easternshoremdfineproperties.com Search Results

$359,900

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: 4108226665

$509,000

Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer, primary bedroom closet organization, all bathrooms refreshed, fenced rear yard and drywalled/painted garage interior. The layout offers traditional rooms that blend together with attractive sight lines and connectivity. Step outside and find a relaxing brick paver patio with mature privacy plantings and a natural gas Weber Grill connected to town gas service all encompassed within the fenced back yard. This is a great house, move in ready for you! 55+ age-restricted section. Community amenities include Clubhouse with meeting room, exercise rooms, library and game rooms, outdoor pool, tennis/pickleball courts, picnic areas and common grounds, putting green, exercise paths, bocce ball, horse shoes and more. Located close to downtown Easton with fine restaurants and shopping and medical facilities, St. Michaels and Oxford. 1.5 hours to MD/DE beaches. 30 minutes to Bay Bridge.

3 Beds ⋅ 3 Baths

Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer, primary bedroom closet organization, all bathrooms refreshed, fenced rear yard and drywalled/painted garage interior. The layout offers traditional rooms that blend together with attractive sight lines and connectivity. Step outside and find a relaxing brick paver patio with mature privacy plantings and a natural gas Weber Grill connected to town gas service all encompassed within the fenced back yard. This is a great house, move in ready for you! 55+ age-restricted section. Community amenities include Clubhouse with meeting room, exercise rooms, library and game rooms, outdoor pool, tennis/pickleball courts, picnic areas and common grounds, putting green, exercise paths, bocce ball, horse shoes and more. Located close to downtown Easton with fine restaurants and shopping and medical facilities, St. Michaels and Oxford. 1.5 hours to MD/DE beaches. 30 minutes to Bay Bridge.

7432 Karen Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$795,000

This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining. Hardwood flooring runs throughout the home. The main level offers a flexible layout with a bedroom just off the entry and a nearby full bath. The kitchen features double wall ovens and a gas cooktop in the island and opens to comfortable living spaces. The living room includes a gas fireplace, while the family room offers custom built-ins, a Vermont wood stove, and direct access to the courtyard and backyard. Upstairs, the primary suite includes a large bath with soaking tub, stall shower, and double vanity. A second en-suite bedroom currently serves as an office with extensive custom built-in cabinetry and could easily convert back to bedroom use. A mudroom off the attached two-car garage provides access to the side yard and leads to a staircase accessing a finished bonus room above the garage. This flexible space features independent heating and hot water and offers excellent options for guests, workspace, or additional living area. Custom built-ins are also found in the garage, family room, bedroom, and office. Additional improvements include a roof replacement in 2025, upgraded heating system in 2020, and a Rinnai hot water system. The property also features an irrigation system to maintain the beautifully landscaped grounds. Cooke’s Hope residents enjoy walking trails, tennis courts, fitness center, dog park, and well-maintained community green spaces.

4 Beds ⋅ 4 Baths

This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining. Hardwood flooring runs throughout the home. The main level offers a flexible layout with a bedroom just off the entry and a nearby full bath. The kitchen features double wall ovens and a gas cooktop in the island and opens to comfortable living spaces. The living room includes a gas fireplace, while the family room offers custom built-ins, a Vermont wood stove, and direct access to the courtyard and backyard. Upstairs, the primary suite includes a large bath with soaking tub, stall shower, and double vanity. A second en-suite bedroom currently serves as an office with extensive custom built-in cabinetry and could easily convert back to bedroom use. A mudroom off the attached two-car garage provides access to the side yard and leads to a staircase accessing a finished bonus room above the garage. This flexible space features independent heating and hot water and offers excellent options for guests, workspace, or additional living area. Custom built-ins are also found in the garage, family room, bedroom, and office. Additional improvements include a roof replacement in 2025, upgraded heating system in 2020, and a Rinnai hot water system. The property also features an irrigation system to maintain the beautifully landscaped grounds. Cooke’s Hope residents enjoy walking trails, tennis courts, fitness center, dog park, and well-maintained community green spaces.

