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Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If you're searching for an escape - this just might be it!

2 Beds ⋅ 2 Baths

Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If you're searching for an escape - this just might be it!

8805 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

$365,000

Rarely available three-level townhome offering approximately 2,258 square feet, 3 bedrooms, 3.5 baths, and a distinctive, exceptionally flexible floor plan. The first and second floors have been freshly painted, luxury vinyl plank flooring installed on the first floor, the landscaping has been refreshed, and the few items identified during a recent home inspection have been addressed. The main level features comfortable living and dining spaces, a well-appointed kitchen with maple cabinetry, granite countertops, ceramic tile flooring, and updated appliances, plus access to the rear deck and fenced yard. The spacious second-floor primary suite offers a private bath with dual sinks, tub/shower surround, and walk-in closet. The third level is a true retreat, complete with a gas fireplace, full bath, walk-in closet, and abundant possibilities as an ensuite bedroom, game room, studio, home office, or private space for multigenerational living. An exceptionally generous “sky attic” provides valuable storage for seasonal items and more. A newer roof and hot water heater add further appeal. Pinehurst Circle is located within the sought-after Easton Club community, where residents enjoy a community pool, tennis and pickleball courts, trash removal, snow removal, yard maintenance, and common-area maintenance through the HOA. Easton Utilities provides electric service, natural gas, water, sewer, cable, and high-speed Easton Velocity internet. Convenient access to Route 50 makes this an excellent location for commuting, while downtown Easton’s restaurants, boutiques, galleries, Academy Art Museum, and Avalon Theatre are just minutes away. With multiple ensuite possibilities and generous living and storage space across three levels, this move-in-ready townhome, backing to the woods presents a rare opportunity.

3 Beds ⋅ 4 Baths

Rarely available three-level townhome offering approximately 2,258 square feet, 3 bedrooms, 3.5 baths, and a distinctive, exceptionally flexible floor plan. The first and second floors have been freshly painted, luxury vinyl plank flooring installed on the first floor, the landscaping has been refreshed, and the few items identified during a recent home inspection have been addressed. The main level features comfortable living and dining spaces, a well-appointed kitchen with maple cabinetry, granite countertops, ceramic tile flooring, and updated appliances, plus access to the rear deck and fenced yard. The spacious second-floor primary suite offers a private bath with dual sinks, tub/shower surround, and walk-in closet. The third level is a true retreat, complete with a gas fireplace, full bath, walk-in closet, and abundant possibilities as an ensuite bedroom, game room, studio, home office, or private space for multigenerational living. An exceptionally generous “sky attic” provides valuable storage for seasonal items and more. A newer roof and hot water heater add further appeal. Pinehurst Circle is located within the sought-after Easton Club community, where residents enjoy a community pool, tennis and pickleball courts, trash removal, snow removal, yard maintenance, and common-area maintenance through the HOA. Easton Utilities provides electric service, natural gas, water, sewer, cable, and high-speed Easton Velocity internet. Convenient access to Route 50 makes this an excellent location for commuting, while downtown Easton’s restaurants, boutiques, galleries, Academy Art Museum, and Avalon Theatre are just minutes away. With multiple ensuite possibilities and generous living and storage space across three levels, this move-in-ready townhome, backing to the woods presents a rare opportunity.

28461 Pinehurst Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$365,000

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

4 Beds ⋅ 3 Baths

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

408 Crowberry Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$354,500

Updated 2-bedroom, 2-bath home featuring a number of improvements and upgrades completed since December 2023. A bright front sunroom provides an inviting entry and features a custom built-in window bench seat. The adjoining living and dining areas offer comfortable everyday living space, accented by a custom stained-glass window. The renovated kitchen features new custom cabinetry, quartz countertops, stainless steel appliances, new flooring, a pantry, and a breakfast nook. The primary bedroom includes an en-suite bath with a glass-enclosed shower and double vanity. A second bedroom and full bath complete the home's living spaces. Additional improvements include upgraded electrical, new vinyl replacement windows, a new mini-split heating and air conditioning system, new water heater, ceiling fans, and a new front storm door. Just off the kitchen, the carport provides convenient covered parking with the flexibility to serve as additional outdoor living or entertaining space. Vinyl fencing and gates help define this area from the spacious backyard, offering plenty of room to enjoy the property outdoors. Some furniture and furnishings are available. Conveniently located with quick access to Route 50, the home offers an easy connection to downtown Easton, Cambridge, St. Michaels and surrounding Mid-Shore destinations.

