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$354,900
3 Beds 2 Baths
🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

29316 Will St, Easton

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

$799,999
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: 4108226665

$6,995,000
7 Beds 6 Baths
Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence provides thoughtful design and enduring craftsmanship. The home was built for hosting and gathering. Seven ensuite bedrooms welcome family and friends, while soaring ceilings, three fireplaces, and a cozy morning room with a wood stove set the tone for gracious living. The turret, perched to catch the last rays of daylight, reminds one that every detail was designed around the water. The accessory structures and outdoor areas for entertaining are well-positioned to capture broad views and an immense water presence. From the waterside deck of the residence to the pool house with bathroom, loft, kitchenette, and outdoor grill, to the riverfront fire pit, the focal point is Broad Creek. The broad water portion of the shoreline is protected with 1,900 feet of stone revetment, and the remaining 2,500 feet of shoreline along Bridge Creek provides a natural setting. The farm has 13 acres under cultivation, with 3.5 acres in pasture. In addition, a 40 x 60 pole barn, featuring a second-floor caretaker apartment, provides ample space for the hobby enthusiast, complete with a workshop and off-season storage.

24390 Deep Neck Farm Ln, Royal Oak

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

$2,995,000
3 Beds 5 Baths
"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

6906 Travelers Rest Cir, Easton

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

$415,000
4 Beds 3 Baths
Welcome Home to a beautifully maintained home tucked away on a quiet cul-de-sac in an established neighborhood conveniently located within minutes of RT50 for easy commuting to Easton, Cambridge or the beach. This spacious 4 Bedroom, 3 Full Bath home offers the flexibility todays buyer's are looking for with a potential 5th main level bedroom thanks to a dining room with closet access and adjacent full bath. Designed for comfortable everyday living and effortless entertaining, the main level features 9 foot ceilings, crown molding and generous living spaces including an open kitchen with island, plenty of cabinets, dining and living area that flows seamlessly for gatherings both large and small. Step outside to a beautiful 17 x 15 screened in porch with ceiling fan to create a perfect spot for morning coffee or quiet evenings overlooking beautifully landscaped, fenced back yard. Upper level you will find a spacious primary suite with 2 separate closets, the primary suite includes a double sink, soaking tub and separate shower. Upper level laundry area is convenient for the 3 additional upper level bedrooms. The added feature of this home is the upper level 23 x 15 Bonus room with vaulted ceilings. Some facts about this home - Upper level A/C is 1 year old, Main level A/C is 2 years old.

3868 Marvel Dr, Trappe

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$993,000
3 Beds 2 Baths
Nestled in the serene enclave of Bozman, this exquisite 1940s bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen features rich wood cabinetry and ample counter space, while the family room, conveniently located off the kitchen, invites relaxation with its warm ambiance. The primary bedroom, a true sanctuary, offers breathtaking waterfront views, allowing you to wake up to the gentle sounds of nature. The interior is adorned with beautiful wood floors that exude warmth and sophistication, complemented by ceiling fans that enhance the airy feel throughout. The bathrooms are thoughtfully designed, featuring a luxurious walk-in shower and a stall shower, ensuring a spa-like experience at home. An attic provides additional storage, while the main floor laundry adds convenience to your daily routine. Outside, the property is a true oasis, set on a generous 0.58+/-acre lot that is cleared and beautifully landscaped. The sloping rear yard leads to 98+/- feet of pristine waterfront along Harris Creek, where you can indulge in the tranquility of water views framed by lush trees and woods. This unique setting not only offers a picturesque backdrop but also provides navigable water access, perfect for kayaking or leisurely afternoons by the water. The exterior features include a charming outbuilding and a shed shop, ideal for hobbies or additional storage. An attached garage with front entry and an asphalt driveway ensures ample parking for you and your guests. Located in a peaceful riverfront community, this property is not just a home; it's a lifestyle. Enjoy the serenity of nature while being just a short drive from local amenities and attractions. Experience the perfect blend of luxury, comfort, and natural beauty in this exceptional Bozman residence, where every detail has been meticulously crafted for an exclusive living experience.

