Caroline County, VA Real Estate Search

Caroline County, VA 5 Bedroom Homes for Sale

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Newest Caroline County, VA 5 Bedroom Homes for Sale

5 Beds ⋅ 6 Baths

Waterfront living in Lake Land’Or with open-water views and outdoor spaces designed to make the most of the setting. This distinctive home offers four bedrooms, an additional NTC bedroom in the finished walkout basement, four full baths and two half baths across three levels. Hardwood floors extend throughout the main living areas, where the family room features a wood-burning fireplace and opens to a wraparound deck overlooking the water. The remodeled kitchen includes upgraded countertops, newer appliances, an island with a wine refrigerator and a backup gas cooktop. The upper-level primary suite enjoys water views, a sitting area, private deck access, an updated bath with an oversized shower and double vanity, and conveniently located laundry. The walkout basement adds a family room with wet bar, game room, full bath and access to the lower deck. Outside, enjoy multiple decks, a waterfront swimming area, dock platform and two swim ladders. Additional highlights include an oversized two-car garage, newer roof and gutters, recessed lighting and abundant storage.

12 Mahon Cir, Ruther Glen

Listing courtesy of Century 21 Redwood Realty. Contact:

5 Beds ⋅ 2 Baths

4.93 Acres of Possibility! Bring your vision and a little imagination to this charming Cape Cod nestled on 4.93 acres, where classic character meets endless potential. This spacious 5-bedroom, 2-full-bath home offers the perfect opportunity to restore, refresh, and create a home that truly reflects your style. Inside, you'll find original hardwood floors, an inviting eat-in kitchen, separate dining room, and a comfortable living room and family room featuring a classic brick fireplace—all the elements of a home with timeless charm and plenty of room to make it your own. With an unfinished basement full of possibilities. Outside is where this property really shines with possibilities. A 3-car detached carport provides ample covered parking, while the multi-room outbuilding offers flexible space for storage, a workshop, hobby space, or even the potential to be converted into stalls. And tucked away on the back side of the property sits the old cattle barn, patiently waiting for someone to bring it back to life. With nearly five acres, multiple outbuildings, and a home filled with original character, this property offers something increasingly hard to find—space, privacy, history, and potential all in one place. This isn't a cookie-cutter property. It's a diamond waiting for someone to give it its shine. Bring your ideas, your creativity, and your vision, and unlock everything this special property has to offer!

5148 Fredericksburg Tpke Tpke, Woodford

Listing courtesy of Coldwell Banker Elite. Contact:

5 Beds ⋅ 3 Baths

If you've been dreaming of peaceful country living without giving up the convenience of town, this beautifully maintained Colonial in the desirable Lister Estates community may be exactly what you've been waiting for. Enjoy the feeling of space and privacy while still being close to a quaint town square, local shopping, churches, schools, parks, and major commuter routes. From the moment you arrive, you'll appreciate how exceptionally clean and well cared for this 5-bedroom, 2.5-bath home is. Freshly painted interiors, almost-new gleaming oak hardwood floors, a beautiful newer front door that fills the entry with natural sunlight, and several recent updates make this home truly move-in ready. The inviting main level offers a comfortable, flexible layout designed for both everyday living and entertaining. The centrally located kitchen flows easily into the breakfast area and spacious family room, creating a wonderful gathering space. The kitchen features a new refrigerator, new dishwasher, and new garbage disposal. Just off the kitchen, you'll find a generous dining room plus a formal front room that can easily serve as a den, office, sitting room. Upstairs, the spacious primary suite provides a peaceful retreat with a walk-in closet and private bath featuring double vanities. Four additional bedrooms offer plenty of room for family, guests, hobbies, or working from home. The lower level provides even more possibilities. Finish or customize the basement/rec area to fit your lifestyle—whether you envision a recreation room, home gym, workshop, media area, or simply need additional storage. A two-car garage and abundant storage add to the home's functionality. Step outside to the spacious backyard, where you'll have room for summer cookouts, gardening, play, and outdoor gatherings. Additional comfort and efficiency features include a UV air-cleaning system that is professionally maintained twice yearly, helping improve indoor air quality as part of the home's HVAC system. This is the kind of home that offers the best of both worlds: room to breathe, a peaceful neighborhood setting, and the convenience of being close to the places you need and the small-town amenities you enjoy.