2 Beds ⋅ 2 Baths

Updated 2-bedroom, 2-bath home featuring a number of improvements and upgrades completed since December 2023. A bright front sunroom provides an inviting entry and features a custom built-in window bench seat. The adjoining living and dining areas offer comfortable everyday living space, accented by a custom stained-glass window. The renovated kitchen features new custom cabinetry, quartz countertops, stainless steel appliances, new flooring, a pantry, and a breakfast nook. The primary bedroom includes an en-suite bath with a glass-enclosed shower and double vanity. A second bedroom and full bath complete the home's living spaces. Additional improvements include upgraded electrical, new vinyl replacement windows, a new mini-split heating and air conditioning system, new water heater, ceiling fans, and a new front storm door. Just off the kitchen, the carport provides convenient covered parking with the flexibility to serve as additional outdoor living or entertaining space. Vinyl fencing and gates help define this area from the spacious backyard, offering plenty of room to enjoy the property outdoors. Some furniture and furnishings are available. Conveniently located with quick access to Route 50, the home offers an easy connection to downtown Easton, Cambridge, St. Michaels and surrounding Mid-Shore destinations.

29336 Hawkes Hill Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$350,000

Great opportunity in Easton! This spacious 4-bedroom, 2-bath rancher offers nearly 2,000 square feet of comfortable one-level living on approximately half an acre. The inviting floor plan features a generously sized kitchen with quartz countertops, ample cabinetry, a large pantry and plenty of space for everyday living and entertaining. The primary bedroom offers a vaulted ceiling, skylight, huge walk-in closet and private full bath with custom shower. Three additional bedrooms provide flexibility for family, guests or a home office. Outside, enjoy the spacious yard, patio/deck area and storage shed. The attached one-car garage provides additional storage and convenience. Ideally located with easy access to Easton, shopping, dining, St. Michaels, airport, new hospital and golf course! A wonderful opportunity to enjoy space, comfort and one-level living just minutes from all that Easton has to offer!

4 Beds ⋅ 2 Baths

Great opportunity in Easton! This spacious 4-bedroom, 2-bath rancher offers nearly 2,000 square feet of comfortable one-level living on approximately half an acre. The inviting floor plan features a generously sized kitchen with quartz countertops, ample cabinetry, a large pantry and plenty of space for everyday living and entertaining. The primary bedroom offers a vaulted ceiling, skylight, huge walk-in closet and private full bath with custom shower. Three additional bedrooms provide flexibility for family, guests or a home office. Outside, enjoy the spacious yard, patio/deck area and storage shed. The attached one-car garage provides additional storage and convenience. Ideally located with easy access to Easton, shopping, dining, St. Michaels, airport, new hospital and golf course! A wonderful opportunity to enjoy space, comfort and one-level living just minutes from all that Easton has to offer!

10225 Ocean Gtwy, Easton

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

$350,000

Solid brick 3-bedroom, 2-bath rancher situated on a quiet street just behind the hospital. This well-maintained home features a newer roof, soffits, and gutters, along with a vapor barrier, energy-efficient windows, and sliding door. The updated kitchen includes stainless steel appliances. Enjoy a gravel driveway plus convenient street parking. Ideally located close to the hospital and just minutes from downtown restaurants, shops, and amenities.

3 Beds ⋅ 2 Baths

Solid brick 3-bedroom, 2-bath rancher situated on a quiet street just behind the hospital. This well-maintained home features a newer roof, soffits, and gutters, along with a vapor barrier, energy-efficient windows, and sliding door. The updated kitchen includes stainless steel appliances. Enjoy a gravel driveway plus convenient street parking. Ideally located close to the hospital and just minutes from downtown restaurants, shops, and amenities.

