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This private retreat, ideally positioned between historic Easton and St. Michaels, offers the rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on more than six beautifully landscaped acres, the property includes a striking 4,800‑square‑foot all‑brick Colonial residence, an expansive concrete pool with a screened entertainment pavilion, a versatile 60' x 30' Morton building, and frontage on a freshwater pond with peaceful views extending toward the Miles River. The residence was just connected to our county sewer system which provides ultimate flexibility for future expansion of the home if desired. * The home’s exterior is designed for low‑maintenance living with full brick construction, a new roof, a paved drive and circular turnaround, generous parking, brick walkways, and a concrete pool surround. Inside, the first floor features oak hardwood floors, high ceilings, and impressive room sizes. The living room with fireplace, formal dining room, and private office or den with powder room create an elegant and functional layout. The renovated gourmet kitchen includes granite countertops, a tile backsplash, stainless appliances, and opens to a breakfast room and a spacious family room with a vaulted ceiling and cozy fireplace. The first‑floor primary suite serves as a true retreat with a vaulted ceiling, fireplace, oversized walk‑in closet, luxurious bath, and an adjoining flex room ideal for a gym, office, studio, or hobby space. A well‑designed mudroom, laundry with cabinetry and sink, and an additional powder room connect conveniently to the oversized two‑car garage. * The second floor offers a private guest suite with its own bath, two additional bedrooms, a hall bath, and a large bonus or game room. Dual staircases — a formal front staircase and a back staircase leading to the kitchen and family room — enhance both convenience and privacy. * Outdoor living is a highlight of this property. The large concrete pool and screened pavillion create an inviting setting for warm‑weather enjoyment. Mature, thoughtful landscaping surrounds the home, while the Morton building with four overhead doors provides exceptional flexibility for boats, RVs, car storage, or workshop needs. The freshwater pond at the edge of the property adds a serene natural element, with pondside views stretching toward the Miles River. * The home has been meticulously maintained and significantly improved. Recent upgrades include a renovated kitchen and dining area with new fixtures, backsplash, wallpaper, and stainless appliances; a 5‑ton Carrier high‑efficiency heat pump for 1st floor installed in 2011; Bryant 2.5‑ton upstairs AC unit installed in 2018; 2023 electric hot water heater; fresh exterior painting of the house, cabana, and barn trim in 2016; and a new GAF Weather Stopper 50‑year roof with transferable warranty added in 2018. The Morton building received a new steel roof in 2019. An 18.6 kW grid‑tied solar array was installed on the barn roof, covering approximately 90 percent of the home’s annual electric use. Atlantic Broadband service was extended to the property for reliable internet access. Additional enhancements include custom mosquito curtains for the cabana, a new pantry under the stairs, a fully remodeled downstairs bath, and an upgraded primary bath with new double vanity, granite, fixtures, and mirrors. Extensive landscaping improvements include new trees, raised garden beds with irrigation, refreshed poolside plantings, a new picket fence with hydrangeas and iris, and upgraded perennial gardens featuring a wide variety of seasonal blooms. Quarterly public sewer fee $231.25.

4 Beds ⋅ 5 Baths

This private retreat, ideally positioned between historic Easton and St. Michaels, offers the rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on more than six beautifully landscaped acres, the property includes a striking 4,800‑square‑foot all‑brick Colonial residence, an expansive concrete pool with a screened entertainment pavilion, a versatile 60' x 30' Morton building, and frontage on a freshwater pond with peaceful views extending toward the Miles River. The residence was just connected to our county sewer system which provides ultimate flexibility for future expansion of the home if desired. * The home’s exterior is designed for low‑maintenance living with full brick construction, a new roof, a paved drive and circular turnaround, generous parking, brick walkways, and a concrete pool surround. Inside, the first floor features oak hardwood floors, high ceilings, and impressive room sizes. The living room with fireplace, formal dining room, and private office or den with powder room create an elegant and functional layout. The renovated gourmet kitchen includes granite countertops, a tile backsplash, stainless appliances, and opens to a breakfast room and a spacious family room with a vaulted ceiling and cozy fireplace. The first‑floor primary suite serves as a true retreat with a vaulted ceiling, fireplace, oversized walk‑in closet, luxurious bath, and an adjoining flex room ideal for a gym, office, studio, or hobby space. A well‑designed mudroom, laundry with cabinetry and sink, and an additional powder room connect conveniently to the oversized two‑car garage. * The second floor offers a private guest suite with its own bath, two additional bedrooms, a hall bath, and a large bonus or game room. Dual staircases — a formal front staircase and a back staircase leading to the kitchen and family room — enhance both convenience and privacy. * Outdoor living is a highlight of this property. The large concrete pool and screened pavillion create an inviting setting for warm‑weather enjoyment. Mature, thoughtful landscaping surrounds the home, while the Morton building with four overhead doors provides exceptional flexibility for boats, RVs, car storage, or workshop needs. The freshwater pond at the edge of the property adds a serene natural element, with pondside views stretching toward the Miles River. * The home has been meticulously maintained and significantly improved. Recent upgrades include a renovated kitchen and dining area with new fixtures, backsplash, wallpaper, and stainless appliances; a 5‑ton Carrier high‑efficiency heat pump for 1st floor installed in 2011; Bryant 2.5‑ton upstairs AC unit installed in 2018; 2023 electric hot water heater; fresh exterior painting of the house, cabana, and barn trim in 2016; and a new GAF Weather Stopper 50‑year roof with transferable warranty added in 2018. The Morton building received a new steel roof in 2019. An 18.6 kW grid‑tied solar array was installed on the barn roof, covering approximately 90 percent of the home’s annual electric use. Atlantic Broadband service was extended to the property for reliable internet access. Additional enhancements include custom mosquito curtains for the cabana, a new pantry under the stairs, a fully remodeled downstairs bath, and an upgraded primary bath with new double vanity, granite, fixtures, and mirrors. Extensive landscaping improvements include new trees, raised garden beds with irrigation, refreshed poolside plantings, a new picket fence with hydrangeas and iris, and upgraded perennial gardens featuring a wide variety of seasonal blooms. Quarterly public sewer fee $231.25.

8466 Aveley Farm Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,495,000

Welcome to this beautifully maintained 4/5 BR/3.5BA waterfront residence in desirable Oxford, offering timeless coastal appeal and the relaxed lifestyle that defines Maryland's Eastern Shore. Thoughtfully designed for both comfortable everyday living and gracious entertaining, the home features a desirable main-level primary suite with tranquil water views, a large walk-in closet, and a spacious ensuite bath with double-sink vanity. Upstairs, a second primary suite, two additional guest bedrooms, a full bath, and a versatile bonus room provide exceptional flexibility for family and guests. Filled with natural light, the home offers a seamless blend of traditional design and inviting gathering spaces. The gourmet kitchen features a center island, custom glass-front cabinetry, and opens to a charming breakfast room where peaceful water views create the perfect backdrop for morning coffee. A formal dining room is ideal for special occasions, while the dramatic vaulted living room showcases a gas-burning fireplace with custom surround and built-in entertainment center. Double sliding doors open to the patio and gardens, creating an effortless connection between indoor and outdoor living. A separate mudroom provides convenient interior access to the attached 2-car garage, which also offers a full staircase to wonderful attic storage above. Outside, a waterside screened porch invites you to relax and enjoy gentle Eastern Shore breezes and ever-changing views across Boone Creek. The beautifully landscaped grounds are enhanced by mature trees, flowering gardens, and expansive lawn leading to the water's edge. Complete with a private pier featuring two slips and a boat lift, approximately 3.5+ feet of MLW, riprapped shoreline, and picturesque views along Boone Creek, this exceptional waterfront property offers an ideal setting for boating, entertaining, and embracing the best of Oxford's waterfront lifestyle.

4 Beds ⋅ 4 Baths

Welcome to this beautifully maintained 4/5 BR/3.5BA waterfront residence in desirable Oxford, offering timeless coastal appeal and the relaxed lifestyle that defines Maryland's Eastern Shore. Thoughtfully designed for both comfortable everyday living and gracious entertaining, the home features a desirable main-level primary suite with tranquil water views, a large walk-in closet, and a spacious ensuite bath with double-sink vanity. Upstairs, a second primary suite, two additional guest bedrooms, a full bath, and a versatile bonus room provide exceptional flexibility for family and guests. Filled with natural light, the home offers a seamless blend of traditional design and inviting gathering spaces. The gourmet kitchen features a center island, custom glass-front cabinetry, and opens to a charming breakfast room where peaceful water views create the perfect backdrop for morning coffee. A formal dining room is ideal for special occasions, while the dramatic vaulted living room showcases a gas-burning fireplace with custom surround and built-in entertainment center. Double sliding doors open to the patio and gardens, creating an effortless connection between indoor and outdoor living. A separate mudroom provides convenient interior access to the attached 2-car garage, which also offers a full staircase to wonderful attic storage above. Outside, a waterside screened porch invites you to relax and enjoy gentle Eastern Shore breezes and ever-changing views across Boone Creek. The beautifully landscaped grounds are enhanced by mature trees, flowering gardens, and expansive lawn leading to the water's edge. Complete with a private pier featuring two slips and a boat lift, approximately 3.5+ feet of MLW, riprapped shoreline, and picturesque views along Boone Creek, this exceptional waterfront property offers an ideal setting for boating, entertaining, and embracing the best of Oxford's waterfront lifestyle.

26226 Langs Landing Rd, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$1,450,000

A rare chance to own 44.28± acres of productive farmland located in the sought-after Chapel School District, just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: - 70± stall main barn with pasture access - Dry cow barn - 120' x 50' heifer barn - 10-cow swing parlor - 800-gallon milk tank - 350,000-gallon Slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.

5 Beds ⋅ 3 Baths

A rare chance to own 44.28± acres of productive farmland located in the sought-after Chapel School District, just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: - 70± stall main barn with pasture access - Dry cow barn - 120' x 50' heifer barn - 10-cow swing parlor - 800-gallon milk tank - 350,000-gallon Slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.

10380 Chapel Rd, Easton

Listing courtesy of The Land Group. Contact:

Selling Office: The Land Group.

$1,450,000

Waterfront Retreat in Cooke’s Hope – Perfectly positioned along Easton’s sought-after Oxford Road corridor, this custom waterfront home in Cooke’s Hope offers timeless design and a relaxed Eastern Shore lifestyle just minutes from downtown Easton. Designed by Pam Gardner, the home features 3 bedrooms, 2.5 baths and an open floor plan filled with natural light and beautiful water views. A dramatic two-story foyer leads to the vaulted waterfront living room with skylights and wood floors, creating an inviting setting for everyday living and entertaining. The waterside primary suite offers a private retreat with a fireplace and spa-inspired bath featuring a steam shower and soaking tub. The kitchen is designed for both everyday living and entertaining with granite countertops, bar seating and casual dining space. A private den with built-ins and fireplace offers a comfortable office or reading retreat, while the light-filled cupola room provides flexible space for a studio, lounge or creative escape. A separate bedroom wing ensures privacy for family or guests while a detached one-bedroom guest apartment offers additional accommodations. Outdoor living includes a screened porch and waterside deck overlooking the tranquil setting. A two-car garage provides excellent storage for vehicles and waterfront gear. The leased boat slip with water and electric at the community pier (available 2026) offers easy access to the surrounding waterways. A rare opportunity to enjoy waterfront living just minutes from Easton, Oxford and St. Michaels!

4 Beds ⋅ 4 Baths

Waterfront Retreat in Cooke’s Hope – Perfectly positioned along Easton’s sought-after Oxford Road corridor, this custom waterfront home in Cooke’s Hope offers timeless design and a relaxed Eastern Shore lifestyle just minutes from downtown Easton. Designed by Pam Gardner, the home features 3 bedrooms, 2.5 baths and an open floor plan filled with natural light and beautiful water views. A dramatic two-story foyer leads to the vaulted waterfront living room with skylights and wood floors, creating an inviting setting for everyday living and entertaining. The waterside primary suite offers a private retreat with a fireplace and spa-inspired bath featuring a steam shower and soaking tub. The kitchen is designed for both everyday living and entertaining with granite countertops, bar seating and casual dining space. A private den with built-ins and fireplace offers a comfortable office or reading retreat, while the light-filled cupola room provides flexible space for a studio, lounge or creative escape. A separate bedroom wing ensures privacy for family or guests while a detached one-bedroom guest apartment offers additional accommodations. Outdoor living includes a screened porch and waterside deck overlooking the tranquil setting. A two-car garage provides excellent storage for vehicles and waterfront gear. The leased boat slip with water and electric at the community pier (available 2026) offers easy access to the surrounding waterways. A rare opportunity to enjoy waterfront living just minutes from Easton, Oxford and St. Michaels!

6780 Cookes Hope Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Monument Sotheby's International Realty.

$1,395,000

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

3 Beds ⋅ 3 Baths

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 W Chestnut, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,350,000

Beyond the white picket fence, a storybook garden unfolds—lush, curated, and unmistakably Oxford. Perfectly positioned just moments from the beach, ferry, and waterfront park, 208 Factory Street offers a rare blend of timeless village charm and sophisticated modern comfort. Thoughtfully enhanced with updated mechanical systems since 2019, this three-bedroom residence has been meticulously maintained and beautifully reimagined for effortless living. Sunlight pours into the airy, open- concept living, dining, and kitchen spaces, where hardwood flooring flows seamlessly throughout and every room feels connected to the outdoors. Designed with exceptional flexibility, the home features two private primary suites—one conveniently located on the main level and a second occupying the upper floor. The upstairs retreat serves as a true sanctuary, complemented by a beautifully renovated spa-inspired bath featuring a glass-enclosed porcelain tile steam shower. The main-level suite offers its own renovated bath and charming loft area, creating an equally inviting private escape. Just off the kitchen, a dedicated office provides the ideal work-from-home setting, while multiple outdoor living spaces invite relaxation and entertaining throughout the seasons. Enjoy quiet mornings on the intimate sitting porch overlooking the pool, gather with friends on the screened porch, or simply savor the beauty of the impeccably landscaped cottage gardens that envelop the property. Completing the offering is a detached one-car garage and an enviable location in the heart of Oxford. A home that captures the very essence of Eastern Shore living—elegant yet approachable, refined yet welcoming, and perfectly connected to one of Maryland’s most treasured waterfront communities. Here, every detail has been thoughtfully curated to create a lifestyle as beautiful as its surroundings. ---{Luxury & Special Features} Electric retractable awnings | Heated floor in second-floor primary bath | Glass-enclosed steam shower with rain shower in second-floor primary bath | Towel warmer in second-floor primary bath | Tesla charger in detached garage | Moen smart water shutoff valve | Water pressure booster pump | Lawn irrigation system | Updated mechanical systems since 2019 | Hardwood flooring throughout | Two primary suites, including a main-level primary | Dedicated office/flex room | Screened porch | Poolside sitting porch | Detached one-car garage | Cottage gardens and white picket fence setting |

