Caroline VA 3500+ Sq. Ft. Real Estate, Homes, Condos for Sale

5 Beds ⋅ 5 Baths ⋅ MDCM2007560 MLS

" 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

$1,200,000

4 Beds ⋅ 4 Baths ⋅ VACV2010578 MLS

Bayfront living with exceptional waterfront amenities! This home offers a rare opportunity to enjoy water views, a boat dock with slip, and a private beach area. The sunroom/sun porch provides the perfect space to relax, entertain, or simply take in the peaceful waterfront setting. The home features a desirable first-floor primary suite with its own private exterior entrance and generous closet space. A separate suite over the garage, also with its own private entry, adds wonderful flexibility for guests, extended living, a home office, studio, or private retreat. With a spacious and versatile layout, multiple private-entry living areas, and direct access to the water, this property is full of potential and ready for its next chapter.

30019 Goose Point Ct, Port Royal

$600,000

5 Beds ⋅ 4 Baths ⋅ VACV2010568 MLS

With over 4,600 finished square feet, 5 bedrooms, 3.5 baths, and a fully finished walk-out basement, this spacious home offers room for everyone. A welcoming covered front porch leads into a bright, open floor plan featuring luxury vinyl plank flooring, a gas fireplace, and a beautifully updated kitchen with granite countertops, large island, double wall ovens, pantry, and new backsplash. The adjoining sunroom with cathedral ceiling fills the home with natural light and opens to the covered rear porch. Upstairs, the primary suite features cathedral ceilings, a large sitting area, oversized walk-in closet, and a spa-inspired bath with jetted tub, dual vanities, and separate shower. Three additional bedrooms, a full bath, and an upstairs laundry room complete the level. The walk-out basement is ideal for multigenerational living or guests, offering a bedroom with its own full bath, kitchenette, second gas fireplace, spacious recreation area, abundant storage, and unfinished space with potential for a sixth bedroom. Outside, enjoy a fully fenced backyard designed for entertaining with a covered porch, stamped concrete patio, and a professionally serviced 10,000-gallon in-ground pool. Major recent updates include two new HVAC systems (2025), water heater (2023), kitchen backsplash, fresh paint, soft-washed exterior, and upgraded dryer venting. A huge plus are the Solar panels for added energy savings. Conveniently located in Maury Heights, just minutes from downtown Bowling Green, I-95, and an easy commute to Fredericksburg, Richmond, Dahlgren, and Ashland. Spacious, updated, and move-in ready—this home truly has it all.

18015 Jackson Dr, Bowling Green

$2,500,000

4 Beds ⋅ 5 Baths ⋅ MDCM2006946 MLS

Welcome to a rare opportunity to own a premier 105+/- acre agricultural estate combining modern comfort, income-producing farmland, and outstanding infrastructure. Ideally situated in a peaceful rural setting, this remarkable property features approximately 70± acres of fully irrigated, tillable land—perfect for high-yield row crops or specialty farming. At the heart of the farm sits a stunning 6,500 sq ft custom-built home, offering a perfect balance of elegance and functionality. Designed for gracious living and entertaining, the home includes expansive living spaces, a gourmet kitchen, multiple fireplaces, generous bedrooms, and panoramic views of the surrounding countryside. The agricultural infrastructure includes a 60x100 machine shed, providing ample space for equipment storage, workshop needs, or additional agricultural operations. Whether you're seeking a productive working farm, a private family retreat, or a multi-use investment opportunity, this exceptional property delivers.

28219 Bridgeville Road, Federalsburg

$630,000

4 Beds ⋅ 4 Baths ⋅ MDCM2007462 MLS

Nestled on 5 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and country living. Approximately 1.8 acres are wooded, providing a peaceful backdrop and frequent visits from local wildlife, while the remaining acreage is cleared and ideal for outdoor enjoyment. The inviting front porch overlooks the private rural setting, while the interior features an open-concept floor plan with cathedral ceilings that create a bright and airy living space. A separate sitting room offers additional living space for relaxation, a home office, or a den. Designed with flexibility in mind, the home includes two primary suites, each located on opposite ends of the home for added privacy. Two additional bedrooms share a full hall bath. Above the attached two-car garage, you'll find a spacious bonus room with interior access and its own half bath—perfect for a game room, guest space, home office, or hobby area. Step outside and enjoy your own backyard oasis featuring a 20' x 40' in-ground saltwater pool with fenced enclosure and a rear deck ideal for entertaining. The property also includes a 30' x 40' pole barn with concrete flooring and electric service, providing ample space for equipment, hobbies, storage, or livestock needs. Enjoy peaceful country living with deer often seen right in your backyard, all while remaining close to Delaware for shopping, dining, and commuting. This unique property offers the space, privacy, and amenities you've been searching for. Seller is in the process of building there next house and would like to coordinate the time frame for settlement.

26927 Boyce Mill Rd, Greensboro

$994,000

3 Beds ⋅ 2 Baths ⋅ VACV2010384 MLS

Here is your opportunity to own a family compound spanning approximately 6.5 acres over 2 parcels with 2 separate homes! The larger home has an additional guest suite on the main level! The larger home on acreage offers a rare and versatile main-level guest suite or entertainment wing at the rear of the home, complete with its own laundry, kitchenette, living spaces, and two full bathrooms. This flexible layout provides exceptional options for a variety of needs and lifestyles. 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. Step outside and enjoy plenty of room to run, relax, or explore the walking trails created through the wooded portion of the acreage. This smaller home is subject to a lease through November 2026 and will not be sold separately. The home is well kept and shows very well!

22623 & 22617 Telegraph Rd, Ruther Glen

$649,000

5 Beds ⋅ 5 Baths ⋅ VACV2010380 MLS

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

$2,560,000

8 Beds ⋅ 16 Baths ⋅ MDCM2006492 MLS

A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind property. The main residence spans over 9,364 square feet and is thoughtfully designed for refined living and grand-scale entertaining. A dramatic two-story foyer with sweeping double staircases opens to richly appointed formal and informal living spaces accented by custom millwork, crown moldings, hardwood flooring, and four fireplaces. At the heart of the home, the chef’s kitchen impresses with coffered ceilings, expansive island, commercial-grade range, double wall ovens, and premier Viking, Sub-Zero, and Wolf appliances, along with an induction cooktop and icemaker. A well-appointed butler’s pantry ensures seamless entertaining, while the adjoining Grill Room—featuring an infrared grill, Viking beverage cooler, and Sub-Zero icemaker—offers a relaxed gathering space. The primary suite is a private retreat with fireplace, mood lighting, generous walk-in closets, and dual doors leading to a private balcony overlooking the grounds. The spa-inspired bath includes double vanities, a tiled shower, and soaking tub. All additional bedrooms in the main residence are ensuite, offering comfort and privacy for family and guests. Outdoor living rivals a private resort, highlighted by a 40’ x 20’ heated saltwater infinity pool with swim ledge, hot tub, outdoor kitchen, covered porch, expansive patios, and firepit—perfect for year-round enjoyment amid mature landscaping, a tranquil pond, and sweeping rural views. Automobile collectors will appreciate the estate’s unparalleled garage facilities. A detached brick automotive gallery features a nine-bay, climate-controlled showcase garage with CHI aluminum tinted glass doors, polished concrete floors, and premium climate control—ideal for preserving and displaying a museum-quality collection. Above, a fully appointed three-bedroom, two-bath guest residence offers a kitchen and multiple living spaces. Two additional fully insulated, climate-controlled 50’ x 75’ garages with 12-foot overhead doors and professional-grade lifts provide exceptional flexibility. An oversized storage building and run-in to the rear further enhances the property’s versatility. Hobbyists, from automobile collectors to equestrian enthusiasts, will be delighted to make use of the many large accessory structures on the property. Additional features include a comprehensive security and surveillance system, private gated entrance, 60-zone irrigation system, whole-property surround sound, & Comcast fiber internet. This is more than a home—it is a destination estate offering an elevated lifestyle for those who value privacy, craftsmanship, and automotive excellence in a refined Eastern Shore setting. IMPORTANT NOTES: Property consists of three parcels with separate addresses/taxes, portions of which are leased for agricultural use through December 2025. The irrigation system has a mainline break beneath a garage and will not be repaired by the seller. Quotes for repair or replacement are available for review.in documents. Front garage has suffered water damage and in the process of being remediated but seller will not be making repairs to the garage or apartment. Estimates for the remediation (which seller is doing) and the repair of damaged area is uploaded in MLS disclosure docs. All agents/buyers touring MUST sign a Hold Harmless Document prior to entering the garage/apartment. Property is being sold AS-IS/WHERE-IS with all faults. Contact listing agent(s) with any questions. ***Please do not enter lane to property without a confirmed appointment.

