$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.
$1,350,000 Excellent opportunity to own a 9,000+/- sf warehouse in Easton. Located in the Carlton Business Park. Easy access and plenty of parking. Includes: two 900+/- sf office areas and 7,200+/- sf of warehouse space with 16' clearing height and clear span. Five OHD, fenced area in the rear of the property. Zoned BC. Excellent opportunity to own a 9,000+/- sf warehouse in Easton. Located in the Carlton Business Park. Easy access and plenty of parking. Includes: two 900+/- sf office areas and 7,200+/- sf of warehouse space with 16' clearing height and clear span. Five OHD, fenced area in the rear of the property. Zoned BC. 29528 Canvasback Dr, Easton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Benson & Mangold, LLC.
$1,350,000 Step into history at the Thomas-Kirby House (c.1860), a charming renovated colonial in the heart of town with picturesque street views toward Saint Michaels Harbor. This light-filled historic residence showcases beautiful hardwood floors, two staircases, detailed millwork, and rich wood accents throughout. The welcoming foyer with its 'Seaport' hand painted mural wallpaper opens to a cozy study with fireplace and custom built-ins. The comfortable dining room flows seamlessly into the updated kitchen, appointed with a new center island, upgraded features and appliances. A double-sided fireplace serves both spaces, adding warmth and character. The light-filled living room, complete with its own fireplace and entertainment center(which conveys), opens through French doors to an extended brick patio, perfect for indoor-outdoor living. Upstairs, the stunning primary suite with its cathedral ceiling, offers large built-in wardroom space, gardens views, a private balcony, and beautiful ensuite bath featuring a clawfoot tub and glass-enclosed shower. Two additional large guest bedrooms share a full bath with a luxurious steam shower, and a conveniently located second-floor laundry room completes this level. Outside, a charming brick footpath winds behind the home, connecting to an off-street brick driveway. The private backyard with its new cedar shed provides a tranquil retreat with mature trees and lush landscaping, while benefiting from the extended view into St Mary's Square. With its historic charm, modern comforts, and extensive renovations made by the current owners, this home offers the perfect opportunity to enjoy the best of Eastern Shore living. *encapsulated crawlspace and attic; new American Standard Platinum 18 SEER System; Aprilene whole house dehumidifiers (2 units); complete restoration and painting of interior and exterior are just some of the Upgrades 3 Beds ⋅ 3 Baths Step into history at the Thomas-Kirby House (c.1860), a charming renovated colonial in the heart of town with picturesque street views toward Saint Michaels Harbor. This light-filled historic residence showcases beautiful hardwood floors, two staircases, detailed millwork, and rich wood accents throughout. The welcoming foyer with its 'Seaport' hand painted mural wallpaper opens to a cozy study with fireplace and custom built-ins. The comfortable dining room flows seamlessly into the updated kitchen, appointed with a new center island, upgraded features and appliances. A double-sided fireplace serves both spaces, adding warmth and character. The light-filled living room, complete with its own fireplace and entertainment center(which conveys), opens through French doors to an extended brick patio, perfect for indoor-outdoor living. Upstairs, the stunning primary suite with its cathedral ceiling, offers large built-in wardroom space, gardens views, a private balcony, and beautiful ensuite bath featuring a clawfoot tub and glass-enclosed shower. Two additional large guest bedrooms share a full bath with a luxurious steam shower, and a conveniently located second-floor laundry room completes this level. Outside, a charming brick footpath winds behind the home, connecting to an off-street brick driveway. The private backyard with its new cedar shed provides a tranquil retreat with mature trees and lush landscaping, while benefiting from the extended view into St Mary's Square. With its historic charm, modern comforts, and extensive renovations made by the current owners, this home offers the perfect opportunity to enjoy the best of Eastern Shore living. *encapsulated crawlspace and attic; new American Standard Platinum 18 SEER System; Aprilene whole house dehumidifiers (2 units); complete restoration and painting of interior and exterior are just some of the Upgrades 204 Mulberry St, Saint Michaels Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Chesapeake Bay Real Estate Plus, 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.
