Refine Search
Map
Sort by
$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
$130,000
2 Beds ⋅ 2 Baths
Priced below appraised value! Step into a new chapter of carefree living in the vibrant Hyde Park/ Sun Community located in Easton, MD. This home with 2 generously sized bedrooms and 2 full baths offers spacious, open living/dining /kitchen, separate laundry room and lots of closets. There is a bright three-seasons room—complete with separate side access. The open-concept living, dining, and kitchen areas are perfect for entertaining, while a roomy detached shed adds valuable storage. Hyde Park offers amenities all included in the monthly ground rent: outdoor pool, clubhouse, shuffleboard courts, trash service, water/sewer, property taxes, snow removal on paved streets, and maintenance of common areas—all managed by an on-site office team. Located just minutes from historic downtown Easton via Route 50, you’ll have easy access to medical facilities, the YMCA, restaurants, shopping, and more—blending tranquility with convenience. This is an estate sale and is being sold "as is". Don’t miss the opportunity to enjoy living in this active lifestyle community making new friends!

68 Park Lane, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$699,999
4 Beds ⋅ 3 Baths
THIS IS IT! 7586 Easton Club is an entertainer’s dream home—so much fun downstairs with open concept living, eat in kitchen with ample bar seating, double door pantry, a stainless wine fridge, natural gas fireplace, a new salt water hot tub, very private backyard and brick patio, garden seating area, huge driveway for lots of guest parking, and more! Upstairs, you can escape the party by enjoying four sizable bedrooms, including a primary en suite with another vaulted ceiling, a custom walk in closet, and bathroom with dual sinks, a walk in shower, deep soaking tub, heated floors, and heated towel rack. This well-maintained, turn-key Master's Village home in Easton Club is also walkable to the community pool and tennis/pickleball courts and minutes to Historic Easton's fabulous shops, restaurants and galleries. It's not just a home; it's a lifestyle! 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 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 (there is cherry hardwood underneath the downstairs LVP if preferred). The upstairs guest bathroom tile flooring was newly installed by the current owners. 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! 1st Floor, bathrooms and primary staged by Wall to Wall Staging, bedrooms three and four are virtually staged. A half dozen of the home's rooms were painted by the sellers within the last few months.

7586 Easton Club Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$399,900
3 Beds ⋅ 4 Baths
Welcome to this spacious, light-filled 3-level townhome in the heart of Easton! Featuring an open and inviting layout, the main level offers a bright living and dining area, along with an eat-in kitchen with granite countertops, ample cabinetry, and a walk-in pantry, plus a cozy family room with fireplace—perfect for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms, including an oversized primary suite with a walk-in closet and private ensuite bath. The conveniently located upper-level laundry adds ease to your daily routine. The lower level offers versatile space ideal for relaxing or hosting overnight guests, complete with a full bathroom and direct access to the fenced backyard—ready for your personal touch. Backing to trees, the setting provides added privacy and a peaceful backdrop. The 2-car garage offers convenience and additional storage space. Enjoy community amenities including a pool and outdoor basketball court. Ideally located within Easton town limits, just minutes to downtown shops and restaurants, and a short drive to St. Michaels. Don’t miss this opportunity to own a beautiful, move-in ready home in a highly desirable location!

29273 Superior Cir, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$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
$699,000
4 Beds ⋅ 2 Baths
Beautiful 4-bedroom, 2-bathroom home on a 1+/- acre parcel with an additional 12.45+/- acre lot included—ideal for expansion, equipment storage, or future investment. The 48' x 60' pole barn features three overhead doors, providing ample space for tools, vehicles, and materials. Outside, enjoy an in-ground pool and a fully fenced backyard. The property is currently served by well and septic, but with the new hospital development nearby, there may be future access to public water and sewer (buyer to verify).

