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$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
$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
$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
$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
$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
$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
$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
$1,195,000
5 Beds ⋅ 6 Baths
Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

110 N Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,195,000
Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers weekend showings. If weekday is only possibility, please allow 24 hours. Thank you

110 N Morris St, Oxford

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
$519,000
3 Beds ⋅ 2 Baths
Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

21869 Albie Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$719,500
3 Beds ⋅ 2 Baths
Wake up to peaceful views of Peachblossom Creek and enjoy the best of Eastern Shore living from this well-maintained 3-bedroom home in the highly sought-after Oxford Road corridor. Included is access to a private waterfront lot, providing the perfect spot to launch a kayak, fish, watch wildlife, or simply take in the beauty of the water. Designed for easy one-level living, the home offers a bright and welcoming floor plan with an open kitchen featuring a marble island, spacious walk-in pantry, and adjoining living room with a gas fireplace. A heated semi-enclosed porch creates an inviting space to enjoy creek views and outdoor living throughout the seasons. The primary suite features a large walk-in closet with custom built-ins and a well-appointed bath with a no-threshold tile shower and double-sink vanity. Additional amenities include a dedicated laundry room, partially floored attic storage, updated metal roof sections installed in 2025, and a fenced rear yard with storage shed. Just minutes from downtown Easton, shopping, the YMCA, parks, and miles of bike trails, this property offers a rare opportunity to enjoy a relaxed waterfront lifestyle without the maintenance and expense of a traditional waterfront home. Excluded : One peony plants and 2 lilies.

28567 Holden Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$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
$475,000
3 Beds ⋅ 3 Baths
Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$925,000
5 Beds ⋅ 3 Baths
Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

28715 Jacks Field Rd, Wye Mills

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$449,000
3 Beds ⋅ 2 Baths
The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substantially lower electric cost to heat and cool the home. Only about 12 miles from the shops and restaurants of charming St Michaels but without St. Michael's town taxes. The village has its own park and playground as well as a public landing with a launch for canoes and kayaks. While currently on a septic system, public sewer is in the process of servicing the town, adding convenience and potentially increasing property value. Overall, this Eastern Shore retreat offers a blend of historical character, modern updates, and a desirable water view location, making it suitable for both full-time residence or part-time retreat. County sewer soon available. Neavitt yard sale moved to September while other village get-togethers/activities remain as scheduled.

6390 Bozman Neavitt Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$845,000
3 Beds ⋅ 2 Baths
Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

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

$515,000
2 Beds ⋅ 2 Baths
Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

6394 Bozman Neavitt Rd, Neavitt

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
$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
$3,100,000
4 Beds ⋅ 4 Baths
Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,195,000
4 Beds ⋅ 4 Baths
Approximately 4400 square feet +/- , 3 Level, newly updated, 4 bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/bedroom. Second floor includes two spacious bedrooms, two baths (both en suite); plus, large bonus/storage room which could easily be converted to a 5th bedroom or in-law suite. Perfect for entertaining- the open floor plan with pass-through, double fireplace between the kitchen and great room connects to an enclosed private sun room leading to a fenced-in, paved patio surrounded by wonderful and private garden with new irrigation system allowing for luxurious indoor/outdoor living. Located on other side of the residence in back is an additional fenced-in private garden. The main level laundry and mud rooms connect to the oversized, two car garage. Very large butler's pantry and wet bar off the kitchen. Light-filled windows with plantation shutters and venetian blinds through-out. This bright and sunny home blends elegance, luxury, and everyday comfort. This home allows for exceptional privacy in a close-knit, water access community. Please inquire about the many other Cooke's Hope amenities.

28711 Hope Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,950,000
5 Beds ⋅ 5 Baths
Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

21485 Island Club Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$3,999,900
4 Beds ⋅ 7 Baths
Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. 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.

27473 Westpoint Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$5,000,000
3 Beds ⋅ 4 Baths
Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$699,000
3 Beds ⋅ 3 Baths
Broker and Public Open 4/23 from 10am to Noon! OCCUPANCY PERMIT in hand, move right in! Nestled in the charming town of Easton Maryland, this exquisite new construction offers a perfect blend of modern luxury and traditional elegance. The sixth of Sandy Lane's ten total homes to be built, this design is the first two story that includes a first-floor primary suite with gorgeous en-suite bath and a huge walk-in closet. There are two additional bedrooms up and a 320sf family room, providing a second spacious gathering place for tv watching, reading, homework, pool table, games, the works! It is a thoughtfully designed custom layout providing plenty of space for privacy, relaxation and entertainment. Step inside to discover an inviting open floor plan that seamlessly connects the gourmet kitchen to the dining and living areas. The kitchen as designed is a cook's dream, with an island providing ample workspace and seating for four. The kitchen is equipped with custom cabinetry and elegant countertops as well as stainless appliances. The kitchen island serves as a focal point for gatherings, while recessed lighting and ceiling fans enhance the ambiance throughout the home. The interior is fitted with luxurious vinyl plank flooring and carpeting, creating a warm and comfortable atmosphere. The first-floor primary suite features a huge walk-in closet and a private, beautifully finished bathroom with a custom-tiled shower. Next to the interior entrance to the garage, you will find a convenient, dedicated laundry room and private powder room. Outside, the property is equally impressive. The extensive hardscape and beautifully landscaped front yard create a picturesque setting, with a rear patio and front porch perfect for outdoor entertaining or quiet evenings spent enjoying the neighborhood views. In addition to an encapsulated and climate-controlled crawl space, features include energy-efficient double-pane windows, Certified IECC Energy Efficient insulation (R-49 ceiling, R 21 walls), exterior lighting, and a well-designed gutter system, ensuring both functionality and aesthetic appeal. Whether you are retired, work from home or have a growing family, this flexible floorplan will suit your needs. Parking is a breeze with an attached garage with electric car charger, driveway space for two vehicles, and additional on-street parking available. Located on a cul-de-sac, this home offers a sense of privacy while still being in the heart of downtown, where the vibrant community life of Easton awaits. You can experience the luxury of modern living in a prime downtown Easton location, where every detail has been meticulously crafted to provide comfort and elegance. Don't miss the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle offered on Sandy Lane. Sandy Lane homes are subject to recorded Covenants and Restrictions (attached in docs) but there is no HOA or fees. Developer: Sandy Lane, LLC, MHBR 9512. Builder: Stansbury and Sons Home Improvement Inc., MHBR 8351. BUILDER CONTRACT REQUIRED.

18 Sandy Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$745,000
4 Beds ⋅ 4 Baths
Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

28933 Jasper Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$3,700,000
5 Beds ⋅ 7 Baths
GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play area. Large garage/barn to store all the water toys and pool equipment. It's currently being used as a Vacation Rental. Showings will be staggered between use.

21721 Heavenly Haven Rd, Sherwood

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

$6,800,000
5 Beds ⋅ 6 Baths
Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

7090 Cooper Point Rd, Bozman

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