109 Walnut St, Ridgely

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

5 Beds ⋅ 3 Baths

Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful .46-acre lot. The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The kitchen provides abundant cabinet storage and plenty of natural light. Downstairs, you'll find two additional bedrooms, a large family room with an electric fireplace, and a charming stone sitting area with a large sliding glass door that opens directly to the backyard and expansive concrete patio. The layout provides great flexibility for guests, a home office, recreation space, or whatever fits your lifestyle. Step outside and enjoy the privacy of the backyard, complete with an above-ground pool and deck, large patio, and plenty of room to create your own outdoor retreat. Imagine summer afternoons by the pool, gatherings on the patio, or adding a firepit area to make the backyard your own. The home is in good condition and is ready for its next owner to add their own personal touches to make the space their next home sweet home. Conveniently located in a quiet neighborhood setting while still offering easy access to Federalsburg, Bridgeville, Seaford, and Denton.

2792 Meadowbrook Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact: 3023600300

5 Beds ⋅ 4 Baths

Welcome home to 18015 Jackson Dr! Tucked on a corner lot, this is one of the neighborhood's original and best-loved homes. This stunning 5 bedroom, 3.5 bath colonial offers the space, quality, and lifestyle that most dream of, all less than 5 minutes from historic downtown Bowling Green. Grab a coffee at The Mix House and browse local shops on Main Street, or enjoy the small town charm that makes this location so special, all just minutes from your front door. From the moment you step onto the inviting front porch, you'll feel the pride of ownership that's gone into this home. Inside; abundance of natural light and cathedral ceilings set the tone for a home that's as beautiful as it is functional. This home has been beautifully crafted with comfort in mind. The main level offers a formal living room , a formal dining space, and a large family room centered around a cozy gas fireplace with beautiful bay windows. The gourmet eat in kitchen is the true showstopper; featuring granite countertops, a large center island, a cooktop, spacious pantry, plenty of counter space for cooking and hosting. The kitchen flows into a stunning sunroom/ eat in space with loads of natural light from windows all around, perfect for gathering with family and friends. Upstairs, retreat to a luxurious primary suite complete with a huge walk-in closet, a private sitting area, and a spa-like bathroom with a soaking tub, separate shower, and linen closet. Three additional bedrooms, a full bath, and a convenient laundry room complete the upper level. The walkout basement adds incredible versatility, with a recreation area, kitchenette, and spacious bedroom with a full bath. Basement also offers incredible storage and gym area; this basment is perfect for multigenerational living, guests, or even a home business. Outside, enjoy a fenced-in yard, a sparkling pool, a Trex deck, and a patio. all the space you need for summer fun and outdoor entertaining. Home also offers a 2 car garage and solar! Come checkout this beautiful home!!

18015 Jackson Dr, Bowling Green

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 5403715220

5 Beds ⋅ 3 Baths

Discover your dream home in this newly built 2024 country ranch located on 2 acres in the picturesque Caroline County, where privacy meets luxurious living. There is no HOA! This stunning 5-bedroom, 3-bathroom residence is a true architectural gem, featuring over 2,800 square feet of finished living space, designed for both modern functionality and elegance. Step inside to experience an open floor plan that brings abundant natural light into the spacious living areas. The vaulted ceiling, adorned with beautifully stained wood beams, infuses a rustic charm that perfectly complements the contemporary design. The kitchen is truly a chef's paradise, featuring luxurious granite countertops, top-of-the-line stainless steel appliances, and a charming farmhouse sink. Rich hardwood floors throughout the home add warmth and character to every room, while the meticulously tiled bathrooms exhibit exceptional attention to detail. One of the standout features of this remarkable residence is the stunning free-standing tub in one of the bathrooms, creating a tranquil retreat for relaxation after a long day. The finished basement enhances the home’s versatility, offering an additional bedroom, a full bathroom, an office/bedroom space, and a spacious recreation room ideal for entertaining family and friends. With an impressive 2,800 square feet of thoughtfully designed living space, this home provides ample room for both relaxation and entertaining. The expansive lot presents endless opportunities for outdoor enjoyment and potential future expansion. This hidden gem is only 6 minutes to Ruther Glen and Interstate 95, under 3 miles to Route 1, and 5 miles to Route 301. It’s just 10 minutes to Ladysmith, 13 minutes to Bowling Green/Fort A.P. Hill, and less than 40 minutes to Fredericksburg and the Dahlgren Naval Base. Additionally, it’s a 35-minute drive to Short Pump/Richmond, and commuter lots are less than 6 miles away. **Don’t miss out on this extraordinary home that effortlessly blends comfort and luxury in every detail** **Some photos feature virtual staging in specific listing images.**