28713 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$489,000

Beautiful end-unit townhome in desirable Easton Club, offering a rare combination of natural light, flexible living space, and sweeping, peaceful nature views. Thoughtfully positioned on one of the larger lots among the original Easton Club townhomes, this home features added side windows that bring in wonderful natural light while capturing the surrounding nature views. The main level offers an inviting living room with solid wood flooring, crown molding, higher baseboards, and a gas fireplace with marble hearth and mantel. An arched opening leads to the formal dining room, creating a gracious flow for everyday living and entertaining. The kitchen features white cabinetry, composite countertops, tile backsplash, tile flooring, newer appliances, and recently installed LED under-cabinet lighting. A spacious first-floor family room provides excellent flexibility and could also serve as a main-level primary bedroom suite, with a full bath and closet for added convenience. Upstairs, the large primary bedroom with sitting area features a walk-in closet, updated walk-in shower, and access to a private balcony with newer polymer membrane, privacy screen, posts, and railings. A second upstairs bedroom and additional full bath complete the upper level. Outdoor spaces include a rear patio overlooking a peaceful lawn, mature trees, and open green space, plus a private balcony for relaxing above it all. Additional conveniences and updates include an attached one-car garage, a newer roof with GAF Silver Pledge warranty, newer gutters and downspouts, newer furnace, newer washer and dryer, recently installed wool stair runner, and an encapsulated crawlspace with dehumidifier. Charming garden accents, including the front yard armillary and backyard concrete bird bath, convey with the home. Enjoy the ease of Easton Club living, where tree-lined surroundings, open green space, panoramic view of expansive open land, and neighborhood amenities create a quiet and convenient setting. The community offers a pool, tennis and pickleball courts, sidewalks, and easy access to downtown Easton, Oxford, shops, dining, and waterfront recreation. With its desirable end-unit location, versatile floor plan, beautiful natural light, and scenic setting, this home is a special opportunity in one of Easton’s established communities. Schedule your private showing today.

3 Beds ⋅ 3 Baths

Beautiful end-unit townhome in desirable Easton Club, offering a rare combination of natural light, flexible living space, and sweeping, peaceful nature views. Thoughtfully positioned on one of the larger lots among the original Easton Club townhomes, this home features added side windows that bring in wonderful natural light while capturing the surrounding nature views. The main level offers an inviting living room with solid wood flooring, crown molding, higher baseboards, and a gas fireplace with marble hearth and mantel. An arched opening leads to the formal dining room, creating a gracious flow for everyday living and entertaining. The kitchen features white cabinetry, composite countertops, tile backsplash, tile flooring, newer appliances, and recently installed LED under-cabinet lighting. A spacious first-floor family room provides excellent flexibility and could also serve as a main-level primary bedroom suite, with a full bath and closet for added convenience. Upstairs, the large primary bedroom with sitting area features a walk-in closet, updated walk-in shower, and access to a private balcony with newer polymer membrane, privacy screen, posts, and railings. A second upstairs bedroom and additional full bath complete the upper level. Outdoor spaces include a rear patio overlooking a peaceful lawn, mature trees, and open green space, plus a private balcony for relaxing above it all. Additional conveniences and updates include an attached one-car garage, a newer roof with GAF Silver Pledge warranty, newer gutters and downspouts, newer furnace, newer washer and dryer, recently installed wool stair runner, and an encapsulated crawlspace with dehumidifier. Charming garden accents, including the front yard armillary and backyard concrete bird bath, convey with the home. Enjoy the ease of Easton Club living, where tree-lined surroundings, open green space, panoramic view of expansive open land, and neighborhood amenities create a quiet and convenient setting. The community offers a pool, tennis and pickleball courts, sidewalks, and easy access to downtown Easton, Oxford, shops, dining, and waterfront recreation. With its desirable end-unit location, versatile floor plan, beautiful natural light, and scenic setting, this home is a special opportunity in one of Easton’s established communities. Schedule your private showing today.

28542 Congressional Ct, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$370,000

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.

3 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: 4108226665

$715,000

This beautifully appointed three-bedroom, two-and-a-half-bath home offers refined comfort, thoughtful design, and effortless Eastern Shore living in the waterfront access community of Easton Village. Built in 2009 and designed for easy everyday living, the home features spacious, light-filled interiors with an open floor plan, formal dining area, and inviting living spaces ideal for both entertaining and relaxed evenings at home. The great room is anchored by a gas fireplace, creating a warm and welcoming atmosphere. The kitchen offers upgraded countertops, generous table space, a cooktop, double oven, built-in microwave, dishwasher, disposal, and refrigerator, perfect for preparing favorite meals, hosting guests, or enjoying casual mornings at home. A main-level primary suite provides comfort and convenience, complete with a walk-in closet and private bath featuring a soaking tub and shower. Upstairs, a spacious loft/family room overlooks the main living area and is complemented by two additional bedrooms, a full bath, and a storage room. Additional highlights include: hardwood, ceramic tile, and carpeted flooring, recessed lighting, ceiling fans, crown molding, chair rail details, first floor laundry room, wired surround sound, extensive hardscape and exterior lighting, private patio for outdoor dining and gatherings, a fully fenced yard with a sprinkler system, and a rear-entry two-car attached garage with garage door opener Located in Easton Village, residents enjoy sidewalks, common grounds, a community center, exercise room, meeting room, picnic area, area, recreational paths, and outdoor pool all close to historic Easton, shopping, dining, and local attractions. A wonderful opportunity to enjoy comfort, convenience, and community in one of Easton’s most charming neighborhoods.

