21645 Homes under $400,000

21645 Homes under $400,000

Welcome to Kennedyville, Maryland, nestled in the picturesque Kent County and proudly bearing the zip code 21645. This charming small town offers a unique blend of rural tranquility and community spirit, making it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Kennedyville is surrounded by the stunning landscapes of the Eastern Shore, with lush farmland, serene waterways, and a rich tapestry of nature. Here, you can enjoy outdoor activities like hiking, fishing, and exploring the nearby Chesapeake Bay. The town's close-knit community fosters a welcoming atmosphere, where neighbors become friends and local businesses thrive.

For homebuyers seeking affordability, Kennedyville presents an impressive selection of homes priced under $400,000. Whether you're a first-time buyer or looking to downsize, you'll find charming residences that boast character and comfort. From cozy cottages to spacious family homes, the real estate options here cater to a variety of tastes and lifestyles. With competitive pricing, you can enjoy the benefits of homeownership without breaking the bank.

Living in Kennedyville means more than just owning a home; it’s about embracing a lifestyle rich in community, nature, and history. With its convenient access to nearby towns and amenities, you can enjoy the best of both worlds—peaceful living with urban conveniences just a short drive away. Explore the possibilities that await you in this delightful corner of Maryland, where your dream home is waiting to be discovered!

Newest 21645 Homes under $400,000

28036 Creamery St, Kennedyville
$224,900
3 Beds ⋅ 1 Baths
Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

28036 Creamery St, Kennedyville

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

11989 Augustine Herman Hwy, Kennedyville
$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:

11989 Augustine Herman Hwy, Kennedyville
$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:

11944 Augustine Herman Hwy, Kennedyville
$399,000
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:

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