4218 Harmony Road, Preston

$1,500,000

3 Beds ⋅ 4 Baths ⋅ MDCM2007284 MLS

Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6” cooling pads, conventional heat, and a 175 kW generator with a Perkins diesel engine and auto transfer switch for efficient and reliable operation. Recent improvements include a new manure shed and updated metal siding on the poultry houses. The operation also benefits from consistent poultry placement through Perdue with chicken deliveries approximately every two weeks. The property offers multiple income streams, including poultry production, rental income from a renovated mobile home, and income from farmland, a grain bin, and a hay shed. The mobile home was renovated around 2015 and features ductless HVAC, propane backup heat, propane range, refrigerator, washer and dryer, and electric water heater. The refurbished 3-bedroom, 3.5-bath farmhouse, originally believed to date back to approximately 1890, was extensively updated in 2024 and blends historic charm with modern comfort and functionality. Multiple outbuildings provide excellent utility, storage, and operational support, with room for future expansion subject to Caroline County approvals. Conveniently located within Maryland’s Eastern Shore agricultural corridor, this farm offers easy access to major routes connecting to the Delaware beaches, Annapolis, Easton, Denton, and the Chesapeake Bay region. Enjoy the privacy and open space of country living while still being within reach of shopping, restaurants, farm supply stores, marinas, and outdoor recreation, hunting, fishing, and boating. The surrounding area is known for its strong farming community, scenic rural landscapes, and access to local parks, waterfront attractions, and small-town amenities. An exceptional opportunity for poultry growers, investors, or owner-operators seeking a turnkey, income-producing agricultural operation with additional rental and farmland income potential. The property is being sold strictly “as-is, where-is.”

7347 Harmony Rd, Preston

$1,550,000

5 Beds ⋅ 5 Baths ⋅ MDCM2006964 MLS

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

$700,000

3 Beds ⋅ 2 Baths ⋅ MDCM2007280 MLS

STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique opportunity features a spacious all-brick home paired with a large commercial building designed for flexibility and function. The commercial space includes a showroom, mechanic area with lift, two offices, two bathrooms, heat and air conditioning, and an expansive paved parking lot. Previously operated as a dealership, the seller still holds a trader’s license, offering exceptional potential for a variety of business uses. The well-maintained home offers 3 spacious bedrooms and 2 full baths, along with a comfortable living room, dining room, and kitchen featuring stainless steel appliances. Additional highlights include hardwood floors beneath the carpet, a welcoming front porch, full basement, attached carport, and paved driveway. Some major improvements have already been completed, including a new roof (2025), new gutters with leaf protection (2025), and a new deep well (2025). The commercial building and home are separately metered and each have their own well and septic systems. The seller was in the process of subdividing the property, with much of the work already completed. This creates additional flexibility and potential for future owners, as a buyer may choose to complete the subdivision process, allowing the house and commercial building to be sold or leased separately. Buyer to verify all zoning, permitted uses, and business opportunities with the county and conduct their own due diligence regarding sudivision status and intended use of the property. Contact me today for more information or to schedule your private tour. Properties like this don’t come around often, act fast and secure your future before it's gone.

14236 Drapers Mill Rd, Greensboro

$599,740

4 Beds ⋅ 3 Baths ⋅ CVR-2612848 MLS

Welcome to the Hanover model, offering a modern open-concept living space designed to meet your family’s needs. The main level features a combined family room and casual dining area, creating a spacious area perfect for entertaining and daily activities. The chef-inspired kitchen boasts a large center island, a walk-in pantry, and ample counter space, making it ideal for cooking and gathering. A formal dining room and office provide additional spaces for both work and relaxation, while a convenient powder room completes the main floor. Upstairs, an additional living space provides even more flexibility, whether you need a home office, play area, or entertainment room. The primary suite is a true retreat, featuring a large walk-in closet 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 space for the whole family.This home is complete with a walk-out basement. The Hanover model offers the perfect live-play-work home, with flexible living spaces, modern amenities, and plenty of room for growing families. Photos and renderings are from builder's library and not a representation of the actual house. This is a to-be-built listing.

6270 Sterling Way, Ruther Glen

$1,250,000

5 Beds ⋅ 5 Baths ⋅ CVR-2611659 MLS

Welcome to your waterfront retreat on the Rappahannock River—where comfort, nature, and thoughtful design meet. This custom all-brick Colonial sits on 3.44 acres, directly across from the Rappahannock River Valley National Wildlife Refuge, offering sweeping river and wildlife views. At the heart of the home, the chef’s kitchen features Silestone countertops, a spacious island for six, a Wolf 5-burner gas range with hood, stainless steel appliances, a butler’s pantry, and elegant tile floors. Whether preparing a meal or entertaining, the river views from the kitchen make it a favorite spot for gathering. The family room is designed for relaxation, with a see-through gas fireplace and floor-to-ceiling windows framing the water. In the primary suite, enjoy trey ceilings, hardwood floors, a wet bar, a see-through fireplace, a custom bath with oversized jetted tub, and your own sitting area—perfect for peaceful river views each morning. Host gatherings or quiet evenings on the brick terrace or covered porch. Launch your boat from the private covered boathouse, with electric and jet ski lifts, or head out for kayaking, paddleboarding, fishing, or just soaking in the sights of ospreys and bald eagles. The dock is perfect for lunch or enjoying sunrises and sunsets. Downstairs, a full basement offers storage, finished living spaces with a kitchenette, a full bath, and separate private access. The Savaria elevator connects all three levels. Upstairs, four large bedrooms with Jack-and-Jill baths welcome family and guests. The fenced wrought iron yard is ideal for pets or children, while the refuge across the street offers hiking and endless views. Located in Port Royal, you’re only 25 miles from Fredericksburg, 17 miles from the Massaponax VRE, 16 miles from Dahlgren, and about an hour from Richmond or DC—a rare blend of privacy, natural beauty, and easy access.

1181 Caroline Street, Port Royal

$585,740

4 Beds ⋅ 3 Baths ⋅ CVR-2612751 MLS

Welcome to the Salem, a beautifully designed home offering a modern open-concept living space that meets all your family’s needs. This spacious home features a family room, kitchen, casual dining space, flex room, laundry room, and powder room on the main level, providing the perfect balance of comfort and functionality. The first-floor primary suite is a true retreat, offering a large walk-in closet and a luxurious bathroom with separate vanities and a private water closet for added convenience. Upstairs, you’ll find a huge bonus room with two walk-in closets, a full bathroom, and three additional bedrooms, offering ample space for your family to spread out and enjoy. The home is complete with a walk-out basement. This home combines open living spaces, modern design, and family-friendly features, making it the ideal choice for families seeking spacious living with plenty of storage and flexible space for all types of activities. Photos and renderings are from builder's library and not a representation of the actual house.

6278 Sterling Way, Ruther Glen

$749,000

7 Beds ⋅ 4 Baths ⋅ VACV2010182 MLS

PRICE REDUCED & UNMATCHED PRIVACY!! Welcome to your secluded 2.8-acre retreat in historic Port Royal! This beautifully and totally renovated 7BR/4BA brick ranch offers the perfect blend of absolute privacy and modern luxury. Enjoy a smooth entrance via the newly paved driveway to a home featuring a brand-new roof, new windows, and elegant flooring throughout. The chef’s kitchen is a culinary masterpiece, fully equipped with premium new appliances and a grand island. NO HOA means complete freedom to enjoy your expansive lot undisturbed. Perfectly positioned for effortless commuting, this rare gem offers peaceful country living with quick, easy access to both Fredericksburg and Richmond via Route 301 and Route 17. Don't miss this incredible value!