$1,320,000 Discover the charm of 213 S Morris Street, an exquisite residence nestled in Oxford, MD's historic district. Originally built in 1870 by a skilled shipwright, this home was meticulously restored with a "down to the studs" renovation, seamlessly blending historic charm with modern luxury. The property boasts a gated brick and river stone driveway, providing off-street parking. The property is fully enclosed by both a historic brick wall and an Oxford-style picket fence ensuring privacy. The grounds are professionally landscaped and irrigated for natural beauty and feature a large blue slate patio for outdoor living. The home features a separate heated and air-conditioned studio/office, perfect for creative pursuits or remote work. Inside, the beautifully decorated interior offers a primary bedroom (with en-suite bath) on the first floor and three additional bedrooms upstairs. With three bathrooms—including two on the second floor, one on the first, plus a powder room—comfort and convenience are paramount. Enjoy cozy evenings by one of the four gas fireplaces or entertain in the stunning family room with vaulted ceilings and clerestory windows that adjoins a gourmet kitchen equipped with a six-burner Wolf stove and top-of-the-line appliances. The home is bathed in natural light, with top-quality windows and doors, and features pristine pine floors throughout. It's a "happy house," radiating warmth and elegance, and its reproduction costs in today's market would far exceed the list price. 4 Beds ⋅ 4 Baths Discover the charm of 213 S Morris Street, an exquisite residence nestled in Oxford, MD's historic district. Originally built in 1870 by a skilled shipwright, this home was meticulously restored with a "down to the studs" renovation, seamlessly blending historic charm with modern luxury. The property boasts a gated brick and river stone driveway, providing off-street parking. The property is fully enclosed by both a historic brick wall and an Oxford-style picket fence ensuring privacy. The grounds are professionally landscaped and irrigated for natural beauty and feature a large blue slate patio for outdoor living. The home features a separate heated and air-conditioned studio/office, perfect for creative pursuits or remote work. Inside, the beautifully decorated interior offers a primary bedroom (with en-suite bath) on the first floor and three additional bedrooms upstairs. With three bathrooms—including two on the second floor, one on the first, plus a powder room—comfort and convenience are paramount. Enjoy cozy evenings by one of the four gas fireplaces or entertain in the stunning family room with vaulted ceilings and clerestory windows that adjoins a gourmet kitchen equipped with a six-burner Wolf stove and top-of-the-line appliances. The home is bathed in natural light, with top-quality windows and doors, and features pristine pine floors throughout. It's a "happy house," radiating warmth and elegance, and its reproduction costs in today's market would far exceed the list price. 213 S Morris St, Oxford Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Unrepresented Buyer Office.
$1,300,000 Don’t miss this rare opportunity to own one of the most prominent retail locations in St. Michaels. Located at the high-traffic corner of Talbot Street (Route 33) and Railroad Avenue, this property offers approximately 6,000 square feet of space and generous off-street parking. Positioned in the heart of town and close to the marina, restaurants, ice cream shop, and the renowned Maritime Museum. Don’t miss this rare opportunity to own one of the most prominent retail locations in St. Michaels. Located at the high-traffic corner of Talbot Street (Route 33) and Railroad Avenue, this property offers approximately 6,000 square feet of space and generous off-street parking. Positioned in the heart of town and close to the marina, restaurants, ice cream shop, and the renowned Maritime Museum. 100 N Talbot, Saint Michaels Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Unrepresented Buyer Office.