3 Beds ⋅ 3 Baths

This beautifully appointed three-bedroom, two-and-a-half-bath home offers refined comfort, thoughtful design, and effortless Eastern Shore living in the waterfront access community of Easton Village. Built in 2009 and designed for easy everyday living, the home features spacious, light-filled interiors with an open floor plan, formal dining area, and inviting living spaces ideal for both entertaining and relaxed evenings at home. The great room is anchored by a gas fireplace, creating a warm and welcoming atmosphere. The kitchen offers upgraded countertops, generous table space, a cooktop, double oven, built-in microwave, dishwasher, disposal, and refrigerator, perfect for preparing favorite meals, hosting guests, or enjoying casual mornings at home. A main-level primary suite provides comfort and convenience, complete with a walk-in closet and private bath featuring a soaking tub and shower. Upstairs, a spacious loft/family room overlooks the main living area and is complemented by two additional bedrooms, a full bath, and a storage room. Additional highlights include: hardwood, ceramic tile, and carpeted flooring, recessed lighting, ceiling fans, crown molding, chair rail details, first floor laundry room, wired surround sound, extensive hardscape and exterior lighting, private patio for outdoor dining and gatherings, a fully fenced yard with a sprinkler system, and a rear-entry two-car attached garage with garage door opener Located in Easton Village, residents enjoy sidewalks, common grounds, a community center, exercise room, meeting room, picnic area, area, recreational paths, and outdoor pool all close to historic Easton, shopping, dining, and local attractions. A wonderful opportunity to enjoy comfort, convenience, and community in one of Easton’s most charming neighborhoods.

28288 Hemmersley St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$385,000

Come experience this beautifully maintained townhome offering an impressive 2,520 square feet of living space, featuring an open-concept floor plan designed for comfortable everyday living and entertaining. The spacious main-level primary suite includes a large walk-in closet, while the inviting second floor loft provides the perfect space to relax, read, or enjoy hobbies. You'll also appreciate a dedicated office/study room on the main level. Additional highlights include a fenced rear yard, cozy gas fireplace, attached garage, Brand-New roof (2026), and a convenient huge walk-in storage room - no attic stairs required. The community's private swimming pool is included with the HOA, providing a wonderful place to cool off and unwind during the summer months. Ideally located with quick and easy access to downtown Easton, you'll enjoy shopping, dining, entertainment, and all the charm that the Easton lifestyle has to offer. Schedule your tour today!

3 Beds ⋅ 3 Baths

Come experience this beautifully maintained townhome offering an impressive 2,520 square feet of living space, featuring an open-concept floor plan designed for comfortable everyday living and entertaining. The spacious main-level primary suite includes a large walk-in closet, while the inviting second floor loft provides the perfect space to relax, read, or enjoy hobbies. You'll also appreciate a dedicated office/study room on the main level. Additional highlights include a fenced rear yard, cozy gas fireplace, attached garage, Brand-New roof (2026), and a convenient huge walk-in storage room - no attic stairs required. The community's private swimming pool is included with the HOA, providing a wonderful place to cool off and unwind during the summer months. Ideally located with quick and easy access to downtown Easton, you'll enjoy shopping, dining, entertainment, and all the charm that the Easton lifestyle has to offer. Schedule your tour today!

