Refine Search
Map
Sort by
$1,035,000
5 Beds ⋅ 4 Baths
Welcome to Pin Oak House, an Easton Federal style white-washed brick property proud to feature the Grand Champion Pin Oak of Talbot County within the confines of its iron-fenced front yard. The spacious corner lot also offers fine gardens, providing colorful foliage nearly year-round. Roses, honeysuckle, tulips, a glorious crepe myrtle, gazebo, irises, stone hardscaping, and a koi pond with waterfall feature are among the many surprises of the enchanting, fairytale-like backyard. The front and backyards are on a multi-zone irrigation system. This property provides ample off street parking for three cars as well as a sizable storage facility that can be converted into a garage if desired. The backyard and main parking area is monitored 24/7 by a Nest Cam security system. The recently installed uplighting in the front and back of the property further adds to the elegance of the home. Enter inside the red solid wood front door and you are greeted by new custom closets and wood doors, new crown molding, a just installed custom sisal stair runner in the foyer; a stunning formal dining room with designer wallpaper and custom window treatments, a beautiful kitchen with granite, dual ovens, a gas stove, new plantation shutters, stainless appliances, and a wet bar/coffee bar; a sizable living room inclusive of custom built in bookcases and a working wood burning fireplace; a cozy family room with a brick floor and warm grasscloth wallpaper; and a darling period-inspired powder room. On the second and third floors are five bedrooms (one being used as an office), three full baths, new paint, designer toile wallpaper, a new custom herringbone runner, new plantation shutters/window treatments, and custom built ins. The entire house offers ample closet space on each floor. Additionally, the dry basement (which is accessible from either inside the home or from the exterior) offers many storage racks, a washer/dryer, a large laundry sink, and sump pump. The backyard is fully fenced with privacy trees along Earle Avenue, so the space cooperates with dog lovers and truly feels like a private, quiet escape in the heart of town. This property is diagonal across the street from the Historic District so is not subject to the restrictions of the town's historic requirements, however, the white-washed Federal style brick blends in seamlessly with the look of the district. The property is a short walk to Easton's renowned restaurants, shops, galleries, downtown events such as Waterfowl Festival, museums, as well as in the opposite direction to Idlewild Park, the YMCA and Rails to Trails. Full list of upgrades can be found in the agent remarks. Owner is a licensed realtor in Maryland.

301 Washington St S, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Weichert, REALTORS.

$1,025,000
3 Beds ⋅ 2 Baths
A lovely waterfront home located in Sailors Retreat. Three bedrooms and two and half baths. primary bedroom, sunroom, and family room have a beautiful view of Island Creek. Nice deck and patio for relaxing Two car garage with walk upstairs to the attic. The dock can accommodate two boats with a water depth of 3'-4' MLW. Buyer must verify the water depth

4752 Sailors Retreat Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$1,009,009
Well-maintained 8-unit apartment building offering immediate income and a history of consistent occupancy. Ideally located approximately one block from Route 50, providing convenient access for commuters while maintaining a neighborhood setting. The property consists of eight 1-bedroom, 1-bath units, including two larger units at approximately 711 sq ft and six units at approximately 650 sq ft . Each unit features a functional layout with open living areas, separate bedrooms, and efficient kitchens. Flooring is a mix of hardwood, carpet, and laminate, with new carpet installed (common areas) throughout both upper and lower levels in 2024. Each apartment is equipped with its own mini-split system for heating and air conditioning, as well as a dedicated hot water heater.

142 Calvert St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,000,000
5 Beds ⋅ 3 Baths
Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef’s kitchen anchors the heart of the home, outfitted with a commercial-grade gas stove, a commercial refrigerator, two dishwashers, granite countertops, and an oversized island perfect for entertaining or casual morning coffee. The main-level primary suite is a private retreat, offering dual walk-in closets, a spa-inspired bath with soaking tub and glass shower, and serene views of the surrounding landscape. A conveniently placed laundry room with a half bath adds thoughtful utility to the main floor, while the upstairs offers flexibility with four generous bedrooms, a shared full bath, and a secondary living space complete with its own kitchenette—ideal for extended guests or multigenerational living. From nearly every room, you're drawn to the shimmering water just beyond the windows. Whether enjoying sunsets from the deck, stargazing from the rooftop deck above the three-car garage, or savoring peaceful mornings with the birdsong of the bay, this home embraces its setting with elegance and ease. Attic storage above the garage ensures ample space for seasonal gear or future creative use. Tilghman Island itself is a captivating enclave, celebrated for its maritime heritage, vibrant wildlife, and relaxed coastal vibe. Here, you’ll enjoy unmatched privacy, historic charm, and proximity to waterfront dining, boutique shops, and world-class boating—just far enough to escape, yet close enough to stay connected. 5520 Leeward Lane isn’t just a home—it’s a lifestyle. A sanctuary where land, sea, and sky converge in perfect harmony. Schedule your private showing and experience Eastern Shore living redefined.