3 Beds ⋅ 4 Baths

Beyond the white picket fence, a storybook garden unfolds—lush, curated, and unmistakably Oxford. Perfectly positioned just moments from the beach, ferry, and waterfront park, 208 Factory Street offers a rare blend of timeless village charm and sophisticated modern comfort. Thoughtfully enhanced with updated mechanical systems since 2019, this three-bedroom residence has been meticulously maintained and beautifully reimagined for effortless living. Sunlight pours into the airy, open- concept living, dining, and kitchen spaces, where hardwood flooring flows seamlessly throughout and every room feels connected to the outdoors. Designed with exceptional flexibility, the home features two private primary suites—one conveniently located on the main level and a second occupying the upper floor. The upstairs retreat serves as a true sanctuary, complemented by a beautifully renovated spa-inspired bath featuring a glass-enclosed porcelain tile steam shower. The main-level suite offers its own renovated bath and charming loft area, creating an equally inviting private escape. Just off the kitchen, a dedicated office provides the ideal work-from-home setting, while multiple outdoor living spaces invite relaxation and entertaining throughout the seasons. Enjoy quiet mornings on the intimate sitting porch overlooking the pool, gather with friends on the screened porch, or simply savor the beauty of the impeccably landscaped cottage gardens that envelop the property. Completing the offering is a detached one-car garage and an enviable location in the heart of Oxford. A home that captures the very essence of Eastern Shore living—elegant yet approachable, refined yet welcoming, and perfectly connected to one of Maryland’s most treasured waterfront communities. Here, every detail has been thoughtfully curated to create a lifestyle as beautiful as its surroundings. ---{Luxury & Special Features} Electric retractable awnings | Heated floor in second-floor primary bath | Glass-enclosed steam shower with rain shower in second-floor primary bath | Towel warmer in second-floor primary bath | Tesla charger in detached garage | Moen smart water shutoff valve | Water pressure booster pump | Lawn irrigation system | Updated mechanical systems since 2019 | Hardwood flooring throughout | Two primary suites, including a main-level primary | Dedicated office/flex room | Screened porch | Poolside sitting porch | Detached one-car garage | Cottage gardens and white picket fence setting |

208 Factory St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,325,000

Some homes check the boxes. Others create a lifetime of memories......Welcome Home to 28091 Oaklands Circle Perfectly situated on over 2.5 beautifully landscaped acres in the highly desirable Oaklands community, this exceptional five-bedroom, four-and-a-half-bath custom home offers the rare combination of luxury, comfort, privacy, and a truly move-in-ready lifestyle. From the moment you arrive, you’ll appreciate the mature trees, manicured landscaping, fresh mulch, and natural privacy that surround this beautifully maintained property. Every detail reflects years of thoughtful care and pride of ownership. Inside, timeless craftsmanship meets thoughtful updates. Rich hardwood flooring flows throughout the home, complemented by replacement windows, recessed LED lighting, custom built-in shelving, window seats with hidden storage, and pocket doors that add both character and functionality. At the heart of the home is the beautifully updated kitchen featuring granite countertops, generous island workspace, coffee bar, breakfast area with lots of natural light and an inviting layout designed for everything from family dinners to holiday gatherings. With five spacious bedrooms, 4 1/2 bathrooms, great room, formal areas, and a fully finished bonus room above the attached three-car garage, the flexible floor plan easily accommodates growing, blended, or multi generational families, overnight guests, a home office, fitness room, or recreation space. Comfort can be found in every season. Enjoy the warmth of both a gas fireplace and a traditional wood-burning fireplace, or gather around the fire pit on cool evenings during cooler months. Just outside you will discover your own private retreat. Relax on the screened-in covered porch, multiple decks, spend afternoons and weekends lounging by the sparkling swimming pool with diving board, featuring a new pool cover and new pool pumps. Explore the custom tree fort and zip line, or simply enjoy the open green space that makes this property so special. Relax on any one of the multiple deck spaces overlooking the peaceful backyard or just simply soak up the AC in the summertime. A large storage shed provides plenty of room for lawn equipment, tools, and outdoor gear. Significant improvements—including replacement windows, approximately three-quarters of the roof replaced, and a whole-house backup generator—offer lasting value and peace of mind. A state-of-the-art security, alarm, and surveillance system adds another level of comfort for today’s homeowners. Located just minutes from historic downtown Easton or the waterfront town of Oxford, both with outstanding restaurants, boutique shopping, access to local healthcare, schools, and the waterfront lifestyle of Maryland’s Eastern Shore, this home offers the perfect balance of convenience and tranquility. Beautifully updated, meticulously maintained, and designed for everyday living as well as unforgettable entertaining, 28091 Oaklands Circle is more than a home—it’s where birthdays are celebrated, holidays are shared, and lifelong memories are made. Come experience the warmth, quality, and lifestyle that make this remarkable property truly one of Easton’s finest.

5 Beds ⋅ 5 Baths

Some homes check the boxes. Others create a lifetime of memories......Welcome Home to 28091 Oaklands Circle Perfectly situated on over 2.5 beautifully landscaped acres in the highly desirable Oaklands community, this exceptional five-bedroom, four-and-a-half-bath custom home offers the rare combination of luxury, comfort, privacy, and a truly move-in-ready lifestyle. From the moment you arrive, you’ll appreciate the mature trees, manicured landscaping, fresh mulch, and natural privacy that surround this beautifully maintained property. Every detail reflects years of thoughtful care and pride of ownership. Inside, timeless craftsmanship meets thoughtful updates. Rich hardwood flooring flows throughout the home, complemented by replacement windows, recessed LED lighting, custom built-in shelving, window seats with hidden storage, and pocket doors that add both character and functionality. At the heart of the home is the beautifully updated kitchen featuring granite countertops, generous island workspace, coffee bar, breakfast area with lots of natural light and an inviting layout designed for everything from family dinners to holiday gatherings. With five spacious bedrooms, 4 1/2 bathrooms, great room, formal areas, and a fully finished bonus room above the attached three-car garage, the flexible floor plan easily accommodates growing, blended, or multi generational families, overnight guests, a home office, fitness room, or recreation space. Comfort can be found in every season. Enjoy the warmth of both a gas fireplace and a traditional wood-burning fireplace, or gather around the fire pit on cool evenings during cooler months. Just outside you will discover your own private retreat. Relax on the screened-in covered porch, multiple decks, spend afternoons and weekends lounging by the sparkling swimming pool with diving board, featuring a new pool cover and new pool pumps. Explore the custom tree fort and zip line, or simply enjoy the open green space that makes this property so special. Relax on any one of the multiple deck spaces overlooking the peaceful backyard or just simply soak up the AC in the summertime. A large storage shed provides plenty of room for lawn equipment, tools, and outdoor gear. Significant improvements—including replacement windows, approximately three-quarters of the roof replaced, and a whole-house backup generator—offer lasting value and peace of mind. A state-of-the-art security, alarm, and surveillance system adds another level of comfort for today’s homeowners. Located just minutes from historic downtown Easton or the waterfront town of Oxford, both with outstanding restaurants, boutique shopping, access to local healthcare, schools, and the waterfront lifestyle of Maryland’s Eastern Shore, this home offers the perfect balance of convenience and tranquility. Beautifully updated, meticulously maintained, and designed for everyday living as well as unforgettable entertaining, 28091 Oaklands Circle is more than a home—it’s where birthdays are celebrated, holidays are shared, and lifelong memories are made. Come experience the warmth, quality, and lifestyle that make this remarkable property truly one of Easton’s finest.

28091 Oaklands Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,280,000

Prime waterfront home in Oxford’s beautiful historic district, faces west overlooking the Tred Avon River. Offering the best in Oxford waterfront with prevailing SW summer breezes, fantastic year-round sunsets, a long dock, patio, old growth large trees, extensive hardscape and off-street parking make this property unique. It has a carport and is located on a significant tree-lined street and lies with the “X” zone on the flood maps. On the first floor is an open, well equipped kitchen that opens to the great room with views overlooking the patio, gardens and the river. One full bath on the first floor with a library/den and front entrance. There is a primary bedroom suite on the second level adjoining a screened porch and deck with views to the Tred Avon beyond. The views are extraordinary! In addition, there is a second bedroom and bath on this level.

2 Beds ⋅ 3 Baths

Prime waterfront home in Oxford’s beautiful historic district, faces west overlooking the Tred Avon River. Offering the best in Oxford waterfront with prevailing SW summer breezes, fantastic year-round sunsets, a long dock, patio, old growth large trees, extensive hardscape and off-street parking make this property unique. It has a carport and is located on a significant tree-lined street and lies with the “X” zone on the flood maps. On the first floor is an open, well equipped kitchen that opens to the great room with views overlooking the patio, gardens and the river. One full bath on the first floor with a library/den and front entrance. There is a primary bedroom suite on the second level adjoining a screened porch and deck with views to the Tred Avon beyond. The views are extraordinary! In addition, there is a second bedroom and bath on this level.

102 Tred Avon Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,270,000

Tucked in a lovely Oxford location just steps from in-town amenities, this completely redone 4 bedroom, 3.5-bath residence offers quaint Eastern Shore living with exceptional charm and flexibility. The light-filled main home features a formal dining room, private office/bedroom, inviting family room with gas fireplace and wet bar with custom built-ins, and a top-of-the-line gourmet kitchen with cathedral ceiling, generous cabinetry, center island, and an adjacent mudroom with additional appliances. Upstairs, the spacious primary suite overlooks the beautifully landscaped rear grounds , pool and features vaulted ceilings, custom built-ins, and a walk-in closet. There is a comfortable guest bedroom and full bath. Outdoor living features a fabulous rear deck overlooking an in-ground swimming pool and manicured gardens—perfect for entertaining or quiet relaxation. A separate guest cottage with murphy bed, full bath and kitchenette adds even more versatility, ideal for guests, extended stays, or a private retreat. Only a couple blocks to town owned waterfront, shops, restaurants, parks, marinas and the local market. Move in ready home.

4 Beds ⋅ 4 Baths

Tucked in a lovely Oxford location just steps from in-town amenities, this completely redone 4 bedroom, 3.5-bath residence offers quaint Eastern Shore living with exceptional charm and flexibility. The light-filled main home features a formal dining room, private office/bedroom, inviting family room with gas fireplace and wet bar with custom built-ins, and a top-of-the-line gourmet kitchen with cathedral ceiling, generous cabinetry, center island, and an adjacent mudroom with additional appliances. Upstairs, the spacious primary suite overlooks the beautifully landscaped rear grounds , pool and features vaulted ceilings, custom built-ins, and a walk-in closet. There is a comfortable guest bedroom and full bath. Outdoor living features a fabulous rear deck overlooking an in-ground swimming pool and manicured gardens—perfect for entertaining or quiet relaxation. A separate guest cottage with murphy bed, full bath and kitchenette adds even more versatility, ideal for guests, extended stays, or a private retreat. Only a couple blocks to town owned waterfront, shops, restaurants, parks, marinas and the local market. Move in ready home.

103 Tred Avon Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Compass.

$1,250,000

The owner must approve all showings, advance notice is preferred. REAL ESTATE ONLY FOR SALE. Positioned in the heart of downtown St. Michaels, 208 N Talbot Street offers a rare opportunity to acquire a premier mixed-use commercial property in one of the Eastern Shore’s most desirable waterfront communities. This 4,111-square-foot building features outstanding visibility along Talbot Street, benefiting from strong pedestrian traffic and close proximity to the waterfront, marinas, boutique shops, and established dining destinations. The property is ideally suited for a restaurant or hospitality concept, featuring a fully built-out commercial kitchen and an impressive total seating capacity of approximately 158 guests across indoor and outdoor dining areas. This allows a new owner to open and operate with minimal additional build-out—an increasingly rare opportunity in this market. A standout feature is the inclusion of 12 dedicated parking spaces, a significant advantage in downtown St. Michaels, enhancing accessibility for both customers and staff. The second level, which has outside access, offers a spacious three-bedroom, three-bathroom apartment, providing excellent flexibility for owner occupancy or future rental income. The apartment kitchen is currently unfinished, needs some remodelling, upstairs offering the opportunity for customization while adding additional long-term value once completed. Whether positioned as a signature dining establishment, boutique hospitality concept, or mixed-use investment, this property delivers a compelling combination of location, infrastructure, and upside potential in a market where inventory remains limited. The property is sold as is. Recommend each individual buyer check with the Town Office for uses for 2nd level.

208 N Talbot, Saint Michaels

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

Selling Office: Non Subscribing Office.

$1,250,000

Prime 82.54± Acre Eastern Shore Farm With Tillable Ground And Hunting This 82.54-acre property in Talbot County, Maryland, offers a highly desirable opportunity to own productive Eastern Shore farmland with strong agricultural value, recreational appeal, and future homesite potential. Situated in a well-regarded farming region, this tract offers a balanced combination of income-producing capability, land investment potential, and outdoor enjoyment. The property is zoned agricultural, allowing continued row-crop production, long-term land ownership, and flexibility for future use. A large portion of the acreage is tillable, supported by soils consisting primarily of Hambrook Sassafras complex and Ingleside sandy loam. These soil types are well known throughout the region for their productivity and drainage, making the farm suitable for consistent agricultural operations. In addition to its farming attributes, the property includes a smaller wooded section that enhances privacy, natural diversity, and wildlife habitat. This wooded section also includes a designated forest conservation area, as shown on the recorded plat. This area represents only a small portion of the overall property and contributes to long-term environmental stewardship while maintaining the farms overall usability and value. Portions of the property were previously enrolled in CRP, offering the potential to further utilize income-producing opportunities on the property while continuing current agricultural practices. The property benefits from excellent access and layout, with road frontage along Bambury Road on the eastern boundary and Kates Point Road along the northern boundary. This dual frontage provides convenient entry points and supports efficient movement for farming operations. A drainage and utility easement is present on the property, typical for farms in the area near county roads, and does not detract from its overall usability. From a recreational standpoint, this property offers exceptional hunting potential. The combination of productive tillable ground, natural edge habitat, and surrounding agricultural landscape creates an ideal environment for attracting and holding whitetail deer and migratory geese. The property has a strong history of producing quality whitetail deer, with the area known for harvesting mature bucks. The layout supports multiple stand and blind locations, allowing for effective setups across different wind directions and seasons. The property also offers strong potential for a future homesite, making it an excellent option for those looking to build a private residence, farmhouse, or retreat surrounded by productive farmland and natural beauty. This blend of usability, privacy, and location creates an appealing setting for both investment and lifestyle buyers. For buyers seeking expansion, this tract is also available in combination with the adjacent 90-acre home farm, creating the potential for a larger, contiguous farming operation with additional improvements. This Talbot County property offers a rare combination of productive farmland, recreational value, and long-term potential in one of Marylands most sought-after rural regions. Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750-B Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Meredith Fine Properties.

