25 properties for sale in Deep Harbor

Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity youre seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original Crescent Moon shutters and leads into a bright open living room with hardwood floors and exposed wood beams ceilings. A cozy waterside den with a double-sided wood-burning fireplace is the perfect place to unwind. The kitchen offers tile floors and white cabinetry and leads to the dining roomcomplete with hardwood floors and a built-in barn wood bar overlooking the backyard and the cove beyond. The first-floor primary suite features hardwood floors, a double sided fireplace and a unique en-suite bath with a tub/shower combo. A second full bath and laundry room complete the main level, while two spacio

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside'River Room. The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crab

Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite

Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/. Acres in the quaint village of Wittman. Offering 1,662+/. Sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provide

A myriad of possibilities come with this unique property. Two homes for the price of one. The main house offers three bedrooms with two full baths plus an attached in-laws/au-pair with two bedrooms, family room with brick hearth fireplace, one full bath, kitchen and sunroom. The main house has gleaming wood floors, kitchen with breakfast area, formal dining and living room with fireplace. Spacious primary suite with walk-in closet. The third floor is great for a workroom, studio, crafting and kids playroom. Situated on 2.1 +/_ acres with a detached 4-car garage and storage shed in a quiet country setting and just minutes to a Talbot County boat ramp

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84 commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights 3 Bedrooms 2 Bathrooms split between two units 0.84 acre parcel with generous yard space Two accessory structures (retail/storage (in need of repair) + versatile garage/ workshop) Strong long-term potential rental market suppo

Embrace the Eastern Shore lifestyle in this private mini retreat, located just minutes outside of historic St. Michaels. Tucked away behind a natural buffer of mature trees and surrounded by beautiful waterfront estates, this property offers peace and privacy. For the outdoor or hobby enthusiast, the property features a versatile 4-stall barn with ample space to store cars, mowers, or your boat. The acreage currently showcases a lush, natural landscape, but offers the perfect canvas to easily revive the past pastures for equestrian or agricultural use. Inside, the home features classic hardwood floors throughout the first level, while the upstairs bedrooms and hallway are finished with carpeting. Ready for your personal touch, the home is being sold as-is and includes an existing flueperfect for hooking up a cozy wood or gas stove. Outside, a private vinyl pool (last serviced and fully operational when closed in October 2023) awaits summer refreshment. Rest easy knowing the core compon

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and f

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 historic home was built by members of the Neavitt family, for who the village was named. The present owner bought it in 1999 and renovated and updated it 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 Some furniture conveys

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 propertys 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 we

Welcome to this extensively renovated 3-bedroom, 2-full-bath home, offering approximately 1,539 sq. Ft. of living space on a spacious, level 0.69-acre lot. Recent updates include: New flooring throughout Fresh interior and exterior paint Updated kitchen with new countertops and appliances Updated bathrooms New deck New dishwasher New washing machine New AC unit Move-in ready with plenty of room inside and out, this home offers comfortable living in a peaceful Eastern Shore settingapproximately 10 minutes from St. Michaels and 5 minutes from Tilghman Island Beach 3 Bedrooms | 2 Full Bathrooms | 1,539 Sq. Ft. 0.69 Acres

Be sure to watch the video tour to experience the property and setting. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owners retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay life

Be sure to watch the video tour to experience the property and setting. Rare opportunity in the coveted Village of Fairbank on Tilghman Island. Set on nearly an acre in a peaceful Eastern Shore setting, this charming 1900 traditional home offers 1,720 square feet of living space with three bedrooms, two full baths, and the warmth and character of a wood-burning fireplace. One of the property's most distinctive features is its setting along Black Walnut Cove, just beyond the backyard, offering an idyllic backdrop for kayaking, canoeing, and enjoying life near the water. The expansive. 93-acre lot provides plenty of room for outdoor entertaining, gardening, or simply relaxing and taking in the natural surroundings. Fairbank on Tilghman is a special community where neighbors know one another and take care of eachother. Whether you're searching for a full-time residence or a weekend retreat, this property offers a wonderful opportunity to enjoy the character of Tilghman Island, the beauty

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, youll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage,

Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors. The list goes on.Tilghman on Chesapeake' has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired

Creekside' is a classic Eastern Shore Waterfront Retreat. Sited on 5 private, partially-wooded acres with extensive shoreline, the 3,800 sq ft main house provides panoramic southerly views across the confluence of Fire Cove and Cummings Creek. The views are exceptional! Sunsets, too! The 4-bedroom, 4-bath home has been lovingly updated and improved, including an outstanding new kitchen, which opens to a spacious'Great Room' w/cathedral ceilings and lots of glass to enjoy the views. So much more: Waterside swimming pool; Detached 3-car garage (w/HVAC); Spacious garage apartment/office above the garage w/full bath; Private 120 ft dock w/two boatlifts and a floating kayak dock. By car, St. Michaels is just 10-minutes away. By Boat, Tilghman Island and Knapps Narrows with its marinas and several waterside restaurants is a short, scenic cruise down-stream. The 5-acre property (approximately 2/3 wooded), is a nature-lovers paradise. You can catch fish and crabs from the dock and/or enjoy wat

