Caroline County, VA Real Estate Search

Caroline County, VA 5 Bathroom Homes for Sale

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Newest Caroline County, VA 5 Bathroom Homes for Sale

5 Beds ⋅ 5 Baths

" Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier.

8821 Dorothy Ln, Denton

Listing courtesy of Wright Real Estate. Contact: (410) 924-3111

5 Beds ⋅ 5 Baths

Exceptional Private Retreat on 10 Acres! Welcome to your own slice of Virginia paradise in the heart of Caroline County. Nestled on 10 picturesque acres surrounded by mature trees, this beautifully updated home offers the perfect blend of privacy, comfort, and convenience. Whether you're looking for room to entertain, explore nature, garden, or simply unwind, this property delivers the lifestyle you've been dreaming of—all while being just minutes from Route 1 and I-95 for an easy commute to Fredericksburg and Richmond. From the moment you step inside, you'll be impressed by the grand two-story foyer and the stunning floor-to-ceiling flagstone fireplace with a custom mantel, creating a warm and inviting focal point. Elegant arched openings between the living and dining rooms add timeless architectural charm and character. Home Features: -Spacious floor plan with **4 bedrooms and 3 full bathrooms** on the upper level. -Luxurious primary suite featuring a private sitting area, oversized walk-in closet, and spa-inspired bath with a soaking tub, separate walk-in shower, and abundant counter space. -Second bedroom with its own private en-suite bathroom—ideal for guests or multi-generational living. -Bright walk-up lower level with a large recreation room, wet bar, full bathroom, and an additional room perfect for a home office, gym, or guest room. -Brand-new hardwood flooring throughout the main level. -Brand-new carpet throughout the upper level and all staircases. Step outside to enjoy the beautifully refinished patio, a basketball court, and a detached garage/large shed overlooking approximately 2 acres of cleared land, offering endless possibilities for outdoor entertaining, gardening, a future pool, or creating your own backyard oasis. Beyond that, the remaining acreage provides your own private playground—perfect for hiking, camping, wildlife watching, or simply enjoying the peace and beauty of nature right outside your door. Opportunities to own a beautifully upgraded home on 10 private acres at such a competitive price are exceptionally rare. If you've been searching for space, privacy, modern updates, and everyday convenience without sacrificing accessibility, this is the home you've been waiting for. Schedule your private showing today before it's gone!

4443 Jericho Rd, Ruther Glen

Listing courtesy of RE/MAX Realty Group. Contact:

7 Beds ⋅ 5 Baths

Rare opportunity to own two fully renovated single-family homes on one property! The main house offers 4 bedrooms, 3 full bathrooms, and 2,092 finished square feet, while the second house features 3 bedrooms, 2 full bathrooms, and approximately 1,000 finished square feet. Both homes have been completely remodeled with new flooring, fresh paint, updated kitchens, new cabinetry, countertops, fixtures, renovated bathrooms with new vanities, new HVAC systems, and new roofs and gutters. The modern open floor plans create a bright and inviting atmosphere, while the peaceful country setting provides privacy and space to enjoy. This unique property is perfect for multi-generational living, accommodating in-laws, or generating rental income to help offset your mortgage. Whether you're looking for additional living space, an investment opportunity, or both, this property offers exceptional flexibility and value. Two homes for the price of one—don't miss this incredible opportunity!

12469 Paige Rd, Woodford

Listing courtesy of Samson Properties. Contact: (703) 378-8810

5 Beds ⋅ 5 Baths

This home on acreage offers a rare and versatile main-level guest suite (with it's own laundry, kitchenette, living spaces and 2 full bathrooms) or entertainment wing at the rear of the home, providing exceptional flexibility for a variety of needs. Step inside from the spacious front porch to 9-foot ceilings and wood floors throughout most of the main level, creating an open and welcoming feel from the moment you enter. Recent updates add to the home’s appeal, including a water filtration system in 2025, quartz kitchen counters, kitchen backsplash, and refrigerator in 2024, wood floors in 2023, garage landing in 2022, paved driveway in 2021, original home HVAC in 2018, original home roof in 2017, and well pump in 2017. With its thoughtful layout, flexible living spaces, and meaningful updates, this home is designed to adapt to a variety of needs and lifestyles. While the original home was built in 1995, the Colonial portion of the home was added in 2010. Step outside and enjoy plenty of room to run, relax, or explore the walking trails created through the wooded portion of the acreage.

22617 Telegraph Rd, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5403717653

5 Beds ⋅ 5 Baths

Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained — nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets — and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras — accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton — an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.

322 S 2nd St, Denton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

4 Beds ⋅ 5 Baths

ROSE HILL ESTATE — 352 ACRES OF HISTORIC ELEGANCE AND AN ELEVATED COUNTRY LIFESTYLE Featured in Architectural Digest, this Amelia T. Handegan–designed residence anchors one of Virginia’s most distinguished country estates. Encompassing 352.24 acres, the property offers timeless elegance, masterful restoration, and unparalleled privacy. Designed for those who value both heritage and luxury, every detail reflects refined craftsmanship and enduring beauty. The estate’s remarkable grounds and gardens were further recognized with the 2016 ASLA Virginia Chapter Merit Award, honoring the property’s exceptional landscape architecture and stewardship. Protected under conservation easement, the estate’s rolling landscape unfolds through two gated entrances across open fields, century-old hardwoods, formal gardens, and a stocked pond—offering a rare balance of seclusion, scale, and natural beauty. Originally built in 1799, the residence was comprehensively restored in 2011 by Tidewater Preservation, Inc., under the direction of acclaimed Charleston designer Amelia T. Handegan. The result is a seamless blend of historic integrity and modern sophistication, enhanced by geothermal climate control and radiant floor heating. The 5,431-square-foot main residence features 4 bedrooms, each with an ensuite bath, and a collection of gracious living spaces defined by hardwood floors, intricate crown molding, chair railing, and custom French wallpaper. Formal rooms include a dining room with fireplace, an elegant living room with built-ins, and a distinctive octagonal music room with English windows and hand-painted geometric floors. The chef’s eat-in kitchen pairs historic character with professional-grade function, offering custom wood cabinetry, a wood-burning fireplace, marble-topped island, Wolf range, paneled appliances, wine refrigerator, and ice machine. A well-appointed mudroom with built-ins and laundry provides convenient access to the gardens. The main-level primary suite is a private retreat, featuring a fireplace, sitting room with built-ins, walk-in closet, and direct access to the outdoors, along with a marble-clad bath complete with dual vanities, soaking tub, and walk-in shower. Additional bedroom suites offer fireplaces, built-ins, and beautifully appointed baths, each capturing sweeping views of the rolling countryside, pond, or historic gardens. Beyond the main residence, a guest cottage with exposed beams, marble finishes, and a fireplace offers refined accommodations for visitors. A Pennsylvania bank barn, relocated in 2009, has been thoughtfully reimagined to include a gym, office with full bath, and loft. Distinctive architectural elements include a Thomas Jefferson–inspired dovecote with Birmingham Rollers and a newly constructed folly overlooking the pond. Outdoor amenities are equally exceptional, featuring a tennis court with pavilion, croquet lawn, riding trails, and formal gardens that have been showcased in Garden Club tours, filled with hydrangeas, peonies, fruit trees, and rose of Sharon. A working barn supports a herd of Belted Galloway cattle, further enhancing the estate’s pastoral character. Utilities include well water, septic, geothermal HVAC, propane heat (two owned tanks: 500 and 1,000 gallons), radiant floor heating, and four hot water tanks. A rare and significant offering, Rose Hill Estate embodies a legacy property—where history, land, and lifestyle converge in extraordinary form.

23348 Tidewater Trl, Rappahannock Academy

Listing courtesy of Coldwell Banker Elite. Contact:

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