Caroline County Public Schools Homes under $400,000

Caroline County Public Schools Homes under $400,000

Welcome to Caroline County, a hidden gem in the heart of Virginia, where the charm of small-town living meets the convenience of modern amenities. One of the standout features of this area is the highly regarded Caroline County Public Schools. This school district is dedicated to providing a nurturing and academically enriching environment for students, ensuring they receive a top-notch education. With a focus on innovation and community involvement, Caroline County Public Schools offers a variety of programs designed to cater to the diverse needs of its students, from advanced placement courses to extracurricular activities that foster growth and creativity.

As you explore the housing market in Caroline County, you’ll be pleased to discover a range of homes available for under $400,000. This affordability allows families and first-time homebuyers to find their dream home without breaking the bank. Whether you’re looking for a cozy single-family residence, a charming cottage, or a spacious townhome, Caroline County has something to offer everyone. The picturesque landscapes, friendly neighborhoods, and access to quality education make it an ideal place to settle down.

Living in Caroline County means enjoying a blend of rural charm and community spirit, all while having access to the educational resources that help shape the future of our children. If you’re ready to make a move, let the welcoming community and excellent school district of Caroline County be your next destination! Your dream home awaits!

Newest Caroline County Public Schools Homes under $400,000

203 Sharp Rd, Denton
$315,000
3 Beds ⋅ 2 Baths
This ranch-style home, nestled on a generous 1.24-acre lot, offers a harmonious blend of comfort with nostalgia. 3 spacious bedrooms and 2 full bathrooms, the open floor plan invites you to experience a warm and inviting atmosphere. Step outside to discover a landscaped exterior featuring a screened porch, ideal for enjoying serene mornings or tranquil evenings. The property is partly wooded, providing a natural backdrop that enhances privacy and tranquility. An outbuilding and shed offer ample storage for your outdoor equipment or hobbies, while the garden area invites leisure and fun. Just blocks away from the picturesque Choptank River, this home offers an exclusive lifestyle, where water activities and nature walks are at your doorstep. The attached carport and expansive driveway ensure convenient parking for you and your guests. Inside, enjoy thoughtful features such as a walk-in closet in the primary suite, a cozy dining area, and ceiling fans that enhance comfort throughout. 203 Sharp is centrally located offering, shopping, entertainment and community parks. Denton Elementary, Choptank River,Sharp and Lions Park are all within walking distance. Food Lion and the Super Walmart are within 2 miles from the house but the house is tucked away in a remote, private setting. New roof installed 11/12/2026

203 Sharp Rd, Denton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

306 Sunrise Ave, Ridgely
$314,900
4 Beds ⋅ 2 Baths
Price improvement! Nestled on a charming corner lot, this delightful ranch-style home offers a perfect blend of comfort and community. Built in 1955, this residence boasts a spacious layout with 1,539 square feet of living space, featuring four inviting bedrooms and two full bathrooms. New $30,000 complete roof with 50-year transferable warranty. The warm ambiance is enhanced by a mix of hardwood and carpet flooring, creating a cozy atmosphere throughout. The exterior, adorned with durable aluminum siding, complements the home's classic design while providing low-maintenance living. The generous lot size of 0.37 acres allows for ample outdoor space, perfect for gardening, play, or simply enjoying the fresh air. Located in a vibrant neighborhood, this home is surrounded by a welcoming community that values connection and engagement. The nearby schools are known for their commitment to education, providing a nurturing environment for students to thrive. Convenience is key in this location, with off-street and on-street parking available, making it easy for guests to visit. The neighborhood is well-served by public services, ensuring that residents have access to essential amenities and resources. This property is not just a house; it's a place where memories are made. The inviting layout and community-oriented surroundings create an ideal setting for gatherings, celebrations, and everyday moments. Whether you're enjoying a quiet evening at home or exploring the local parks, this residence offers a sense of belonging and comfort. With its charming features and prime location, this home is ready to welcome you into a lifestyle filled with warmth and community spirit. Experience the joy of living in a neighborhood that feels like home, where every day brings new opportunities to connect and create lasting memories.

