Deep Point Homes with Cottage Style

Deep Point Homes with Cottage Style

Welcome to Deep Point, a hidden gem nestled in the heart of Woolford, Maryland, where the charm of cottage-style homes meets the serene beauty of Dorchester County. This delightful subdivision offers a unique blend of cozy living and picturesque landscapes, making it an ideal retreat for those seeking tranquility and a sense of community.

Deep Point is characterized by its enchanting cottage-style homes, each designed with an inviting aesthetic that embraces warmth and comfort. These homes feature charming architectural details, including gabled roofs, inviting porches, and beautifully landscaped gardens. The cottages are perfect for families, retirees, or anyone looking to escape the hustle and bustle of city life while enjoying the picturesque surroundings.

As you stroll through the tree-lined streets of Deep Point, you’ll be captivated by the peaceful ambiance and friendly neighbors who make this community truly special. The proximity to the stunning Chesapeake Bay offers endless opportunities for outdoor adventures, from kayaking and fishing to leisurely walks along the shore.

In addition to its natural beauty, Deep Point is conveniently located near local amenities, including shops, restaurants, and recreational facilities, ensuring that residents have everything they need within reach.

Whether you’re looking for a weekend getaway or a permanent residence, Deep Point invites you to experience the charm of cottage-style living in a picturesque setting. Discover your dream home in this idyllic community, where every day feels like a retreat!

Newest Deep Point Homes with Cottage Style

$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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