$1,295,000 One of the most admired buildings is St. Michaels is now offered for sale. 202 S. Talbot Street is the tallest building in town with prominent front windows. The 3 story building is currently occupied by one of St. Michael's finest retailers, "Come By Chance". The 2nd and 3rd floor offer incredible potential for the savvy investor as possible options include short term rental units, apartments, and office space. This a timely and great opportunity for an end-user or investor. One of the most admired buildings is St. Michaels is now offered for sale. 202 S. Talbot Street is the tallest building in town with prominent front windows. The 3 story building is currently occupied by one of St. Michael's finest retailers, "Come By Chance". The 2nd and 3rd floor offer incredible potential for the savvy investor as possible options include short term rental units, apartments, and office space. This a timely and great opportunity for an end-user or investor. 202 Talbot, Saint Michaels Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Meredith Fine Properties.
$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. 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. 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.
$1,202,000 7361 Solitude Road, a single-family waterfront rancher set on 2.4 private acres along Solitude Creek, offering approximately 3’ mean low water, a private dock with boat lift, and a secluded setting just minutes from downtown St. Michaels. The home is designed for comfortable single-story living, featuring hardwood floors throughout, a gas fireplace in the main living area, and a primary suite on waterside. The kitchen and living room also overlook the creek, filling the home with natural light and scenic views enhanced by the southeastern exposure. A sunroom off the primary suite leads directly to a composite deck, creating an easy transition to outdoor living. Exterior highlights include an endless pool, waterside decking, and ample space to enjoy boating, kayaking, and the natural setting. Additional features include a paved driveway, two-car garage and a full basement ideal for storage or future use and a detached shed with electric. Offering first-floor living, quality waterfront, and an unbeatable location near St. Michaels, this Eastern Shore retreat is perfectly suited as a full-time residence or weekend escape. 3 Beds ⋅ 2 Baths 7361 Solitude Road, a single-family waterfront rancher set on 2.4 private acres along Solitude Creek, offering approximately 3’ mean low water, a private dock with boat lift, and a secluded setting just minutes from downtown St. Michaels. The home is designed for comfortable single-story living, featuring hardwood floors throughout, a gas fireplace in the main living area, and a primary suite on waterside. The kitchen and living room also overlook the creek, filling the home with natural light and scenic views enhanced by the southeastern exposure. A sunroom off the primary suite leads directly to a composite deck, creating an easy transition to outdoor living. Exterior highlights include an endless pool, waterside decking, and ample space to enjoy boating, kayaking, and the natural setting. Additional features include a paved driveway, two-car garage and a full basement ideal for storage or future use and a detached shed with electric. Offering first-floor living, quality waterfront, and an unbeatable location near St. Michaels, this Eastern Shore retreat is perfectly suited as a full-time residence or weekend escape. 7361 Solitude Rd, Saint Michaels Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Benson & Mangold, LLC.
$1,195,000 Now under contract & sorry for the last minute cancellation of the Open House. WATERFRONT CHARM! This home was built by Peninsula Construction with care in 2001 for the original and only owners! It boasts an open floor plan with hardwood floors throughout except the carpeted 3 bedrooms. The water views are captivating of Cummings Creek from the open floor plan of the home but you will also enjoy the waterside screened porch with amazing views of the the quiet Creek! Currently a 3 bedroom, 2 bath home all on the first floor, if you need something larger, the second floor is ready for expansion which is plumbed and already has an exercise room ready for you to stay in shape! The barn/shed is being being sold as is but is great for a workshop or your hobbies. The landscaping is beautiful and although there is no pool, there is plenty of room to add one! The boating enthusiast will love the Bailey dock with 3 ft MLW plus a 7 ' mooring! Come take a look! You won't be disappointed! 3 Beds ⋅ 2 Baths Now under contract & sorry for the last minute cancellation of the Open House. WATERFRONT CHARM! This home was built by Peninsula Construction with care in 2001 for the original and only owners! It boasts an open floor plan with hardwood floors throughout except the carpeted 3 bedrooms. The water views are captivating of Cummings Creek from the open floor plan of the home but you will also enjoy the waterside screened porch with amazing views of the the quiet Creek! Currently a 3 bedroom, 2 bath home all on the first floor, if you need something larger, the second floor is ready for expansion which is plumbed and already has an exercise room ready for you to stay in shape! The barn/shed is being being sold as is but is great for a workshop or your hobbies. The landscaping is beautiful and although there is no pool, there is plenty of room to add one! The boating enthusiast will love the Bailey dock with 3 ft MLW plus a 7 ' mooring! Come take a look! You won't be disappointed! 8698 Cummings Rd, Wittman Listing courtesy of Shore Living Real Estate. Contact: Selling Office: Meredith Fine Properties.
$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.
$1,175,000 The Arthur K. Easter House, St. Michaels, Maryland From the moment you arrive, it is clear: this is no ordinary house. Located on one of St. Michaels’ most sought-after streets, the circa 1889 Arthur K. Easter House seems to have stepped from the pages of a storybook—one filled with golden light, quiet elegance, and a sense of belonging. This stylish historic home was relocated to its current site in the 1940s, where it rests on a modern foundation while preserving the grace of its era. Step inside and you’ll find a home that doesn’t shout—but sings. Golden sunburst wallpaper greets you in the entryway, a quiet hint of the artistry to come. Grass cloth walls add texture to the front room, while Asian-themed wallpaper in the powder room nods to a worldly, well-traveled spirit. The kitchen blends form and function with custom cabinetry, Japanese tansu, an antique center island, granite countertops, and stainless-steel appliances. Just beyond lies a laundry room and pantry, offering additional storage and a private side entrance through a door so charming it might have been borrowed from a Hobbit hole. Refinished heart pine floors flow throughout the main level, which includes an elegant living room, a cozy library with built-in bookcases and a wood-burning fireplace, and a dining area ideal for both casual meals and formal gatherings. Just beyond, the sunroom wraps the rear of the house in warmth and light, with a beadboard ceiling, tiled floor, and French doors that blur the line between home and garden. Bathed in natural light and surrounded by greenery, it’s a space that feels less like a room and more like a quiet corner of the outdoors—perfect for morning coffee, afternoon reading, or an evening glass of wine. The living and dining spaces flow easily, whether you're hosting friends or savoring a quiet moment. Upstairs, the primary bedroom serves as a peaceful retreat, with a sitting area, a full wall of closets, and a luminous, sepia-toned mural that evokes a distant landscape seen through time’s soft focus. It’s a space meant not just for rest, but for dreaming. A second bedroom and a beautifully updated bathroom with classic tile finishes and a glass shower complete the upper level. Outdoors, a handcrafted moon gate from Walpole Outdoors beckons you into the garden—a serene and curated landscape designed for both visual delight and peaceful retreat. The current owners, avid gardeners, have begun implementing a landscape plan that adds privacy and seasonal beauty to the in-town lot, with roses, weeping peach, dogwood, crape myrtle, holly, and arborvitae creating a park-like setting. Every feature of this house has been thoughtfully updated over the past four years, including a new HVAC system, faux-slate roof, fresh exterior and interior paint, and a curated collection of wallcoverings. Just down the street lies the harbor, and within a short stroll are the Chesapeake Bay Maritime Museum, the county landing and kayak launch, a scenic nature trail, and the town’s beloved shops and restaurants. The Arthur K. Easter House isn’t just attractive—it is deeply intentional. A canvas for creativity, a haven for quiet living, and a rare opportunity to own a piece of St. Michaels’ history—timelessly updated and ready to welcome its next chapter. 2 Beds ⋅ 2 Baths The Arthur K. Easter House, St. Michaels, Maryland From the moment you arrive, it is clear: this is no ordinary house. Located on one of St. Michaels’ most sought-after streets, the circa 1889 Arthur K. Easter House seems to have stepped from the pages of a storybook—one filled with golden light, quiet elegance, and a sense of belonging. This stylish historic home was relocated to its current site in the 1940s, where it rests on a modern foundation while preserving the grace of its era. Step inside and you’ll find a home that doesn’t shout—but sings. Golden sunburst wallpaper greets you in the entryway, a quiet hint of the artistry to come. Grass cloth walls add texture to the front room, while Asian-themed wallpaper in the powder room nods to a worldly, well-traveled spirit. The kitchen blends form and function with custom cabinetry, Japanese tansu, an antique center island, granite countertops, and stainless-steel appliances. Just beyond lies a laundry room and pantry, offering additional storage and a private side entrance through a