306 Sunrise Ave, Ridgely

Listing courtesy of Samson Properties. Contact:

15416 Tidewater Trl, Fredericksburg
$280,000
3 Beds ⋅ 3 Baths
1 Acre parcel with cape code, 3 bedrooms, primary bedroom and bath on the main floor, with 2 additional beds and full bath on upper level. Attached 2 car garage, with an outbuilding. Being sold As-Is, this property needs work.

15416 Tidewater Trl, Fredericksburg

Listing courtesy of Century 21 Redwood Realty. Contact:

100 American Dr, Ruther Glen
$282,000
3 Beds ⋅ 1 Baths
Enjoy the lake lifestyle for under $300K! This refreshed 3-bedroom, 1-bath ranch in Lake Caroline offers nearly 1,000 finished square feet, extensive updates, and inviting spaces inside and out. A welcoming front porch leads into a bright, airy living room that flows into the spacious eat-in kitchen, complete with access to the back deck. Three bedrooms and a full bathroom are conveniently located down the hall. Updates completed in 2026 include all-new windows, new flooring throughout, new kitchen countertops, freshly painted kitchen cabinets, a new water heater, and a new crawlspace vapor barrier and insulation. The roof was replaced in 2020, and the HVAC was installed in 2021. The septic tank was last pumped in 2025 and is now being completely replaced. Outside, the mostly level lot offers scattered backyard trees, space to relax, and a storage shed for tools and outdoor essentials. Enjoy Lake Caroline’s community pool, beaches, basketball courts, pickleball and tennis courts, and more. With so many updates already completed, this charming home is ready for your personal touches. Schedule your showing and discover everything lake living has to offer!

100 American Dr, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact:

27944 Possum Hill Rd, Federalsburg
$200,000
2 Beds ⋅ 1 Baths
Offering a peaceful country setting, nearly an acre and a half of land, and a rustic barn with an interesting connection to local history, this two-bedroom, one-bath home in Federalsburg, Maryland, presents an opportunity to enjoy country living with plenty of room to make it your own. The home's casual, comfortable interior features a spacious living room with hardwood flooring and vaulted ceilings that create an open, airy feel. A generously sized country kitchen offers ample room for everyday cooking and connects seamlessly to a large dining area, providing an easy, functional flow between the two spaces. Two nicely sized bedrooms offer comfortable accommodations, while a convenient mudroom and laundry area just off the kitchen provides direct access to the backyard. Recent improvements include an upgraded stove, washer, dryer, and hot water heater. Outside, the expansive property offers plenty of open space for gardening, outdoor activities, and a variety of possibilities. Adding character and versatility is the property's rustic barn, complete with electricity and a concrete floor. Steeped in local lore, the barn reportedly once served as the original Smithville Store, with ties to moonshine sales during the Prohibition era. Today, this piece of local history offers practical potential for a workshop, storage, hobbies, or other uses. Located in the rural countryside of Caroline County, just outside Federalsburg, this property combines a relaxed country atmosphere, a generous parcel of land, and an intriguing piece of the area's past, with plenty of opportunity to add your own personal touches. This home is being offered As-Is.

27944 Possum Hill Rd, Federalsburg

Listing courtesy of Northrop Realty. Contact:

23624 File Rd, Bowling Green
$340,000
3 Beds ⋅ 2 Baths
Tucked behind mature hardwoods on 2 private acres in Caroline County, this home offers country living with no HOA. Built in 2014 and well maintained, this move-in-ready 3-bedroom, 2-full-bath ranch offers 1,152 sq ft of easy one-level living. The land around the home is cleared, with open lawn ready for a vegetable garden, a fire pit or room for pets to roam, while the surrounding trees keep it private. Picture slow mornings on the covered front porch, watching the light come through the trees. Inside, an open floor plan lets the family room flow into an eat-in kitchen with granite countertops, a center island, a pantry, recessed lighting, stainless steel appliances and warm wood cabinetry. The dining area opens through sliding doors to the back yard, so you can carry your coffee outside and enjoy the quiet, with nothing but birdsong and rustling leaves around you. At the end of the day, the primary suite offers a peaceful retreat with a walk-in closet and private bath with a walk-in shower. Two more bedrooms share a full hall bath with tub/shower combination and granite countertops. Outside, a detached shed holds the mower, tools and outdoor gear, and the partially fenced yard has space to garden and play. The gravel driveway offers plenty of parking for a trailer, a boat or weekend visitors, and there’s room to expand or add your own garage. Recent updates include a new water heater (2025), new garbage disposal (2025), dishwasher (2022), several replaced windows, fresh paint and a re-graveled driveway. Enjoy true rural privacy about 15 minutes from Bowling Green’s shops, restaurants, schools and a community park. Barn shaped shed does not convey. Other shed conveys ‘as is’. 1-0 Buy down offered by preferred lender.