29049 Superior Cir, Easton

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$599,000

Welcome to the highly desirable 55+ section of Easton Club East. Situated on a premium corner lot, this well-maintained Merion model offers comfortable living both inside and out. Enjoy the beautifully landscaped yard featuring a custom patio, pergola, irrigation system, and plenty of space to relax or entertain. Inside, the bright and inviting floor plan includes a welcoming foyer, formal living and dining rooms, and a spacious family room with a gas fireplace. The kitchen features granite countertops, ample cabinetry, and a layout that opens to the main living areas. Just beyond, the tiled sunroom provides additional living space and overlooks the rear yard. The main-level primary suite is privately located and features a walk-in closet and a large bath with a soaking tub and separate tiled shower. Upstairs, you'll find a loft that's perfect for a sitting area, office, or hobby space, along with two guest bedrooms, a full bath, and convenient walk-up attic storage. Easton Club East residents enjoy an exceptional array of amenities, including a clubhouse with fitness center, library, ballroom, meeting rooms, game room, and billiards room. Outdoor amenities include a swimming pool, tennis and pickleball courts, bocce courts, putting green, walking trails, and scenic ponds. Located just minutes from downtown Easton, you'll have easy access to shopping, restaurants, healthcare, and everyday conveniences. The waterfront towns of St. Michaels and Oxford are nearby for dining, boating, and exploring the best of Maryland's Eastern Shore. For commuters and travelers, the Bay Bridge is approximately 30 minutes away, with Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches all within an easy drive.

3 Beds ⋅ 3 Baths

Welcome to the highly desirable 55+ section of Easton Club East. Situated on a premium corner lot, this well-maintained Merion model offers comfortable living both inside and out. Enjoy the beautifully landscaped yard featuring a custom patio, pergola, irrigation system, and plenty of space to relax or entertain. Inside, the bright and inviting floor plan includes a welcoming foyer, formal living and dining rooms, and a spacious family room with a gas fireplace. The kitchen features granite countertops, ample cabinetry, and a layout that opens to the main living areas. Just beyond, the tiled sunroom provides additional living space and overlooks the rear yard. The main-level primary suite is privately located and features a walk-in closet and a large bath with a soaking tub and separate tiled shower. Upstairs, you'll find a loft that's perfect for a sitting area, office, or hobby space, along with two guest bedrooms, a full bath, and convenient walk-up attic storage. Easton Club East residents enjoy an exceptional array of amenities, including a clubhouse with fitness center, library, ballroom, meeting rooms, game room, and billiards room. Outdoor amenities include a swimming pool, tennis and pickleball courts, bocce courts, putting green, walking trails, and scenic ponds. Located just minutes from downtown Easton, you'll have easy access to shopping, restaurants, healthcare, and everyday conveniences. The waterfront towns of St. Michaels and Oxford are nearby for dining, boating, and exploring the best of Maryland's Eastern Shore. For commuters and travelers, the Bay Bridge is approximately 30 minutes away, with Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches all within an easy drive.

7425 Michael Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$99,000

Come see this charming home located in the sought after 55+ community of Hyde Park a Sun Community in Easton. This home offers lots of updates throughout. Major improvements: new roof (2017), Heat pump (2023) A/C unit (2017) Beautiful Laminate flooring (2017) New deck and sliding door (2017) Some new vinyl windows (2022) New Shed (2017), All newer appliances within 5 yrs to include washer and dryer. Additional upgrades include: Resurfaced Driveway (2020) Upgraded interior lighting (2017) Repainted interior & exterior (2018) New exterior shutters (2022) Upgraded landscaping & exterior lighting (2017). You will find the location in the park unbeatable as it backs up to beautiful trees and views of open farm field beyond! A large rear deck offering a private, functional, and inviting retreat for relaxing and entertainment or just enjoying your morning coffee! A wonderful sunroom offers added living space and with a little heater can be used year round. The ample kitchen boasts plenty of cabinets and work space along with a breakfast bar. Some community amenities include: Club House with exercise room; inground pool; covered pavilion; gazebo; disc golf course; dog park; walking paths; fishing pond and rv & boat storage. Just minutes to local shops, stores, restaurants and all Easton has to offer!

2 Beds ⋅ 1 Baths

Come see this charming home located in the sought after 55+ community of Hyde Park a Sun Community in Easton. This home offers lots of updates throughout. Major improvements: new roof (2017), Heat pump (2023) A/C unit (2017) Beautiful Laminate flooring (2017) New deck and sliding door (2017) Some new vinyl windows (2022) New Shed (2017), All newer appliances within 5 yrs to include washer and dryer. Additional upgrades include: Resurfaced Driveway (2020) Upgraded interior lighting (2017) Repainted interior & exterior (2018) New exterior shutters (2022) Upgraded landscaping & exterior lighting (2017). You will find the location in the park unbeatable as it backs up to beautiful trees and views of open farm field beyond! A large rear deck offering a private, functional, and inviting retreat for relaxing and entertainment or just enjoying your morning coffee! A wonderful sunroom offers added living space and with a little heater can be used year round. The ample kitchen boasts plenty of cabinets and work space along with a breakfast bar. Some community amenities include: Club House with exercise room; inground pool; covered pavilion; gazebo; disc golf course; dog park; walking paths; fishing pond and rv & boat storage. Just minutes to local shops, stores, restaurants and all Easton has to offer!