door so charming it might have been borrowed from a Hobbit hole. Refinished heart pine floors flow throughout the main level, which includes an elegant living room, a cozy library with built-in bookcases and a wood-burning fireplace, and a dining area ideal for both casual meals and formal gatherings. Just beyond, the sunroom wraps the rear of the house in warmth and light, with a beadboard ceiling, tiled floor, and French doors that blur the line between home and garden. Bathed in natural light and surrounded by greenery, it’s a space that feels less like a room and more like a quiet corner of the outdoors—perfect for morning coffee, afternoon reading, or an evening glass of wine. The living and dining spaces flow easily, whether you're hosting friends or savoring a quiet moment. Upstairs, the primary bedroom serves as a peaceful retreat, with a sitting area, a full wall of closets, and a luminous, sepia-toned mural that evokes a distant landscape seen through time’s soft focus. It’s a space meant not just for rest, but for dreaming. A second bedroom and a beautifully updated bathroom with classic tile finishes and a glass shower complete the upper level. Outdoors, a handcrafted moon gate from Walpole Outdoors beckons you into the garden—a serene and curated landscape designed for both visual delight and peaceful retreat. The current owners, avid gardeners, have begun implementing a landscape plan that adds privacy and seasonal beauty to the in-town lot, with roses, weeping peach, dogwood, crape myrtle, holly, and arborvitae creating a park-like setting. Every feature of this house has been thoughtfully updated over the past four years, including a new HVAC system, faux-slate roof, fresh exterior and interior paint, and a curated collection of wallcoverings. Just down the street lies the harbor, and within a short stroll are the Chesapeake Bay Maritime Museum, the county landing and kayak launch, a scenic nature trail, and the town’s beloved shops and restaurants. The Arthur K. Easter House isn’t just attractive—it is deeply intentional. A canvas for creativity, a haven for quiet living, and a rare opportunity to own a piece of St. Michaels’ history—timelessly updated and ready to welcome its next chapter. 205 E Chew, Saint Michaels Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Compass.
$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.
$1,150,000 PRICE REDUCTION! Five diamond resort living meets the Eastern Shore in a relaxed rural setting. This exquisite one-of-a-kind home is situated on just under an acre enveloped by luscious, manicured landscaping, towering pines and open field. Just minutes away provides boating with Wye River Landing, a large public boat ramp. Add the luxury of marina life just miles away at Kent Narrows, St Michaels, and Oxford. This location serves the Eastern Shore and beach areas as well as Annapolis, Baltimore, and Washington DC with a comfortable commute as well as driving distance to BWI and other airports. Escape to a home that was built in 2006 and renovated throughout its lifetime by the renowned custom home builder West and Callahan, Easton, MD. Landscaping has been thoughtfully and meticulously provided and kept by F.A. Hobson Landscaping, Queenstown, MD. The 20’x40’ resort style recently renovated heated and air-conditioned Pebble Sheen pool (new pool salt cell) with large open travertine deck is the combined efforts of Aqua Pools Easton, MD and F.A. Hobson Landscaping. Nestled quietly and privately, the new owner will relax pool side, enjoying the sanctuary of plantings blooming all seasons tucked nicely away from neighbors’ view. This home boasts every upscale detail including crown-mold and chair-rail throughout entire living area, columns, a gourmet chef’s dream kitchen featuring a gas 6 burner and electric griddle Jenn Air range, Jenn Air double wall oven with convection, new Jenn Air dishwasher and new 48” Sub Zero side by side refrigerator. A large granite topped island as part of this country sit-in area kitchen invites entertaining from morning to evening. A whole house sound system pipes music throughout the entire home including the finished basement featuring hand milled bookshelves, cabinetry and fireplace mantel, a rarely seen large scale custom built granite topped bar with stainless Jenn Air dishwasher, full sink, bar refrigerator and ice maker, walk-in custom built wine cellar, Peter Vitale 