27197 Tidewater Trl, Port Royal

$589,740

4 Beds ⋅ 3 Baths ⋅ CVR-2612210 MLS

Welcome to the Hanover model, offering a modern open-concept living space designed to meet your family’s needs. The main level features a combined family room and casual dining area, creating a spacious area perfect for entertaining and daily activities. The chef-inspired kitchen boasts a large center island, a walk-in pantry, and ample counter space, making it ideal for cooking and gathering. A formal dining room and office provide additional spaces for both work and relaxation, while a convenient powder room completes the main floor. Upstairs, an additional living space provides even more flexibility, whether you need a home office, play area, or entertainment room. The primary suite is a true retreat, featuring a large walk-in closet 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 space for the whole family.This home is complete with a walk-out basement. The Hanover model offers the perfect live-play-work home, with flexible living spaces, modern amenities, and plenty of room for growing families. Photos and renderings are from builder's library and not a representation of the actual house.

6250 Sterling Way, Ruther Glen

$599,740

4 Beds ⋅ 3 Baths ⋅ CVR-2612209 MLS

Welcome to the Hanover model, offering a modern open-concept living space designed to meet your family’s needs. The main level features a combined family room and casual dining area, creating a spacious area perfect for entertaining and daily activities. The chef-inspired kitchen boasts a large center island, a walk-in pantry, and ample counter space, making it ideal for cooking and gathering. A formal dining room and office provide additional spaces for both work and relaxation, while a convenient powder room completes the main floor. Upstairs, an additional living space provides even more flexibility, whether you need a home office, play area, or entertainment room. The primary suite is a true retreat, featuring a large walk-in closet 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 space for the whole family.This home is complete with a walk-out basement. The Hanover model offers the perfect live-play-work home, with flexible living spaces, modern amenities, and plenty of room for growing families. Photos and renderings are from builder's library and not a representation of the actual house.

6292 Sterling Way, Ruther Glen

$585,740

4 Beds ⋅ 3 Baths ⋅ CVR-2612067 MLS

Welcome to the Salem, a beautifully designed home offering a modern open-concept living space that meets all your family’s needs. This spacious home features a family room, kitchen, casual dining space, flex room, laundry room, and powder room on the main level, providing the perfect balance of comfort and functionality. The first-floor primary suite is a true retreat, offering a large walk-in closet and a luxurious bathroom with separate vanities and a private water closet for added convenience. Upstairs, you’ll find a huge bonus room with two walk-in closets, a full bathroom, and three additional bedrooms, offering ample space for your family to spread out and enjoy. The home is complete with a walk-out basement. This home combines open living spaces, modern design, and family-friendly features, making it the ideal choice for families seeking spacious living with plenty of storage and flexible space for all types of activities. Photos and renderings are from builder's library and not a representation of the actual house.

6296 Sterling Way, Ruther Glen

$41,500

5 Beds ⋅ 3 Baths ⋅ CVR-2611731 MLS

This well-maintained Colonial in Belmont at Carmel Church offers a main-level primary bedroom with an en-suite bath that includes a soaking tub and separate shower. The main level features hardwood flooring, a center-island kitchen with table space, and a living area with a gas fireplace. Three additional bedrooms and a full bath are located on the upper level. The home includes natural gas utilities, public water and sewer, and a two-car garage with interior access. A fenced rear yard provides outdoor space, and the full unfinished basement with outside access and rough-in plumbing offers options for future expansion. Located about one mile from I-95, the property provides convenient access to restaurants, services, and commuter routes.

10621 Gallant Fox Way, Ruther Glen

$542,000

3 Beds ⋅ 5 Baths ⋅ CVR-2611362 MLS

Well maintained 4500+ finished sqft home on a corner lot with gleaming hardwood flooring & crown molding. This home boasts 9ft ceilings, formal dining room, study with built-in shelving, formal den, an in-law suite, gourmet kitchen, butler pantry, a fully finished walk-out basement with full bath, 6th bedroom, rec room, wet bar, storage room, theater-styled media room with surround sound wiring. The kitchen is finished with beautiful Corian countertops, ceramic tile backsplash, upgraded cabinets, and 2 pantries. Recessed lights are throughout home, tray ceilings and upgraded ceramic tile in mud room, master bath, powder room and in-law suite and a 9 x 14 trex deck! Hardwood upgrade in Foyer, Dining Room, Living Room, Study and Kitchen. Home is within walking distance to the YMCA, the library, and the neighborhood’s private gym, clubhouse, pool, playground, grilling area, amphitheater, dog park and community garden.

7239 Azalea Drive, Ruther Glen

$499,000

MDCM2007026 MLS

Excellent investment opportunity. Also perfect for a homeowner, live in one unit and let the other units pay your mortgage. 4-unit residential apartments fully rented with long-term tenants. Additional office space available. 5 units total. Current income from 4 units is $5,100/month, potentially $6,100/month including the office. Plenty of parking for tenants, guests, and customers. Updated kitchens and bathrooms. New water heaters. Brand new well system with 20-year warranty. Updated electric panels. 6 separate electric meters. 24 hour notice required for all showings. OWNER FINANCING AVAILABLE. CALL FOR DETAILS.

310 Main St, Marydel

$890,000

5 Beds ⋅ 4 Baths ⋅ VACV2010028 MLS

**BACK ON THE MARKET AT NO FAULT OF SELLER** Discover the perfect blend of luxury, comfort, and country living with this exceptional NO HOA 10-acre estate—fully equipped and ready for horses, chickens, and all the animals you can dream of! There is still plenty of wooded area that would be perfect for riding trails or subdivided if you wish. The spacious home features 5 bedrooms, including two large primary suites. One of the primary bedrooms is massive with a sitting room and upgraded designer walk-in closet. All bathrooms have been renovated. New wood flooring on the lower level and upstairs there are elegant Red Oak wood floors. You will also see nice touches throughout such as crown molding and wainscoting. The gourmet kitchen is a chef’s dream, boasting an oversized quartz island, a 6-burner commercial-grade gas range, new kitchen flooring, and a walk-in pantry. Step outside to your private oasis, featuring a heated in-ground pool and hot tub—both only one year old—along with a pool house perfect for entertaining. The deck boards were replaced just two years ago, and roof is only 5 years old with upgraded shingles. Equestrian enthusiasts will appreciate the impressive 4-stall barn complete with water, electricity, storage, a tack room, and a wash stall with a tankless water heater. The property also includes fencing, a chicken coop, and ample space for livestock, making it truly turnkey for farm and animal lovers. Additional highlights include a deep well, a cozy gas fireplace, a Generac whole-home generator for peace of mind, and a spacious three-car garage. Many items will convey with the home such as chicken coop, pool lounges, deck furniture, all lawn equipment (big mower, commercial weed eater, blower, elite drag) and some equestrian items. This extraordinary property offers the ultimate in refined rural living—where luxury meets tranquility. Schedule your private tour today!