5520 Leeward Ln, Tilghman

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$995,000
3 Beds ⋅ 3 Baths
Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining room. Efficient hot-water baseboard heat and 2-zone AC. In addition to an attached garage, there is a detached 3-bay garage/workshop. Asphalt driveway and parking area. Substantial pier w/two boat slips. By boat, Tilghman Island and the open waters of Chesapeake are a short, scenic cruise downstream from the dock. This location is known for great fishing and crabbing!

8684 Sewell Point Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$995,000
Set along the broad waters of the Choptank River, this remarkable 10.88± acre waterfront property in Talbot County offers an uncommon blend of scale, privacy, and panoramic open-water views. With approximately 600± feet of rip-rapped shoreline, the setting provides both protection and an impressive stretch of river frontage rarely available today. A current approval for a 6-bedroom residence allows for the creation of a substantial custom home tailored to your vision. Importantly, the property is not located in a flood zone, so flood insurance is not required—a meaningful advantage for long-term ownership and design flexibility. The wide river exposure captures expansive vistas, steady breezes, and ever-changing light across the water. Boating, sailing, and fishing are easily enjoyed from this stretch of the Choptank, with convenient access to the Chesapeake Bay and nearby waterfront towns such as Oxford and Cambridge. Beyond the river frontage, a scenic 2.5-acre pond enhances the landscape and creates opportunities for thoughtful estate planning. With nearly eleven acres, there is ample room for a guest house, pool, gardens, or additional outbuildings (subject to county approval), allowing the property to evolve into a true Eastern Shore compound. Private yet convenient to Easton and Route 50, this offering represents a rare opportunity to secure significant waterfront acreage in one of Maryland’s most sought-after coastal regions.

29569 Porpoise Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Realty Group.

$983,000
2 Beds ⋅ 2 Baths
Waterfront Retreat with Breathtaking Views Tucked away on a private drive, this charming home, built in 1999, offers the perfect blend of quality construction, thoughtful design, and an unbeatable waterfront location. With peaceful privacy, sweeping water views, and exceptional features throughout, this property is the ideal year-round retreat. The main level features a spacious open kitchen with a large island, elegant granite countertops, and abundant storage, flowing seamlessly into the living room with panoramic water views. Step out to the expansive deck for outdoor dining or relaxation, or enjoy the sunroom with tile flooring that brings in even more natural light. The main level also boasts heated tile flooring, adding warmth and comfort, and a wood-burning stove in the living room creates a cozy, inviting atmosphere. For year-round comfort, heat pumps provide efficient central heat and air. Upstairs, you'll find two spacious bedrooms, a full bath, and a versatile bonus room—ideal for an office, workout space, or walk-in closet. The primary bedroom is a true sanctuary, featuring a private waterview balcony where you can enjoy your morning coffee or relax in the evening while taking in the stunning water views. The upper level also showcases beautiful heart pine wood floors, adding a touch of warmth and elegance to the space. Outdoor living is just as impressive, with a waterside deck that includes an outdoor shower—perfect for rinsing off after a day on the water or simply enjoying the fresh air. The property offers direct access to the water via a private pier, floating dock, and boat ramp (approx. 3’ MLW), ideal for boating and water sports enthusiasts. For gardening lovers, the irrigated raised garden offers an easy-to-maintain space for growing your favorite plants, vegetables, or herbs. Additional highlights include a detached 2-car garage with an large workshop,, auxiliary generator wiring for added peace of mind, and a golf cart for easy property access. The home will soon be connecting to public sewer. This remarkable waterfront home combines comfort, and a truly stunning location.