9’ custom pool table with hand-picked upscale lighting and other amenities. The first-floor great room has floor to 20’ ceiling windows and a fireplace that invites a quiet retreat or large-scale entertaining. The first floor gathering room has painted brick flooring, bead-board hand milled siding, coffered custom made ceiling and giant panoramic windows capturing a one-of-a kind estuary pool side view. Primary bedroom boasts columns large walk-in closet and recently renovated glass walk-in subway tiled shower. All baths within all living areas mimic the primary bath including granite topped, stainless sinks, and Kohler fixtures. Nothing has been compromised. The recently renovated laundry room features highest end Speed Queen pet settings washer and dryer, granite countertop and full-size stainless sink. Invisible fence. Some furnishings included (list will be provided)This must see must have home has been thoughtfully cared for and offers new carpeting and painting throughout. Add every form of eastern shore lifestyle including boating, golf, tennis, pickleball and more within minutes of your new retreat. 5 Beds ⋅ 5 Baths PRICE REDUCTION! Five diamond resort living meets the Eastern Shore in a relaxed rural setting. This exquisite one-of-a-kind home is situated on just under an acre enveloped by luscious, manicured landscaping, towering pines and open field. Just minutes away provides boating with Wye River Landing, a large public boat ramp. Add the luxury of marina life just miles away at Kent Narrows, St Michaels, and Oxford. This location serves the Eastern Shore and beach areas as well as Annapolis, Baltimore, and Washington DC with a comfortable commute as well as driving distance to BWI and other airports. Escape to a home that was built in 2006 and renovated throughout its lifetime by the renowned custom home builder West and Callahan, Easton, MD. Landscaping has been thoughtfully and meticulously provided and kept by F.A. Hobson Landscaping, Queenstown, MD. The 20’x40’ resort style recently renovated heated and air-conditioned Pebble Sheen pool (new pool salt cell) with large open travertine deck is the combined efforts of Aqua Pools Easton, MD and F.A. Hobson Landscaping. Nestled quietly and privately, the new owner will relax pool side, enjoying the sanctuary of plantings blooming all seasons tucked nicely away from neighbors’ view. This home boasts every upscale detail including crown-mold and chair-rail throughout entire living area, columns, a gourmet chef’s dream kitchen featuring a gas 6 burner and electric griddle Jenn Air range, Jenn Air double wall oven with convection, new Jenn Air dishwasher and new 48” Sub Zero side by side refrigerator. A large granite topped island as part of this country sit-in area kitchen invites entertaining from morning to evening. A whole house sound system pipes music throughout the entire home including the finished basement featuring hand milled bookshelves, cabinetry and fireplace mantel, a rarely seen large scale custom built granite topped bar with stainless Jenn Air dishwasher, full sink, bar refrigerator and ice maker, walk-in custom built wine cellar, Peter Vitale 9’ custom pool table with hand-picked upscale lighting and other amenities. The first-floor great room has floor to 20’ ceiling windows and a fireplace that invites a quiet retreat or large-scale entertaining. The first floor gathering room has painted brick flooring, bead-board hand milled siding, coffered custom made ceiling and giant panoramic windows capturing a one-of-a kind estuary pool side view. Primary bedroom boasts columns large walk-in closet and recently renovated glass walk-in subway tiled shower. All baths within all living areas mimic the primary bath including granite topped, stainless sinks, and Kohler fixtures. Nothing has been compromised. The recently renovated laundry room features highest end Speed Queen pet settings washer and dryer, granite countertop and full-size stainless sink. Invisible fence. Some furnishings included (list will be provided)This must see must have home has been thoughtfully cared for and offers new carpeting and painting throughout. Add every form of eastern shore lifestyle including boating, golf, tennis, pickleball and more within minutes of your new retreat. 13543 Rustling Oaks Dr, Wye Mills Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Keller Williams Select Realtors of Annapolis.
$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.
$1,130,000 Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns. Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting. Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay. Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision. This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland. 3 Beds ⋅ 3 Baths Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns. Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting. Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay. Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision. This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland. 24318 Oakwood Park Rd, Saint Michaels Listing courtesy of Compass. Contact: Selling Office: Meredith Fine Properties.
$1,118,892 Fabulous waterfront townhome in an exceptional St. Michaels setting, adjacent to the Inn at Perry Cabin with tranquil water views. Designed for comfort and easy living, this 2-bedroom, 2.5-bath residence offers a thoughtfully designed open layout with hardwood floors, fireplace, and sun-filled interiors throughout. Professional photos coming next week. The well-appointed kitchen features Silestone quartz countertops, stainless steel appliances and generous cabinetry, flowing seamlessly into the living and dining areas for effortless everyday living and entertaining. A sunroom with wet bar extends the interior living space and opens to waterside deck. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Recent updates include dual-zone HVAC systems. The property includes a deep-water boat slip (#320) , along with access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. Ideal location close to St. Michaels restaurants, shops and harbor! 2 Beds ⋅ 3 Baths Fabulous waterfront townhome in an exceptional St. Michaels setting, adjacent to the Inn at Perry Cabin with tranquil water views. Designed for comfort and easy living, this 2-bedroom, 2.5-bath residence offers a thoughtfully designed open layout with hardwood floors, fireplace, and sun-filled interiors throughout. Professional photos coming next week. The well-appointed kitchen features Silestone quartz countertops, stainless steel appliances and generous cabinetry, flowing seamlessly into the living and dining areas for effortless everyday living and entertaining. A sunroom with wet bar extends the interior living space and opens to waterside deck. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Recent updates include dual-zone HVAC systems. The property includes a deep-water boat slip (#320) , along with access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. Ideal location close to St. Michaels restaurants, shops and harbor! 320 Perry Cabin, Saint Michaels Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Keller Williams Select Realtors of Easton.
$1,100,000 Beautifully updated home on Easton's premier residential block. a short distance to the downtown, Idlewild Park the "Y", and the Academy Art Museum. Brick and flagstone walkways. Traditional center-hall colonial with 9 ft ceilings and oak floors. Oversize crown moldings in LR, DR and PBR. Living Room with fireplace. Dining Room, with built in corner cupboards. Eat-in kitchen with top-of-the-line refrigerator, decorative tiles. Cheery sunroom with south bay window. Three or four Bedrooms, 2 1/2 baths. Principal Bedroom has four closets, and newly remodeled principal Bath has heated tile floor, marble shower surround. Third story can be utilized as a large home office or as a dormitory. Central A/C. Third story and sunroom heated/cooled by mini-split heat pump supplemented by e.b.b. heat Third story is 20' x 31', irregular dimensions. . Hardwood floors. Newly installed "Levelor" privacy blinds. Screened porch. Detached garage, beautiful flower garden with fenced yard. Brick and flagstone walkways. Alley in rear. 4 Beds ⋅ 3 Baths Beautifully updated home on Easton's premier residential block. a short distance to the downtown, Idlewild Park the "Y", and the Academy Art Museum. Brick and flagstone walkways. Traditional center-hall colonial with 9 ft ceilings and oak floors. Oversize crown moldings in LR, DR and PBR. Living Room with fireplace. Dining Room, with built in corner cupboards. Eat-in kitchen with top-of-the-line refrigerator, decorative tiles. Cheery sunroom with south bay window. Three or four Bedrooms, 2 1/2 baths. Principal Bedroom has four closets, and newly remodeled principal Bath has heated tile floor, marble shower surround. Third story can be utilized as a large home office or as a dormitory. Central A/C. Third story and sunroom heated/cooled by mini-split heat pump supplemented by e.b.b. heat Third story is 20' x 31', irregular dimensions. . Hardwood floors. Newly installed "Levelor" privacy blinds. Screened porch. Detached garage, beautiful flower garden with fenced yard. Brick and flagstone walkways. Alley in rear. 221 S Harrison St, Easton Listing courtesy of Shoreline Realty. Contact: Selling Office: Meredith Fine Properties.
$1,077,500 Tucked away on Elbert’s Cove, this one-level waterfront home offers a peaceful retreat on approximately 3 acres. With 3 bedrooms and 3 full bathrooms, the layout is thoughtfully designed for comfort and easy living. Multiple living spaces include a large recreation room with pool table, a living room with a cozy brick fireplace, and a waterside family room with built-ins and an adjacent dining area. The open kitchen, featuring two breakfast bars, flows seamlessly into the living and dining spaces—perfect for gatherings. A spacious screened porch and brick patio overlook the water, ideal for outdoor dining or relaxing after a day on the water. Enjoy the best of Eastern Shore living with a private pier offering approximately 3’ MLW, a rip-rapped shoreline, Jet Dock, and kayak and boat launch—right outside your back door. Seller has recent septic approval for 5 Bedrooms. 3 Beds ⋅ 3 Baths Tucked away on Elbert’s Cove, this one-level waterfront home offers a peaceful retreat on approximately 3 acres. With 3 bedrooms and 3 full bathrooms, the layout is thoughtfully designed for comfort and easy living. Multiple living spaces include a large recreation room with pool table, a living room with a cozy brick fireplace, and a waterside family room with built-ins and an adjacent dining area. The open kitchen, featuring two breakfast bars, flows seamlessly into the living and dining spaces—perfect for gatherings. A spacious screened porch and brick patio overlook the water, ideal for outdoor dining or relaxing after a day on the water. Enjoy the best of Eastern Shore living with a private pier offering approximately 3’ MLW, a rip-rapped shoreline, Jet Dock, and kayak and boat launch—right outside your back door. Seller has recent septic approval for 5 Bedrooms. 6379 Cedar Cove Rd, Royal Oak Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Phoenix Real Estate.
$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.
$1,075,000 Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family room provide a central gathering space with expansive water views, granite countertops, and custom cabinetry. A secondary kitchen provides added convenience for entertaining. The owners have invested in significant updates, including new two-stage heat pumps with UV filter and whole-house dehumidifier, fresh interior paint throughout, refinished hardwood floors, and an encapsulated crawlspace for efficiency. The second floor offers three bedrooms and full bath. On the third floor you will find your Owner's Suite with views to your private dock and en-suite bathroom with tile shower. Outdoor amenities include a boat ramp, dock with water and electric, and floating dock making days on the water simple and enjoyable. The side yard of the home offers a firepit and ample space for a pool. With over 3,500 square feet and these amenities, this home presents a great opportunity for your Eastern Shore retreat or short term vacation rental, with approval. 4 Beds ⋅ 3 Baths Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family room provide a central gathering space with expansive water views, granite countertops, and custom cabinetry. A secondary kitchen provides added convenience for entertaining. The owners have invested in significant updates, including new two-stage heat pumps with UV filter and whole-house dehumidifier, fresh interior paint throughout, refinished hardwood floors, and an encapsulated crawlspace for efficiency. The second floor offers three bedrooms and full bath. On the third floor you will find your Owner's Suite with views to your private dock and en-suite bathroom with tile shower. Outdoor amenities include a boat ramp, dock with water and electric, and floating dock making days on the water simple and enjoyable. The side yard of the home offers a firepit and ample space for a pool. With over 3,500 square feet and these amenities, this home presents a great opportunity for your Eastern Shore retreat or short term vacation rental, with approval. 21368 Fairbank Cir, Tilghman Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: AB & Co Realtors, Inc..