This beautifully maintained 4-bedroom, 3-full-bath home offers approximately 3,348 square feet of living space in desirable Bozman, Maryland. Surrounded by mature trees, the property offers a peaceful, private setting while staying close to downtown St. Michaels. The home has been thoughtfully updated, with improvements including a roof installed in 2020, replacement windows in 2017, public sewer connection completed in 2026, a professionally installed water-filtration system in 2022, upgraded kitchen appliances in 2022, an upstairs air handler and heat pump installed in 2017, and a downstairs air handler replaced in 2025. Interior features include bamboo flooring in the kitchen, kitchenette, foyer, and hallway; tiled bathrooms and laundry room; and wall-to-wall carpeting in additional rooms. The primary bathroom features a Jacuzzi tub and glass-enclosed shower. Another bathroom offers a decorative vanity and distinctive river-rock flooring. Additional conveniences include pantry stora

Tucked away beneath a canopy of mature trees, 6114 Sunset Lane feels like a storybook retreat along the shores of the Chesapeake Bay. A tree-lined, pebbled circular driveway welcomes you home, setting the tone for the quiet beauty and sense of escape found throughout this special waterfront property. Surrounded by nature and framed by peaceful water views, the home offers a slower, more intentional way of living. Begin your mornings with sunlight dancing across the bay, spend your afternoons enjoying the gentle rhythm of the water, and end each day beneath the soft colors of an Eastern Shore sunset. Inside, abundant natural light pours through the home, creating bright, inviting spaces that feel effortlessly connected to the surrounding landscape. The thoughtfully renovated three-bedroom, two-full-bathroom residence blends timeless character with elevated modern comfort. At the heart of the home is the beautifully renovated kitchen, where rich soapstone countertops bring natural warmth

Price reduced significantly! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ens

This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic'W' homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bathideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacksthe last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air

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 deckperfect 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 awningan ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a

Grafton Manour EstateA Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86-acre peninsula wrapped by approximately 1.5 miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86 acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6 acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5 acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemet

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to 227 Dorchester Road a nicely updated 3-bedroom, 3-full-bath split foyer tucked on a private, fenced lot in the water-oriented community of Kent Island Estates. The main level features new LVP flooring, a bright kitchen with painted cabinetry, 3 bedrooms and 2 full baths, including a fully renovated primary bath with a custom tiled shower. The hall bath has also been refreshed with updated flooring and paint. The finished lower level offers fantastic flexible living space and was substantially renovated in 2023 with new drywall, electrical, flooring and paint, plus a cozy pellet stove and an existing third full bath. Outside, enjoy the fenced backyard, a large deck with access to the yard and eat-in dining area, a concrete patio and plenty of room for entertaining, gardening or play. There's even a chicken coop that conveys and the chickens can convey too! The STEP sewer system was installed in 2018, taking one more major item off the list. And when you're ready to get out an

Sellers have found home of choice! Now $469,900 + seller offering $10,000 toward buyer closing costs or rate buy down with acceptable offer! Built in 2021 and Move-in ready with garage, fenced yard, 3 bedrooms and 2.5 baths offers nearly 1,700 sq. Ft. of comfortable living space with a bright, open floor plan and thoughtful upgrades throughout. The main level features durable LVP flooring and an open kitchen with granite countertops, tile backsplash, large island, stainless steel appliances and plenty of space for gathering and entertaining. Upstairs, the spacious primary suite offers a walk-in closet and a generously sized private bath with double vanity, soaking tub and separate stand-up shower. Two additional bedrooms, another full bath and conveniently located upstairs laundry complete the second level. Additional features include a whole-house water filtration system with softener and chemical feeder, an encapsulated crawl space, attached garage and a fenced backyard improved with

Brand new home on kent island for under $500,000! This modern farm house is well appointed with LVP throughout the 1st floor and bathrooms, quartz countertops, full stainless steel kitchen appliance suite, white shaker cabinets, 2nd floor laundry, and double vanity in master bathroom, peaceful front porch, and more. Energy efficient new home for low maintenance and low energy bills. Short walk to the Romancoke Fishing Pier. South Island Trail is at your fingertips with this home!

Privacy & serenity you've been searching for on coveted Kent Island in this beautifully maintained ONE-LEVEL rancher, offering over 1,700 square feet of comfortable living on a secluded 0.65-acre homesite. Featuring 3 spacious bedrooms, 2 baths, an updated kitchen (2025), renovated full bath (2023), Roof (2015), NEW 100' well (2022), this move-in-ready home combines modern updates with everyday convenience. Step outside to your own private retreat with a fenced backyard, sparkling in-ground pool, shady gazebo, and ample room to entertain or simply unwind. A wide concrete driveway provides generous parking, while the rear wheelchair ramp adds accessibility and flexibility. Perfectly positioned just blocks from the Cross Island Trail and Romancoke Pier, with multiple public boat ramps nearby, you'll enjoy the very best of the Kent Island lifestyle. Local shopping, restaurants, waterfront recreation, and an easy commute to both work and play are all just minutes away. Sunporch off kitchen