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Located in the community of Gentle Winds just minutes from the Eastern Shore and 10 minutes to Middletown, Delaware, this 2.88-acre private lot is shaped like a baseball field (and approximately the same size as a professional baseball field). Enclosed by mature trees for maximum privacy and complimented by 2 large beautiful trees (similar to large bonsai trees), this land is the ideal setting for your dream home. This lot was improved in 1995, when the entire development was landscaped with trees that were already 20 years old, transplanted from Angelica Nursery. You cannot buy this growth on a lot. Magnolias are 65 feet tall and redwoods are 80 feet tall. The entire lot is screened with this kind of growth. The address marker (Lot 18) is numbered and the entrance is paved into the site. Home prices in the Gentle Winds community average over $900,000 and all homes are a minimum of 3,000 square feet. The community is 3 minutes to 301 and 6 minutes to the Delaware State line outside of Middletown for tax free shopping. You will not find an opportunity like this lot with privacy and convenience in a 19-lot development. The Gentle Winds Community in Kent County, Maryland, offers a unique blend of natural beauty, historic charm, and modern potential. Situated near the quaint town of Galena, this community offers: • Stunning Natural Surroundings: Expansive, picturesque landscapes with rolling hills, woodlands, and water views, ideal for residential, agricultural, or recreational use. • Generously Sized Lots: Plenty of space for privacy and creativity, whether for a custom home or a weekend retreat. • Outdoor Lifestyle: Easy access to hiking, birdwatching, kayaking, and boating on the nearby Sassafras River and Chesapeake Bay. • Convenient Location: Minutes from Galena's boutiques and dining, close to Chestertown’s cultural offerings, and near top-rated schools and landmarks like Eastern Neck National Wildlife Refuge. Community Values and Investment Potential Gentle Winds fosters a peaceful, close-knit environment with sustainable infrastructure and community amenities, such as gardens and trails. It’s not just a place to live—it’s an excellent investment in a growing area with lasting appeal. Don’t miss your chance to own a piece of this serene and vibrant community. Gentle Winds is where history, nature, and opportunity meet to create a lifestyle like no other.

14075 Crataegus Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$200,000

Multiple offers received- Highest and best due by 9/29 at noon! Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 bedroom downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Recently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash or renovation financing only—will not qualify for traditional financing. Priced to move!

4 Beds ⋅ 1 Baths

Multiple offers received- Highest and best due by 9/29 at noon! Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 bedroom downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Recently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash or renovation financing only—will not qualify for traditional financing. Priced to move!

223 Mount Vernon Ave, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$179,900

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

2 Beds ⋅ 1 Baths

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

21324 Persimmon Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

$145,000

Amazing commercial opportunity just minutes from Route 301 and Middletown, DE. This old creamery building has since been used as a fish farm and auto shop. The property is conveniently located adjacent to the railroad and just off Route 313. The block structure has high ceilings and has a versatile layout perfect for many uses.

32920 Maryland Line Rd, Massey

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$50,000

House with public water and sewer needs major renovation or tear down and replace with new home.

3 Beds ⋅ 1 Baths

House with public water and sewer needs major renovation or tear down and replace with new home.

21447 E Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$40,000

Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

Tonopah Rd., Chestertown

Listing courtesy of The Hogans Agency. Contact:

$25,000

Don’t miss this rare opportunity to own 1.72 acres on Galena Rd. Perfect for a commercial or business development, this property offers excellent visibility and accessibility, just off Route 313 and minutes from Massey and Galena. Nearby landmarks include the Massey Aerodrome & Air Museum, combining convenience with local charm.

12374 Galena Rd, Massey

Listing courtesy of EXP Realty, LLC. Contact:

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