6271 Neavitt Manor Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Compass.

$979,000
3 Beds ⋅ 3 Baths
Just Listed! Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, closets design by California Closets, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The third bedroom features a Murphy bed which gives this room multiple uses. The guest bathroom is beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

204 Brookletts Ave, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$970,000
4 Beds ⋅ 5 Baths
Set on 2.8± private acres along the highly sought-after Oxford Corridor, this spacious residence offers the perfect blend of comfort, space, and timeless Eastern Shore appeal. A welcoming rocking-chair front porch, huge fenced rear yard with expansive rear deck perfect for entertaining with a custom retractable awning, , paver patio, and in-ground saltwater pool create an ideal setting for relaxed luxury living and effortless entertaining. Inside, the spacious floor plan is thoughtfully designed for both comfortable everyday living and effortless entertaining. The inviting family room features custom built-ins and a fireplace, seamlessly flowing into the gourmet kitchen appointed with custom cabinetry, Caesarstone countertops, center island, oversized walk-in pantry, and Viking gas cooktop. A formal living provides additional gathering area. The first-floor owner’s suite offers a custom ceiling detail, private remodeled bath, walk-in closet, and direct access to the rear deck, creating a peaceful retreat. Upstairs, three generously sized en-suite bedrooms provide comfort and privacy for family and guests alike, including a spacious bonus room ideally suited as a private guest area or flex space over garage. Completing the property is an attached 3-car garage and beautifully landscaped grounds, ideally located just moments from the shops, dining, and amenities of Historic Easton and close to the waterfront charm of Oxford . Wood floors in all rooms except primary bedroom. Gas fireplace never used going "as is". BAT septic system serviced 5/26/26. Irrigation never used, going "as is" Electric dog fence does not work. Crawlspace and attic have been conditioned . New roof recently added.

27939 Waverly Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

$969,000
3 Beds ⋅ 3 Baths
This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

504 Seymour Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

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

$947,000
3 Beds ⋅ 3 Baths
Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood, the living room has a wood burning fireplace for cozy evenings, there is a separate laundry room and an eat in kitchen. The community offers access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. This unit is ideally located for the best views and privacy. Ideal location close to St. Michaels restaurants, shops and harbor. Take advantage of the Inn at Perry Cabin for dining and the luxurious spa! Minutes away is the Links at Perry Cabin premier golf destination designed by the legendary Pete Dye. This 18-hole championship course offers a challenging and picturesque experience.

360 Perry Cabin, Saint Michaels

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

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$910,000
5 Beds ⋅ 5 Baths
Welcome to 13532 Rustling Oaks Drive: where meticulous pride of ownership truly shows on this classic Cape Cod in the land of pleasant living on the Eastern Shore. Situated on over an acre of land with towering pines providing excellent shade and privacy, this 5 bedroom, 5,500+ square foot home has been recently upgraded and offers something for the whole family. 10 foot ceilings, hardwood floors, arched hallways, crown moldings, columns, chair rails, are just a few of the timeless interior finishes while a brand new saltwater gunite pool elevates the exterior space. Inside, an expansive first floor primary suite offers total main level living and complete privacy. With a tray ceiling, bay window and double walk-in closets, it is a retreat in its own; punctuated by an updated ensuite bath with double vanity, soaking tub, and oversized glass walk-in shower. The true heart of the main level is the upgraded kitchen and living room areas. These large complementing spaces are perfect for entertaining and everyday living. The kitchen has all new stainless steel appliances including a double wall oven and is finished with wood cabinets and granite countertops. The large island has a propane cooktop and overhanging bar seating. A breakfast area looks through a large bay window to the back yard. A new wood burning stove insert with wood mantel is the centerpiece of the living room just off the kitchen. A formal dining room and separate laundry/mud room complete the first floor. The main living area seamlessly flows into everyone's favorite space: the back yard, anchored by a brand new saltwater gunite pool and sweeping patio with lounging, grilling and fire pit areas. An additional screened-in porch with a tv is perfect for summertime crab feasts or morning coffee. Back inside, the basement is another world of its own with 9 foot ceilings and over 2,000 finished square feet. A 2nd full kitchen opens the possibilities to a private guest space or mother-in-law suite. There is a large game area, a private home office, a 5th bedroom with full bath and an unfinished utility space with room for more storage or workout equipment. Moving upstairs to the 2nd floor, one will find an additional primary bedroom with ensuite bath, two more generously sized guest bedrooms, a shared bath and a comfortable reading area atop the stairs. In addition to the two-car attached garage, a detached two-car garage with space above offers additional storage and workshop potential. A large garden shed and underground sprinkler system completes the backyard. A few of the recent updates include a saltwater gunite pool (2024), all new stainless steel kitchen appliances (2024), updated primary bath (2025), first floor dual-fuel 5-ton high efficiency heat pump (2025), fireplace wood stove insert (2023), leaf gutter guards (2025). Minutes away from a public boat ramp serving the picturesque Wye River and the enduring beauty of the Wye Island Nature Preserve. Major marinas are close by at Kent Narrows, St Michaels, or Oxford. This centrally located Eastern Shore getaway serves the lower beaches and the Chesapeake's tributaries well yet is still an easy commute to Annapolis, Baltimore or D.C. 10 minutes to downtown Easton and all the shopping you might need. The property across the street is open community space and will not be built upon. This tastefully updated and diligently maintained home offers a unique blend of amenities and functionality for the laid-back Eastern Shore lifestyle. Much more info and professional photos to come. Stay tuned!!