$1,250,000

A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the waterfront experience. Gracious, private, and full of soul, this rare Broad Cove property offers the presence and romance of a true dream home. Note: Original section of home has asbestos-cement exterior shingles.

4 Beds ⋅ 3 Baths

A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the waterfront experience. Gracious, private, and full of soul, this rare Broad Cove property offers the presence and romance of a true dream home. Note: Original section of home has asbestos-cement exterior shingles.

21408 Broad Cove Ln, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: Northrop Realty.

$1,225,000

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.

2 Beds ⋅ 3 Baths

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.

106 Chestnut St E, Saint Michaels

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$1,190,000

Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. NEW ROOF and Pool Equipment 2026, HVAC 2019 & 2021. Inside, the home features a well-designed floor plan with abundant natural light and timeless appeal. The open kitchen connects seamlessly to a casual dining and living area highlighted by a vaulted ceiling, creating an inviting space for everyday living and entertaining. Formal living and dining rooms offer elegant settings for gatherings, while the expansive deck, fenced backyard, and in-ground pool extend the living space outdoors. The first-floor primary suite provides convenience and privacy. Upstairs, you’ll find spacious guest suites, a dedicated office, and a flexible family room ideal for work, relaxation, or hobbies. A large walk-up attic offers excellent storage and future expansion potential. Ideally positioned within the Oxford corridor, this home allows easy access to the waterfront town of Oxford and the shopping, dining, and cultural amenities of Easton. Enjoy the best of rural living with proximity to modern conveniences, all within a peaceful and sought-after neighborhood.

4 Beds ⋅ 4 Baths

Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. NEW ROOF and Pool Equipment 2026, HVAC 2019 & 2021. Inside, the home features a well-designed floor plan with abundant natural light and timeless appeal. The open kitchen connects seamlessly to a casual dining and living area highlighted by a vaulted ceiling, creating an inviting space for everyday living and entertaining. Formal living and dining rooms offer elegant settings for gatherings, while the expansive deck, fenced backyard, and in-ground pool extend the living space outdoors. The first-floor primary suite provides convenience and privacy. Upstairs, you’ll find spacious guest suites, a dedicated office, and a flexible family room ideal for work, relaxation, or hobbies. A large walk-up attic offers excellent storage and future expansion potential. Ideally positioned within the Oxford corridor, this home allows easy access to the waterfront town of Oxford and the shopping, dining, and cultural amenities of Easton. Enjoy the best of rural living with proximity to modern conveniences, all within a peaceful and sought-after neighborhood.

28028 Playtor Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Washington Fine Properties, LLC.

$1,187,500

3 Beds ⋅ 3 Baths

344 Perry Cabin Dr, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,175,000

Set on 2.14 beautifully maintained acres, this exceptional 6-bedroom home offers the perfect blend of space, comfort, and outdoor living. A thoughtfully designed layout features a desirable first-floor master suite, providing privacy and convenience with generous proportions and serene views of the surrounding landscape. The home’s expansive interior includes multiple living and entertaining areas, ideal for both everyday living and hosting guests. Large windows throughout invite natural light and showcase the property’s stunning grounds. Step outside to your own private retreat, complete with a sparkling pool and extensive landscaping that creates a peaceful, park-like setting. Whether relaxing poolside or enjoying the open green space, this property offers endless opportunities for outdoor enjoyment. A detached two-car garage adds functionality and additional storage, complementing the home’s impressive features. With six spacious bedrooms and ample acreage, this property provides flexibility for a variety of lifestyles—all in a picturesque and private setting.

6 Beds ⋅ 6 Baths

Set on 2.14 beautifully maintained acres, this exceptional 6-bedroom home offers the perfect blend of space, comfort, and outdoor living. A thoughtfully designed layout features a desirable first-floor master suite, providing privacy and convenience with generous proportions and serene views of the surrounding landscape. The home’s expansive interior includes multiple living and entertaining areas, ideal for both everyday living and hosting guests. Large windows throughout invite natural light and showcase the property’s stunning grounds. Step outside to your own private retreat, complete with a sparkling pool and extensive landscaping that creates a peaceful, park-like setting. Whether relaxing poolside or enjoying the open green space, this property offers endless opportunities for outdoor enjoyment. A detached two-car garage adds functionality and additional storage, complementing the home’s impressive features. With six spacious bedrooms and ample acreage, this property provides flexibility for a variety of lifestyles—all in a picturesque and private setting.

8464 Aveley Farm Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

$1,152,500

The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.

3 Beds ⋅ 3 Baths

The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.

114 E Chew Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,150,000

This home checks ALL the boxes! Over 400ft of waterfront overlooking Bolingbroke Creek with Pier and Floating jet ski dock. Beautiful and Inviting Front Porch that leads into this Custom-built Cape Cod located on Very Private 12.77 acres with many recent upgrades. Features include 4 Bedrooms, 3-1/2 Baths. This open floor plan features large kitchen with Granite countertops and plenty of cabinets and Lots of Storage. Primary Bedroom on the first floor with Full Bath, deck and Hot Tub overlooking the water. Family Room with wood burning Fireplace. Waterside glassed in porch and first floor laundry with built-in Pet Bathing Station. Separate Dining Room / Office. Gorgeous Luxury Vinyl Planking floors throughout. Upstairs you will find...3 Bedrooms, 1 Full Bath, Large Rec Room, and a Breezeway that leads you to Finished Space above Garage-Currently a bonus room with Full Bath. Room could easily be a Workout Room / Office / Game Room. Outdoor Features Include... Geothermal HVAC, Shed, Fire Pit, Entertaining Space surrounded by Beautiful Landscaping. Custom walkway to the water for all your boating and Fishing needs. Minutes to Scenic Choptank River, Sand Bar, and all Cambridge has to offer. In addition, there is plenty of acreage for Hunting or Gardening which includes a Garage w/ lean to attached and a small Greenhouse. Currently a Perc pending for additional dwelling. Home is situated within 15 minutes to Easton or Cambridge. One hour to Maryland and Delaware Beaches. Call Today!! You will not be disappointed.

4 Beds ⋅ 4 Baths

This home checks ALL the boxes! Over 400ft of waterfront overlooking Bolingbroke Creek with Pier and Floating jet ski dock. Beautiful and Inviting Front Porch that leads into this Custom-built Cape Cod located on Very Private 12.77 acres with many recent upgrades. Features include 4 Bedrooms, 3-1/2 Baths. This open floor plan features large kitchen with Granite countertops and plenty of cabinets and Lots of Storage. Primary Bedroom on the first floor with Full Bath, deck and Hot Tub overlooking the water. Family Room with wood burning Fireplace. Waterside glassed in porch and first floor laundry with built-in Pet Bathing Station. Separate Dining Room / Office. Gorgeous Luxury Vinyl Planking floors throughout. Upstairs you will find...3 Bedrooms, 1 Full Bath, Large Rec Room, and a Breezeway that leads you to Finished Space above Garage-Currently a bonus room with Full Bath. Room could easily be a Workout Room / Office / Game Room. Outdoor Features Include... Geothermal HVAC, Shed, Fire Pit, Entertaining Space surrounded by Beautiful Landscaping. Custom walkway to the water for all your boating and Fishing needs. Minutes to Scenic Choptank River, Sand Bar, and all Cambridge has to offer. In addition, there is plenty of acreage for Hunting or Gardening which includes a Garage w/ lean to attached and a small Greenhouse. Currently a Perc pending for additional dwelling. Home is situated within 15 minutes to Easton or Cambridge. One hour to Maryland and Delaware Beaches. Call Today!! You will not be disappointed.

2195 Quail Run Dr, Trappe

Listing courtesy of Brenton Realty Group. Contact:

Selling Office: Benson & Mangold, LLC.

$1,138,000

Gorgeous waterfront home! Rancher, one level living on over 2 acres in Royal Oak. Get ready, properties like these don't come around too often!

2 Beds ⋅ 2 Baths

Gorgeous waterfront home! Rancher, one level living on over 2 acres in Royal Oak. Get ready, properties like these don't come around too often!

6706 Thorneton Rd, Royal Oak

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$1,135,000

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

2 Beds ⋅ 2 Baths

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

107 E Chestnut, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: RE/MAX Executive.

$1,075,000

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

4 Beds ⋅ 4 Baths

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

114 W Chestnut St, St Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$1,055,000

Experience exceptional waterfront living in this custom-built home set on a private, 3-acre lot. Designed to maximize comfort and connection to the outdoors. The spacious floor plan includes a dedicated office, a cozy den and a gourmet kitchen. The oversized garage and separate laundry room are an added bonus to this perfect property. This custom designed and built - one of a kind home is conveniently located between Easton and St. Michaels. Large primary bedroom with ensuite bath. Every bedroom features direct access to the expansive deck, creating a seamless indoor–outdoor lifestyle and offering the perfect place to enjoy quiet moments. Step outside to your own resort-like escape. The very large deck provides ample room for dining, relaxing, and entertaining, while the in-ground pool invites you to enjoy warm days in total privacy. A rare combination of craftsmanship, serenity, and recreation, this waterfront property delivers an unparalleled living experience—perfect as a year-round residence or private retreat.

3 Beds ⋅ 3 Baths

Experience exceptional waterfront living in this custom-built home set on a private, 3-acre lot. Designed to maximize comfort and connection to the outdoors. The spacious floor plan includes a dedicated office, a cozy den and a gourmet kitchen. The oversized garage and separate laundry room are an added bonus to this perfect property. This custom designed and built - one of a kind home is conveniently located between Easton and St. Michaels. Large primary bedroom with ensuite bath. Every bedroom features direct access to the expansive deck, creating a seamless indoor–outdoor lifestyle and offering the perfect place to enjoy quiet moments. Step outside to your own resort-like escape. The very large deck provides ample room for dining, relaxing, and entertaining, while the in-ground pool invites you to enjoy warm days in total privacy. A rare combination of craftsmanship, serenity, and recreation, this waterfront property delivers an unparalleled living experience—perfect as a year-round residence or private retreat.

7605 Pendleton Farm Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,050,000

Welcome to this one-of-a-kind custom-built home by Paquin Design Build, ideally situated in the sought-after waterfront access community of Easton Village. This exceptional 4-bedroom, 3.5-bath home with a bonus room and office showcases high-end craftsmanship and extensive post-construction upgrades throughout. Interior highlights include a gourmet kitchen with an oversized waterfall-edge island, high-end inset cabinets extending up to the 10ft ceilings, pantry, and stainless-steel appliances. The kitchen opens to a spacious family room with a gas fireplace and built-in storage. There is a primary suite on both the first and second floor, and the second floor suite includes a private balcony, wood-paneled ceiling, and a spa-inspired bath. A sunroom enhanced by custom windows fills the home with natural light, while solid core doors, Cat6 wiring, and a Control4 whole-home audio/visual system elevate everyday living. Outdoor spaces are equally impressive, featuring a welcoming front porch with swing and fan, a professionally designed backyard complete with an extended brick patio, pergola, fire pit with custom sitting wall and a natural gas grill. The Control4 audio extends to the outdoor living areas/porches and the landscaped yard is upgraded with uplighting and WiFi-controlled irrigation. Additional highlights include an encapsulated crawlspace with waterproofing, dual-zone HVAC, Rinnai tankless water heater, and an epoxy-coated garage floor with Gorilla Track storage system. This is a rare opportunity to own a custom-built, impeccably designed home in one of Easton's premier communities. Enjoy all that Easton Village has to offer, including waterfront access with community boat slips, kayak launch, clubhouse and outdoor pool, walking trails, and scenic green spaces along the Tred Avon River. Conveniently located just minutes from downtown Easton's shops, dining, and cultural attractions, this home offers the perfect blend of luxury, comfort and Eastern Shore lifestyle.

4 Beds ⋅ 4 Baths

Welcome to this one-of-a-kind custom-built home by Paquin Design Build, ideally situated in the sought-after waterfront access community of Easton Village. This exceptional 4-bedroom, 3.5-bath home with a bonus room and office showcases high-end craftsmanship and extensive post-construction upgrades throughout. Interior highlights include a gourmet kitchen with an oversized waterfall-edge island, high-end inset cabinets extending up to the 10ft ceilings, pantry, and stainless-steel appliances. The kitchen opens to a spacious family room with a gas fireplace and built-in storage. There is a primary suite on both the first and second floor, and the second floor suite includes a private balcony, wood-paneled ceiling, and a spa-inspired bath. A sunroom enhanced by custom windows fills the home with natural light, while solid core doors, Cat6 wiring, and a Control4 whole-home audio/visual system elevate everyday living. Outdoor spaces are equally impressive, featuring a welcoming front porch with swing and fan, a professionally designed backyard complete with an extended brick patio, pergola, fire pit with custom sitting wall and a natural gas grill. The Control4 audio extends to the outdoor living areas/porches and the landscaped yard is upgraded with uplighting and WiFi-controlled irrigation. Additional highlights include an encapsulated crawlspace with waterproofing, dual-zone HVAC, Rinnai tankless water heater, and an epoxy-coated garage floor with Gorilla Track storage system. This is a rare opportunity to own a custom-built, impeccably designed home in one of Easton's premier communities. Enjoy all that Easton Village has to offer, including waterfront access with community boat slips, kayak launch, clubhouse and outdoor pool, walking trails, and scenic green spaces along the Tred Avon River. Conveniently located just minutes from downtown Easton's shops, dining, and cultural attractions, this home offers the perfect blend of luxury, comfort and Eastern Shore lifestyle.