47 Park Ln, Easton

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

$299,900

Huge price improvement 5/21/26! Welcome to 8186 June Way, #307 in Easton—a move-in ready, spacious and bright three-bedroom end townhome located just one mile from downtown Easton. This beautifully situated unit offers the best location in the townhome section of Waylands, featuring a large backyard bordered by trees and a private side deck off the kitchen/dining area overlooking peaceful greenspace. Inside, you’ll find a well-designed floor plan with a first-floor primary suite, open kitchen with breakfast bar flowing into the dining area, a large living room, and convenient laundry on the main level. Upstairs includes two generously sized bedrooms with plenty of closet space and a full hall bath. Additional highlights include ample storage in the attic, a large detached backyard shed, and crawl space access at the rear of the home. Conveniently located near shopping (Giant, Walmart, and more) and with quick access to Route 50 for commuters.

3 Beds ⋅ 2 Baths

Huge price improvement 5/21/26! Welcome to 8186 June Way, #307 in Easton—a move-in ready, spacious and bright three-bedroom end townhome located just one mile from downtown Easton. This beautifully situated unit offers the best location in the townhome section of Waylands, featuring a large backyard bordered by trees and a private side deck off the kitchen/dining area overlooking peaceful greenspace. Inside, you’ll find a well-designed floor plan with a first-floor primary suite, open kitchen with breakfast bar flowing into the dining area, a large living room, and convenient laundry on the main level. Upstairs includes two generously sized bedrooms with plenty of closet space and a full hall bath. Additional highlights include ample storage in the attic, a large detached backyard shed, and crawl space access at the rear of the home. Conveniently located near shopping (Giant, Walmart, and more) and with quick access to Route 50 for commuters.

8186 June Way Unit #307, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$699,999

PRICED TO SELL! SELLERS NOW OFFERING A $2500 CREDIT AT CLOSING FOR ANY BUYER TO PUT TOWARDS A CHAIR LIFT to more easily access upstairs bedrooms, should that be desired. 7586 Easton Club is an entertainer’s dream home—so much fun downstairs with open concept living, eat in kitchen with ample bar seating, natural gas fireplace, a salt water hot tub, private backyard and brick patio, garden seating area, huge driveway for lots of guest parking, and more! 1st Floor, bathrooms and primary staged by Wall to Wall Staging, bedrooms three and four are virtually staged. Rare opportunity to purchase this well-maintained turn-key Master's Village home in Easton Club on one of the most private backyard lots in the community, all walkable to the community pool and tennis/pickleball courts. It's not just a home; it's a lifestyle! Set back off the road and on a wide lot, the property is professionally landscaped with a rear yard that is among the most private in all of Easton Club, with professional landscaping including many large trees, underground sprinkler system throughout the yard, patio pavers and a separate outdoor seating area as well as a new salt water hot tub to use on those chilly nights or to relax any time of year. The brick front of the traditional home is stately. The front door entrance brings you into a grand two-story foyer which leads into a formal sitting area and dining room with tray ceiling to the right, powder room, laundry, interior access to the garage, family room with gas fireplace and eat-in chef's kitchen to the left with stainless steel appliances, large island, wall oven/microwave, wine fridge and enormous pantry. Ceilings are at a generous 9' height, with a higher vaulted ceiling over the eat-in area of the kitchen. The window shades by the eat-in area are electronic. Downstairs, over a half a dozen windows are new, put in by the current owners. Upstairs are all four sizable bedrooms. The large primary suite can easily accommodate a king sized bed with room to spare and offers vaulted ceiling, a custom built walk in closet. double vanity, heated floors, heated towel rack, large soaking tub, and walk in shower. Within the last few years the HVAC, kitchen and baths have been updated and the current owner has put new LVP floors throughout the entire upstairs, new LVP downstairs (the downstairs LVP flooring is not glued nor nailed and is over stunning hardwood cherry floors that match the powder room flooring, so should the buyer prefer hardwood, they are easily removed). The upstairs guest bathroom tile flooring was newly installed by the current owners. Sellers made some roof repairs early spring 2026. The roof is original and that is factored into the new listing price. Easton Club offers so many desirable amenities, including a clubhouse, pool, tennis court/pickleball, sidewalks, common areas with ponds and much green space & the community is mere minutes from Historic Downtown Easton's restaurants, shops, museums, doctor offices, hospital, and a short drive to Oxford and St Michaels and approximately 1.5 hrs to Washington DC, Bethesda and Baltimore, less than 1 hr to Annapolis!