20029 Jericho Woods Ln, Ruther Glen

$1,695,000

4 Beds ⋅ 4 Baths ⋅ VACV2009396 MLS

A Majestic private estate with expansive acreage, refined living spaces, and room for horses & family play! Welcome to Southbrook Plantation c.1813, a stunning combination of a grand historic home and elegant renovations. This remarkable property, comprised of three parcels totaling 41.97 acres, offers 4 bedrooms, 3.5 bathrooms, and 4,064 square feet above grade, plus a partially finished (1,300 sq ft.) basement. It is complete with a renovated detached 5-car garage (2022), and a six-stall horse barn (built in 2023), all thoughtfully designed for both elegant entertaining and comfortable everyday living. A grand foyer makes a striking first impression, illuminated by dual chandeliers and framed by a sweeping L-shaped staircase, while 12-foot ceilings throughout the main level and enhance the home’s sense of openness and light. Rich hardwood floors and detailed wood trim extend throughout the home, reflecting timeless craftsmanship and architectural elegance. The formal dining room provides an elegant setting for gatherings, framed by dramatic floor-to-ceiling windows and enhanced by a chandelier, detailed millwork, and a gas fireplace, with direct outdoor access. The newly renovated kitchen (2025) centers around an expansive island with seating. It is appointed with a 6-burner KitchenAid gas range, custom hood, double ovens, built-in microwave, refrigeration drawers, paneled dishwasher, and custom white extended-height cabinetry. Quartz countertops extend to the wall as a full-height backsplash, creating a refined aesthetic. Just off the kitchen, the updated laundry room (2021) features tile flooring, a Samsung washer and dryer (2025), ceiling fan, mini-split system, and secondary exterior entrance. The formal living room flows into the spacious family room, creating inviting areas for gathering and entertaining. Both rooms feature fireplaces, including gas logs (2022) in the front living room. A beautiful half bath is located near the staircase. At the first landing, an inviting room with hardwood floors and wall sconces provides the perfect space for a reading retreat, home office, or private fitness area. Upstairs, the spacious primary suite offers dual closets and a beautifully renovated bathroom (2021) with tile flooring, a clawfoot soaking tub, a dual-sink vanity, and a walk-in shower with glass doors and white subway tile. The second level features 10-foot ceilings, enhancing the sense of space throughout. Hardwood flooring continues throughout the additional bedrooms, two of which feature dual closets and fireplaces, while another bedroom also includes a fireplace and generous closet space. A large hall bath with a tub/shower combination and linen storage serves secondary bedrooms. The partially finished basement, remodeled in (2024, includes a recreation or playroom with a full bath and an additional room currently used as a home gym, offering flexible space for a variety of uses. Unfinished areas provide storage and house the mechanical systems, including a Culligan water treatment system and tankless water heater (2021). A brick patio and mature flower garden with a pergola offer a peaceful retreat, while apples, peach, and 40 pecan trees add seasonal beauty throughout the property. Equestrian amenities include a six-stall horse barn, two covered porches, and black wood fencing enclosing the 6-acre pasture—ideal for horses or hobby farming. Recent improvements include 5-car garage, upstairs HVAC (2025), REME HALO air purification systems (2021), septic system (2021) with updated hardware (2025), refinished hardwood floors (2021), fiber optic internet (2021), electrical and plumbing (2021), full exterior paint and window reglazing (2024), whole-house generator (2022), 330-gallon propane tank (2022), flat roof replacement (2021), Radon mitigation (2021) and gutter guards (2021). This exceptional property blends classic elegance, open land, and equestrian living.

8065 Macedonia Rd, Woodford

$1,150,000

4 Beds ⋅ 4 Baths ⋅ MDCM2006446 MLS

Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished wood floors (2023), freshly replastered / painted walls (2023), updated marble bathrooms, brand new gas stove (2025), HVAC split systems (2019), roof (2016), septic (2009), well (2013), pool liner (2020), and a new propane tank and pool heater (2022) for the in-ground pool. Additional outlets, recessed lighting, and ceiling fans have also been added for modern convenience (2022). Outdoors, enjoy the best of Eastern Shore living—fishing, boating, kayaking, or swimming right from your backyard dock on the scenic Choptank River. Relax poolside, gather around the firepit, or simply take in the tranquil water views. With a strong history as an income-generating Airbnb, this property offers exceptional versatility as a private retreat, family estate, or investment opportunity. And to top it off, enjoy a day of golf right next door at Caroline Country Club! Don’t miss your chance to own a piece of Maryland history—and let the riverfront veranda echo with history while you sip your morning coffee.

24800 Pealiquor Road, Denton

$740,000

5 Beds ⋅ 4 Baths ⋅ MDCM2006916 MLS

Back on the Market at No Fault of the Seller! Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‑concept living. To your right, a versatile flex room offers the perfect space for a home office, formal dining, or private study. Forward lies the heart of the home — a spacious living area seamlessly connected to the kitchen and breakfast room beneath soaring vaulted ceilings with skylights and abundant natural light. Custom built‑ins add character and thoughtful storage, while generous cabinetry and direct access to the backyard and pool make the kitchen a chef’s delight and entertainer’s dream. Enjoy floor heating throughout the family room, and sunroom for year‑round comfort. The primary suite offers peaceful backyard views, a private bath, and a walk‑in closet — a true owner’s retreat. Upstairs, an airy den provides a perfect media or lounge space, ideal for family, study, or hobbies. Plumbing is roughed in upstairs for a future bar, adding even more entertaining potential. The L-shaped floorplan flows seamlessly into a cozy family room and a sun-drenched sunroom, complemented by an attached three-car garage for ample parking and storage. Sited on approximately 2 acres, the fenced backyard feels like a private oasis — featuring a concrete pool with regular maintenance and a brand-new pump, lush Bermuda grass, and a shed for storage or gardening tools — all without the restrictions of an HOA. Brand new screens are also included (still in boxes in the attic), ready for installation. Located in charming Denton, Maryland, this home places you in a community rich with small‑town character and natural beauty. Within walking distance to the Caroline Country Club & Events Center, enjoy nearby parks, recreational fields, tennis and pickleball courts, picnic areas, and trails for outdoor fun, as well as easy access to fishing, boating, and stunning sunsets along the historic Choptank River. This is a rare opportunity to own a home where spacious design, thoughtful amenities, and idyllic surroundings come together — a place where you’ll love to live and entertain for years to come.

24764 Pealiquor Rd, Denton

$710,000

6 Beds ⋅ 5 Baths ⋅ MDCM2004710 MLS

BACK ON THE MARKET AND READY TO GO.....Buyers Financing fell through. All inspections (Home, Septic & Well) are completed and any issues have been addressed. Seller says "COME ON DOWN AND LETS MAKE A DEAL". Gorgeous 12.12 acre tree lined property. This privately built home has features one could only dream of...consisting of 5,000 plus sq. ft. , this home has a total of 6bd &4.5ba. It is perfect for family and friends alike. The property, is almost equally split between open/tillable & wooded land. A chef inspired eat-in kit w/granite, double oven w/air fryer & convention, range, microwave, double sink, trash comp, 2 refrigerator/freezer & tons of cabinet & drawers. Just off the kitchen is the main level laundry room. Recent upgrades include the roof, LVP Flooring in portions of main level, Fresh Paint and Crown Molding throughout. This home consists of a Huge LR, FR & study. Listing photos show off room sizes as well as virtual de-core, to demonstrate possible furniture placement. The property is equipped with a conventional Well, being fed from an aquifer. This well is drilled 385ft and is capable of pumping 75 gallons/minute. The septic has a 1500 gal tank with 400 feet of drain field . Septic has been professionally inspected, cleaned and scoped. Another unique feature of this home is the option to heat this beautiful home with wood fired or oil baseboard hydronic (water) heat. The hydronic systems have 7 zones. An alternative heating/cooling option is available by way of 3 new Ultra Efficient Bryant Infinity Heat Pump Systems. The heat pumps have 3 zones. This is not just a house, it has its own identity, when you go behind the walls or beneath the house. In addition to this lovely home the property also contains a 60X42 Morton Building with electric & heat as well as an outdoor pavilion equipped with a subzero fridge which could be used for a variety of activities. A deeded driveway leads back to this secluded oasis with a paved circular driveway and tons of parking. A perfect backdrop to get away from the hustle and bustle of daily life, and enjoy he beauty and quiet of nature. Not only is property perfect for large families, with a little effort it could be an event space for parties, bbq's and/or special events. How about hosting retreats for all sorts of organizations or clubs, perhaps home based business such as daycare provider or landscaper company? There is always the option adding few horses for your enjoyment. The possibilities are endless. Please note this property is not sub-dividable. However the addition of ADU's are possible with county approval. 6 acres of the property have been assessed forestation for a slight reduction in property taxes. County property taxes could be lowered if you file to change to a non residential classification. Please note tractor and accessories and trailer are negotiable. Call to see this property today.