8099 Fox Squirrel Way, Easton

Listing courtesy of ERA Martin Associates. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,050,000

Waterfront living on Glebe Creek! Set on 1.7 elevated acres overlooking scenic Glebe Creek, this updated 3-bedroom, 2-bath rancher offers expansive southern-facing water views and effortless Eastern Shore living. The single-story layout is designed for comfort and connection to the outdoors, with large windows throughout that capture natural light and sweeping creek views. The heart of the home features a fully renovated kitchen with new cabinetry, stainless steel appliances, quartz countertops, tile flooring, and a stylish backsplash, opening into inviting living spaces with refinished hardwood floors, custom built-ins, and a charming gas fireplace. One of the standout spaces is the expansive rear sunroom, complete with vaulted ceilings, exposed beams, luxury vinyl plank flooring, and walls of windows that flood the room with natural light while framing peaceful water views. Recent improvements throughout the home include a brand-new roof (2026), fresh interior paint, refinished hardwood floors, a renovated shared bath with new tile and shower, making this home move-in ready. Outside, enjoy the best of waterfront living with a private dock and boat lift, perfect for exploring Glebe Creek and beyond. The property also includes a detached 2-car garage connected by a breezeway, offering convenience and additional storage. Just a short drive from both downtown Saint. Michaels and downtown Easton, this property provides the ideal blend of waterfront tranquility and access to the Eastern Shore’s restaurants, shops, and amenities.

3 Beds ⋅ 2 Baths

Waterfront living on Glebe Creek! Set on 1.7 elevated acres overlooking scenic Glebe Creek, this updated 3-bedroom, 2-bath rancher offers expansive southern-facing water views and effortless Eastern Shore living. The single-story layout is designed for comfort and connection to the outdoors, with large windows throughout that capture natural light and sweeping creek views. The heart of the home features a fully renovated kitchen with new cabinetry, stainless steel appliances, quartz countertops, tile flooring, and a stylish backsplash, opening into inviting living spaces with refinished hardwood floors, custom built-ins, and a charming gas fireplace. One of the standout spaces is the expansive rear sunroom, complete with vaulted ceilings, exposed beams, luxury vinyl plank flooring, and walls of windows that flood the room with natural light while framing peaceful water views. Recent improvements throughout the home include a brand-new roof (2026), fresh interior paint, refinished hardwood floors, a renovated shared bath with new tile and shower, making this home move-in ready. Outside, enjoy the best of waterfront living with a private dock and boat lift, perfect for exploring Glebe Creek and beyond. The property also includes a detached 2-car garage connected by a breezeway, offering convenience and additional storage. Just a short drive from both downtown Saint. Michaels and downtown Easton, this property provides the ideal blend of waterfront tranquility and access to the Eastern Shore’s restaurants, shops, and amenities.

8987 Glebe Creek Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,049,000

Privately situated along the Oxford Road corridor, Heron Rest is a custom Pam Gardner–designed waterfront home that beautifully blends Eastern Shore charm with modern functionality. Built in 1995 and set on approximately two acres overlooking Peachblossom Creek, this property embodies the essence of relaxed waterfront living. The home features cathedral ceilings and hardwood floors throughout the great room and dining area, anchored by a striking wood-burning marble fireplace. The spacious kitchen is equipped with double wall ovens, a gas cooktop, generous cabinetry, and a walk-in pantry with wine storage. A butler’s pantry, laundry room, and mudroom/side entry add convenience and thoughtful flow to the layout. The primary suite includes an adjoining library with custom built-ins and a vaulted ceiling, while two additional bedrooms share a hall bath. A large screened porch features tile floors, rattan shades, and a gas fireplace, an inviting retreat with tranquil water views. A detached three-car garage includes second floor storage for an office or studio. The waterside deck and gently sloping lawn lead to a private pier on Peachblossom Creek. Located just minutes from downtown Easton and Oxford, Heron Rest offers a rare combination of privacy, craftsmanship, and timeless Eastern Shore beauty.

3 Beds ⋅ 2 Baths

Privately situated along the Oxford Road corridor, Heron Rest is a custom Pam Gardner–designed waterfront home that beautifully blends Eastern Shore charm with modern functionality. Built in 1995 and set on approximately two acres overlooking Peachblossom Creek, this property embodies the essence of relaxed waterfront living. The home features cathedral ceilings and hardwood floors throughout the great room and dining area, anchored by a striking wood-burning marble fireplace. The spacious kitchen is equipped with double wall ovens, a gas cooktop, generous cabinetry, and a walk-in pantry with wine storage. A butler’s pantry, laundry room, and mudroom/side entry add convenience and thoughtful flow to the layout. The primary suite includes an adjoining library with custom built-ins and a vaulted ceiling, while two additional bedrooms share a hall bath. A large screened porch features tile floors, rattan shades, and a gas fireplace, an inviting retreat with tranquil water views. A detached three-car garage includes second floor storage for an office or studio. The waterside deck and gently sloping lawn lead to a private pier on Peachblossom Creek. Located just minutes from downtown Easton and Oxford, Heron Rest offers a rare combination of privacy, craftsmanship, and timeless Eastern Shore beauty.

28701 Edgemere Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Keller Williams Select Realtors of Cambridge.

$1,048,000

Historic Charm Meets Endless Potential in Easton Welcome to this beautifully renovated home situated on a highly desirable, deep double corner lot in Easton's Historic District. Inside, you are greeted by bright, airy spaces that perfectly balance historic character with modern flair, featuring gorgeous hardwood floors, classic moldings, and elegant fireplaces. Main House Highlights: Inviting Living Spaces: Multiple sitting areas offer cozy fireplaces and glass doors that seamlessly blend indoor and outdoor living. Brand new HVAC. Chef’s Kitchen: A large, fully equipped kitchen boasts crisp white cabinetry, stainless steel appliances, a center island with seating, and striking granite countertops, flowing easily into a separate dining room. Versatile Upper Level: Features spacious bedrooms (including a bold, stylish primary suite), flexible space for a dedicated home office, and a beautiful sunroom bathed in natural light from three sides. Updated Baths: Two charming and light-filled bathrooms complete the interior. Outdoor Oasis: Step outside to enjoy a very private, fenced yard complete with a patio, a relaxing side porch, extensive landscaping, greenhouses, landscape lighting, and the convenience of off-street parking. The home also features Lutron lighting throughout to perfectly set the mood. The Bonus Opportunity—A Ready-to-Build Guest House: The property includes an existing barn/shop outbuilding, and the current owners have already done the heavy lifting to envision its future. Schematic architectural plans for a complete barn conversion by John Hutchison Architecture are available for the new owner! The Vision: The proposed design transforms the space into a stunning guest house or accessory dwelling. First Floor: Designed to feature a living area with a gas fireplace, a kitchenette, and two bathrooms. Second Floor: Expertly planned to accommodate custom built-in beds and bunks. Premium Finishes: Planned materials include James Hardie vertical board and batten siding, Andersen 400 series windows, and engineered hardwood flooring. Turnkey Potential: A comprehensive construction estimate from KRM Construction is also on file, making this an easy, ready-to-execute project for the visionary buyer. (Further adding to the property's incredible potential, existing condition architectural plans have also been drafted for a future main house addition.)