8090 Bozman Neavitt Rd, Bozman

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

$4,495,000
5 Beds 4 Baths
Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

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

$2,495,000
4 Beds 4 Baths
Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Lane Ln, Trappe

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$269,500
3 Beds 2 Baths
Important Georgian residence built in 1763 by Quaker Emanuel Jenkinson. House contains much original raised paneling, built-in cupboard, paneled doors, wide-board flooring etc. The house sits on a 1660s land-grant called "Edmondson's Freshes". Today the neighborhood is known as "Stoney Ridge" Seller has the brass front door lock and other useful 18th C, hardware. No restriction against moving the house to a waterfront building site . . . Listing agent is owner. The house was largely re-wired in the 1980s. In 2009 the windows were rebuilt using mahogany, with salvaged wavy glass, The roof is of unknown age, but is over eighteen years. Seller purchased the property in 2008 for $140,000 and can document over $150,000 on restoration: repointing the brick, restoring the windows, and cornices, installing French drains,, taking down trees, The house was last occupied in 2007. It requires extensive further renovations and the task is not for the faint of heart. The bathroom water pipes froze and burst in 2007 and have not been replaced, but that is not a difficult job. for a plumber. The property is not subject to the covenants and restrictions of Stoney Ridge A former owner removed the wide yellow poplar floorboards from one of the third story bedrooms to create a cathedral ceiling in the room below. Replacing the missing flooring would be an easy job. Despite its condition, the house is worthy of restoration and is just waiting for an old house lover to complete the restoration. Brick portion exterior measures 19' x 33 1/2'.

7346 Shirley Dr, Easton

Listing courtesy of Shoreline Realty. Contact: 410-822-7556

$2,275,000
3 Beds 3 Baths
Welcome to Soleil on the Bay! Nestled on nearly 7 acres along the calm, deep waters of Maxmore Creek—just off the Tred Avon River—this exceptional west-facing waterfront property offers the most gorgeous sunsets and wide-open water views providing the perfect blend of privacy, natural beauty, and endless potential. Ideally located between Easton and St. Michaels, it provides easy access to the best of Maryland’s Eastern Shore. Enter your future family estate down a beautiful, private, tree-lined, fully paved driveway. Extensive site planning and improvements have already been completed, and the County and MDE have approved a septic expansion to support up to 8 bedrooms. The estate is beautifully appointed with mature trees, a 20’x40’ waterside pool, and a brand-new, 185- foot, deep-water dock featuring 6’ mean low water, floating docks, fully connected with electrical and water, a jet ski lift, kayak launch, and a 20,000+ pound boat lift with 30 amp, 220 electrical outlet to charge your boat. Two charming guest cottages totaling approximately 2,600 sq. ft. have been remodeled and enhance the property; providing unique opportunities each with its own fully equipped kitchen and multiple bedrooms and bathrooms. Includes oversized 3 car attached garages. Imagine your friends and family enjoying their own cottage for the utmost in privacy on this family compound. Additional highlights include 550’ of rip-rapped shoreline, extensive stone hardscaping, brick and paver walkways and patios, and a paved blacktop driveway, making this an extraordinary offering with unlimited potential in a prime waterfront setting. The grounds are mostly flat with available buildable lot coverage. The main residence needs to be remodeled or rebuilt and presents a unique opportunity to create your dream home. Architectural plans are already in place for a stunning new main house or design your own dream home. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

6976 Travelers Rest Cir, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$599,000
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

$695,000
3 Beds 3 Baths
Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water.

32930 Oyster Bank Ter, Easton

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

$749,900
3 Beds 2 Baths
Beautifully crafted “Oxford Cottage,” just a few blocks from waterfront park access, downtown Oxford, the Oxford Bellevue Ferry, and the Strand beach. Built in 2023, this builder’s personal home is being offered for the first time. Upstairs features two spacious bedrooms, a full bath, and a convenient laundry area. The main level offers flexible living space with the option for an additional bedroom, home office, or expanded living area, along with a full bath. Enjoy the inviting eat-in kitchen that opens to a large screened porch—perfect for relaxing or entertaining. The property also includes a detached garage with plenty of room for both your vehicle and recreational gear. Outside, cedar-raised flower beds beautifully frame the home, while the welcoming front porch is ideal for unwinding and enjoying the peaceful surroundings.