15184 Jarrell Road, Goldsboro

$435,000

5 Beds ⋅ 4 Baths ⋅ MDCM2006444 MLS

Welcome to this spacious beautiful family home in a desirable subdivision. This 5 bedroom 3.5 bathroom home is inviting the inut you walk through the door. This home boats a first and second floor primary suite tha is perfect for in laws or guests. If closet space is essential to you than you will love the closet space in the 2nd floor primary suite. It's a dream space for anyone with an expansive wardrobe because there is more than enough room for every thing. This stunning home is the largest in the community and provides over 4000 sq feet in addition to a three car garage. This beautiful home is overloaded with so much character as well as a commodious entertainment/recreation room. There's a patio that overlooks the mature trees for a peaceful and serene setting for entertaining, grilling. or just relaxing outside.

1233 Painted Fern Road, Denton

$1,200,000

6 Beds ⋅ 3 Baths ⋅ MDCM2005608 MLS

Back on the Market due to Buyer's FSA financing falling through. SELLER NOW OFFERING A $20,000 CREDIT TOWARDS FRESH PAINT & NEW CARPET! Welcome to Thanksgiving Farm, an exceptional opportunity to own nearly 100 acres of prime Eastern Shore farmland just minutes from charming small towns and within easy reach of Ocean City, Annapolis, and major airports. This versatile estate includes two parcels – one is a separate, buildable 13.81-acre lot, offering future flexibility or potential multi-generational living. Tucked at the end of a long private drive, the main home is a thoughtfully designed farmhouse that perfectly blends classic charm and practical living. The home features four spacious bedrooms upstairs, including a private primary suite with a sitting area, large bathroom, and direct access to a massive bonus room – perfect for a home office, yoga studio, sewing room, or playroom. The bonus room also has its own private staircase, making it a truly flexible space. On the main level, enjoy hardwood floors throughout, a light-filled kitchen that opens to a casual dining area and cozy family room with a wood stove. Just off the family room, a large screened-in porch overlooks the property’s picturesque fields, gardens, mature trees, and classic barn. A formal living room and dining room round out the main level, ideal for gatherings and entertaining. There’s also a convenient first-floor bedroom. The unfinished attic—with walk-up stairs, windows, and skylights—offers the potential for a bunk room, office, or gym, while the walk-out basement is ideal for a workshop or storage and connects directly to the attached garage. Outdoors, the land itself is the true star. Of the 99.81± total acres, approximately 70 are tillable—ideal for row crops or converting to a regenerative farm. Several low-lying areas create opportunities for duck ponds or managed impoundments. The remainder of the property is wooded and absolutely teeming with wildlife—whitetail deer, turkey, and more—making it a hunter’s paradise. A large equipment shed offers ample space for tractors, ATVs, RVs, boats, and anything else you can imagine. Whether you’re looking to work the land, create a multigenerational retreat, or simply unwind in the heart of Maryland’s farm country, Thanksgiving Farm offers endless possibilities.

14271 Cedar Lane, Greensboro

$514,900

5 Beds ⋅ 4 Baths ⋅ VACV2009238 MLS ⋅ Newland Communities BLDG.

Welcome to 17182 Perinchief Street! A beautifully refreshed and thoughtfully upgraded home in the heart of Ladysmith Village, where modern comfort meets timeless community charm. Step inside to soaring 10-foot ceilings, freshly painted rooms, new carpet throughout, and new hardwood flooring on the main level, creating a warm, bright, and welcoming atmosphere from the moment you arrive. The home has been meticulously maintained and enhanced, featuring a whole-house water softener, reverse osmosis system, and a 2021 water heater, offering everyday comfort and peace of mind. Major systems are in great shape as well, with the roof and HVAC both replaced in 2011. The gourmet kitchen is ideal for both relaxed weeknights and lively gatherings, complete with a butler’s pantry and seamless flow into the open living spaces. The home is pre-wired for HDMI and CAT5, and the downstairs media room comes wired for surround sound, making movie nights and game days feel like a true cinematic experience. Curtain rods and curtains will convey for an effortless move-in. Outdoor living shines here: enjoy a newer deck with pergola (2024) constructed using locally sourced treated lumber from Madison Wood Preservers, a new rear door leading outside, and an expansive stamped concrete patio with fire pit, perfect for quiet evenings under the stars or entertaining friends all weekend long. Upstairs, soaring 9-foot ceilings enhance the spacious bedrooms with an airy openness, filling them with natural light while offering comfort and versatility—perfectly completing the home’s inviting design. Beyond your front door, Ladysmith Village offers some of the region’s best community amenities: an outdoor theater, multiple playgrounds, a dog park, pools, fitness room, clubhouse, walking trails, and even a YMCA on site. With quick access to I-95 and Route 1, commuting, shopping, and weekend adventures are easy and convenient. At 17182 Perinchief Street, every detail has been thoughtfully selected to elevate your lifestyle! Whether you’re hosting, relaxing, or enjoying the vibrant community around you.

17182 Perinchief Street, Ruther Glen

$750,000

5 Beds ⋅ 4 Baths ⋅ CVR-2600132 MLS

**ASSUMABLE LOAN***Welcome to Lakeside Living! This Stately Brick Waterfront Home on Beautiful Lake Caroline offers more than what you see from a picture or from the street! Take a real look at this 1.15-acre entertaining paradise that offers 180 feet of shoreline with beautiful lake views. This renovated raised ranch features 2-level living including 5-bedrooms, 3.5-baths with space for all your family & friends to enjoy. Lovely open concept living spaces, The Custom Kitchen features granite countertops, SS appliances, tons of storage and a spacious island for entertaining. The primary suite is complete with custom marble, double vanity, large Oval Soaker Tub. The basement offers a "NEW FULL BATH" entertaining areas, media room, lots of storage wood fireplace and more. And don't forget the MULTI-CRAFT DOCK , firepits, horseshoe pit, fruit trees, flower / vegetable gardens and... the icing on the Cake.... The detached garage! 24’x24’ with 200-amp service, with a 24' x 16' added workshop in the back! With a fenced area for any additional storage needs. Side area on the right of the garage was created for an RV/Bus in mind. Plenty of room for all of your toys, cars and equipment! 24/7 Gated community, 2 boat ramps, 2 sandy beaches, playgrounds, pool, clubhouse and courts for tennis, pickleball, and basketball—all while embracing an active lake lifestyle with boating, swimming, and kayaking at your doorstep. Your Lakeside Paradise Awaits! This extraordinary waterfront retreat blends luxury, comfort, and recreation into one breathtaking property. Schedule your private showing today! Lake Caroline is located just off I-95 between Ashland & Fredericksburg for easy commuting all around. Close by you will find: Shopping, Pendleton Golf, Library, Community Theatre, Farmer's Market & YMCA, Just down the road a bit - Kings Dominion, the Virginia State Fair, Dominion Raceway & New Kalahari Water Park Coming Soon ! Come check out this gorgeous property in Caroline County's Best Kept SECRET ! LAKE CAROLINE

20 LAKE CAROLINE DRIVE, Ruther Glen

$781,000

4 Beds ⋅ 4 Baths ⋅ VACV2008336 MLS

This stunning waterfront home in the gated community of Lake Caroline sits on 1.3 acres on a triple lot with 220 feet of shoreline and a boat dock. It features an open floor plan with vaulted ceilings and seven skylights throughout. You will love the abundance of natural light throughout! Custom kitchen includes granite countertops, stainless steel appliances, a double-door pantry, and a large island adjoining the great room with its four retractable skylights. From the great room step onto the screen porch or spacious deck which open to the luxuriously landscaped backyard. Easy-care perennial plantings throughout the property. The primary bedroom on main level includes full bath with custom shower and a walk-in closet. Second floor features a bedroom, full bath and a loft overlooking the great room. A major remodel in 2008 added a suite above the attached side-loaded two-car garage. The suite includes two bedrooms, a large sitting room, full bath, and is equipped with separate heating and AC. This serene home is a beautiful place to live, entertain and relax.