10118 Hiners Ln, Easton

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 porch 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 primary bath, encapsulated basement, redecked pier, plus more1!-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
$6,495,000
4 Beds ⋅ 5 Baths
Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

24679 Deep Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$4,395,000
4 Beds ⋅ 6 Baths
Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

27029 Miles River Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$3,249,000
4 Beds ⋅ 4 Baths
Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4346 Southside Ln, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,495,000
4 Beds ⋅ 4 Baths
Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

28910 Jennings Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$559,000
3 Beds ⋅ 3 Baths
Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‑level residence in the sought‑after Easton Club community. Built in 1995, this home blends timeless style with an open, light‑filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite bath, creating a private retreat. A separate guest wing includes a second bedroom and full bath—ideal for visitors. The living room, home office, and primary suite all open onto a full‑width deck overlooking the property and community grounds, providing a perfect setting for entertaining or quiet outdoor relaxation. Upstairs, a skylit TV room expands your living space, accompanied by a third bedroom, full bath, and climate‑controlled storage. An attached side‑load two‑car garage adds everyday convenience. The Easton Club is a picturesque neighborhood originally designed around a golf course and now reimagined as open green space with cart paths, abundant wildlife, and scenic views along the Tred Avon River. Residents enjoy outstanding amenities including a swimming pool, tennis and pickleball courts, sidewalks, and public water and sewer. This home offers a rare opportunity to enjoy resort‑style living in one of Easton’s most desirable communities, all just minutes from town conveniences.

28642 Clubhouse Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$480,000
3 Beds ⋅ 3 Baths
Chesapeake by Del Webb. Popular 2-story Wittman model. Spacious 3 bedroom, 3 bath home. Great room with gas fireplace, office, large kitchen with center island, granite countertops and breakfast nook. Primary bedroom suite with walk-in closet, bath with separate vanities, separate shower and soaking tub. Guest bedroom, hall bath with walk-in tub and laundry room. Sunroom, enclosed porch overlooking your own private fenced in-ground pool. 2nd floor features large loft, guest bedroom and bath perfect for visitors or separate living area. newer roof (approx. 7 years old). Economical gas heat. Recent interior painting of some rooms. Attached 2-car garage, patio and irrigation system. Sited on a corner lot close to the community amenities which include a Clubhouse, tennis/pickleball courts, exercise trails, community pool, bocce ball, picnic areas, putting green. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. NOTE: Coastal Pools is in the process of completing extensive renovation of the pool

29638 Janets Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$7,900,000
8 Beds ⋅ 6 Baths
"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$2,149,000
3 Beds ⋅ 3 Baths
NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

7149 Drum Point, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$1,195,000
4 Beds ⋅ 5 Baths
Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.

114 W Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$7,950,000
7 Beds ⋅ 9 Baths
Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft caretaker's house. The main parcel is 10.48 acres with an additional 7.1-acre tree lined drive with a perpetual easement. This is a one-of-a-kind property and a true Talbot County piece of History. Furniture is negotiable.

26546 Presquile Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$799,000
4 Beds ⋅ 4 Baths
📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

8050 Easton Village Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$499,000
4 Beds ⋅ 4 Baths
RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE

1215 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$499,000
4 Beds ⋅ 4 Baths
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application and payment of applicable fees. The property features two mirror-image units, each offering: Kitchen with a cozy breakfast area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath This duplex presents an excellent investment opportunity with a strong rental history. Both units are currently tenant-occupied and rent well. Additional opportunity: The neighboring duplex at 1215 is also available for purchase (MLS #MDTA2012950).UST REDUCED - DONT WAIT TO LOOK AT THIS DESIREABLE RIO VISTA LIVING -MOVE

1211 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$489,990
3 Beds ⋅ 2 Baths
Ideally located in a prime cul-de-sac, this main level living home showcases a sophisticated interior with artisan trim and impressive 10-foot ceilings throughout. The welcoming covered entry leads you to the heart of the home: a spacious family room open to a chef-inspired kitchen and a comfortable dining area. The kitchen is a highlight, featuring a substantial island, abundant white cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package with range hood, and a large walk-in pantry. Extend your living space to the rear screened porch, accessible from the family room and dining room. A dedicated study offers a quiet sanctuary for work or hobbies. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole and Bark park, playground and racquet sports courts. An immersive lakeside experience also in the works! Ask about special fixed rate financing and closing costs!

1549 Lake Tahoe Dr, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$425,000
4 Beds ⋅ 4 Baths
PRICE IMPROVEMENT*** Discover the charm of Lakelands at Easton, where community spirit meets modern living in this stunning coastal-style townhouse. Built in 2010, this beautifully maintained home boasts 4 spacious bedrooms and 3.5 bathrooms, offering ample space for relaxation and entertainment. The inviting exterior features well-kept sidewalks that encourage evening strolls and friendly neighborly chats. Step outside to enjoy the community amenities, including basketball courts and a refreshing outdoor pool, perfect for summer gatherings and active lifestyles. The vibrant neighborhood is designed for connection, with parks nearby that provide green spaces for picnics, playdates, and outdoor activities. The community's commitment to safety and convenience is evident, with public services readily accessible, making daily life a breeze. Inside, the home features a cozy gas fireplace, ideal for creating warm memories during chilly evenings. The improved basement offers additional living space, while the attached garage and driveway provide ample parking for guests. With a lot size of 0.09 acres, this property strikes the perfect balance between manageable upkeep and outdoor enjoyment. Embrace a lifestyle where community, comfort, and convenience come together seamlessly in Lakelands at Easton. Don't miss your chance to make this delightful townhouse your new home! **New AC 2024, Five New windows with warranty, New Roof Ridge top peak and vents through Marasun 2025, Gas Fireplace-all new parts 2026, 2019 Replaced wood Decking with Trex decking, Only One of 4 units that has 4 bedrooms.**

29197 Superior Cir, Easton

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

$564,000
5 Beds ⋅ 4 Baths
TILGHMAN ISLAND. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantry—perfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for family or guests, while the remaining bedrooms offer ample space and versatility for a home office, gym, or guest accommodations. Situated in the tranquil Tilghman on Chesapeake community, residents enjoy access to exceptional amenities, including a community pool, clubhouse, and deep-water boat slips available through the HOA. Ideally located near the Chesapeake Bay and surrounding tributaries, this home offers unparalleled access to boating, deep-water fishing, crabbing, and scenic coastal adventures. Miles of open bike trails and the peaceful charm of Tilghman Island complete the experience, making this property the perfect blend of luxury, comfort, and true Bay living.

5559 Trafalgar Cir, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$11,000,000
4 Beds ⋅ 5 Baths
Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700
$475,000
3 Beds ⋅ 3 Baths
Chesapeake By Del Webb. Popular 2 story Wittman model. Great room with gas fireplace, dining room, large eat-in kitchen with breakfast nook and center island, sunroom, office, 1st floor primary suite with walk-in closet and bath with walk-in shower and soaking tub, guest bedroom, hall bath and laundry. 2nd floor is perfect for guests with a loft, bedroom and bath. Features a 2 car rear loading garage, patio and lawn irrigation. Improvements include roof (2020), water heater (2019) and HVAC (November 2016). This is an active 55+ adult community with Clubhouse, outdoor pool, tennis/pickleball courts, putting green, bocce ball, picnic areas, gazebos and exercise paths. Close to downtown Easton with nice restaurants, medical facilities, YMCA, churches, parks and more. This one owner home has been immaculately maintained.

7344 Casey Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$7,500,000
6 Beds ⋅ 8 Baths
Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

7508 Cooper Point Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$449,000
3 Beds ⋅ 2 Baths
No neighbors, private and set back off the road. Beautifully Updated Split-Level Retreat on Nearly an Acre Along Route 50! Set back on a private, wooded lot just under an acre, this beautifully remodeled 3-bedroom, 2.5-bath split-level home offers the perfect blend of comfort, style, and outdoor enjoyment. A long circular driveway welcomes you home, setting the tone for the peaceful setting that surrounds this 2,676 sq. ft. property. Inside, the home has been thoughtfully updated since purchase, including new replacement windows, mini-splits, new paint, new LVP flooring, a fully remodeled bathroom, and a vapor barrier with insulated crawl space—providing both modern comfort and long-term peace of mind. The main level features bright, open living spaces with sliding doors from both the living and dining rooms leading to the screened-in porch. From here, you can relax while overlooking the serene pond and the inviting in-ground pool—an ideal setup for entertaining or unwinding after a long day. The finished lower level expands your living possibilities with a cozy den complete with a bar area, a utility/laundry room, and two bonus rooms that can easily be converted into a large fourth bedroom or additional sleeping quarters. Sliding doors from the den offer direct access to the pool area, creating a seamless indoor-outdoor flow. Additional highlights include a wood-burning stove, ample storage, and the flexibility to add 1–2 more bedrooms if desired. With professional photos coming soon, this move-in-ready home is sure to draw attention quickly. A rare combination of privacy, upgrades, and lifestyle amenities—this one truly won’t last. Pool will be open soon.

7364 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$575,000
4 Beds ⋅ 3 Baths
Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

316 Spring Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272