3 Beds ⋅ 3 Baths

Historic Charm Meets Endless Potential in Easton Welcome to this beautifully renovated home situated on a highly desirable, deep double corner lot in Easton's Historic District. Inside, you are greeted by bright, airy spaces that perfectly balance historic character with modern flair, featuring gorgeous hardwood floors, classic moldings, and elegant fireplaces. Main House Highlights: Inviting Living Spaces: Multiple sitting areas offer cozy fireplaces and glass doors that seamlessly blend indoor and outdoor living. Brand new HVAC. Chef’s Kitchen: A large, fully equipped kitchen boasts crisp white cabinetry, stainless steel appliances, a center island with seating, and striking granite countertops, flowing easily into a separate dining room. Versatile Upper Level: Features spacious bedrooms (including a bold, stylish primary suite), flexible space for a dedicated home office, and a beautiful sunroom bathed in natural light from three sides. Updated Baths: Two charming and light-filled bathrooms complete the interior. Outdoor Oasis: Step outside to enjoy a very private, fenced yard complete with a patio, a relaxing side porch, extensive landscaping, greenhouses, landscape lighting, and the convenience of off-street parking. The home also features Lutron lighting throughout to perfectly set the mood. The Bonus Opportunity—A Ready-to-Build Guest House: The property includes an existing barn/shop outbuilding, and the current owners have already done the heavy lifting to envision its future. Schematic architectural plans for a complete barn conversion by John Hutchison Architecture are available for the new owner! The Vision: The proposed design transforms the space into a stunning guest house or accessory dwelling. First Floor: Designed to feature a living area with a gas fireplace, a kitchenette, and two bathrooms. Second Floor: Expertly planned to accommodate custom built-in beds and bunks. Premium Finishes: Planned materials include James Hardie vertical board and batten siding, Andersen 400 series windows, and engineered hardwood flooring. Turnkey Potential: A comprehensive construction estimate from KRM Construction is also on file, making this an easy, ready-to-execute project for the visionary buyer. (Further adding to the property's incredible potential, existing condition architectural plans have also been drafted for a future main house addition.)

209 Goldsborough St, Easton

Listing courtesy of Compass. Contact:

Selling Office: Douglas Realty LLC.

$1,035,000

Welcome to Pin Oak House, an Easton Federal style white-washed brick property proud to feature the Grand Champion Pin Oak of Talbot County within the confines of its iron-fenced front yard. The spacious corner lot also offers fine gardens, providing colorful foliage nearly year-round. Roses, honeysuckle, tulips, a glorious crepe myrtle, gazebo, irises, stone hardscaping, and a koi pond with waterfall feature are among the many surprises of the enchanting, fairytale-like backyard. The front and backyards are on a multi-zone irrigation system. This property provides ample off street parking for three cars as well as a sizable storage facility that can be converted into a garage if desired. The backyard and main parking area is monitored 24/7 by a Nest Cam security system. The recently installed uplighting in the front and back of the property further adds to the elegance of the home. Enter inside the red solid wood front door and you are greeted by new custom closets and wood doors, new crown molding, a just installed custom sisal stair runner in the foyer; a stunning formal dining room with designer wallpaper and custom window treatments, a beautiful kitchen with granite, dual ovens, a gas stove, new plantation shutters, stainless appliances, and a wet bar/coffee bar; a sizable living room inclusive of custom built in bookcases and a working wood burning fireplace; a cozy family room with a brick floor and warm grasscloth wallpaper; and a darling period-inspired powder room. On the second and third floors are five bedrooms (one being used as an office), three full baths, new paint, designer toile wallpaper, a new custom herringbone runner, new plantation shutters/window treatments, and custom built ins. The entire house offers ample closet space on each floor. Additionally, the dry basement (which is accessible from either inside the home or from the exterior) offers many storage racks, a washer/dryer, a large laundry sink, and sump pump. The backyard is fully fenced with privacy trees along Earle Avenue, so the space cooperates with dog lovers and truly feels like a private, quiet escape in the heart of town. This property is diagonal across the street from the Historic District so is not subject to the restrictions of the town's historic requirements, however, the white-washed Federal style brick blends in seamlessly with the look of the district. The property is a short walk to Easton's renowned restaurants, shops, galleries, downtown events such as Waterfowl Festival, museums, as well as in the opposite direction to Idlewild Park, the YMCA and Rails to Trails. Full list of upgrades can be found in the agent remarks. Owner is a licensed realtor in Maryland.

5 Beds ⋅ 4 Baths

Welcome to Pin Oak House, an Easton Federal style white-washed brick property proud to feature the Grand Champion Pin Oak of Talbot County within the confines of its iron-fenced front yard. The spacious corner lot also offers fine gardens, providing colorful foliage nearly year-round. Roses, honeysuckle, tulips, a glorious crepe myrtle, gazebo, irises, stone hardscaping, and a koi pond with waterfall feature are among the many surprises of the enchanting, fairytale-like backyard. The front and backyards are on a multi-zone irrigation system. This property provides ample off street parking for three cars as well as a sizable storage facility that can be converted into a garage if desired. The backyard and main parking area is monitored 24/7 by a Nest Cam security system. The recently installed uplighting in the front and back of the property further adds to the elegance of the home. Enter inside the red solid wood front door and you are greeted by new custom closets and wood doors, new crown molding, a just installed custom sisal stair runner in the foyer; a stunning formal dining room with designer wallpaper and custom window treatments, a beautiful kitchen with granite, dual ovens, a gas stove, new plantation shutters, stainless appliances, and a wet bar/coffee bar; a sizable living room inclusive of custom built in bookcases and a working wood burning fireplace; a cozy family room with a brick floor and warm grasscloth wallpaper; and a darling period-inspired powder room. On the second and third floors are five bedrooms (one being used as an office), three full baths, new paint, designer toile wallpaper, a new custom herringbone runner, new plantation shutters/window treatments, and custom built ins. The entire house offers ample closet space on each floor. Additionally, the dry basement (which is accessible from either inside the home or from the exterior) offers many storage racks, a washer/dryer, a large laundry sink, and sump pump. The backyard is fully fenced with privacy trees along Earle Avenue, so the space cooperates with dog lovers and truly feels like a private, quiet escape in the heart of town. This property is diagonal across the street from the Historic District so is not subject to the restrictions of the town's historic requirements, however, the white-washed Federal style brick blends in seamlessly with the look of the district. The property is a short walk to Easton's renowned restaurants, shops, galleries, downtown events such as Waterfowl Festival, museums, as well as in the opposite direction to Idlewild Park, the YMCA and Rails to Trails. Full list of upgrades can be found in the agent remarks. Owner is a licensed realtor in Maryland.

301 Washington St S, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Weichert, REALTORS.

$1,025,000

A lovely waterfront home located in Sailors Retreat. Three bedrooms and two and half baths. primary bedroom, sunroom, and family room have a beautiful view of Island Creek. Nice deck and patio for relaxing Two car garage with walk upstairs to the attic. The dock can accommodate two boats with a water depth of 3'-4' MLW. Buyer must verify the water depth

3 Beds ⋅ 2 Baths

A lovely waterfront home located in Sailors Retreat. Three bedrooms and two and half baths. primary bedroom, sunroom, and family room have a beautiful view of Island Creek. Nice deck and patio for relaxing Two car garage with walk upstairs to the attic. The dock can accommodate two boats with a water depth of 3'-4' MLW. Buyer must verify the water depth

4752 Sailors Retreat Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$1,012,000

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

3 Beds ⋅ 3 Baths

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

925 Riverview Ter, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,009,009

Well-maintained 8-unit apartment building offering immediate income and a history of consistent occupancy. Ideally located approximately one block from Route 50, providing convenient access for commuters while maintaining a neighborhood setting. The property consists of eight 1-bedroom, 1-bath units, including two larger units at approximately 711 sq ft and six units at approximately 650 sq ft . Each unit features a functional layout with open living areas, separate bedrooms, and efficient kitchens. Flooring is a mix of hardwood, carpet, and laminate, with new carpet installed (common areas) throughout both upper and lower levels in 2024. Each apartment is equipped with its own mini-split system for heating and air conditioning, as well as a dedicated hot water heater.

142 Calvert St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

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