241 Brookwood Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$350,000

Assumable 2.75% FHA interest rate. Seller offering $5,000 seller credit toward buyer closing cost or rate buydown with acceptable offer. BRAND NEW ROOF INSTALLED SEPTEMBER 2026 & NEW HVAC 2025. Enjoy the freedom of main-level living without giving up the space to host family and friends. This beautifully maintained Lakelands home offers a first-floor primary suite, generous guest accommodations, flexible loft space, a private fenced yard, and the low-maintenance lifestyle so many Easton buyers are searching for. Additional features include multiple storage closets, a dedicated laundry room, a two-car garage, and a fully fenced backyard with patio ideal for outdoor entertaining, pets, or gardening.

3 Beds ⋅ 3 Baths

Assumable 2.75% FHA interest rate. Seller offering $5,000 seller credit toward buyer closing cost or rate buydown with acceptable offer. BRAND NEW ROOF INSTALLED SEPTEMBER 2026 & NEW HVAC 2025. Enjoy the freedom of main-level living without giving up the space to host family and friends. This beautifully maintained Lakelands home offers a first-floor primary suite, generous guest accommodations, flexible loft space, a private fenced yard, and the low-maintenance lifestyle so many Easton buyers are searching for. Additional features include multiple storage closets, a dedicated laundry room, a two-car garage, and a fully fenced backyard with patio ideal for outdoor entertaining, pets, or gardening.

29053 Superior Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$349,900

Recently updated and move-in ready, this one-level home offers 3 bedrooms and 2 full baths with LVP flooring throughout most of the home, kitchen with newer appliances, separate dining area, and a spacious living room. The primary bedroom includes a private bath. Major 2025 -2026 improvements include a new HVAC system with updated ductwork and vents, an encapsulated crawl space, a new roof, new siding, new windows, and new doors. Outside, you'll find a storage shed and a gravel driveway with ample parking. Conveniently located near downtown Trappe with fabulous dining options and two parks..See list of improvements. Close to public boat ramp. This home is ideally situated between Easton and Cambridge. A well-maintained, updated home offering excellent value and easy living on Maryland's Eastern Shore.

3 Beds ⋅ 2 Baths

Recently updated and move-in ready, this one-level home offers 3 bedrooms and 2 full baths with LVP flooring throughout most of the home, kitchen with newer appliances, separate dining area, and a spacious living room. The primary bedroom includes a private bath. Major 2025 -2026 improvements include a new HVAC system with updated ductwork and vents, an encapsulated crawl space, a new roof, new siding, new windows, and new doors. Outside, you'll find a storage shed and a gravel driveway with ample parking. Conveniently located near downtown Trappe with fabulous dining options and two parks..See list of improvements. Close to public boat ramp. This home is ideally situated between Easton and Cambridge. A well-maintained, updated home offering excellent value and easy living on Maryland's Eastern Shore.

4072 Main St, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$349,000

🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

3 Beds ⋅ 2 Baths

🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

29316 Will St, Easton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$344,900

Welcome to this extensively renovated 3-bedroom, 2-full-bath home, offering approximately 1,539 sq. ft. of living space on a spacious, level 0.69-acre lot. ✨ Recent updates include: • New flooring throughout • Fresh interior and exterior paint • Updated kitchen with new countertops and appliances • Updated bathrooms • New deck • New dishwasher • New washing machine • New AC unit Move-in ready with plenty of room inside and out, this home offers comfortable living in a peaceful Eastern Shore setting—approximately 10 minutes from St. Michaels and 5 minutes from Tilghman Island Beach 3 Bedrooms | 2 Full Bathrooms | 1,539 Sq. Ft. | 0.69 Acres

3 Beds ⋅ 2 Baths

Welcome to this extensively renovated 3-bedroom, 2-full-bath home, offering approximately 1,539 sq. ft. of living space on a spacious, level 0.69-acre lot. ✨ Recent updates include: • New flooring throughout • Fresh interior and exterior paint • Updated kitchen with new countertops and appliances • Updated bathrooms • New deck • New dishwasher • New washing machine • New AC unit Move-in ready with plenty of room inside and out, this home offers comfortable living in a peaceful Eastern Shore setting—approximately 10 minutes from St. Michaels and 5 minutes from Tilghman Island Beach 3 Bedrooms | 2 Full Bathrooms | 1,539 Sq. Ft. | 0.69 Acres

8490 Tilghman Island Rd, Wittman

Listing courtesy of Johnson-Needham Realty LLC. Contact:

$342,500

Motivated Seller. Sold As Is with Great Potential for Rehab...This is a Great Opportunity to make this your Forever Home. Great remodel and expansion potential in this Brick home on a large corner lot with Water Views. Home is in need of a Total Renovation. Just off of St. Michaels Rd. looking across to Oak Creek. With nearly 3/4 of an acre and no Flood Zone this is centrally located between Easton and St. Michaels. Property is being offered "As Is" !

3 Beds ⋅ 2 Baths

Motivated Seller. Sold As Is with Great Potential for Rehab...This is a Great Opportunity to make this your Forever Home. Great remodel and expansion potential in this Brick home on a large corner lot with Water Views. Home is in need of a Total Renovation. Just off of St. Michaels Rd. looking across to Oak Creek. With nearly 3/4 of an acre and no Flood Zone this is centrally located between Easton and St. Michaels. Property is being offered "As Is" !

25911 River Rd, Newcomb

Listing courtesy of Coldwell Banker Realty. Contact:

$340,000

Residential lot available minutes from St Michaels. .56 of an acre with 200 feet water frontage. Public water and sewer hookup is available. Build your waterfront dream home here!!!!!!

Main Street, Neavitt

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

$340,000

Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

2 Beds ⋅ 1 Baths

Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

11994 Cordova Rd, Cordova

Listing courtesy of Coldwell Banker Realty. Contact:

$335,000

Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

6 Beds ⋅ 3 Baths

Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

4096 Main St, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

$334,290

Large 3 bed Townhouse 2,254 sq ft - July Delivery! Open plan kitchen, Stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

3 Beds ⋅ 3 Baths

Large 3 bed Townhouse 2,254 sq ft - July Delivery! Open plan kitchen, Stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

1217 Loch Ness Ln, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$329,000

This attractive end-unit townhouse is located in the desirable Easton Club community offering well-maintained, move-in ready living just minutes from historic downtown Easton. The home features a welcoming front porch that leads to the foyer and spacious kitchen, complete with granite counters, a pantry, breakfast bar, ample cabinet and counter space and appliances that are all less than two years old. The spacious living room offers flexible space for both living and dining and features two sliding glass doors leading to the rear deck overlooking ponds and a wooded setting. Upstairs, the primary suite features a large walk-in closet and spacious private bath, while the second bedroom also includes its own full bath and walk-in closet. Bedroom-level laundry adds everyday convenience. An attached outdoor storage shed provides ample space for tools, bikes, seasonal decor or any of your storage needs. A new roof was installed in June 2026 giving a buyer peace of mind for years to come. Residents of Easton Club enjoy a newly refinished in-ground pool, newly refinished tennis and pickleball courts and multiple ponds throughout the community, all just minutes from downtown Easton's charming boutiques, restaurants and local attractions. Downtown Oxford is approximately 10 minutes away where you can enjoy local waterfront dining, the beach at “The Strand” and so much more.

2 Beds ⋅ 3 Baths

This attractive end-unit townhouse is located in the desirable Easton Club community offering well-maintained, move-in ready living just minutes from historic downtown Easton. The home features a welcoming front porch that leads to the foyer and spacious kitchen, complete with granite counters, a pantry, breakfast bar, ample cabinet and counter space and appliances that are all less than two years old. The spacious living room offers flexible space for both living and dining and features two sliding glass doors leading to the rear deck overlooking ponds and a wooded setting. Upstairs, the primary suite features a large walk-in closet and spacious private bath, while the second bedroom also includes its own full bath and walk-in closet. Bedroom-level laundry adds everyday convenience. An attached outdoor storage shed provides ample space for tools, bikes, seasonal decor or any of your storage needs. A new roof was installed in June 2026 giving a buyer peace of mind for years to come. Residents of Easton Club enjoy a newly refinished in-ground pool, newly refinished tennis and pickleball courts and multiple ponds throughout the community, all just minutes from downtown Easton's charming boutiques, restaurants and local attractions. Downtown Oxford is approximately 10 minutes away where you can enjoy local waterfront dining, the beach at “The Strand” and so much more.