13532 Rustling Oaks Dr, Wye Mills

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

Selling Office: Benson & Mangold, LLC.

$900,000
4 Beds ⋅ 4 Baths
Charming 4 bedroom, 3.5-bath Cape Cod set on a parklike 2.4± acre lot overlooking the Talbot Country Club golf course. This home has seen recent updates including new roof, all new interior and exterior lighting, interior paint along with front of house, and paved parking. Featuring an updated kitchen with large marble center island with bar seating and stainless steel appliances. The living room offers floor to ceiling built-ins and a wood burning fireplace adjoining to a bright sunroom with vaulted ceiling. The first-floor primary suite offers a newly renovated bath with soaking tub, heated floors, and steam shower, while the second-floor primary includes a walk-in closet and private bath. A finished room above the garage provides ideal bonus space for an office, media room, or playroom. The property also includes a large yard with invisible fence, patio, shed for storage, and attached garage all within close proximity to downtown Easton.

6372 Country Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$900,000
SIGNIFICANT PRICE REDUCTION!! Amazing investment opportunity!! 23.06 Acres of commercial property situated with 500 +/- ft. of direct frontage along busy Rt. 50 with 30,000+ AADT. Located less than 2 miles from the heart of Cambridge, Maryland, this versatile property features 3 vehicular ingress / egress points and is zoned Limited Commercial (LC), which is characterized by low intensity commercial, neighborhood-oriented businesses. The once bustling Talbot Landing Motel, with more than 8,000 square feet, features 4 buildings with 19 total guest rooms plus a roomy owner's suite, and could be perfect for revitalization or redevelopment. There is existing well and septic in use on the property. This is a phenomenal opportunity to acquire significant acreage along Rt.50.

1730 Ocean Gtwy, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Realty.

$900,000
SIGNIFICANT PRICE REDUCTION!! Amazing investment opportunity!! 23.06 Acres of commercial property situated with 500 +/- ft. of direct frontage along busy Rt. 50 with 30,000+ AADT. Located less than 2 miles from the heart of Cambridge, Maryland, this versatile property features 3 vehicular ingress / egress points and is zoned Limited Commercial (LC), which is characterized by low intensity commercial, neighborhood-oriented businesses. The once bustling Talbot Landing Motel, with more than 8,000 square feet, features 4 buildings with 19 total guest rooms plus a roomy owner's suite, and could be perfect for revitalization or redevelopment. There is existing well and septic in use on the property. This is a phenomenal opportunity to acquire significant acreage along Rt.50.

1730 Ocean Gtwy, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

$877,000
5 Beds ⋅ 5 Baths
Welcome to 24896 Back Creek Drive Saint Michaels, a coastal home with one of the most beautiful back yard pond views available in the entire community! This property has so much a buyer may desire--modern, coastal design, open concept living, soaring ceilings, a large fenced back yard, broad views of a beautiful pond, water access approx 0.2 miles down the community pathway to San Domingo Creek for kayaking/paddleboarding, an abundance of space, a kitchen with a spectacular gas stove and two ovens, a gas fireplace, recently planted privacy trees, an encapsulated crawl space and so much more! You will be the envy of family and/or friends as you all sit around the enormous 90" flat screen television over the fireplace to take in sporting events or shows (television conveys with the property) or when you sit around the new hardscape fire pit boasting a new, large pellet/wood burning stove (which also conveys, along with the four new Adirondack chairs)! If you prefer to take in the spectacular water view from the nice deck or the large four season sunroom, either is an excellent option! The primary suite is on the main floor with all other bedrooms upstairs. There is an option to have an upstairs primary en suite if you prefer being on the same floor as other bedrooms. This property has sold in past listed as a five bedroom property so is listed as such again. Please be advised two of the five bedrooms do not have closets; wardrobes have been used in past listing of the property. Closets can easily be built in those two bedrooms--there is tremendous space to do so. Recent seller upgrades include a newly paved driveway, fire pit hardscape and pellet/wood fire pit (which conveys with the sale of the property), kitchen cabinet handles/pulls, entire exterior of the home was power washed, The crawl space is encapsulated. This property is very close to a grocery store, coffee place, bank and gas station. St Michaels' Historic District can be reached in mere minutes by car or on foot. The Y, community pool, Miles River Yacht Club, Chesapeake Bay Maritime Museum, Inn at Perry Cabin, golf, are all in proximity.

24896 Back Crk, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

$875,000
3 Beds ⋅ 3 Baths
This charming Victorian house is located in the Historic District of Oxford and has resided with the current owner for several decades. A front porch overlooks a beautifully landscaped garden and lawn while the rear lawn is surrounded by gardens for beauty and privacy. A stunning water fountain with trickling water works perfectly for a quiet time on the sun porch or the second floor deck with sliding shades for the late afternoon sun. A garden shed/shop and a single car garage with a studio/apartment on the second floor round out this beautifully decorated home. A full size modern kitchen with top of the line appliances, dining room, and formal living room are on the first floor. Three bedrooms and two modern baths are located on the second floor. The house enjoys the benefits of a geothermal well system, 9’ ceilings and two fireplaces. The garage and garden shed are accessed by an alley which also allows for additional off street parking, a rarity in the Historic District. All of this sits on high ground in the “X” flood zone. Enjoy easy access to local shops, restaurants, the waterfront park, Oxford Market, and the beloved Scottish Highland Creamery.

226 S Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$875,000
5 Beds ⋅ 3 Baths
Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

28715 Jacks Field Rd, Wye Mills

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Real Estate Professionals, Inc..

$850,000
4 Beds ⋅ 4 Baths
Easton Club. This beautiful 3300 sq. ft. home has been extensively renovated. Living room, formal dining room, upgraded kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

28391 Masters Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$830,000
4 Beds ⋅ 3 Baths
Easton Village. Desirable waterfront community located minutes from downtown Easton, St. Michaels and Oxford. Enjoy access to the Tred Avon River, community pier, clubhouse, outdoor pool, bocce court, kayak launch, 3+ miles of trails and 50 acres of open space. This custom built, one owner home features a living/dining room combo, family room with gas fireplace and built-ins, open gourmet kitchen with center island, primary suite, guest bedroom or office. 2nd floor offers a large loft, 2 additional guest bedrooms, bath and attic storage. 2 car rear loading garage with built-in cabinets and work bench, screened porch, patio, fenced backyard, irrigation system and extensive landscaping. LVP flooring throughout first floor living areas. This home is beautiful and is in move-in condition.

28254 Knapps, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

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

$825,000
3 Beds ⋅ 4 Baths
Built in the early 1900s and thoughtfully renovated over the past 20 years, this charming home beautifully combines historic character with modern amenities. Situated on a half-acre lot, the property features 3 bedrooms with the potential for a 4th bedroom, along with 3.5 bathrooms. Each bedroom includes its own private bath, and the bedrooms offer access to relaxing balconies. The updated kitchen is equipped with granite countertops, stainless steel appliances, and tile floors. Hardwood flooring that continues throughout the home. Outside, the property also includes a potting shed and a machine shed, providing additional storage and workspace. A standout feature is the impressive 1,500-square-foot attached garage. This two-story space includes three garage doors, three passenger doors, and a dedicated office area, offering exceptional versatility for hobbies, work, or storage. With its timeless old-world charm and carefully integrated updates, this home offers the perfect blend of classic style and modern comfort.

10494 Rich Neck Rd, Claiborne

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

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$825,000
4 Beds ⋅ 4 Baths
Easton Club. Boasting an open layout, the home features a great room with vaulted ceiling, completely remodeled kitchen (Kitchen Creations) with quartz countertops, stainless appliances (6 burner Wolf stove, double wall oven, GE profile refrigerator, Bosch dishwasher), breakfast area and morning room with Palladian windows, formal dining room, 1st floor primary suite with walk-in closets, primary bath with soaking tub, separate shower and vanities. 1st floor office/5th bedroom and full bath. 2nd floor offers 3 more spacious bedrooms and 2 additional baths and a large family/game room perfect for guests and children. Additional features include an attached 2-car garage, asphalt driveway, screened porch, deck, lawn irrigation system and private backyard. The community includes a pool and tennis/pickleball court. Close to downtown Easton and all its amenities, on the sought-after Oxford corridor.

