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

315 Hughlett St, Preston
$399,000
5 Beds ⋅ 4 Baths
Coming Soon! More Photos Coming Soon! Take advantage of this wonderful opportunity to own a spacious, beautifully updated home in Tidewater Farms! The sellers are downsizing, creating an exciting opportunity for the next owner to enjoy all this home has to offer. Welcome to this spacious 5-bedroom, 3.5-bath home in Tidewater Farms, offering a versatile layout with room for everyone! Featuring two en-suite bedrooms—one conveniently located on the main level and another on the second floor—this home offers flexibility for a variety of living arrangements. Enjoy peace of mind with a **new roof installed 2025 and HVAC system installed in 2024**. Thoughtful updates throughout include additional cabinetry in the dining room, updated lighting and/or ceiling fans in every room, and dusk-to-dawn exterior lighting for added convenience. Step outside to enjoy the fenced-in backyard, complete with an above-ground pool and deck—perfect for relaxing, entertaining, and making the most of the warmer months. The pool also features a separate electrical service. With five bedrooms, multiple en-suite options, important recent updates, and inviting outdoor amenities, this Tidewater Farms home offers space, comfort, and functionality.

315 Hughlett St, Preston

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

120 Lacy Ln, Bowling Green
$650,000
5 Beds ⋅ 5 Baths
This custom brick Cape Cod sits on a full acre in a quiet cul-de-sac surrounded by distinctive homes and classic Southern charm. A large concrete driveway leads to an impressive matching three-car detached brick garage with a full LUXURY APARTMENT above. Even the detached shed was thoughtfully designed to complement the home, complete with a hip roof, dentil moulding, brick water table and matching lighting. Inside, the quality of the custom construction is immediately apparent. Warm oak hardwood floors, detailed trim and moulding, dual fireplaces, granite countertops, and timeless finishes carry throughout the home. The main level includes a bedroom as well as a private study featuring a beautiful marble-surround fireplace. The basement offers significant additional potential and is already framed and drywalled into multiple rooms, providing a strong head start toward future finished living space. Out back, a substantial deck creates is finished with premium Brazilian hardwood decking designed for exceptional durability and longevity, it is another example of the craftsmanship and attention to detail found throughout this one-of-a-kind property. Additional features include multiple laundry hook ups and washer/dryers, 3 refrigerators, a ducted & thermostatically controlled pellet stove in the basement heats the basement and main level.

120 Lacy Ln, Bowling Green

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

13110 Courtland Ln E Unit 00000, Ruther Glen
$375,000
5 Beds ⋅ 3 Baths
INVESTOR SPECIAL — WILL NOT QUALIFY FOR NORMAL FINANCING! Bring your vision to this property (OVER 4,000SQ. FT.) and situated on over 5 acres, offering recent improvements and an unfinished two-level addition with room to expand. Updates to the double-wide include a new roof, siding, and gutters. A new survey is also available. The main finished home’s heat pump is approximately 7 years old, and a new Mitsubishi unit serves the smaller double-wide addition. Built approximately 9 years ago, the unfinished addition features a brick fireplace on each level and sliding exterior doors on both levels. HVAC ductwork and much of the electrical wiring have already been run, and a heat pump/furnace has been installed but has never been operated. This space offers an opportunity for the next owner to complete the project to suit their needs, subject to county requirements and approvals. The county has the addition’s plans on file and has indicated that completing it to include an additional bedroom would require upgrading or replacing the septic system with a larger system. The current septic system serves a 3-bedroom, 2-bathroom home. The siding contractor lost the double-wide’s HUD certification label during siding replacement. With acreage, recent exterior improvements, and expansion potential, this property is ready for an investor with a plan. Buyers should verify permits, completion requirements, septic capacity, and HUD documentation.

13110 Courtland Ln E Unit 00000, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact:

6269 Sterling Way, Ruther Glen
$493,640
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. The 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:

6302 Sterling Way, Ruther Glen
$581,640
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:

6176 Discovering Ridge Dr, Ruther Glen
$531,640
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 home is complete with a walk-out 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 and renderings are from builder's library, actual selections and finishes may vary.

6176 Discovering Ridge Dr, Ruther Glen

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

6245 Sterling Way, Ruther Glen
$516,640
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:

17376 Pirogue Ln, Ruther Glen
$531,640
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 are from builder's library, actual selections and finishes may vary.

17376 Pirogue Ln, Ruther Glen

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

6317 Sterling Way, Ruther Glen
$493,740
5 Beds ⋅ 3 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.

6317 Sterling Way, Ruther Glen

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

17470 Clark And York Blvd, Ruther Glen
$493,740
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. The 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.

17470 Clark And York Blvd, Ruther Glen

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

109 Walnut St, Ridgely
$419,000
5 Beds ⋅ 3 Baths
5 BEDROOMS — 2,250 SQ FT — MOVE-IN READY — 2-CAR GARAGE — ESTABLISHED LISTER ESTATES Looking for the space of a larger home without the wait, construction process, or uncertainty of new construction? Why wait for new construction when you can enjoy the space, comfort and established charm of a beautifully maintained Colonial in desirable Lister Estates? Offering 5 bedrooms, 2.5 baths and approximately 2,250 square feet, this spacious home provides the room today's buyers are looking for—whether you need bedrooms for family, guests, a home office, hobbies or simply more breathing room. From the moment you arrive, you'll appreciate the pride of ownership. The home features a beautiful newer front door that welcomes natural light, gleaming oak hardwood floors, freshly painted interiors and a well-maintained, move-in-ready presentation. The kitchen offers convenient everyday functionality, while the home's generous floor plan provides plenty of space for both comfortable living and entertaining. Need even more room? The lower level offers valuable additional unfinished space and storage with the potential to be customized to suit your needs, subject to buyer's plans and applicable requirements. Outside, enjoy the convenience of an attached 2-car garage, established landscaping and the ease of living in a neighborhood setting while remaining close to Ridgely's quaint town center, shopping, churches, schools, parks and major commuter routes. If you're comparing new construction, smaller homes or properties requiring major updates, be sure to see what 109 Walnut Street has to offer. Five bedrooms, generous living space, a 2-car garage and move-in-ready condition make this a home worth seeing in person!

109 Walnut St, Ridgely

Listing courtesy of Coldwell Banker Realty. Contact:

18015 Jackson Dr, Bowling Green
$550,000
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 built by Aaronal 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 and growth 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 and the biggest table you can think of. 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 its own full bath. Basement also offers incredible storage and gym area; this basement 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, I promise you will not be disappointed!!

18015 Jackson Dr, Bowling Green

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

6323 Sterling Way, Ruther Glen
$493,740
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:

17456 Clark And York St, Ruther Glen
$493,740
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:

66 Albertson Ct, Ruther Glen
$489,500
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:

222 S 2nd St, Denton
$314,000
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:

407 W Sunset Ave, Greensboro
$280,000
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:

6289 Sterling Way, Ruther Glen
$493,640
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:

24276 Asbury Dr, Denton
$595,000
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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