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$740,000
3 Beds ⋅ 3 Baths
Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a wood-burning fireplace, and an enclosed sunroom overlooking the water. Step outside to the expansive Trex deck with a recessed hot tub, then follow the path directly to the river. With three bedrooms, three full bathrooms, a walkout lower level, two bonus space, and a two-car garage, this home delivers the space, finishes, and lifestyle you’ve been waiting for. Schedule your private tour today and experience this waterfront retreat for yourself. Furniture is available for purchase as well!

14540 Stirrup Lane Ln, Galena

Listing courtesy of Keller Williams Flagship. Contact:

$625,000
It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with. Build the house of your dreams and be able to work and play where you live. Short drive to tax free shopping in Middletown DE.

14200 Metasequoia Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$95,000
Welcome to Wilson Point Estates! A 14 Lot Custom Home Eastern Shore Community. Designed for those who value craftsmanship and intention, Wilson Point Estates is not a production neighborhood, it’s a place where each home is purposefully designed to complement the character of the Shore. Picture gracious porches, elevated coastal details, and interiors tailored to how you truly live, entertain, and unwind. The setting offers easy access to the Sassafras River, nearby marinas, and the charm of historic Galena and Chestertown. Perfect for boating days, waterfront dining, and peaceful evenings close to home. Whether you’re building a primary residence or an Eastern Shore retreat, this location delivers both serenity and convenience. All homes within the community are guided custom builds. Buyers may bring their own architectural plans for approval or work directly with the development’s design team to create a home uniquely their own. Construction Concierge by Conestoga manages the development, design coordination, and architectural review, ensuring a seamless and elevated building experience from start to finish. This listing is for Lot 2, located on Sassafras Cove Road. Home is TO BE BUILT. LOT PRICE is $95,000.00. Listing Photos depict possible models to be built. For full details on the homesite, design guidelines, and custom building process, contact Construction Concierge by Conestoga at 410.512.6800. This is more than a lot—it’s the foundation for a lifestyle defined by timeless design, thoughtful living, and the best of the Eastern Shore. Images are artist renderings and AI generated for marketing purposes only. Finishes, features, and details are subject to change. House is to be built, Concierge Homes is the Builder.

2 Sassafras Cove Rd, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact: 4108851606