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406 E Baker St, Gordonsville
$439,900
5 Beds ⋅ 2 Baths ⋅ CVR-2622018 MLS
History and heart, beautifully preserved. Welcome to 406 E Baker St, a tastefully remodeled circa-1900 home set on just over an acre (1.02 acres) in the historic town of Gordonsville, Virginia. This 5-bedroom, 2-bathroom home offers a total of 2900 square feet across four stories plus a basement — a rare blend of turn-of-the-century character and thoughtful modern updates. Step through the large entry foyer into a home where tall ceilings carry the eye upward through all three stories. The kitchen has been fully updated with new appliances, and fresh paint runs through the interior and exterior, giving the home a crisp, move-in-ready feel. Yet the details that made this house special in 1900 are still here to enjoy: an original winding wooden staircase, classic pocket doors, and two fireplaces that anchor the living spaces in warmth and history. Outdoor living is just as generous. Three large porches — front, side, and back — wrap the home and open onto a gorgeous, sprawling backyard, ideal for entertaining, gardening, or simply enjoying Virginia's changing seasons. Set just a short walk from Main Street, 406 E Baker St puts you close to Gordonsville's historic downtown shops, restaurants, and wineries, with easy access to Route 15/33 and I-64, and about a 20-mile drive to Charlottesville. The home falls within the Orange County Public Schools district. Homes that pair authentic 1900 craftsmanship with a tasteful modern remodel rarely come up in Gordonsville — schedule your private showing today. The property also includes an additional dwelling/trailer that offers potential for renovation and possible future rental or income-producing use. New HVAC, and Water heater

406 E Baker St, Gordonsville

236 Caroline St, Orange
$999,000
7 Beds ⋅ 6 Baths ⋅ VAOR2014482 MLS
Nestled in the heart of Orange, Virginia, Chestnut Hill is a serene, picturesque property awaiting its next chapter. Once a nationally recognized and cherished bed and breakfast, this historic gem offers an extraordinary opportunity to restore it to its former glory—or reimagine it entirely. With Seven bedrooms and six bathrooms, nearly three acres of land, sidewalk access to local schools, shopping, and restaurants, as well as a private driveway and ample parking, the potential is truly endless. The property also features two outbuildings that provide additional versatility. Though the home has faced challenges, including a fire that required extensive renovations, its foundation remains strong, ready for a visionary owner to bring it back to life. Thoughtful renovations, modern updates, and curated landscaping could transform Chestnut Hill into a breathtaking retreat once again. Whether you envision it as a boutique bed and breakfast, a private residence, or any other inspired use, the possibilities are limitless with the proper approvals. Since the restoration is only partially complete, there’s a unique opportunity to customize the space to perfectly suit your needs. Imagine the possibilities—restoring it to its former status as a nationally recognized destination, creating a timeless retreat for guests seeking memorable stays, or reimagining the space for personal or professional purposes. With the right vision, this historic property can be transformed to achieve its full potential. Seize this chance to make your mark on an award-winning historic property. Chestnut Hill is ready to inspire your creativity and vision. Contact us today to explore the potential of this remarkable property and take the first step toward turning opportunity into reality.

236 Caroline St, Orange

102 Flat Run, Locust Grove
$975,000
4 Beds ⋅ 4 Baths ⋅ VAOR2014324 MLS
Welcome to 102 Flat Run, a stunning waterfront home that offers captivating 180-degree lake views, including both sunrises and sunsets. Perfectly positioned to maximize privacy from the road and scenic views toward the lake, this residence delivers an exceptional blend of comfort and low-maintenance lakeside living. Gleaming hardwood floors run throughout all living areas (excluding bathrooms), adding warmth and elegance. The first level features an inviting living room/office with a grand fireplace. A few steps then lead you to the expansive family room and dining area, highlighted by a dramatic wall of windows and doors that flood the space with natural light and showcase the breathtaking views. The well-appointed kitchen includes an island and a bright breakfast room, ideal for casual meals while enjoying the water. Step outside to the stunning composite deck overlooking the lake — the perfect spot for morning coffee or evening entertaining. The massive primary bedroom suite is a true retreat, complete with a luxurious bath featuring a soaking tub, separate shower, and two large walk-in closets. A second bedroom, full bath, and a half bath with laundry area complete the main level. The fully finished lower level offers outstanding versatility and space for guests or relaxation. It includes a spacious rec room, two additional bedrooms, a flex room with its own exterior door (ideal for a home office, gym, or guest suite), and another full bath. A huge screened porch runs the entire length of the house, providing even more outdoor living space protected from the elements. Direct access to the three-car garage is conveniently located on this level. Outside, the home boasts a maintenance-free yard with no grass to mow. Enjoy the stunning, colorful landscape, composite decking on the dock, a generous paver patio, and an electric boat lift — everything you need for effortless lakeside enjoyment. This exceptional waterfront property offers move-in-ready space with panoramic views, abundant natural light, and a lifestyle of relaxation and recreation. Don’t miss the opportunity to make this your new lake home. Located in a private, gated, secure community, Lake of the Woods offers anything and everything you could want. Home to two lakes (the 550-acre main lake and a 35-acre "fishing lake"), a golf course, an equestrian center, a fire and rescue department, and a church all within the gates, Lake of the Woods simply has it all. Whether your passion is boating, water skiing, kayaking, golfing, horseback riding, or simply taking in the breathtaking views from the clubhouse while enjoying a fabulous meal, from your deck or yard, or from one of the beaches, you won't be disappointed! Perhaps you'd like a game of bridge or volunteer your time and talents...Lake of the Woods offers more than 60 clubs and organizations. Located in Orange County, we are fortunate to enjoy low real estate taxes. Coupled with home prices ranging from $300,000+ to over $2,000,000, Lake of the Woods is the perfect community for full-time residents and weekenders. But don't take my word for it, please come see for yourself!