28491 Pinehurst Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$329,000

This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a wonderful starter or retirement home.

3 Beds ⋅ 1 Baths

This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a wonderful starter or retirement home.

3900 Harrison Cir, Trappe

Listing courtesy of Mr. Lister Realty. Contact:

$325,000

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

4 Beds ⋅ 2 Baths

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

619 Goldsborough St, Easton

Listing courtesy of Next Step Realty. Contact:

$325,000

Charming Cape Cod Near Historic Downtown Easton Warm, welcoming, and full of character, this beautifully updated Cape Cod offers comfortable living spaces and a wonderful location just a short stroll from historic downtown Easton. Inside, beautiful hardwood floors add warmth and character, while the bright, inviting kitchen and updated HVAC provide everyday comfort. The spacious second level offers exceptional flexibility with a large bedroom, separate office or sitting area, walk-in closet, and abundant additional storage, ideal for a home office, reading nook, hobby space, or quiet retreat. Outdoor living is just as inviting. Enjoy morning coffee or watch the world go by from the classic front porch and porch swing. In the beautifully landscaped backyard, a newer deck and patio provide plenty of space for outdoor dining, entertaining, gardening, or simply relaxing. A large storage shed with attic space offers excellent additional storage for bikes, tools, hobbies, and seasonal items. Best of all is the location. Downtown Easton’s restaurants, boutiques, galleries, and year-round events are close at hand, with parks, shopping, schools, and major routes conveniently nearby. Move-in ready, full of charm, and close to the heart of Easton, come take another look and see all this home has to offer. Advance notice required for showings - please contact your agent to schedule your appointment.

2 Beds ⋅ 1 Baths

Charming Cape Cod Near Historic Downtown Easton Warm, welcoming, and full of character, this beautifully updated Cape Cod offers comfortable living spaces and a wonderful location just a short stroll from historic downtown Easton. Inside, beautiful hardwood floors add warmth and character, while the bright, inviting kitchen and updated HVAC provide everyday comfort. The spacious second level offers exceptional flexibility with a large bedroom, separate office or sitting area, walk-in closet, and abundant additional storage, ideal for a home office, reading nook, hobby space, or quiet retreat. Outdoor living is just as inviting. Enjoy morning coffee or watch the world go by from the classic front porch and porch swing. In the beautifully landscaped backyard, a newer deck and patio provide plenty of space for outdoor dining, entertaining, gardening, or simply relaxing. A large storage shed with attic space offers excellent additional storage for bikes, tools, hobbies, and seasonal items. Best of all is the location. Downtown Easton’s restaurants, boutiques, galleries, and year-round events are close at hand, with parks, shopping, schools, and major routes conveniently nearby. Move-in ready, full of charm, and close to the heart of Easton, come take another look and see all this home has to offer. Advance notice required for showings - please contact your agent to schedule your appointment.

347 N Washington St, Easton

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

9531 Quail Hollow Dr Unit 405, St Michaels

$319,900

Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

2 Beds ⋅ 3 Baths

Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit 405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$315,000

Located in the heart of Easton’s medical and healthcare district—and just moments from Route 50—this 1,500± sq. ft. end-unit commercial condo offers an exceptional opportunity for medical, dental, or professional office use. If you’re ready to own instead of rent, this space delivers the flexibility, infrastructure, and location your business needs. Thoughtfully designed with a highly functional layout, the unit features a welcoming waiting room, dedicated reception area, two restrooms, five office/exam rooms, break room, equipment room, sterilization area, and mechanical room. Every treatment room includes a sink and is fully plumbed for dental chairs with water, suction, and air at both ends. Wiring is already in place for digital dentistry, panoramic X-ray, and data systems. All rooms also include Radon fans installed during COVID to create negative pressure—an added layer of safety and value. Additional perks include 220V service for autoclaves and laundry hookups. Interior walls can be easily reconfigured to suit your practice or workflow. Recent updates include a new roof and freshly repaved parking lot. Shared operating costs—trash, lawn care, landscaping, and water—are divided among the four units based on square footage.With ample parking and a prime location surrounded by established healthcare providers, this space is a rare chance to elevate your business while building equity. Perfect for medical, dental, therapy, or professional users looking to stop paying rent and secure a smart long-term investment. Bring your buyers. Bring your business.