210 Lake Caroline Drive, Ruther Glen

$402,000

4 Beds ⋅ 3 Baths ⋅ MDCM2006308 MLS

Some homes just have that “stop everything and take a closer look” vibe and this is one of them. Discover a home that blends space, comfort, and small-town charm on Maryland’s beloved Eastern Shore. This 4-bedroom, 2.5-bath beauty offers thoughtful design, oversized rooms, and a backyard retreat you’ll never want to leave. Step inside through the soaring two-story foyer and you’re greeted by hardwood floors that flow through the kitchen, breakfast area, and entryway. The kitchen is the heart of the home—complete with an expansive center island, coffee bar, abundant prep space, and a pantry large enough to hold everything you need and then some!. A spacious laundry room doubles as additional storage, while a versatile main-level flex room is perfect for a home office, guest suite, or in-law living space. Upstairs, the open loft fills the home with natural light and connects four oversized bedrooms—each with its own walk-in closet. The primary suite is a true retreat, featuring a spa-like bath with soaking tub, separate shower, an enormous walk-in closet, and even room for a cozy sitting area. Out back, you’ll find your private sanctuary: a vinyl-fenced yard with specialty trees, shrubs, and plants, a patio with built-in BBQ, and plenty of room for entertaining or relaxing outdoors. The rare three-car garage offers unparalleled convenience and storage. Tucked away on a quiet street yet minutes from everything, this home gives you the best of both worlds: peaceful surroundings with easy access to nearby parks, Martinak State Park, Tuckahoe State Park, and Adkins Arboretum. Enjoy the charm of Denton’s historic downtown, or take a short drive to the beaches of Ocean City and Delaware. Here, you’ll experience small-town living with a strong sense of community, surrounded by nature, recreation, and all the beauty of the Eastern Shore.

1111 Daylily Lane, Denton

$940,000

4 Beds ⋅ 4 Baths ⋅ MDCM2005578 MLS

Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural light and showcasing stunning views of the surrounding landscape. Perfect for both relaxation and entertaining, the open-concept main living area flows seamlessly into the dining room and a gourmet kitchen equipped with a large center island, custom cabinetry, abundant storage, and a bright breakfast area. Four fireplaces—including one in the cozy family room—add warmth and character throughout the home. A dedicated billiard room with direct outdoor access offers a versatile space that could also serve as an art studio, media room, or more. The expansive primary suite is a true retreat, featuring a private marble bath, separate workout and tanning rooms, and peaceful garden views. Bedroom flexibility, built-in features, and an upstairs suite with en suite bath offer options for multi-generational living or hosting guests with ease. Outdoors, enjoy your private, fenced backyard oasis complete with a sparkling in-ground pool and a deep-water dock—ideal for boating, kayaking, or simply soaking in the tranquil beauty of the riverfront setting. Additional amenities include a detached garage with a second-floor loft perfect for storage, studio space, or a workshop, and a separate shed for tools and equipment. Located just outside the town of Denton, you’re only minutes from charming shops, dining, and state parks, all while enjoying the privacy and serenity of a secluded waterfront lifestyle. This is a rare opportunity to own a truly remarkable Eastern Shore property where luxury meets nature.

8816 Dorothy Lane, Denton

$450,000

4 Beds ⋅ 2 Baths ⋅ CVR-2523723 MLS

Gorgeous & recently updated, this move-in ready rambler is set against one of the most peaceful landscapes you’ll find. From the moment you arrive, the welcoming front porch invites you home, while modern updates inside create a bright and refreshing space you’ll be proud to call your own. Hardwood and luxury vinyl plank floors flow through the main living areas, while the light-filled kitchen boasts new white cabinetry, granite counters, and abundant prep space, making everyday living and entertaining effortless. Four spacious bedrooms on the main level are complemented by two beautifully updated baths with stylish fixtures. Upstairs, two versatile bonus rooms offer endless possibilities—home office, playroom, or even another bedroom—providing flexibility to fit your lifestyle. The expansive full-footprint basement is bright and inviting, featuring a cozy fireplace and space for recreation, hobbies, or future finishing. Multiple internet options make working or streaming from home simple. Resting on over an acre and bordered by Virginia Land Trust–protected land, the property ensures lasting privacy and natural beauty with no risk of development. The wide-open yard is a blank canvas for gardens, play areas, or even a hobby farm, while a respected local farmer maintains the surrounding fields. Despite its tranquil “middle of nowhere” feel, you’re just 25 minutes from Fredericksburg or Tappahannock, 40 minutes to Dahlgren, and within reach of Richmond, La Plata, and Washington, DC. Both Andrews and Langley Air Force Bases are just over an hour away, making this an excellent choice for military families. With no immediate neighbors yet a welcoming community nearby in Bowling Green, Caroline, and Lake Land’Or, you’ll enjoy the rare balance of privacy, space, and small-town charm. More than just a house, this is a beautifully updated home offering modern comforts inside and endless opportunities outside.

19248 Passing Road, Milford

$475,000

5 Beds ⋅ 6 Baths ⋅ VACV2005786 MLS

Timberlake Manor - Step into a slice of history nestled in the heart of Port Royal! This remarkable home, steeped in the rich tapestry of the 18th and 19th centuries, epitomizes timeless charm and architectural splendor. Upon entering, you're welcomed by a magnificent great hall, boasting a marble floor that sets the stage for the captivating history and elegance that flows throughout this residence. Sprawling rooms and charming fireplaces scattered throughout invite you to envision the countless tales woven into the fabric of this home over the centuries. Spanning nearly 6,000 square feet, this expansive abode offers abundant space for living, entertaining, and crafting cherished memories with loved ones. A modern family room, added in the 1990s, seamlessly melds contemporary comfort with the home's enduring allure. While restoration is needed to restore this gem to its former glory—calling for a new roof and some carpentry work—the potential is boundless. Surrounded by the quaint charm of a historic town and mere steps from a 125-acre wildlife refuge, this residence offers a peaceful retreat into nature's embrace. Its proximity to other historic homes further enhances its allure, providing a glimpse into the captivating history of Port Royal. Experience the enchantment of this historic treasure firsthand. Schedule your showing today and embark on a journey through time as you discover the timeless beauty and endless possibilities that await within this magnificent home."

909 Caroline Street, Port Royal

$2,400,000

8 Beds ⋅ 9 Baths ⋅ CVR-2525654 MLS

Step into a world of peace and tranquility at this exquisite Virginia estate, beautifully reimagined and redesigned to serve as the ultimate retreat center. Nestled in a picturesque country setting, this 184-acre property offers endless possibilities for relaxation, recreation, and rejuvenation. The newly remodeled main house epitomizes modern luxury with its 8 spacious bedrooms, 8.5 elegantly updated bathrooms, and a gourmet kitchen featuring all new appliances. Every corner of this home has been thoughtfully updated to blend contemporary comfort with timeless elegance. In addition to the main house, the estate includes a contemporary two-bedroom villa and a charming three-bedroom guest house, providing ample space for guests or extended family. For those seeking a unique experience, the property also features five glamping tents and an adobe hut, each ready to be transformed into personalized retreats. Outdoor amenities are designed for ultimate comfort and enjoyment. A custom-built swimming pool offers a private oasis for relaxation, while numerous walking trails invite exploration and connection with nature. The expansive rolling pastures are perfect for horses or cattle, adding to the estate's charm and versatility.

14186 Devils Three Jump Road, Milford

$225,000

MDCM2005270 MLS

THIS HOME IS BACK ON THE MARKET DUE TO A BREACH. FROM NO FAULT OF THE SELER. This home is located in Downtown Denton close to and within walking distance to most everything. The home has lots of potential to be and easily transformable to a Duplex or maybe additional units. Live either on the upper level or lower level and rent the other. Also offers a full Attic . Lots of Possibilities . Seller will consider all reasonable offers. Home is sold As Is

505 Market Street, Denton

$6,900,000

4 Beds ⋅ 5 Baths ⋅ VACV2008326 MLS ⋅ Rose Hill BLDG.

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

$494,000

4 Beds ⋅ 4 Baths ⋅ MDCM2005366 MLS

Check out this beautiful 2023 build. With a wrap around front porch and 24'x 30' pole barn with 2 14' pull through doors. Currently finished off as a 3 bed/ 2.5 Bath on the main floor with the upstairs roughed in for a 4/5th bedroom and a full bath or optional bonus room. Wide open floor plan, spacious kitchen great for entertaining with stainless appliances, granite counters, bar height end top, 2 large islands. Durable LVP Flooring through out the main living area with carpeted bedrooms. Supplemental pellet stove heat for those super chilly days. Large primary with walk in closets and an over sized bath, dual vanities, large tile shower with dual shower heads & built in's. 2nd bath close proximity to the 2nd & 3rd bedrooms. Full sized laundry room with sink. Outside you'll find side walks taking you out to your large shop or pool with wrap around deck and swings. Plenty of room out back for all your animals, large fenced in area and a chicken coop. Also a second outdoor shed with lean-too for even more storage.

25879 Brookwood Road, Greensboro

$619,999

5 Beds ⋅ 4 Baths ⋅ CVR-2521684 MLS

LAST 3-CAR GARAGE HOME! AMAZING PRIVATE LOT! Welcome to this 5 bedroom, 3.5 bath, Hemingway home boasting over 3700 square feet and nestled on a private, wooded cul-de-sac lot. Lovely Curb appeal, Craftsman-style exterior and an inviting front porch greet you to your home. Main level features a study area, chef’s gourmet kitchen with custom-curved quartz island, which opens to the spacious family room with a cozy fireplace. From the kitchen, dine or relax in your sunroom with picturesque windows and transom(s) that overlook your very private yard. Oak stairs lead you upstairs, and you are welcomed by an airy loft, three well-appointed bedrooms, laundry room, hall bath and the luxurious primary suite. Primary bath is a must-see with the showstopper ‘Spa Shower’, expansive double vanity, private water closet and huge WIC. The finished basement offers plenty of space to relax or entertain with a massive, finished rec room, full bath and 5th bedroom. Ample storage with the 3-car garage and huge basement!! Come see this one today before it is gone! READY NOW!

7086 Braxton Court, Ladysmith

$600,000

6 Beds ⋅ 5 Baths ⋅ VACV2008242 MLS

TWO HOMES FOR PRICE OF ONE! ...Opportunity to own a property where historic charm meets modern opportunity in downtown Bowling Green! The main house boasts over 2927Sq Ft with 4 Beds and 3 baths PLUS an additional 1800Sq Ft 2 bed 2 bath Income Property that would make the perfect In-Law Suite or Short Term Rental. This beautiful Queen Anne Victorian Home sits on just under 4 acres, built in the 1900s, and still has a lot of the original charm. Features include original hardwood floors, exquisite detailing, grand staircase, built ins, pocket doors, open kitchen with pantry, sunroom, five unique fireplaces, den/office space, and so much more. There is a main floor primary suite as well as additional large bedrooms upstairs. Formal dining room. Custom windows throughout with tons of natural light! This home has a large country front porch, side fenced area/deck for your pups, and large enclosed back porch with fans/speakers that would be perfect for entertaining. The second home on the property has its own separate parking lot and was renovated as a wedding venue in 2014. This home features beautiful windows, LVP Flooring, its own kitchen, and set up with two primary beds/baths. This multifunctional property could be used as wedding venue, apartments, in-law suite, or a short term rental property for extra cash flow! Plus there is a detached 2 car garage with shed/workshop with electric and second storage shed. Lot is beautifully landscaped with patio areas, sprinkler system, and plenty of space for family fun. Dual HVAC. NEW ROOF! Located in the heart of Bowling Green this home is walkable to restaurants, shopping, town square, and entertainment. Central location only 30 minutes to Fredericksburg and 30 minutes to Richmond. Excellent location trash/leaf removal is included in town taxes. (Assessed value is $496,200 plus added $168,900 for second home with old address of 117 E Broaddus = Priced below taxed assessed!!)

115 E Broaddus Avenue, Bowling Green

$1,875,000

4 Beds ⋅ 3 Baths ⋅ CVR-2520067 MLS

Auburn Hill is a 397-acre farm that blends history, natural beauty, and recreational appeal. Located in Caroline County, this property offers an exceptional lifestyle, with wildlife and outdoor recreation at its core. The centerpiece of the property is a historic residence, originally built by Edmund Pendelton in 1740. This home has been carefully restored to preserve its original charm while integrating modern comforts. It features two upstairs bedrooms, a finished children’s attic, and two additional bedrooms in the finished basement. The restoration showcases original heart pine floors, exposed beams, high ceilings, and original brickwork The grounds include a saltwater pool, a garden, and a brick terrace—perfect for outdoor gatherings or relaxation. Several restored outbuildings, including barns, sheds, a corn crib, and a two-story tobacco barn, provide additional space for entertaining. Auburn Hill includes a diverse mix of cropland, wildlife food plots, hardwood slopes, managed pine stands, and wetlands. Maracossic Creek borders the property to the east, and Doctors Creek lies to the south, enhancing its privacy. For outdoor recreation, Auburn Hill is second to none. Over the past decade, the current owner has carefully managed the land to support thriving deer and turkey populations. Extensive food plots, habitat corridors, and a long-term harvest plan contribute to healthy wildlife populations. The property features two stocked ponds ideal for fishing and a wetland complex that provides additional waterfowl habitat. An extensive network of trails winds throughout the property, including a maintained beach and picnic area along Maracossic Creek. About half of the property is protected by a Virginia Outdoors Foundation (VOF) conservation easement, ensuring its preservation for future generations. Auburn Hill offers a rare opportunity to own a property that has history, natural beauty, and close proximity to Richmond and Fredericksburg, making it a perfect retreat, recreational haven, and wildlife sanctuary.

23390 Mt Cloud Road, Bowling Green

$907,650

4 Beds ⋅ 3 Baths ⋅ MDCM2005584 MLS

This 20.2 acre farm includes a second parcel of 49.99 acres that is all woods. Fenced in for horses, cattle or sheep with a pole shed for protection , hay and equipment storage. A two story home with 4 bedrooms and 3 baths. Also an apartment above the garage for an additional bed and bath. More pictures to come. Not available to be shown until April 21, 2025

21710 Marsh Creek Road, Preston

$835,000

5 Beds ⋅ 5 Baths ⋅ MDCM2005396 MLS

Welcome to 22879 Stevenson Road, Ridgely, MD – a private oasis nestled down a winding country lane. This exquisite residence, adorned with elegant Hardie board siding, captivates from the moment you arrive with its inviting front porch and meticulous attention to detail. Step inside to discover the grandeur of a spacious 5,328 +/- square-foot home, where gorgeous bamboo hardwood floors and rich, warm tones create a welcoming ambiance. The main living area boasts a stunning stone gas fireplace with a live edge mantel, set against soaring ceilings and spaces filled with natural light. The open floor plan flows graciously to the dining space and well-equipped kitchen with counter seating. This chef’ s dream offers ample cabinetry, granite workspaces, and a full suite of stainless-steel appliances including a gas stove and double wall oven. Located directly off the kitchen is a slate-tiled mudroom with laundry and built-in cabinetry. Also found on this level is the inviting den space with vaulted ceilings and access to a cozy deck offering the perfect place to enjoy morning coffee or cool beverages at the end of the day. Completing the first floor is the restful primary suite complete with a private, four-piece bathroom and three large closets. Upon continuing through the home and up the gorgeous staircase, the second floor unveils a spacious loft area, a charming princess suite with a Jack and Jill bath, and two additional bedrooms or flexible spaces, offering versatility for any lifestyle need. There is also access to the full-height, floored attic area. Back downstairs, you will find an epic daylight basement with a custom epoxy floor, that provides versatile options for a home theater, gym, or entertaining area, while still offering extensive storage solutions. There is a powder room and access to the backyard and pool as well for seamless entertainment. For added convenience, the front-load garage features two oversized bays, as well as built-in cabinetry and a work sink. Just above this space is the large in-law apartment or guest suite. This private bonus space offers its occupants a kitchen plus living and dining areas, as well as, a large bedroom and bathroom, ensuring ample room for guests or extended family. There is even dedicated separate laundry and attic storage for this unit. Outside, a spectacular living area awaits, designed for both leisure and entertainment. With extensive hardscaping, paver and concrete patios surrounding an inviting in-ground concrete pool, this area is perfect for hosting gatherings or enjoying quiet relaxation. This home is more than just a residence; it's a lifestyle. Experience the blend of elegance and functionality in this remarkable property, where every corner speaks to luxury and thoughtful design.

22879 Stevenson Road, Ridgely

$637,000

6 Beds ⋅ 3 Baths ⋅ MDCM2005496 MLS

This is a WOW!!! Looking for Space??? Let me present to you "24656 White Dogwood Drive". Home Features 6 Bedrooms, 3 Full & 1 Half Bath. Large Eat-in Kitchen with lots of Storage with Center Island with an adjacent Breakfast Nook. Separate Dining Room , Spacious Family Room which leads to Patio and Large level Lot. Primary Bedroom on First Floor with Super Bath to include Walk-in Shower with separate tub and vanities. Nice Walk in Closet, and a short hallway to an Office area with lots of light .Bedroom #2 on the First floor also! Upstairs you will find an Open area for Office, Bedrooms 3, 4 & 5 - an additional Bonus Room or Bedroom #6. Full Bathroom and a Walk-in Attic space. Crawlspace has recently been fully encapsulated Outdoors you will find a 40x30 Pole Building. (Currently used for a Party Room) Easily can be brought back to a Garage. Home is very Private and centrally located within 45 minutes to the Bay Bridge. Maryland and Delaware beaches within an Hour!! Choptank River right up the street for the boating enthusiasts. Come Check this out Today. Alot of Bang for your Buck!!!

24656 White Dogwood Drive, Denton

$718,200

3 Beds ⋅ 3 Baths ⋅ VACV2006864 MLS

REAL WOOD not plastic or vinyl is found at the house at Auburn. A unique floor plan, not a cookie-cutter tract house is found at Auburn. The NUMBERS are impressive: Including the land, this offering is at $181 per square foot. A value of $170,000 for the 17 acres of usable, mostly level land in a classic small town near shopping and amenities is reasonable. Factor that value out of the price and the house is at $140 per square foot for a house built with REAL WOOD. A classic example of Greek Revival architecture with tasteful additions is one of the reasons Auburn is on both the Virginia and National Registers of Historic Places. It is an outstanding property in a wonderful setting of fields and woods, all in the classic small town of Bowling Green; about 1 hour to downtown Richmond, about 20 to Fredericksburg, about 29 minutes to VRE and AMTRAK at 425 Princess Anne St. (Google map), which can take you to Washington, DC or points north. You can add-on to the house or tear it down. Only zoning and subdivision ordinances of the Town of Bowling Green apply with other ordinances. The state and federal governments have no authority of what you can do with the house, unless you want to participate in the tax credit programs. The house and 17.2 acres are not subject to any conservation easements. A great feature of being on the historic registers is, if someone chooses, to grant a conservation easement to generate federal tax deductions and Virginia tax credits. Home improvement projects might qualify for a 25% Virginia tax credit. Wood floors have a patina, luster which is warm and a contrast to other flooring types. Rooms are well proportioned. A large, screened porch in the back of the house provides great views of the gardens, fields, and woods. The sunroom with many windows is a great source of warmth and light in fall, winter, and spring. Photos of magnificent flower gardens are found in the books opened in the kitchen. Heat is mostly radiator, hot water with heat pumps in some rooms and providing air conditioning. The county kitchen is large with many windows, is off the dining room and a screened-in porch overlooking fields, woods, and if you choose to continue, gardens. STAIRS are unique to the second floor. Instead of a long steep staircase, a short set of stairs leads to a landing and then to the main bedroom. The second set of stairs goes from that landing to a hall and the other two bedrooms. Stairs are much more manageable with short sections and a landing. There is more privacy with the other two bedrooms off at a slightly higher level. Kitchen and public rooms are spacious with large windows. A separate two car garage is toward the back of the house and behind the garage is a shed for tools. The dog lot is near the garage. About 13 acres is farmed with the rental agreement year to year at $1,000 per year. Real estate taxes are lower with the farmland taxed lower. The farmer has the right to harvest his crops. The Owner will pay no roll-back taxes. The property has three (3) tax maps, the tax parcel with the main house and outbuildings and two other tax parcels of record which might be buildable house lots. Please see the Narrative in the Document Section of Bright. Go to "Virtual Tours" for link to photos, Videos, and 3D Matterport tour. Go to Documents in Bright at top of listing for detailed Narrative with hot links to other information. Please use the detailed Narrative found in the Document Section of Bright. PLEASE remove your shoes when going inside the house. First impressions count. Please have your realtor get the key from the back door, and then open and enter the front door to the great hall.

320 N Main N Street, Bowling Green

$175,000

MDCM2004882 MLS

123/123A/125 N Main Street, Federalsburg

$165,000

4 Beds ⋅ 2 Baths ⋅ MDCM2005208 MLS

Lots of local History!! Most recently -Town Office! Located on Main Street close to all the Shops, Restaurant's and Parks.....Not to mention the Choptank River! This is a Perfect spot for you to make your HOME or BUSINESS. First Floor offers Spacious Foyer Entry , Two Large Parlors, Full Kitchen, Bathroom and enclosed Sun Room/Conference Room. Upstairs includes Four Office/Bedrooms and a Full Bath. Huge walk up attic for extra storage. Entire property has hard wood floors. Full Dry Basement. 2 Car Detached Garage. Property has many opportunities-. Call today! Sold strictly AS-IS (Mold has been detected on second floor)

113 N Main Street, Greensboro

$630,000

6 Beds ⋅ 3 Baths ⋅ MDCM2005170 MLS

Welcome to 13869 Drapers Mill Road, Greensboro, MD—a home where space, style, and serenity come together! This stunning 6-bedroom, 3.5-bathroom home spans approximately 3,806 square feet, offering all the room you need to live, entertain, and make lifelong memories. Situated on 8.2 acres, the property provides endless opportunities to create your dream outdoor retreat—think pool, pole barn, or even a garden oasis! Step inside and be captivated by the thoughtfully designed floor plan, featuring fresh paint and modern finishes. At the heart of the home is the chef-inspired kitchen, complete with granite countertops, ample cabinetry with under-cabinet lighting, and a flood of natural light to brighten every culinary creation. The primary suite offers a peaceful getaway with a spacious walk-in closet and a luxurious en-suite bathroom, making it the perfect place to relax and recharge. Additional highlights: Generously sized bedrooms for family and guests. Multiple living areas, including a versatile bonus room with a bar—perfect for game nights or gatherings. A new septic system was installed for peace of mind and long-term convenience. This is located just 1.5 hours from Ocean City, MD, and BWI Airport, offering the perfect balance of rural charm and accessibility. If you're ready to experience all this exceptional property has to offer, schedule your private showing today!

13869 Drapers Mill Road, Greensboro

$515,000

5 Beds ⋅ 4 Baths ⋅ CVR-2506193 MLS

Welcome to Your Dream Home! This stunning colonial, nestled in a peaceful cul-de-sac, offers elegance and modern updates throughout. The first floor boasts beautiful hardwood floors and soaring 9-foot ceilings, creating a spacious and inviting atmosphere. The newly remodeled kitchen features sleek stainless steel appliances, perfect for any home chef. Upstairs, the luxurious primary suite includes a large dressing area, a walk-in closet, and a beautifully updated en-suite bath. The fully finished basement provides additional living space, complete with a fifth bedroom and a full bath. Cozy up by the gas fireplace in the family room or admire the triple crown molding and tray ceilings in the living room. With stylish upgrades and plenty of space, this home is truly a must-see!

7246 Watkins Court, Ruther Glen

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