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

$450,000

1 Beds ⋅ 1 Baths

Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

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

$799,999

3 Beds ⋅ 2 Baths

SEIZE THE SUNSET! Enjoy waterfront tranquility right at your back door—and don’t miss this significant price improvement! If you’ve been searching for an immaculate, move-in-ready waterfront home with exceptional first-floor living, this may be the one. Major interior renovations were completed in 2022, and this beautifully updated and meticulously maintained 3-bedroom, 2-bath home offers more than 2,300 square feet of bright, inviting living space designed to showcase the beauty of the Eastern Shore. Panoramic waterfront views greet you from nearly every room, with the living room overlooking the breathtaking vistas of Fishing Creek. Two spacious living areas, each featuring a cozy fireplace, provide plenty of room to relax, entertain, and enjoy the changing seasons.The open gourmet kitchen is the heart of the home, featuring custom finishes, modern updates, and a built-in wine cooler—perfect for preparing meals, gathering with friends, or simply enjoying a quiet evening while taking in the view. Major systems and improvements have already been taken care of, offering peace of mind for the next owner. The roof was replaced in 2018, the HVAC system in 2022, and new thermostats were installed in 2024. An updated sprinkler system, new French gutter drains installed in 2025, and an improved Dry-Zone encapsulated crawl space further enhance the home's efficiency and long-term protection. The crawl space also features a new dehumidifier installed on a raised platform, new insulation, and an indoor monitoring system, all completed in 2026. For additional peace of mind, the home includes transferable USAA flood insurance along with annual Dry-Zone, HVAC, and pest control inspection contracts. Connected to public sewer, this home offers the convenience of simplified ownership from day one.Ideally located just a short distance from historic Cambridge and the Hyatt Regency Chesapeake Bay Golf Resort, with easy access to Easton, Oxford, and St. Michaels. Nature lovers will appreciate the close proximity to Blackwater Wildlife Refuge, where you can explore scenic trails, enjoy kayaking and biking, observe abundant wildlife, and perhaps catch a glimpse of the area's magnificent bald eagles. This is more than a home—it’s an opportunity to embrace the peaceful waterfront lifestyle, spectacular sunsets, and timeless charm of Maryland’s Eastern Shore, with the comfort and confidence of a home where many of the major updates have already been completed.

1318 Bell Ln, Woolford

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

Start Your Search