23624 File Rd, Bowling Green

Listing courtesy of Keller Williams Richmond West. Contact:

202 Buena Vista Ave, Federalsburg
$242,000
4 Beds ⋅ 2 Baths
The back deck might be your favorite spot at 202 Buena Vista Ave. It overlooks a large, fenced-in yard with plenty of room for the dogs to run and friends to come over for a cookout. Inside, this well-maintained Federalsburg home has the character you’d hope for in an older home, with real hardwood floors, newer windows, and a kitchen finished with quartz countertops and tile flooring. There are four bedrooms, one and a half baths, and a full basement with laundry and room for storage. A detached one-car garage and a separate carport give you two covered parking spots. The seller is finishing a few small projects to help keep financing options open.

202 Buena Vista Ave, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

11 Boston Cv, Ruther Glen
$345,900
3 Beds ⋅ 2 Baths
Charming Rambler on a Private Half-Acre Cul-de-Sac Lot!!! This Well-Maintained 3-Bedroom, 2-Full-Bath Beauty Offers the Perfect Combination of Comfort, Privacy and Convenience. Home has Many Updates to Include New Flooring, Fresh Paint, New Roof and New Air Handler. Only Minutes to the Lake and Front Gate. Relax and Unwind on the Country Front Porch or Entertain in the Park-Like Backyard or on the Spacious Private Deck. Plenty of Parking. Shed Included. Move-In Ready with So Much to Offer!!! Schedule Your Private Showing Today!!!

11 Boston Cv, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

4972 Preston Rd, Federalsburg
$299,900
3 Beds ⋅ 2 Baths
Enjoy country living in this charming, recently updated 3 bedroom, 2 bath Cape Cod situated on a corner lot. The home offers a spacious living room, a kitchen that opens to the family room and a separate dining room with access to the rear deck, perfect for outdoor dining or relaxing with family and friends. Conveniently located near Federalsburg and Hurlock, approximately 20 minutes from Easton, Seaford, Denton and Cambridge.

4972 Preston Rd, Federalsburg

Listing courtesy of Meredith Fine Properties. Contact:

4280 Nichols Rd Unit LOT 16, Federalsburg
$109,900
3 Beds ⋅ 2 Baths
Brand New Single Wide home **TO BE PLACED** on leased ground in Meadowbrook Court. Features 3BR, 2BA, gas heat, central air, and an 8x10 shed. Trash is $27.00/month. Monthly metered water fee TBD. **Home has NOT been ordered yet, customization options MAY be available.**

4280 Nichols Rd Unit LOT 16, Federalsburg

Listing courtesy of CALLAWAY FARNELL AND MOORE. Contact:

4270 Nichols Rd Unit LOT 11, Federalsburg
$149,900
3 Beds ⋅ 2 Baths
Brand New Double Wide home **TO BE PLACED** on leased ground in Meadow Brook Mobile Park. Features 3BR, 2BA, gas heat, central air, and an 8x10 shed. Trash is $27.00/month. Monthly metered water fee TBD. **Home has NOT been ordered yet, customization options MAY be available.**

4270 Nichols Rd Unit LOT 11, Federalsburg

Listing courtesy of CALLAWAY FARNELL AND MOORE. Contact:

290 Cedar Ridge Dr, Ruther Glen
$335,000
3 Beds ⋅ 2 Baths
This is one you do not want to miss. Freshly pained, new floors thru out and ready for you to make this your home. 3 bedrooms, 2 baths, large living room, cozy kitchen area, deck and not to mention the 2 car attached garage with storage shed in back all of this sitting on a large lot in a gated community.

290 Cedar Ridge Dr, Ruther Glen

Listing courtesy of LJ Realty Company, Inc.. Contact:

Start Your Search

How much is your home worth?

Get instant property value now!