Deep Point Homes for Sale

Welcome to Deep Point, an enchanting subdivision nestled in the heart of Woolford, Maryland, within picturesque Dorchester County. This charming community offers a unique blend of serene countryside living and modern conveniences, making it an ideal location for families, retirees, and anyone seeking a tranquil lifestyle.

Deep Point is characterized by its stunning waterfront properties that provide breathtaking views of the Choptank River. Imagine waking up to the gentle sounds of nature, with the sun rising over the water, casting a warm glow on your home. The subdivision boasts a variety of homes for sale, each designed to cater to diverse tastes and lifestyles. From cozy cottages to spacious family homes, there’s something for everyone here.

Residents of Deep Point enjoy a close-knit community atmosphere, with friendly neighbors and a strong sense of belonging. The area is perfect for outdoor enthusiasts, offering ample opportunities for fishing, kayaking, and hiking along scenic trails. The nearby towns of Cambridge and Easton provide additional amenities, including shopping, dining, and cultural attractions, ensuring that you have everything you need just a short drive away.

Whether you're looking to settle down or invest in a vacation home, Deep Point is a gem waiting to be discovered. Don't miss your chance to find your dream home in this idyllic subdivision. Explore our listings today and experience the charm of Deep Point for yourself!

Newest Deep Point Homes for Sale

$475,000

1 Beds ⋅ 1 Baths

Exceptional waterfront opportunity with gorgeous water views, deep water access, and extensive boating amenities in a welcoming, waterfront neighborhood known for its friendly and laid-back atmosphere. This fully ADA-compliant 1-bedroom home features a thoughtfully renovated full bath with roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. Relax on the enclosed porch overlooking the water or head outside to the impressive pier offering approximately 6’ MLW, a lookout platform, and four boat lifts including two 1,500lb jet ski lifts, an 8,000lb lift, and a 20,000lb lift installed in 2022—an incredible setup for boating, fishing, and enjoying life on the water. Additional improvements include a new 50-year architectural shingle roof with transferable warranty installed in 2023 and a new well in 2024, plus public sewer service. Wheelchair ramp and lift convey. Detached garage/workshop with concrete floors and newer electric panel offers excellent storage and workspace potential, plumbing in workshop is currently disconnected- but could be hooked up by the new owner. There is an additional storage shed near the pier perfect for kayaks, fishing gear, and outdoor equipment. Bring your personal touches and bring this home to life! Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

Listing courtesy of Sharon Real Estate P.C.. Contact:

$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

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