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First time offered in 30 years, this stately brick Colonial is set on approximately 7± acres in the desirable Ashby neighborhood. Designed with both comfort and functionality in mind, the home offers 5 bedrooms and 3.5 bathrooms, including an expansive primary suite with two walk-in closets, a private den, dedicated vanity/dressing room, soaking tub, and glass-enclosed shower. An additional bedroom also features its own en-suite, while three more bedrooms provide ample space for family or guests. The heart of the home is the spacious family room, filled with natural light and anchored by a brick fireplace. Two sliding glass doors extend the living space to the back deck, making it perfect for entertaining or enjoying peaceful views. A breakfast area also opens to the deck, while thoughtful details such as built-in bookcases, storage window benches, and abundant closet space reflect the home’s smart design. Additional highlights include a 3-car garage, generous outdoor space, and a large deck ideal for gatherings or everyday living. This home combines timeless Colonial architecture with modern comfort in one of the area’s most sought-after locations.

5 Beds ⋅ 4 Baths

First time offered in 30 years, this stately brick Colonial is set on approximately 7± acres in the desirable Ashby neighborhood. Designed with both comfort and functionality in mind, the home offers 5 bedrooms and 3.5 bathrooms, including an expansive primary suite with two walk-in closets, a private den, dedicated vanity/dressing room, soaking tub, and glass-enclosed shower. An additional bedroom also features its own en-suite, while three more bedrooms provide ample space for family or guests. The heart of the home is the spacious family room, filled with natural light and anchored by a brick fireplace. Two sliding glass doors extend the living space to the back deck, making it perfect for entertaining or enjoying peaceful views. A breakfast area also opens to the deck, while thoughtful details such as built-in bookcases, storage window benches, and abundant closet space reflect the home’s smart design. Additional highlights include a 3-car garage, generous outdoor space, and a large deck ideal for gatherings or everyday living. This home combines timeless Colonial architecture with modern comfort in one of the area’s most sought-after locations.

9900 Eagle Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,055,000

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

3 Beds ⋅ 3 Baths

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

7605 Pendleton Farm Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,050,000

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

4 Beds ⋅ 4 Baths

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

8099 Fox Squirrel Way, Easton

Listing courtesy of ERA Martin Associates. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,050,000

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

3 Beds ⋅ 2 Baths

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

8987 Glebe Creek Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,050,000

Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

3 Beds ⋅ 3 Baths

Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

6050 Sunset Ln, Tilghman

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

Selling Office: Benson & Mangold, LLC.

$1,049,000

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

3 Beds ⋅ 2 Baths

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

28701 Edgemere Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Keller Williams Select Realtors of Cambridge.

$1,048,000

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

3 Beds ⋅ 3 Baths

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

209 Goldsborough St, Easton

Listing courtesy of Compass. Contact:

Selling Office: Douglas Realty LLC.

$1,045,000

Located in one of the county’s most coveted areas along the Oxford Corridor, this 4-bedroom, 3.5-bathroom custom home offers a spacious layout with a flexible design for modern living. The open floor plan seamlessly connects the kitchen, dining area, and vaulted-ceiling living room with fireplace, creating a functional space ideal for everyday living and entertaining. The updated kitchen features stainless steel appliances, Silestone countertops, an island, and a breakfast nook. Just off the foyer, a private office with French doors provides a quiet workspace, and a formal dining room offers room for gatherings. The main-level primary suite includes two walk-in closets, two vanities, a soaking tub, a walk-in shower, and direct access to the back patio. Upstairs, an en-suite bedroom serves well as a second primary suite, along with two additional bedrooms and a large bonus or recreation room. A cozy sunroom overlooks the elaborate stone patio and outdoor fireplace, offering a peaceful view of the surrounding 2.6± acre property. In addition to the attached 2-car garage, the property includes an oversized detached equipment building—well-suited for boat restoration, woodworking, recreation, or storage. A deeded right of way provides direct water access to Boone Creek, perfect for kayaking or fishing.

