39 properties for sale in Deep Harbour Farm Estates

Price improvement*. Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marinaperfect for boating, entertaining, and leisure. Whether youre looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! New roof & fireplace 2024, new appliances 2019

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family me

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family me

Are you looking for serenity? Tucked away at the end of a picturesque crepe myrtlelined drive is a breath of fresh air with its peacefully remote surroundings that many people are looking for. 12 miles to St. Michaels, close to Easton and Oxford, This exceptional waterview retreat offers a rare combination of privacy, scenic beauty, and convenience. The property is overlooking Black Walnut Creek, with glimpses of the Chesapeake Bay beyond, this property delivers a true sense of escape. Whether you are seeking a full-time residence, a weekend getaway, or an income-producing short-term rental, the setting and lifestyle here are simply unmatched. Even better, there is no HOA, allowing you the freedom to fully enjoy and personalize your property. Located in FEMA Flood Zone X, with no history of water intrusion, this home provides both peace of mind and long-term value in one of the Eastern Shores most desirable destinations. Inside, thoughtful design meets everyday comfort. The home welcom

Located in the heart of historic Sherwood Village, this beautifully restored Eastern Shore home blends classic architecture with thoughtful modern updates. The charming faade, covered entry, and detached garage/workshop with electric set the tone, while inside youll find sun-filled rooms, warm wood floors, shiplap accents, exposed beams, and a brick hearth with gas stove insert. The dining room opens through French doors to a spacious screened porch, creating effortless indoor-outdoor living. The kitchen features cherry cabinetry, granite countertops, and generous storage. A first-floor full bath offers a subway-tiled walk-in shower, while upstairs two comfortable bedrooms share a bath with walk-in shower and clawfoot tub. Recent improvements include an encapsulated crawlspace, 2025 standing seam metal roof, new BAT septic system, new well, updated HVAC, and Rinnai tankless hot water heater. Mature landscaping provides privacy, and residents enjoy access to the nearby community dock wi

Price improvement*. Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! New roof & fireplace 2024, new appliances 2019

Price improvement Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! New roof & fireplace 2024, new appliances 2019

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 pantryperfect 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

If no contract by April 24, 2026, Seller will be removing home from market. Looking for a home with a private setting, water views, a pool, and no HOA all within easy reach of the charm and activities of St. Michaels and Easton? Interested in a quiet home retreat or a short term rental? Look no further! Enjoy privacy, water views, and the freedom of no HOA at this tucked-away property located at the end of a Crepe Myrtlelined drive. Surrounded by mature trees and overlooking Black Walnut Creek with glimpses of the Chesapeake Bay, this home offers a peaceful setting that feels like a private retreat while still being close to the vibrant waterfront towns of St. Michaels and Easton, known for their dining, shopping, boating, and year-round events. Located in FEMA Flood Zone X (no flood insurance required and no history of water intrusion), the property also offers excellent potential as a weekend getaway, second home, or short-term rental in one of the Eastern Shores most desirable desti

Offered for the first time in over 50 years, this 13+u002F. Acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+u002F. Feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 fullu002F1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a seco

Just a 10-minute drive from Historic St. Michaels, MD (approximately 6 miles), this attractive 1-level, 3-bedroom, two bath home is in'turn-key/move-in condition. Extensively updated 2025-26, the house shows like brand new! Inside: New luxury vinyl floors throughout; All-new kitchen cabinets, quartzite countertops, Frigidaire stainless appliances, New bathrooms. Great floor plan includes a Living Room w/brick wood-burning fireplace; spacious Family Room w/cathedral ceiling and lots of glass, including a large Palladian Window. Primary bedroom w/ensuite bath and 2 guest bedrooms. Outside: New roof shingles on the house and on the detached 2-car garage. New BAT septic system! Large, partly/mostly wooded lot. Nearly 5-acres. Community waterfront lot/picnic area with a substantial dock on Harris Creek. Just listed and PRICED TO SELL @ $499,000

Irish Creek Waterfront Estate Set along more than 1,000 +u002F. Feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +u002F. 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 roo

Enjoy water-privileged living just minutes from downtown St. Michaels. This beautifully maintained one-level home sits on a well manicured lot directly across from the communitys waterfront parcel, offering water views and easy water access. A welcoming front porch leads into a bright foyer and on to the living room, featuring vaulted ceilings, hardwood floors and a gas fireplace. The kitchen was tastefully renovated in 2020 and features quartz countertops, tile backsplash, an island with bar seating, under-cabinet lighting, glass-front display cabinetry with interior lighting and stainless steel appliances. The adjoining dining area includes a coffee bar with a beverage fridge and opens to the rear deck through sliding glass doors. The home offers three bedrooms and two updated bathrooms, including a lovely primary suite with a walk-in closet and an attached bath featuring a glass and tile shower with a stone floor. The primary suite also connects to the sunroom, an ideal place to rel

Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathr