Kent County Public Schools Homes under $400,000

Kent County Public Schools Homes under $400,000

Welcome to the picturesque Kent County, Maryland, where the charm of small-town living meets the vibrancy of a close-knit community. Nestled along the scenic shores of the Chesapeake Bay, Kent County is not just a beautiful place to call home, but it also boasts an exceptional educational system—Kent County Public Schools.

Kent County Public Schools is renowned for its commitment to academic excellence and holistic development. With a range of educational programs that cater to diverse learning needs, this school district ensures that every child receives a quality education. From dedicated teachers to innovative learning environments, students are encouraged to explore their interests and talents. The district also emphasizes extracurricular activities, providing students with opportunities to engage in sports, arts, and community service, fostering well-rounded individuals ready to make their mark in the world.

For families seeking affordable housing options in this idyllic setting, you’ll be pleased to discover that Kent County offers homes under $400,000. Whether you’re looking for a charming cottage, a cozy family home, or a modern townhouse, there’s something for everyone. These homes not only provide excellent value but also place you within reach of the district’s top-notch schools.

Imagine the joy of living in a community where your children can thrive academically while you enjoy the beauty of nature and the warmth of local culture. Kent County is more than just a place to live; it’s a place to grow, learn, and create lasting memories. Come explore the possibilities today!

Newest Kent County Public Schools 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:

234 N Kent St, Chestertown
$325,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

8820 Cumberland St, Chestertown
$312,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

103 Metcalf Rd, Chestertown
$259,900
3 Beds ⋅ 3 Baths
Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

14 Third Ave, Betterton
$245,000
3 Beds ⋅ 3 Baths
A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. ft., featuring a completed exterior and an unfinished interior that gives the next owner the opportunity to finish and customize the home to their own style. Designed for 3 bedrooms and 3 full bathrooms, with the potential for a 4th bedroom or additional living space above the garage. The unfinished interior features open stud walls with roughed-in plumbing and electric, underground electric with 200-amp service, 2x6 exterior walls, 9-foot ceilings on the first floor and basement, Andersen windows, steel entry doors, and an oversized garage door. A beautiful wrap-around porch, attached side-entry garage, and cleared, level 0.24-acre lot add to the possibilities. Located just 3 short blocks from the Chesapeake Bay and a short walk to Betterton Beach, enjoy convenient access to the beach, boardwalk, boat ramp, fishing, swimming, basketball and tennis courts, picnic pavilions, and a town playground. Whether you're envisioning a year-round residence, vacation getaway, or investment opportunity, much of the vision is already in place. Bring your ideas and make this unique property near the Bay your own!

14 Third Ave, Betterton

Listing courtesy of Foraker Realty Co.. Contact:

25094 Reeds Mdw, Worton
$389,000
3 Beds ⋅ 3 Baths
Nestled in the community of Reeds Meadows, this contemporary residence offers a blend of modern convenience and comfortable living. Built in 2020, this meticulously maintained home spans 1,974 square feet, providing ample space for relaxation and entertainment. As you approach the property, you are greeted by a charming exterior with durable vinyl siding, complemented by well-maintained entry. The newly paved road invites leisurely strolls in a pleasant setting. An asphalt driveway leads to an attached garage featuring convenient inside access as well as access to the rear of the property. A garage door with remote opener ensures effortless entry and exit. Step inside to discover a thoughtfully designed layout that emphasizes both functionality and style. The heart of the home is the kitchen, equipped with stainless appliances including a built-in microwave, sleek dishwasher, and a classic range hood. The new refrigerator and stove make meal preparation a delight, while the adjacent laundry area with half bath is conveniently located on the main floor. Natural light pours through large windows, enhancing the warm ambiance throughout. The absence of a fireplace allows for a clean, modern aesthetic, while the contemporary design elements provide a timeless appeal. Retreat to the tranquil first floor master suite, complete with an en-suite bathroom featuring luxurious finishes. Two additional bedrooms, a bonus room, and a well-appointed full-bath ensure comfort and privacy for all. Step outside onto the custom deck, perfect for alfresco dining or simply enjoy the peaceful surroundings of your 0.32-acre lot. This outdoor space is ideal for hosting summer barbecues or unwinding with a good book in the fresh air. Experience the lifestyle that you deserve.  Don't miss the opportunity to make this residence your own. Located about 10 minutes from historic Chestertown on the Chester River, this tidy subdivision 's location offers quick access to public landings for fishing and boating fun, beautiful farms, including Red Acres, which offers beautiful produce, flowers, and retail products. Located between Chestertown/Galena, and Betterton, and also close to Rock Hall which boasts good shopping, restaurants and loads of fun on the Chesapeake Bay.

25094 Reeds Mdw, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

22974 Bay Shore Rd, Chestertown
$329,900
2 Beds ⋅ 2 Baths
Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

21899 Lovers Ln, Rock Hall
$131,000
2 Beds ⋅ 1 Baths
Welcome to peaceful country living in this cozy 2-bedroom, 1-bath manufactured home. Nestled in a serene setting, this home offers several recent improvements. Major updates include a new roof installed in 2026 with a lifetime warranty, newly installed storm door, insulated pipes, hot water heater, and gutters. Step outside and enjoy the covered rear porch—perfect for relaxing and taking in the tranquil surroundings. The partially fenced backyard provides additional outdoor space, while the detached shed offers convenient storage and is equipped with electricity and cable-ready connections. With its recent updates, peaceful setting, and outdoor amenities, this home is ready for its next owner to make it their own. Property is being sold strictly as-is.

21899 Lovers Ln, Rock Hall

Listing courtesy of Coldwell Banker Realty. Contact:

25690 Meadow Rd, Worton
$284,000
3 Beds ⋅ 2 Baths
Ranch style home offering plenty of parking, three bedrooms and two full baths and a lot of outdoor living space on decks and the covered front porch. Located at end of cul-de-sac for privacy. Not much to do here to make this your new home! Property strictly sold as is. HUD CASE#241-778774 . Please see website hudhomestore for details.

25690 Meadow Rd, Worton

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

8732 Elm Rd, Chestertown
$289,000
3 Beds ⋅ 2 Baths
Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

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

25373 Worton Lynch Rd, Worton
$175,000
1 Beds ⋅ 1 Baths
Charming "TINY" house within quiet community of Worton off the main thoroughfare. Woods, public water and sewer, mature trees, deck with view of woods. One bedroom and bath, eat-in kitchen. Separate laundry/utility room. Not fancy by delightful on large lot. Only ten minutes from Historic Chestertown where one can find all daily needs plus many year-round cultural events including live performances. Washington College, tenth oldest college in America, offers programs and events continually. Minutes from Lockbriar (Pick Your Own) Farm and rest of beautiful County of Kent. Bettertown sandy Public beach on Chesapeake Bar and modern playground is nearby. Weekends? Year-round living?

25373 Worton Lynch Rd, Worton

Listing courtesy of Maryland Heritage Properties. Contact:

34155 Bradford Johnson Rd, Galena
$55,000
1 Beds ⋅ 1 Baths
Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

34155 Bradford Johnson Rd, Galena

Listing courtesy of Taylor Properties. Contact:

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