4 Beds ⋅ 4 Baths

Located in one of the county’s most coveted areas along the Oxford Corridor, this 4-bedroom, 3.5-bathroom custom home offers a spacious layout with a flexible design for modern living. The open floor plan seamlessly connects the kitchen, dining area, and vaulted-ceiling living room with fireplace, creating a functional space ideal for everyday living and entertaining. The updated kitchen features stainless steel appliances, Silestone countertops, an island, and a breakfast nook. Just off the foyer, a private office with French doors provides a quiet workspace, and a formal dining room offers room for gatherings. The main-level primary suite includes two walk-in closets, two vanities, a soaking tub, a walk-in shower, and direct access to the back patio. Upstairs, an en-suite bedroom serves well as a second primary suite, along with two additional bedrooms and a large bonus or recreation room. A cozy sunroom overlooks the elaborate stone patio and outdoor fireplace, offering a peaceful view of the surrounding 2.6± acre property. In addition to the attached 2-car garage, the property includes an oversized detached equipment building—well-suited for boat restoration, woodworking, recreation, or storage. A deeded right of way provides direct water access to Boone Creek, perfect for kayaking or fishing.

26604 E Bonfield Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,035,000

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

5 Beds ⋅ 4 Baths

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

301 Washington St S, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Weichert, REALTORS.

$1,025,000

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

3 Beds ⋅ 2 Baths

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

4752 Sailors Retreat Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$1,012,000

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

3 Beds ⋅ 3 Baths

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

925 Riverview Ter, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

$1,009,009

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

142 Calvert St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,000,000

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

2 Beds ⋅ 3 Baths

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

100 Grace St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$1,000,000

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5 Beds ⋅ 3 Baths

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5520 Leeward Ln, Tilghman

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$995,000

Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

3 Beds ⋅ 3 Baths

Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

8684 Sewell Point Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$995,000

Set along the broad waters of the Choptank River, this remarkable 10.88± acre waterfront property in Talbot County offers an uncommon blend of scale, privacy, and panoramic open-water views. With approximately 600± feet of rip-rapped shoreline, the setting provides both protection and an impressive stretch of river frontage rarely available today. A current approval for a 6-bedroom residence allows for the creation of a substantial custom home tailored to your vision. Importantly, the property is not located in a flood zone, so flood insurance is not required—a meaningful advantage for long-term ownership and design flexibility. The wide river exposure captures expansive vistas, steady breezes, and ever-changing light across the water. Boating, sailing, and fishing are easily enjoyed from this stretch of the Choptank, with convenient access to the Chesapeake Bay and nearby waterfront towns such as Oxford and Cambridge. Beyond the river frontage, a scenic 2.5-acre pond enhances the landscape and creates opportunities for thoughtful estate planning. With nearly eleven acres, there is ample room for a guest house, pool, gardens, or additional outbuildings (subject to county approval), allowing the property to evolve into a true Eastern Shore compound. Private yet convenient to Easton and Route 50, this offering represents a rare opportunity to secure significant waterfront acreage in one of Maryland’s most sought-after coastal regions.

29569 Porpoise Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Realty Group.

$983,000

Waterfront Retreat with Breathtaking Views Tucked away on a private drive, this charming home, built in 1999, offers the perfect blend of quality construction, thoughtful design, and an unbeatable waterfront location. With peaceful privacy, sweeping water views, and exceptional features throughout, this property is the ideal year-round retreat. The main level features a spacious open kitchen with a large island, elegant granite countertops, and abundant storage, flowing seamlessly into the living room with panoramic water views. Step out to the expansive deck for outdoor dining or relaxation, or enjoy the sunroom with tile flooring that brings in even more natural light. The main level also boasts heated tile flooring, adding warmth and comfort, and a wood-burning stove in the living room creates a cozy, inviting atmosphere. For year-round comfort, heat pumps provide efficient central heat and air. Upstairs, you'll find two spacious bedrooms, a full bath, and a versatile bonus room—ideal for an office, workout space, or walk-in closet. The primary bedroom is a true sanctuary, featuring a private waterview balcony where you can enjoy your morning coffee or relax in the evening while taking in the stunning water views. The upper level also showcases beautiful heart pine wood floors, adding a touch of warmth and elegance to the space. Outdoor living is just as impressive, with a waterside deck that includes an outdoor shower—perfect for rinsing off after a day on the water or simply enjoying the fresh air. The property offers direct access to the water via a private pier, floating dock, and boat ramp (approx. 3’ MLW), ideal for boating and water sports enthusiasts. For gardening lovers, the irrigated raised garden offers an easy-to-maintain space for growing your favorite plants, vegetables, or herbs. Additional highlights include a detached 2-car garage with an large workshop,, auxiliary generator wiring for added peace of mind, and a golf cart for easy property access. The home will soon be connecting to public sewer. This remarkable waterfront home combines comfort, and a truly stunning location.

2 Beds ⋅ 2 Baths

Waterfront Retreat with Breathtaking Views Tucked away on a private drive, this charming home, built in 1999, offers the perfect blend of quality construction, thoughtful design, and an unbeatable waterfront location. With peaceful privacy, sweeping water views, and exceptional features throughout, this property is the ideal year-round retreat. The main level features a spacious open kitchen with a large island, elegant granite countertops, and abundant storage, flowing seamlessly into the living room with panoramic water views. Step out to the expansive deck for outdoor dining or relaxation, or enjoy the sunroom with tile flooring that brings in even more natural light. The main level also boasts heated tile flooring, adding warmth and comfort, and a wood-burning stove in the living room creates a cozy, inviting atmosphere. For year-round comfort, heat pumps provide efficient central heat and air. Upstairs, you'll find two spacious bedrooms, a full bath, and a versatile bonus room—ideal for an office, workout space, or walk-in closet. The primary bedroom is a true sanctuary, featuring a private waterview balcony where you can enjoy your morning coffee or relax in the evening while taking in the stunning water views. The upper level also showcases beautiful heart pine wood floors, adding a touch of warmth and elegance to the space. Outdoor living is just as impressive, with a waterside deck that includes an outdoor shower—perfect for rinsing off after a day on the water or simply enjoying the fresh air. The property offers direct access to the water via a private pier, floating dock, and boat ramp (approx. 3’ MLW), ideal for boating and water sports enthusiasts. For gardening lovers, the irrigated raised garden offers an easy-to-maintain space for growing your favorite plants, vegetables, or herbs. Additional highlights include a detached 2-car garage with an large workshop,, auxiliary generator wiring for added peace of mind, and a golf cart for easy property access. The home will soon be connecting to public sewer. This remarkable waterfront home combines comfort, and a truly stunning location.

6271 Neavitt Manor Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Compass.

$980,000

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

3 Beds ⋅ 3 Baths

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

9251 Mallard Point Ct, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$979,000

Just Listed! Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, closets design by California Closets, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The third bedroom features a Murphy bed which gives this room multiple uses. The guest bathroom is beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

3 Beds ⋅ 3 Baths

Just Listed! Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, closets design by California Closets, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The third bedroom features a Murphy bed which gives this room multiple uses. The guest bathroom is beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

204 Brookletts Ave, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$975,000

Pictures will be taken end of week of 10/6-10/11. Discover timeless charm and modern luxury in this beautifully appointed 4-bedroom, 2.5-bathroom Colonial nestled on 2.2 acres between the coveted towns of St. Michaels and Easton. This farmhouse-style gem features a seamless blend of hardwood and luxury vinyl flooring, creating a warm and inviting atmosphere throughout. The heart of the home is a gourmet kitchen with a large quartz island, gas cooking stove, and stainless-steel appliances, perfect for hosting gatherings or enjoying quiet family meals. Spacious bedrooms and updated baths offer comfort and style, while the open layout ensures effortless flow. Step outside to your private oasis: an in-ground saltwater pool surrounded by lush landscaping and expansive grounds ideal for entertaining, gardening, or simply soaking in the serenity of the Eastern Shore. This property combines rural elegance with unbeatable location—just minutes from waterfront dining, boutique shopping, and historic charm. This beautiful home is exactly what you've been waiting for, call today for your private showing.

4 Beds ⋅ 3 Baths

Pictures will be taken end of week of 10/6-10/11. Discover timeless charm and modern luxury in this beautifully appointed 4-bedroom, 2.5-bathroom Colonial nestled on 2.2 acres between the coveted towns of St. Michaels and Easton. This farmhouse-style gem features a seamless blend of hardwood and luxury vinyl flooring, creating a warm and inviting atmosphere throughout. The heart of the home is a gourmet kitchen with a large quartz island, gas cooking stove, and stainless-steel appliances, perfect for hosting gatherings or enjoying quiet family meals. Spacious bedrooms and updated baths offer comfort and style, while the open layout ensures effortless flow. Step outside to your private oasis: an in-ground saltwater pool surrounded by lush landscaping and expansive grounds ideal for entertaining, gardening, or simply soaking in the serenity of the Eastern Shore. This property combines rural elegance with unbeatable location—just minutes from waterfront dining, boutique shopping, and historic charm. This beautiful home is exactly what you've been waiting for, call today for your private showing.

8534 Northbend Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$970,000

Set on 2.8± private acres along the highly sought-after Oxford Corridor, this spacious residence offers the perfect blend of comfort, space, and timeless Eastern Shore appeal. A welcoming rocking-chair front porch, huge fenced rear yard with expansive rear deck perfect for entertaining with a custom retractable awning, , paver patio, and in-ground saltwater pool create an ideal setting for relaxed luxury living and effortless entertaining. Inside, the spacious floor plan is thoughtfully designed for both comfortable everyday living and effortless entertaining. The inviting family room features custom built-ins and a fireplace, seamlessly flowing into the gourmet kitchen appointed with custom cabinetry, Caesarstone countertops, center island, oversized walk-in pantry, and Viking gas cooktop. A formal living provides additional gathering area. The first-floor owner’s suite offers a custom ceiling detail, private remodeled bath, walk-in closet, and direct access to the rear deck, creating a peaceful retreat. Upstairs, three generously sized en-suite bedrooms provide comfort and privacy for family and guests alike, including a spacious bonus room ideally suited as a private guest area or flex space over garage. Completing the property is an attached 3-car garage and beautifully landscaped grounds, ideally located just moments from the shops, dining, and amenities of Historic Easton and close to the waterfront charm of Oxford . Wood floors in all rooms except primary bedroom. Gas fireplace never used going "as is". BAT septic system serviced 5/26/26. Irrigation never used, going "as is" Electric dog fence does not work. Crawlspace and attic have been conditioned . New roof recently added.

4 Beds ⋅ 5 Baths

Set on 2.8± private acres along the highly sought-after Oxford Corridor, this spacious residence offers the perfect blend of comfort, space, and timeless Eastern Shore appeal. A welcoming rocking-chair front porch, huge fenced rear yard with expansive rear deck perfect for entertaining with a custom retractable awning, , paver patio, and in-ground saltwater pool create an ideal setting for relaxed luxury living and effortless entertaining. Inside, the spacious floor plan is thoughtfully designed for both comfortable everyday living and effortless entertaining. The inviting family room features custom built-ins and a fireplace, seamlessly flowing into the gourmet kitchen appointed with custom cabinetry, Caesarstone countertops, center island, oversized walk-in pantry, and Viking gas cooktop. A formal living provides additional gathering area. The first-floor owner’s suite offers a custom ceiling detail, private remodeled bath, walk-in closet, and direct access to the rear deck, creating a peaceful retreat. Upstairs, three generously sized en-suite bedrooms provide comfort and privacy for family and guests alike, including a spacious bonus room ideally suited as a private guest area or flex space over garage. Completing the property is an attached 3-car garage and beautifully landscaped grounds, ideally located just moments from the shops, dining, and amenities of Historic Easton and close to the waterfront charm of Oxford . Wood floors in all rooms except primary bedroom. Gas fireplace never used going "as is". BAT septic system serviced 5/26/26. Irrigation never used, going "as is" Electric dog fence does not work. Crawlspace and attic have been conditioned . New roof recently added.

27939 Waverly Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

$969,000

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

3 Beds ⋅ 3 Baths

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

504 Seymour Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

9792 Martingham Cir Unit B-4, Saint Michaels

$965,000

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

3 Beds ⋅ 3 Baths

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

9792 Martingham Cir Unit B-4, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$950,000

Nestled in the heart of Easton’s Historic District, 205 S Hanson Street is a beautifully preserved early-20th-century home that exudes timeless charm and sophistication. Built around 1910, this elegant Colonial Revival offers approximately 2,520 square feet of refined living space with original hardwood floors, detailed millwork, and gracious proportions that reflect its rich architectural heritage. Set on a rare double lot of roughly 0.41 acres, the property provides an exceptional sense of space and privacy. The expansive backyard is a true sanctuary, featuring a sparkling in-ground pool surrounded by mature landscaping, including shade-giving trees, colorful garden beds, and manicured hedges. This lush outdoor setting offers the perfect backdrop for entertaining, quiet afternoons by the pool, or al fresco dining under the canopy of established magnolias. Inside, the home offers a warm and inviting layout. A central hallway opens to formal living and dining rooms, a cozy family room, and a thoughtfully updated kitchen that blends modern amenities with historic character. The upstairs features a spacious primary suite with an en-suite bath, along with three additional bedrooms and a shared hall bath—ideal for family living, guests, or a home office setup. Located just a few blocks from Easton’s vibrant downtown, this residence offers walkable access to shops, restaurants, art galleries, and cultural attractions, all while providing a peaceful retreat on one of the town’s most charming streets. With its rare double lot, resort-style pool, and meticulously landscaped grounds, 205 S Hanson Street is a one-of-a-kind property that combines historic elegance with everyday comfort and convenience.

4 Beds ⋅ 3 Baths

Nestled in the heart of Easton’s Historic District, 205 S Hanson Street is a beautifully preserved early-20th-century home that exudes timeless charm and sophistication. Built around 1910, this elegant Colonial Revival offers approximately 2,520 square feet of refined living space with original hardwood floors, detailed millwork, and gracious proportions that reflect its rich architectural heritage. Set on a rare double lot of roughly 0.41 acres, the property provides an exceptional sense of space and privacy. The expansive backyard is a true sanctuary, featuring a sparkling in-ground pool surrounded by mature landscaping, including shade-giving trees, colorful garden beds, and manicured hedges. This lush outdoor setting offers the perfect backdrop for entertaining, quiet afternoons by the pool, or al fresco dining under the canopy of established magnolias. Inside, the home offers a warm and inviting layout. A central hallway opens to formal living and dining rooms, a cozy family room, and a thoughtfully updated kitchen that blends modern amenities with historic character. The upstairs features a spacious primary suite with an en-suite bath, along with three additional bedrooms and a shared hall bath—ideal for family living, guests, or a home office setup. Located just a few blocks from Easton’s vibrant downtown, this residence offers walkable access to shops, restaurants, art galleries, and cultural attractions, all while providing a peaceful retreat on one of the town’s most charming streets. With its rare double lot, resort-style pool, and meticulously landscaped grounds, 205 S Hanson Street is a one-of-a-kind property that combines historic elegance with everyday comfort and convenience.

205 S Hanson St, Easton

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$947,000

Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood, the living room has a wood burning fireplace for cozy evenings, there is a separate laundry room and an eat in kitchen. The community offers 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. This unit is ideally located for the best views and privacy. Ideal location close to St. Michaels restaurants, shops and harbor. Take advantage of the Inn at Perry Cabin for dining and the luxurious spa! Minutes away is the Links at Perry Cabin premier golf destination designed by the legendary Pete Dye. This 18-hole championship course offers a challenging and picturesque experience.

3 Beds ⋅ 3 Baths

Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood, the living room has a wood burning fireplace for cozy evenings, there is a separate laundry room and an eat in kitchen. The community offers 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. This unit is ideally located for the best views and privacy. Ideal location close to St. Michaels restaurants, shops and harbor. Take advantage of the Inn at Perry Cabin for dining and the luxurious spa! Minutes away is the Links at Perry Cabin premier golf destination designed by the legendary Pete Dye. This 18-hole championship course offers a challenging and picturesque experience.

360 Perry Cabin, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$945,000

Best value!! An amazing chance to renovate or construct a new home! This stunning 1.77-acre property sits on the Choptank River, offering breathtaking western views. The house includes a generous great room, a large eat-in kitchen, 4 bedrooms, 3 bathrooms, a den, an office, a recreation room, as well as a carport and storage shed. Enjoy outdoor living with a deck and patio. The septic system was replaced in 2019, and the HVAC was updated in 2020. Revel in spectacular sunset views, a private pier, rip-rap shoreline, and a sandy beach. Located on a private road, it's just a short distance from the historic towns of Oxford and Easton, with nearby parks, marinas, and dining options.

4 Beds ⋅ 3 Baths

Best value!! An amazing chance to renovate or construct a new home! This stunning 1.77-acre property sits on the Choptank River, offering breathtaking western views. The house includes a generous great room, a large eat-in kitchen, 4 bedrooms, 3 bathrooms, a den, an office, a recreation room, as well as a carport and storage shed. Enjoy outdoor living with a deck and patio. The septic system was replaced in 2019, and the HVAC was updated in 2020. Revel in spectacular sunset views, a private pier, rip-rap shoreline, and a sandy beach. Located on a private road, it's just a short distance from the historic towns of Oxford and Easton, with nearby parks, marinas, and dining options.

26361 Chanticleer Rd, Oxford

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

Selling Office: Shore Living Real Estate.