508 Cynwood Dr Unit A, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$310,000

This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street.. The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property.

3 Beds ⋅ 2 Baths

This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street.. The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property.

409 Railroad Ave, St Michaels

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

$300,000

REAL ESTATE AUCTION featuring ON SITE and SIMULCAST BIDDING!! Online Bidding Opens - Thursday, October 29, 2026. Live On Site Auction - Friday, October 30, 2026 at 12:00 noon. List price is opening bid only. Live Auction Bidders – A $40,000 deposit, payable by cashier’s check, will be required of the purchaser at time and place of sale. Online Auction Bidders – A $40,000 deposit, payable by cashier’s check or wire transfer, is due from all online bidders prior to bidding platform approval. That deposit to be applied to the purchase price for the purchaser, and all other deposits returned within 1 business day. A once in a lifetime opportunity to purchase a waterfront restaurant building with tiki bar in one of the most sought after locations on Maryland’s Eastern Shore. Located at the gateway to Tilghman Island and facing the Tilghman Island Drawbridge, considered to be the busiest on the East Coast, the property features ample exposure to both boat and vehicle traffic. The auction provides an opportunity for both users and investors to purchase a trophy waterfront property in a truly unique, desirable location with extensive long-term potential.

6136 Tilghman Island Rd, Tilghman

Listing courtesy of A.J. Billig & Company. Contact:

$299,900

Welcome home to this charming 3-bedroom, 2-full-bath home offering a comfortable and functional layout with the convenience of a main-level primary bedroom. The spacious primary bedroom features a private full bath and direct access to the deck, creating an easy connection to the outdoors. The main level also offers a welcoming living area, kitchen and dining space, along with convenient main-level laundry. The kitchen and dining area provide additional access to the deck, making outdoor entertaining or enjoying your morning coffee a breeze. Upstairs, you’ll find two additional bedrooms and a full bathroom, providing plenty of space for family, guests, a home office or flex space.This desirable end-unit home offers added privacy and extra outdoor space, including a side yard and backyard—perfect for relaxing, entertaining, or enjoying some fresh air. Updates include an HVAC system that is only one year old and a new washing machine, providing added peace of mind. Come see all this home has to offer!

3 Beds ⋅ 2 Baths

Welcome home to this charming 3-bedroom, 2-full-bath home offering a comfortable and functional layout with the convenience of a main-level primary bedroom. The spacious primary bedroom features a private full bath and direct access to the deck, creating an easy connection to the outdoors. The main level also offers a welcoming living area, kitchen and dining space, along with convenient main-level laundry. The kitchen and dining area provide additional access to the deck, making outdoor entertaining or enjoying your morning coffee a breeze. Upstairs, you’ll find two additional bedrooms and a full bathroom, providing plenty of space for family, guests, a home office or flex space.This desirable end-unit home offers added privacy and extra outdoor space, including a side yard and backyard—perfect for relaxing, entertaining, or enjoying some fresh air. Updates include an HVAC system that is only one year old and a new washing machine, providing added peace of mind. Come see all this home has to offer!

8186 June Way Unit 307, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

$299,000

This charming Colonial is ideally located in downtown Easton, just off the Rails to Trails, only a block from Idlewild Park and conveniently located between both of Easton's YMCA facilities. Inside, the welcoming first floor offers a spacious living room with French doors opening to a cozy den that could also serve as a home office, playroom or quiet retreat. The kitchen flows into a large dining area with French doors leading to a bright sunroom overlooking the fenced rear yard. A spacious laundry/mudroom and updated half bath complete the first floor. Upstairs, three comfortable bedrooms share an updated full bath. Original hardwood floors flow throughout most of the home, adding character to the inviting interior. A large walk-up attic provides abundant storage space for seasonal items. The fenced backyard offers a brick patio for outdoor entertaining, a separate fire pit area ready to be brought back to life and a storage shed. Beyond the rear fence, a private alley presents the opportunity to create off-street parking, an added bonus in town. The roof was replaced in 2017. With its convenient location, flexible living spaces and inviting outdoor areas, this charming Easton home offers the best of in-town living with close proximity to parks, trails, dining, boutique shops and everyday amenities just moments away.