7588 Easton Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

$800,000
Explore an exceptional investment opportunity with this 2.09+/- acre waterfront lot in Sailors Retreat. With approximately 189 feet of water frontage on Island Creek and a six-bedroom perc approval, this property is primed for development. Its high elevation and protected shoreline, complemented by mature oak trees, offer a serene environment just minutes away from local amenities in Oxford and Easton. This is a unique chance to create your dream home in a desirable location. #RealEstate #WaterfrontProperty #InvestmentOpportunity #HomeBuilding #ChesapeakeBay

0000 Sailors Retreat Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$795,000
4 Beds ⋅ 4 Baths
Under Contract, can be shown for backup offers. Open House cancelled for 4/26/26. This stunning center hall colonial, in the sought after community of Thread Haven, seamlessly blends timeless architecture with a complete, top-to-bottom renovation, delivering a truly exceptional living experience in one of Easton’s most established neighborhoods. Every detail has been thoughtfully curated with an uncompromising commitment to design, quality, and craftsmanship. From the moment you enter, you are welcomed by rich heart of pine flooring, refined finishes, and a cohesive, designer-selected color palette that carries throughout the home. The traditional floor plan has been reimagined for modern living while preserving its classic charm. At the heart of the home is the show-stopping gourmet kitchen, expertly designed with all-new double-tiered custom cabinetry, pull-out drawers, and striking display features. Outfitted with GE Café smart Wi-Fi appliances, including a gas range, this space is as functional as it is beautiful. A generous center island with seating anchors the room, while a built-in window seat nestled between custom display cabinetry adds a warm, inviting touch. The kitchen flows effortlessly into the spacious family room, where a gas fireplace framed by custom built-ins creates the perfect gathering space, with direct access to the screened porch and backyard beyond. The main level also offers a beautifully appointed dining room with statement lighting and exquisite millwork, a formal living room, and a richly detailed den featuring exposed beam ceilings and wood-paneled walls, an ideal retreat for work, reading, or quiet moments. A well-placed powder room completes the main level. Upstairs, the primary suite is a true sanctuary, featuring a spa-inspired ensuite bath with dual vanities, a walk-in shower, soaking tub, and elegant tile finishes. Three additional bedrooms are thoughtfully designed with refined detailing and share a beautifully updated hall bath complete with shiplap accents, tile flooring, and a built-in laundry area with cabinetry and folding station for added convenience. A standout feature is the expansive bonus room over the garage, complete with its own full bath and charming sloped ceilings perfect as a playroom, guest suite, or private retreat. Outside, the property is equally impressive. Set on a beautifully landscaped, mature lot, the home is framed by blooming cherry blossoms and lush greenery. The fully fenced backyard offers both privacy and space, enhanced by thoughtful hardscaping, stone wall seating, and an inviting patio ideal for entertaining. The screened porch provides a peaceful vantage point to enjoy the surroundings year-round. Completing the property is an exceptional three-car garage with extra depth, offering ample space for vehicles, storage, or a workshop. This is a rare opportunity to own a fully renovated, design-forward home in an established Easton neighborhood, where classic elegance meets modern luxury in every detail. Located within Easton town limits in the community of Thread Haven, the home enjoys close proximity to all that Easton has to offer including: the newly renovated YMCA, just a few blocks to Idlewild Park and downtown amenities, and offers easy access to the best shops, restaurants, and entertainment, including the Avalon Theatre and the Academy of the Arts. A full list of upgrades & renovations is available in the documents section.

53 Londonderry Dr, Easton

Listing courtesy of Northrop Realty. Contact:

Selling Office: Bayside Realty.

$785,000
3 Beds ⋅ 3 Baths
Located in the sought-after Martingham community and close proximity to downtown Saint Michaels, 24822 Swan Road offers the perfect balance of privacy, convenience, and Eastern Shore charm. Designed for comfortable single-level living, the home features 3 bedrooms and 3 full baths, including a spacious primary suite with a walk-in closet and an updated en-suite bath. The main living area is open-concept and features a family room with wood burning fireplace, parquet oak flooring leading into the recently renovated kitchen which serves as the heart of the home, blending style and functionality for everyday living and entertaining. There is also a sunroom which flanks the back of the house offering plenty of natural light and access to the covered back deck. A standout feature is the large detached two-car garage with a fully finished, conditioned space above, adding an additional 1,200 square feet of living space and bringing the total finished living area to 3,600 square feet. A workshop space is attached to the back of the garage, along with an additional 12' x 16' storage shed, providing even more room for a tractor, garden equipment, or general storage. There are peaceful water views from the back porch, creating an ideal backdrop for morning coffee or relaxed evenings outdoors. Residents enjoy access to a community waterfront park with a kayak launch, right down the street. With a brand-new roof being installed (2026), public water and sewer, mature landscaping, and a location minutes from waterfront dining, marinas, boutiques, and golf, this property delivers both lifestyle and peace of mind. Whether you are seeking a full-time residence or a weekend retreat near the water, 24822 Swan Road is a rare opportunity to enjoy the very best of Saint Michaels living. See documents for full list of updates.