101 Tilghman St, Oxford

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

$5,995,000
6 Beds 6 Baths
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

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

$492,440
4 Beds 4 Baths
Brand‑new Torrington with a main‑level primary bedroom—now under construction and available for a fall move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and presents a rare opportunity to personalize your interior selections while construction is underway. Choose your own cabinetry, countertops, and flooring and create a home that truly reflects your style. The open main level features volume ceilings in the great room, creating an airy and inviting living space. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Step outside to the rear sundeck, perfect for enjoying peaceful outdoor moments or entertaining guests. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation. Current community amenities include: Resort‑style swimming pool Bathhouse with fitness room Ping pong & cornhole Playground & sports courts Dedicated Bark Park An immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. ✨ Ask about builder incentives!

231 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$799,900
3 Beds 3 Baths
***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

807 Radcliff Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$598,000
3 Beds 2 Baths
Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

204 Lincoln, Saint Michaels

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

$795,000
4 Beds 3 Baths
Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

9359 Martingham, Saint Michaels

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

$699,999
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

$799,900
4 Beds 3 Baths
Brand new roof just completed! Extremely well maintained Skipton Estates colonial situated on a wooded 2 acre lot which offers loads of privacy and plenty of bird watching. Upon entering this spacious home you are greeted by a bright, open 2 story foyer with hardwood flooring that's open to the office/study and formal dining room. Continuing into the home features a generous family room that has cathedral ceilings and 2nd floor overlook, gas fireplace and is directly located off the kitchen and sunroom. The kitchen which is perfect for entertaining, offers cooktop with wall oven, tile flooring with an island and bar area with seating. Finishing off the 1st floor offers an oversized laundry room with cabinet storage, the primary bedroom with primary bath, tub, separate shower and double vanity and a walk in closet with sitting room. The 2nd floor offers 3 additional bedrooms as well as a spacious bonus room over the garage. The exterior offers private deck with sunroom and primary bedroom access, 3 car garage and utility shed. Situated in the Chapel School District and 10 minutes to Easton or Centreville and 20 minutes to the Bay Bridge.

29583 Skipton Estates Dr, Cordova

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

$550,000
4 Beds 3 Baths
Tucked away in a quiet country setting just minutes from downtown Easton and convenient access to Rt. 50, this well-maintained Cape Cod offers the perfect balance of privacy and accessibility. Set on a .63-acre lot backing to open space, the home features a bright and inviting main living area with wood flooring, a wood-burning fireplace, and soaring cathedral ceilings that create an open, airy feel. The layout flows easily into the dining area and kitchen, making it well-suited for both everyday living and entertaining. Offering 4 bedrooms and 2.5 bathrooms, the home also includes a versatile bonus room. Recent updates include a new rear deck, ideal for outdoor dining or relaxing while overlooking the peaceful backyard, as well as a new washer and dryer installed in 2024 and a vapor barrier added in the crawlspace for improved efficiency and maintenance. Additional features include a spacious 2-car garage and a functional layout that offers both comfort and flexibility. Backing to open space and surrounded by a quiet setting, this property delivers a more relaxed pace of living while still being just minutes from Easton’s shops, restaurants, and everyday conveniences.

10490 Longwoods Rd, Easton

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

$3,495,000
11 Beds 11 Baths
Nestled on a sprawling 42-acre estate adjacent to the historic Wye Heights Plantation, this stately 8-bedroom mansion offers an unparalleled blend of elegance, comfort, and tranquility. The grand interior is marked by soaring ceilings and meticulous detailing, with an elevator providing convenient access across multiple levels. The heart of the home is designed for both relaxation and entertaining, featuring a fully finished basement with a cozy pub and kitchenette. A guest apartment over the garage offers additional private quarters, ideal for hosting family or friends. Outside, a picturesque pond with a charming bridge adds to the serene beauty of the grounds, while the enclosed garden sunroom and an additional sunroom off the breakfast area both offer sweeping views of the gardens and pond. Expansive screened-in porches on both the main and upper levels invite you to savor the peaceful surroundings year-round. Whether you're seeking a private retreat or a magnificent estate for entertaining, this exceptional property provides an exquisite lifestyle amid nature and history.

11470 Wye Heights Rd, Easton

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

$895,000
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

$1,995,000
6 Beds 5 Baths
Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

7421 Quaker Neck Rd, Bozman

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

$6,250,000
5 Beds 6 Baths
Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$2,395,000
4 Beds 4 Baths
Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344