4 Beds ⋅ 3 Baths

PRICED TO SELL! SELLERS NOW OFFERING A $2500 CREDIT AT CLOSING FOR ANY BUYER TO PUT TOWARDS A CHAIR LIFT to more easily access upstairs bedrooms, should that be desired. 7586 Easton Club is an entertainer’s dream home—so much fun downstairs with open concept living, eat in kitchen with ample bar seating, natural gas fireplace, a salt water hot tub, private backyard and brick patio, garden seating area, huge driveway for lots of guest parking, and more! 1st Floor, bathrooms and primary staged by Wall to Wall Staging, bedrooms three and four are virtually staged. Rare opportunity to purchase this well-maintained turn-key Master's Village home in Easton Club on one of the most private backyard lots in the community, all walkable to the community pool and tennis/pickleball courts. It's not just a home; it's a lifestyle! Set back off the road and on a wide lot, the property is professionally landscaped with a rear yard that is among the most private in all of Easton Club, with professional landscaping including many large trees, underground sprinkler system throughout the yard, patio pavers and a separate outdoor seating area as well as a new salt water hot tub to use on those chilly nights or to relax any time of year. The brick front of the traditional home is stately. The front door entrance brings you into a grand two-story foyer which leads into a formal sitting area and dining room with tray ceiling to the right, powder room, laundry, interior access to the garage, family room with gas fireplace and eat-in chef's kitchen to the left with stainless steel appliances, large island, wall oven/microwave, wine fridge and enormous pantry. Ceilings are at a generous 9' height, with a higher vaulted ceiling over the eat-in area of the kitchen. The window shades by the eat-in area are electronic. Downstairs, over a half a dozen windows are new, put in by the current owners. Upstairs are all four sizable bedrooms. The large primary suite can easily accommodate a king sized bed with room to spare and offers vaulted ceiling, a custom built walk in closet. double vanity, heated floors, heated towel rack, large soaking tub, and walk in shower. Within the last few years the HVAC, kitchen and baths have been updated and the current owner has put new LVP floors throughout the entire upstairs, new LVP downstairs (the downstairs LVP flooring is not glued nor nailed and is over stunning hardwood cherry floors that match the powder room flooring, so should the buyer prefer hardwood, they are easily removed). The upstairs guest bathroom tile flooring was newly installed by the current owners. Sellers made some roof repairs early spring 2026. The roof is original and that is factored into the new listing price. Easton Club offers so many desirable amenities, including a clubhouse, pool, tennis court/pickleball, sidewalks, common areas with ponds and much green space & the community is mere minutes from Historic Downtown Easton's restaurants, shops, museums, doctor offices, hospital, and a short drive to Oxford and St Michaels and approximately 1.5 hrs to Washington DC, Bethesda and Baltimore, less than 1 hr to Annapolis!

7586 Easton Club Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$895,000

Effortless Lifestyle — Deeded Boat Slip with Lift in Easton Village Tucked into one of Talbot County’s most coveted waterfront community, 8020 Easton Village Drive delivers what Eastern Shore buyers search for: a deeded boat slip with electric lift on the Tred Avon, a turn-key home, and close proximity to historic downtown Easton. This 5-bedroom, 3.5-bath Colonial offers a wraparound covered porch and hardwood floors throughout the main level. The open kitchen features granite counters, butcher-block island, stainless appliances, gas cooking, and a coffee bar. A formal dining room, gas-fireplace family room, main-level bonus room (5th bedroom or office), and powder room complete the first floor. Upstairs, the primary suite has vaulted ceilings, two walk-in closets, soaking tub, and double vanity, plus three additional bedrooms and two full baths. The detached two-car garage includes a private guest suite with full bath above — ideal for in-laws or visitors. Major systems include a whole-house standby generator, Rinnai tankless water heater, whole-house alarm system, as well as natural gas forced air, central A/C, and central vacuum. The home has been thoughtfully updated with an improved kitchen, along with new lighting and ceiling fans. The fenced backyard features extensive stone hardscape, a gazebo, and built-in stone grill. The rare and sought-after deeded boat slip with electric lift gives direct access to the Oxford and St Michaels' marinas via the scenic Tred Avon River. Easton Village is known for its top-notch amenities which include an in-ground pool, the clubhouse, a fitness center, kayak launch, trails, and so much more.

5 Beds ⋅ 4 Baths

Effortless Lifestyle — Deeded Boat Slip with Lift in Easton Village Tucked into one of Talbot County’s most coveted waterfront community, 8020 Easton Village Drive delivers what Eastern Shore buyers search for: a deeded boat slip with electric lift on the Tred Avon, a turn-key home, and close proximity to historic downtown Easton. This 5-bedroom, 3.5-bath Colonial offers a wraparound covered porch and hardwood floors throughout the main level. The open kitchen features granite counters, butcher-block island, stainless appliances, gas cooking, and a coffee bar. A formal dining room, gas-fireplace family room, main-level bonus room (5th bedroom or office), and powder room complete the first floor. Upstairs, the primary suite has vaulted ceilings, two walk-in closets, soaking tub, and double vanity, plus three additional bedrooms and two full baths. The detached two-car garage includes a private guest suite with full bath above — ideal for in-laws or visitors. Major systems include a whole-house standby generator, Rinnai tankless water heater, whole-house alarm system, as well as natural gas forced air, central A/C, and central vacuum. The home has been thoughtfully updated with an improved kitchen, along with new lighting and ceiling fans. The fenced backyard features extensive stone hardscape, a gazebo, and built-in stone grill. The rare and sought-after deeded boat slip with electric lift gives direct access to the Oxford and St Michaels' marinas via the scenic Tred Avon River. Easton Village is known for its top-notch amenities which include an in-ground pool, the clubhouse, a fitness center, kayak launch, trails, and so much more.

8020 Easton Village Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$480,000

Chesapeake by Del Webb. Popular 2-story Wittman model. Spacious 3 bedroom, 3 bath home. Great room with gas fireplace, office, large kitchen with center island, granite countertops and breakfast nook. Primary bedroom suite with walk-in closet, bath with separate vanities, separate shower and soaking tub. Guest bedroom, hall bath with walk-in tub and laundry room. Sunroom, enclosed porch overlooking your own private fenced in-ground pool. 2nd floor features large loft, guest bedroom and bath perfect for visitors or separate living area. newer roof (approx. 7 years old). Economical gas heat. Recent interior painting of some rooms. Attached 2-car garage, patio and irrigation system. Sited on a corner lot close to the community amenities which include a Clubhouse, tennis/pickleball courts, exercise trails, community pool, bocce ball, picnic areas, putting green. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. NOTE: Coastal Pools is in the process of completing extensive renovation of the pool

3 Beds ⋅ 3 Baths

Chesapeake by Del Webb. Popular 2-story Wittman model. Spacious 3 bedroom, 3 bath home. Great room with gas fireplace, office, large kitchen with center island, granite countertops and breakfast nook. Primary bedroom suite with walk-in closet, bath with separate vanities, separate shower and soaking tub. Guest bedroom, hall bath with walk-in tub and laundry room. Sunroom, enclosed porch overlooking your own private fenced in-ground pool. 2nd floor features large loft, guest bedroom and bath perfect for visitors or separate living area. newer roof (approx. 7 years old). Economical gas heat. Recent interior painting of some rooms. Attached 2-car garage, patio and irrigation system. Sited on a corner lot close to the community amenities which include a Clubhouse, tennis/pickleball courts, exercise trails, community pool, bocce ball, picnic areas, putting green. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. NOTE: Coastal Pools is in the process of completing extensive renovation of the pool

29638 Janets Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$249,000

ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY. IT IS SURROUNDED BY BEAUTIFUL HOMES MINUTES TO HISTORIC ST MICHAELS WITH ITS SHOPS, RESTAURANTS, MUSEUM, YACHTCLUB AND WATERFRONT PARKS. THE LOT BACKS UP TO COMMON SPACE THAT IS A NATURAL HABITAT FOR ULTIMATE PRIVACY AND WILDLIFE.

Deepwater Point, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$799,000

📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

4 Beds ⋅ 4 Baths

📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

8050 Easton Village Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,945,000

Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

6 Beds ⋅ 6 Baths

Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

228 Perry Cabin Dr Unit #228 / 226, Saint Michaels

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

$455,000

Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins, and seamless access to a private rear patio overlooking peaceful common space. The stunning kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options for guests or primary use. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, along with a second guest suite offering its own private bath. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage,plus paved parking. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value.

3 Beds ⋅ 3 Baths

Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins, and seamless access to a private rear patio overlooking peaceful common space. The stunning kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options for guests or primary use. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, along with a second guest suite offering its own private bath. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage,plus paved parking. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value.

9518 Quail Hollow Unit #702, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$1,679,000

Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

4 Beds ⋅ 4 Baths

Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

24390 Oakwood Park Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$1,195,000

Approximately 4400 square feet +/- , 3 Level, newly updated, 4 bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/bedroom. Second floor includes two spacious bedrooms, two baths (both en suite); plus, large bonus/storage room which could easily be converted to a 5th bedroom or in-law suite. Perfect for entertaining- the open floor plan with pass-through, double fireplace between the kitchen and great room connects to an enclosed private sun room leading to a fenced-in, paved patio surrounded by wonderful and private garden with new irrigation system allowing for luxurious indoor/outdoor living. Located on other side of the residence in back is an additional fenced-in private garden. The main level laundry and mud rooms connect to the oversized, two car garage. Very large butler's pantry and wet bar off the kitchen. Light-filled windows with plantation shutters and venetian blinds through-out. This bright and sunny home blends elegance, luxury, and everyday comfort. This home allows for exceptional privacy in a close-knit, water access community. Please inquire about the many other Cooke's Hope amenities.

4 Beds ⋅ 4 Baths

Approximately 4400 square feet +/- , 3 Level, newly updated, 4 bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/bedroom. Second floor includes two spacious bedrooms, two baths (both en suite); plus, large bonus/storage room which could easily be converted to a 5th bedroom or in-law suite. Perfect for entertaining- the open floor plan with pass-through, double fireplace between the kitchen and great room connects to an enclosed private sun room leading to a fenced-in, paved patio surrounded by wonderful and private garden with new irrigation system allowing for luxurious indoor/outdoor living. Located on other side of the residence in back is an additional fenced-in private garden. The main level laundry and mud rooms connect to the oversized, two car garage. Very large butler's pantry and wet bar off the kitchen. Light-filled windows with plantation shutters and venetian blinds through-out. This bright and sunny home blends elegance, luxury, and everyday comfort. This home allows for exceptional privacy in a close-knit, water access community. Please inquire about the many other Cooke's Hope amenities.

28711 Hope Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,950,000

Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

5 Beds ⋅ 5 Baths

Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

21485 Island Club Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$374,000

REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort, and scenic beauty. Enjoy stunning golf course views from the second floor, while the first-floor living spaces benefit from a private, landscaped setting. The thoughtfully designed open floor plan seamlessly connects the living and dining areas, highlighted by a cozy fireplace and sliding glass doors that open to the screened porch—an ideal space for relaxing or entertaining. The well-appointed kitchen features granite countertops and a dedicated breakfast area, while the bathrooms also showcase attractive granite finishes. A one-car garage and an additional designated parking space provide convenience and practicality. Residents of Martingham enjoy exclusive access to a private waterfront park, along with abundant opportunities for walking, biking, and enjoying the area's natural beauty. Located just minutes from the charming waterfront town of St. Michaels, this remarkable home offers the perfect combination of luxury, recreation, and Eastern Shore living.

2 Beds ⋅ 3 Baths

REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort, and scenic beauty. Enjoy stunning golf course views from the second floor, while the first-floor living spaces benefit from a private, landscaped setting. The thoughtfully designed open floor plan seamlessly connects the living and dining areas, highlighted by a cozy fireplace and sliding glass doors that open to the screened porch—an ideal space for relaxing or entertaining. The well-appointed kitchen features granite countertops and a dedicated breakfast area, while the bathrooms also showcase attractive granite finishes. A one-car garage and an additional designated parking space provide convenience and practicality. Residents of Martingham enjoy exclusive access to a private waterfront park, along with abundant opportunities for walking, biking, and enjoying the area's natural beauty. Located just minutes from the charming waterfront town of St. Michaels, this remarkable home offers the perfect combination of luxury, recreation, and Eastern Shore living.

9545 Quail Hollow Unit #205, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283