24822 Swan Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Waterman Realty.

$775,000
4 Beds ⋅ 3 Baths
OPEN HOUSE Saturday June 27 2pm-4pm. SERIOUS 70k price reduction, best deal in Cooke's Hope Village! NEW 50 YR ROOF 2026 CertainTeed Landmark architectural shingles. Discover this exceptional listing in one of Talbot County’s most desirable neighborhoods of Cooke’s Hope. Ideally situated just off Oxford Road in Easton, the community offers numerous amenities and unmatched convenience, located only five minutes from both downtown Easton and Talbot Country Club. Set on quiet Wheeler Park Circle, one of the community’s most sought-after village locations, this home offers just under 3,000 square feet of finished living space. Broad double covered front porches create a welcoming front exterior, while at the rear of the home a large, private screened porch off the kitchen opens to a fully fenced backyard with patio—ideal for outdoor living and entertaining. The main level features a first-floor primary suite with a lovely, updated bath and huge walk-in closet. Hardwood floors enhance the rest of the first floor including the beautiful light-filled living room with gas fireplace, a formal dining room, convenient powder room and a spacious den with built ins that flows into a beautifully updated eat-in kitchen with mostly new appliances. A large separate first floor laundry/mud room provides not only washer and dryer but abundant cabinetry and a utility sink for added convenience. Upstairs, a wide hardwood hallway leads to three additional bedrooms, a full bath, and spacious fully insulated storage room complete with a mini split system, space easily finished if desired. An oversized attached two car garage, accessed by a private concrete drive from the rear alley, completes this well-designed home. Owner has meticulously maintained this property since purchase in 2018 including new kitchen appliances (2026), all hvac=two air-condition units & furnace ("TRANE" 2023), interior paint, etc. The Cooke’s Hope HOA maintains a reserve fund, manages community operations and common areas, oversees the community waterfront park and dock, and supports additional amenities including a gym, mail room, tennis/pickleball court, dog park, over three miles of walking paths, ponds, picnic areas, roads, trash service, and snow removal. The HOA has a set yearly fee for these services and provides front and side yard maintenance at a reasonable additional cost to the property owners. The community is served by Easton Utilities, providing electric, water, sewer, natural gas, and fiber optic high-speed internet. Extra refrigerator and two custom carpets for living and dining rooms included.

7106 Wheeler Park Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Monument Sotheby's International Realty.

$765,000
3 Beds ⋅ 3 Baths
Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully maintained single-family home features a covered front porch, ideal for relaxing, entertaining, or enjoying quiet mornings. Inside, the flexible floor plan includes a main-level living room or home office with pocket doors, a formal dining room, and an open-concept kitchen and great room — a layout highly sought after by today’s buyers. The kitchen offers ample cabinetry, generous counter space, and a large center island with seating, making it perfect for everyday living and entertaining. The great room opens to a covered rear porch overlooking community ponds, with western exposure and sunset views. A private patio and pollinator garden enhance the outdoor living space. The first-floor primary suite is a standout feature, offering a walk-in closet with custom built-ins and an updated en-suite bath. Additional main-level highlights include a powder room, laundry room, and continuous flooring throughout, creating a seamless flow. Upstairs, you’ll find two spacious bedrooms with large closets, a full bath, and a large bonus room ideal for guests, a media room, home gym, or second family room. A walk-in attic provides excellent storage, a rare and valuable feature. Back Creek Landing is a planned residential community offering walking trails, scenic ponds, picnic areas, and water access to San Domingo Creek, complete with a community dock and kayak storage — perfect for buyers seeking the Eastern Shore lifestyle with kayaking, nature, and outdoor recreation. Freshly painted and move-in ready, this St. Michaels home combines main-level living, outdoor spaces, water access, and proximity to town — a highly desirable combination that is rarely available. 📍 St. Michaels, MD 21663 💲 $795,000 🛏 3 Bedrooms | 🛁 2.5 Bathrooms | 📐 3,166 sq ft Don’t miss your opportunity to tour this exceptional Back Creek Landing home. Schedule your private showing today.