$926,000

3 Beds ⋅ 2 Baths

203 Mulberry, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$910,000

Welcome to 13532 Rustling Oaks Drive: where meticulous pride of ownership truly shows on this classic Cape Cod in the land of pleasant living on the Eastern Shore. Situated on over an acre of land with towering pines providing excellent shade and privacy, this 5 bedroom, 5,500+ square foot home has been recently upgraded and offers something for the whole family. 10 foot ceilings, hardwood floors, arched hallways, crown moldings, columns, chair rails, are just a few of the timeless interior finishes while a brand new saltwater gunite pool elevates the exterior space. Inside, an expansive first floor primary suite offers total main level living and complete privacy. With a tray ceiling, bay window and double walk-in closets, it is a retreat in its own; punctuated by an updated ensuite bath with double vanity, soaking tub, and oversized glass walk-in shower. The true heart of the main level is the upgraded kitchen and living room areas. These large complementing spaces are perfect for entertaining and everyday living. The kitchen has all new stainless steel appliances including a double wall oven and is finished with wood cabinets and granite countertops. The large island has a propane cooktop and overhanging bar seating. A breakfast area looks through a large bay window to the back yard. A new wood burning stove insert with wood mantel is the centerpiece of the living room just off the kitchen. A formal dining room and separate laundry/mud room complete the first floor. The main living area seamlessly flows into everyone's favorite space: the back yard, anchored by a brand new saltwater gunite pool and sweeping patio with lounging, grilling and fire pit areas. An additional screened-in porch with a tv is perfect for summertime crab feasts or morning coffee. Back inside, the basement is another world of its own with 9 foot ceilings and over 2,000 finished square feet. A 2nd full kitchen opens the possibilities to a private guest space or mother-in-law suite. There is a large game area, a private home office, a 5th bedroom with full bath and an unfinished utility space with room for more storage or workout equipment. Moving upstairs to the 2nd floor, one will find an additional primary bedroom with ensuite bath, two more generously sized guest bedrooms, a shared bath and a comfortable reading area atop the stairs. In addition to the two-car attached garage, a detached two-car garage with space above offers additional storage and workshop potential. A large garden shed and underground sprinkler system completes the backyard. A few of the recent updates include a saltwater gunite pool (2024), all new stainless steel kitchen appliances (2024), updated primary bath (2025), first floor dual-fuel 5-ton high efficiency heat pump (2025), fireplace wood stove insert (2023), leaf gutter guards (2025). Minutes away from a public boat ramp serving the picturesque Wye River and the enduring beauty of the Wye Island Nature Preserve. Major marinas are close by at Kent Narrows, St Michaels, or Oxford. This centrally located Eastern Shore getaway serves the lower beaches and the Chesapeake's tributaries well yet is still an easy commute to Annapolis, Baltimore or D.C. 10 minutes to downtown Easton and all the shopping you might need. The property across the street is open community space and will not be built upon. This tastefully updated and diligently maintained home offers a unique blend of amenities and functionality for the laid-back Eastern Shore lifestyle. Much more info and professional photos to come. Stay tuned!!