22309 Great Falls Way, Ruther Glen

Listing courtesy of Story House Real Estate. Contact: 8554500442

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6323 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

Welcome to this spacious and beautifully updated 5-bedroom, 4-bathroom home, perfectly situated on a large lot within walking distance of the lake. Offering an ideal blend of comfort, functionality, and charm, this property features a welcoming wraparound porch, a screened rear porch, and a fenced backyard that’s perfect for relaxing, entertaining, or enjoying the outdoors. Inside, you’ll find a freshly painted interior complemented by brand-new carpet throughout, creating a move-in-ready feel. The spacious kitchen offers plenty of room for cooking and gathering, while the oversized primary suite provides a true retreat with generous closet space. Large closets throughout the home ensure you’ll have abundant storage for every need. Additional highlights include a NEW ROOF (August 2026), a nearly new driveway, seasonal winter water views, and a layout designed to accommodate both everyday living and entertaining. With its combination of updates, space, and desirable location near the lake, this home is one you won’t want to miss!

408 Land Or Dr, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact: 8668257169

5 Beds ⋅ 3 Baths

Now selling in the newest section of the Ladysmith Subdivision! Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The home is complete with a walkout basement. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos are from builder's library, actual selections and finishes may vary.

6302 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Photos are from builder's library, actual finishes and features may vary.

17456 Clark And York St, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 3 Baths

Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos and renderings are from builder's library, actual finishes and features may vary.

17417 Riverside Dr, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 3 Baths

Rare find! A split foyer Lake Retreat with 5 bedrooms! This home has nice finishes, open floorplan, 2 car garage, back deck, nice yard. If you are looking for space, then this one needs to be on the must-see list. A great balance of Lake living with everyday convenience. CLOSE TO GOLF, WINERY, SHOPPING, YMCA, LIBRARY, CAROLINE COUNTY AGRICULTURE FAIR, CAROLINE COMMUNITY THEATER, FARMERS MARKET, KINGS DOMINION, MEADOW EVENT PARK, DOMINION RACEWAY & NEW KALAHARI RESORT WATERPARK COMING SOON ONLY 10 MILES NORTH !! LOT'S TO DO !!

66 Albertson Ct, Ruther Glen

Listing courtesy of Hometown Realty Services, Inc.. Contact:

5 Beds ⋅ 2 Baths

This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history. Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding. The house offers something that many two-story homes do not - a spacious first floor bedroom with a full bathroom nearby. Kids and guests will have the privacy of their own floor with 4 bedrooms and a full bathroom upstairs. The walk up attic, air-conditioned and heated, provides storage and an opportunity to create more living space. The partial basement offers storage plus utility access. Outdoor lovers can relax on the screened porch, or in the fenced backyard that is big enough for activities, but small enough for easy maintenance. And it’s a short walk to the library, restaurants, and shops. Check out 222 S. 2nd St. and see what it has to offer you.-- Within walking distance to Shops, Restaurants, Library, and Parks. Minutes to Public Boat ramp, Choptank River, and State Parks. Come check this out... You won't be disappointed!

222 S 2nd St, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663

5 Beds ⋅ 2 Baths

Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing & electrical, new flooring & paint, jacuzzi, and much more. OWNER FINANCING AVAILABLE. Call for details.

407 W Sunset Ave, Greensboro

Listing courtesy of R&R Executive Realty. Contact: 4104321223

5 Beds ⋅ 3 Baths

Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos and renderings are from builder's library, actual finishes and features may vary.

6245 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6289 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2211 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6269 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 3 Baths

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

24276 Asbury Dr, Denton

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

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