24912 Back Creek Dr, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$755,000
3 Beds ⋅ 3 Baths
Move In Ready!! Please try 3-D virtual tour. This gorgeous Hanover design by Koch Homes is the needle in the haystack you've been looking for. New Construction that is 100% complete in the highly sought after Cooke's Hope community. This home focuses on main-level living, while having two bedrooms and one bath upstairs for family and friends. An open floorplan flows beautifully from the foyer entrance, past the home office, and into the dining and great room. Our 19 x 10 morning room is filled with windows to soak up the eastern shore sunlight. Get a great night's rest in the 1st floor owners suite and then hit the tennis courts (only steps away) for a match with a friend. Fishing, boating, golfing, and all outdoor activities are more enjoyable when the day starts and ends in your new Koch Home at Cooke's Hope...

7015 Cheston Way, Easton

Listing courtesy of Koch Realty, Inc.. Contact:

Selling Office: Benson & Mangold, LLC.

$750,000
3 Beds ⋅ 2 Baths
Positioned along the picturesque 5th fairway of the prestigious Talbot Country Club, this comprehensively renovated Easton residence blends timeless Eastern Shore charm with elevated modern design. Privately set on beautifully landscaped grounds with sweeping golf course vistas, the property offers refined one-level living in one of Talbot County’s most desirable country club settings. Thoughtfully reimagined from top to bottom, the home showcases a sophisticated, light-filled interior highlighted by white oak hardwood flooring throughout, curated West Elm lighting, custom millwork, and seamless indoor-outdoor flow. A dramatic 15-foot sliding glass door anchors the rear living spaces, opening effortlessly to the expansive terrace and manicured grounds beyond. At the center of the home is a stunning designer kitchen featuring Borghini Gold quartz countertops, custom cabinetry, premium GE Profile appliances, a 36-inch Verona range, beverage refrigeration, floating wood shelving, and an oversized center island designed for both entertaining and everyday living. Kohler faucets and fixtures throughout the home further elevate the carefully curated finish package. The gracious living room is centered around a striking marble fireplace surround with custom built-ins, creating a warm yet sophisticated focal point for gathering and entertaining. The thoughtfully designed floor plan offers generously sized bedrooms, beautifully renovated baths, and a spacious primary suite retreat with a boutique hotel feel. Beyond the cosmetic renovation, the property also benefits from a brand-new septic system and freshly refreshed gravel driveway, providing both style and peace of mind in equal measure. Combining understated luxury, turnkey condition, and premier golf course positioning just minutes from downtown Easton’s celebrated restaurants, boutiques, galleries, and waterfront amenities, this exceptional offering captures the very best of Eastern Shore living.

6524 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

$740,000
3 Beds ⋅ 2 Baths
Enjoy water-privileged living just minutes from downtown St. Michaels. This beautifully maintained one-level home sits on a well manicured lot directly across from the community’s waterfront parcel, offering water views and easy water access. A welcoming front porch leads into a bright foyer and on to the living room, featuring vaulted ceilings, hardwood floors and a gas fireplace. The kitchen was tastefully renovated in 2020 and features quartz countertops, tile backsplash, an island with bar seating, under-cabinet lighting, glass-front display cabinetry with interior lighting and stainless steel appliances. The adjoining dining area includes a coffee bar with a beverage fridge and opens to the rear deck through sliding glass doors. The home offers three bedrooms and two updated bathrooms, including a lovely primary suite with a walk-in closet and an attached bath featuring a glass and tile shower with a stone floor. The primary suite also connects to the sunroom, an ideal place to relax and enjoy views of the backyard and visiting wildlife. The home further features two guest rooms and an additional bathroom. A separate laundry room and an oversized attached 2-car garage with workshop space complete this home. Step outside and experience the property’s exceptional outdoor living. A hot tub is conveniently situated between the deck and sunroom and a large paver patio adjoins the large rear deck. Out front, a hardscaped fire pit and patio provide the perfect place to unwind and take in water views of the creek. The property also includes two storage sheds, a run-in shed for equipment or vehicle storage, raised garden beds with blueberry and black raspberry bushes and apple and pear trees. Additional updates include a new roof in 2024 and fresh exterior paint in 2025. Located less than two miles from historic St. Michaels, residents can enjoy all the charm this iconic Eastern Shore town offers, boutique shopping, award-winning restaurants, waterfront dining, the Chesapeake Bay Maritime Museum, marinas, festivals and year-round events. Known for its walkability, vibrant small-town atmosphere and scenic harbor, St. Michaels is a coveted destination while remaining close to Annapolis, Baltimore, Northern Virginia and both BWI and Dulles international airports.

23869 Mount Misery Rd, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.