3 Beds ⋅ 2 Baths

This charming Colonial is ideally located in downtown Easton, just off the Rails to Trails, only a block from Idlewild Park and conveniently located between both of Easton's YMCA facilities. Inside, the welcoming first floor offers a spacious living room with French doors opening to a cozy den that could also serve as a home office, playroom or quiet retreat. The kitchen flows into a large dining area with French doors leading to a bright sunroom overlooking the fenced rear yard. A spacious laundry/mudroom and updated half bath complete the first floor. Upstairs, three comfortable bedrooms share an updated full bath. Original hardwood floors flow throughout most of the home, adding character to the inviting interior. A large walk-up attic provides abundant storage space for seasonal items. The fenced backyard offers a brick patio for outdoor entertaining, a separate fire pit area ready to be brought back to life and a storage shed. Beyond the rear fence, a private alley presents the opportunity to create off-street parking, an added bonus in town. The roof was replaced in 2017. With its convenient location, flexible living spaces and inviting outdoor areas, this charming Easton home offers the best of in-town living with close proximity to parks, trails, dining, boutique shops and everyday amenities just moments away.

313 Linden Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$295,000

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home on 0.84± commercially zoned acreage with premier road frontage presents a compelling opportunity for investors seeking rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights • 3 Bedrooms 2 Bathrooms split between two units • 0.84± acre parcel with generous yard space • Two accessory structures (retail/storage in need of repair + versatile workshop ) • Strong long-term rental market supported by local workforce and regional amenities • Minutes to marinas, dining, recreation, and Chesapeake Bay attractions • Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable rental property in the Eastern Shore’s highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

22314 Pot Pie Rd, Wittman

Listing courtesy of Meredith Fine Properties. Contact:

$295,000

A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot, the property provides remarkable flexibility for home placement, architectural style, and outdoor living spaces. The generous buildable envelope allows for a variety of layouts, and driveway access can be configured from Miles Avenue, Canton Street, or both, depending on the design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$295,000

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights • 3 Bedrooms 2 Bathrooms split between two units • 0.84± acre parcel with generous yard space • Two accessory structures (retail/storage (in need of repair) + versatile garage/ workshop) • Strong long-term potential rental market supported by local workforce and regional amenities • Minutes to marinas, dining, recreation, and Chesapeake Bay attractions • Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable potential rental property in the Eastern Shore’s highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

3 Beds ⋅ 2 Baths

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights • 3 Bedrooms 2 Bathrooms split between two units • 0.84± acre parcel with generous yard space • Two accessory structures (retail/storage (in need of repair) + versatile garage/ workshop) • Strong long-term potential rental market supported by local workforce and regional amenities • Minutes to marinas, dining, recreation, and Chesapeake Bay attractions • Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable potential rental property in the Eastern Shore’s highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

22314 Pot Pie Rd, Wittman

Listing courtesy of Meredith Fine Properties. Contact:

$289,900

Professional photos and detailed description coming soon!

3 Beds ⋅ 2 Baths

Professional photos and detailed description coming soon!

3967 Harrison Cir, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

$279,000

Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot provides ample outdoor space for potential landscaping or recreational activities, enhancing the property's appeal. Homeowners or Investors will appreciate the potential to transform this property into your personal residence or investment property. Being sold As Is condition.

3 Beds ⋅ 2 Baths

Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot provides ample outdoor space for potential landscaping or recreational activities, enhancing the property's appeal. Homeowners or Investors will appreciate the potential to transform this property into your personal residence or investment property. Being sold As Is condition.

210 Brooks Ln, St Michaels

Listing courtesy of Meredith Fine Properties. Contact:

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