5 Beds ⋅ 5 Baths

Welcome to 13532 Rustling Oaks Drive: where meticulous pride of ownership truly shows on this classic Cape Cod in the land of pleasant living on the Eastern Shore. Situated on over an acre of land with towering pines providing excellent shade and privacy, this 5 bedroom, 5,500+ square foot home has been recently upgraded and offers something for the whole family. 10 foot ceilings, hardwood floors, arched hallways, crown moldings, columns, chair rails, are just a few of the timeless interior finishes while a brand new saltwater gunite pool elevates the exterior space. Inside, an expansive first floor primary suite offers total main level living and complete privacy. With a tray ceiling, bay window and double walk-in closets, it is a retreat in its own; punctuated by an updated ensuite bath with double vanity, soaking tub, and oversized glass walk-in shower. The true heart of the main level is the upgraded kitchen and living room areas. These large complementing spaces are perfect for entertaining and everyday living. The kitchen has all new stainless steel appliances including a double wall oven and is finished with wood cabinets and granite countertops. The large island has a propane cooktop and overhanging bar seating. A breakfast area looks through a large bay window to the back yard. A new wood burning stove insert with wood mantel is the centerpiece of the living room just off the kitchen. A formal dining room and separate laundry/mud room complete the first floor. The main living area seamlessly flows into everyone's favorite space: the back yard, anchored by a brand new saltwater gunite pool and sweeping patio with lounging, grilling and fire pit areas. An additional screened-in porch with a tv is perfect for summertime crab feasts or morning coffee. Back inside, the basement is another world of its own with 9 foot ceilings and over 2,000 finished square feet. A 2nd full kitchen opens the possibilities to a private guest space or mother-in-law suite. There is a large game area, a private home office, a 5th bedroom with full bath and an unfinished utility space with room for more storage or workout equipment. Moving upstairs to the 2nd floor, one will find an additional primary bedroom with ensuite bath, two more generously sized guest bedrooms, a shared bath and a comfortable reading area atop the stairs. In addition to the two-car attached garage, a detached two-car garage with space above offers additional storage and workshop potential. A large garden shed and underground sprinkler system completes the backyard. A few of the recent updates include a saltwater gunite pool (2024), all new stainless steel kitchen appliances (2024), updated primary bath (2025), first floor dual-fuel 5-ton high efficiency heat pump (2025), fireplace wood stove insert (2023), leaf gutter guards (2025). Minutes away from a public boat ramp serving the picturesque Wye River and the enduring beauty of the Wye Island Nature Preserve. Major marinas are close by at Kent Narrows, St Michaels, or Oxford. This centrally located Eastern Shore getaway serves the lower beaches and the Chesapeake's tributaries well yet is still an easy commute to Annapolis, Baltimore or D.C. 10 minutes to downtown Easton and all the shopping you might need. The property across the street is open community space and will not be built upon. This tastefully updated and diligently maintained home offers a unique blend of amenities and functionality for the laid-back Eastern Shore lifestyle. Much more info and professional photos to come. Stay tuned!!

13532 Rustling Oaks Dr, Wye Mills

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Benson & Mangold, LLC.

$900,000

This expansive 10,000 square foot commercial building on US Route 50 in Easton is set on a generous 1.17-acre lot. Built in 1974, the heavy duty structure features enormous metal beams and a robust concrete floor, providing a solid foundation for your commercial business. The open layout allows for versatile configurations, whether you envision an open area or several rooms . The below-average exterior condition presents an exciting chance to customize and elevate the property to meet your aspirations, making it a true reflection of your style and purpose. The surrounding area boasts a traffic signal, ample parking with a convenient driveway and overhead door, ensuring easy access for clients and guests alike. The expansive outdoor space offers room for landscaping, outdoor seating, or even a tranquil garden retreat, enhancing the overall appeal of the property. The potential for growth and development in this area is immense, making it an ideal investment for those looking to capitalize on the evolving landscape. Whether you're an entrepreneur seeking a new venture or an investor looking for a promising opportunity, this property stands ready to accommodate your ideas.

7793 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$900,000

Charming 4 bedroom, 3.5-bath Cape Cod set on a parklike 2.4± acre lot overlooking the Talbot Country Club golf course. This home has seen recent updates including new roof, all new interior and exterior lighting, interior paint along with front of house, and paved parking. Featuring an updated kitchen with large marble center island with bar seating and stainless steel appliances. The living room offers floor to ceiling built-ins and a wood burning fireplace adjoining to a bright sunroom with vaulted ceiling. The first-floor primary suite offers a newly renovated bath with soaking tub, heated floors, and steam shower, while the second-floor primary includes a walk-in closet and private bath. A finished room above the garage provides ideal bonus space for an office, media room, or playroom. The property also includes a large yard with invisible fence, patio, shed for storage, and attached garage all within close proximity to downtown Easton.

4 Beds ⋅ 4 Baths

Charming 4 bedroom, 3.5-bath Cape Cod set on a parklike 2.4± acre lot overlooking the Talbot Country Club golf course. This home has seen recent updates including new roof, all new interior and exterior lighting, interior paint along with front of house, and paved parking. Featuring an updated kitchen with large marble center island with bar seating and stainless steel appliances. The living room offers floor to ceiling built-ins and a wood burning fireplace adjoining to a bright sunroom with vaulted ceiling. The first-floor primary suite offers a newly renovated bath with soaking tub, heated floors, and steam shower, while the second-floor primary includes a walk-in closet and private bath. A finished room above the garage provides ideal bonus space for an office, media room, or playroom. The property also includes a large yard with invisible fence, patio, shed for storage, and attached garage all within close proximity to downtown Easton.

6372 Country Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

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