Refine Search
Map
Sort by
$245,000
2 Baths
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$245,000
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$515,000
4 Beds ⋅ 2 Baths
Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and dryer. Could be returned to full bath when relocating washer and dryer to basement. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park area. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

14136 Kentmore Park Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$382,500
4 Beds ⋅ 3 Baths
Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

11901 Dairy St, Kennedyville

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

$430,000
4 Beds ⋅ 2 Baths
Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm. Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat. Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage. Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

11944 Augustine Herman Hwy, Kennedyville

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

$75,000
Seller Says Bring All Offers! This rural 0.38-acre lot presents a unique investment opportunity in a quaint small-town atmosphere. The property is cleared and ready for your building plans, offering a blank canvas for various residential projects. With road frontage, it ensures easy access and visibility, enhancing its appeal for future buyers or renters. Notably, the lot is not currently in development, allowing for flexibility in planning and construction. The absence of existing structures means lower initial costs and the potential for higher returns on investment. The cleared land allows for immediate construction, reducing time to market and maximizing rental income or resale value. Sellers have already invested in the public water/sewer setup allocation and with this property's strategic location positions it as a lucrative opportunity for savvy investors looking to expand their portfolios. With the right vision and execution, this lot can yield significant financial returns in a competitive real estate market. Don't miss out on the chance to secure a valuable asset with great potential.

11930 Kennedyville Rd, Kennedyville

Listing courtesy of Remax Vision. Contact: