Deep Point Homes for Sale

Deep Point Homes for Sale

Welcome to Deep Point, a hidden gem nestled in the serene landscapes of Woolford, Maryland. This charming subdivision in Dorchester County offers a unique blend of tranquility and community spirit, making it an ideal place for families, retirees, and anyone looking to embrace a peaceful lifestyle.

Deep Point is characterized by its picturesque surroundings, where the lush greenery meets the sparkling waters of the Chesapeake Bay. Residents enjoy a close-knit neighborhood feel, where friendly faces and a sense of belonging are part of everyday life. The area is perfect for outdoor enthusiasts, with ample opportunities for fishing, boating, and leisurely strolls along scenic trails.

When it comes to homes for sale in Deep Point, prospective buyers will find a variety of options to suit their needs and preferences. From charming single-family homes to spacious waterfront properties, each residence is designed to offer comfort and style. Many homes feature modern amenities, open floor plans, and beautiful outdoor spaces, perfect for entertaining or enjoying a quiet evening under the stars.

Living in Deep Point means embracing a lifestyle that balances nature and community. With easy access to local shops, restaurants, and recreational activities, residents can enjoy the best of both worlds. Whether you’re looking to settle down or invest in a vacation home, Deep Point is a wonderful choice. Explore the homes for sale in this delightful subdivision and discover the perfect place to call your own in the heart of Maryland. Your dream home awaits!

Newest Deep Point Homes for Sale

$849,500
3 Beds 2 Baths
Improved Pricing! Was $875,000 now $849,500. Major Interior Renovations completed in 2022 (see attachment for full list). This beautifully updated and meticulously maintained, 3-bedroom, 2-bath home offers over 2,300 square feet of bright living space designed to capture the beauty of waterfront living. Panoramic water views greet you from nearly every room, with the living room highlighting breathtaking vistas of Fishing Creek. Two spacious living areas, each with a cozy fireplace, make relaxing or entertaining effortless year-round. The open gourmet kitchen features custom finishes, modern updates, and a built-in wine cooler—perfect for gathering with family and friends. The primary suite includes a private bath, while the open floor plan provides both functionality and seamless flow. Major systems have already been taken care of for you—roof replaced in 2018, HVAC replaced in 2022, and new thermostats installed in 2024—so you can move in with confidence. A new sprinkler system, plus all French gutter drains installed in 2025 and an improved Dry-Zone encapsulated crawl space further enhance efficiency and long-term protection. For added reassurance, the home includes transferable flood insurance and annual Dry-Zone, HVAC and pest control inspection contracts. Home is connected to public sewer, helping to simplify ownership from day one. Ideally located just a short distance from historic Cambridge, the Hyatt Regency Chesapeake Bay Golf Resort, and within easy reach of Easton, Oxford, and St. Michaels, you’ll also enjoy close proximity to Blackwater Wildlife Refuge—perfect for exploring nature, spotting eagles’ nests, or enjoying canoeing, biking, and hiking trails.

1318 Bell Ln, Woolford

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

Start Your Search