102 Flat Run, Locust Grove

21731 Berry Run Rd, Orange
$225,000
3 Beds ⋅ 2 Baths ⋅ VAOR2013990 MLS
Location, Location, Location! If you are looking for privacy and convivence this is the property for you. Welcome to this beautifully maintained 3-bedroom, 2-bath home situated on just over 2 acres of peaceful, private land. Built approximately 5 years ago, this home offers modern comfort with thoughtful design throughout. Step inside to find durable luxury vinyl plank (LVP) flooring and an open, inviting layout ideal for everyday living. The home features exposed beams that add warmth and character, creating a stylish yet comfortable at atmosphere. The spacious kitchen, with a large island and living areas flow seamlessly, while the bedrooms provide ample space and functionality. The kitchen features beautiful cabinets and a farm sink. The primary suite includes a walking closet, a private bath, offering a relaxing retreat, with a soaking tub, separate tile shower and double vanity. Additionally, there are two more guest rooms with large closets and a lovely bathroom with a tub/shower combination to accommodate guests. Outside, enjoy the expansive yard and natural surroundings, perfect for outdoor activities, gardening, or simply taking in the quiet setting. There's a beautiful front deck and rear deck that is perfect for entertaining. The property offers a balance of open space and wooded privacy, giving you room to spread out while still feeling tucked away. If you’re looking for a newer home in excellent condition with acreage and a peaceful setting, this property is must-see.

21731 Berry Run Rd, Orange

18184 Crawford Ln, Gordonsville
$650,000
4 Beds ⋅ 4 Baths ⋅ VAOR2013652 MLS
WOW! Great Price!! Custom Home on 13+ Wooded Acres with Mountain Run Frontage! This beautiful barndo home was built in 2023 offering a rare blend of rustic charm and modern craftsmanship. Designed with style and function in mind, the home features a striking metal and wood exterior, durable metal roof, cathedral and two-story ceilings, exposed steel beams, and wood-slatted accent walls that elevate its character. Step inside to a spacious foyer that opens into a light-filled great room with oversized windows and a gas fireplace adorned with decorative wood surround, mantel, and raised hearth. The open-concept kitchen includes an island, pantry, and eat-in area—perfect for everyday living and entertaining. The main-level primary suite offers comfort and convenience with two story ceilings and sliding doors to outside. A primary bath offers a double vanity, soaking tub, and room for a future walk-in shower. The home is designed with a private in-law suite featuring its own entrance, a mini kitchen and living area, two bedrooms (or one bedroom and an office), and a full bath. A unique half bath with a petrified wood sink adds personality and warmth. On the upper level you'll find another bedroom with a private bath and a loft area overlooking the great room—ideal as a second living space, creative retreat, or reading nook. This home was ideal for multigenerational living space and for entertaining guests. Enjoy the outdoors from the welcoming covered front porch or explore the 13+ wooded acres that stretch along the year-round waters of Mountain Run—perfect for the nature lover, adventurer, or anyone seeking a peaceful escape. Additional features include a tankless hot water heater, whole-house water filtration system, and available broadband internet. This truly special property offers unique living with privacy, beauty, and room to grow. Come experience all it has to offer!

18184 Crawford Ln, Gordonsville

1206 Eastover Pkwy, Locust Grove
$685,000
3 Beds ⋅ 3 Baths ⋅ VAOR2012556 MLS
Welcome to this beautiful Keaton Lake waterfront in Lake of the Woods! This completely renovated 3-bedroom, 2.5-bathroom prow-style home blends modern comfort with breathtaking lake views and timeless charm. Step inside the spacious foyer, where a built-in bench and coat hooks offer a warm and practical welcome. Kick off your shoes and get ready to fall in love with the details throughout this thoughtfully reimagined home. Laminate plank flooring stretches across the main living areas, tying the open-concept design together seamlessly. The heart of the home—the farmhouse-style kitchen—features stainless steel appliances, a deep farm sink, gas cooking, and ample counter and cabinet space. It’s both beautiful and functional, ideal for the home chef or anyone who loves to entertain. The adjacent dining area and great room are bathed in natural light from the floor-to-ceiling windows and bay window with sliding doors, offering stunning lake views from nearly every angle. The living room centers around a cozy gas fireplace, creating a serene balance of fire and water elements that make this space truly special. All three bedrooms are conveniently located on the main level, including a spacious primary suite with two walk-in closets, a spa-inspired ensuite bath, and private deck access—the perfect spot to start or end your day overlooking the water. You’ll also appreciate the centrally located laundry room, perfectly positioned near all the bedrooms for effortless access. This space includes built-in shelving for organization and a dedicated folding area, making everyday tasks both simple and stylish. A home theater with bar area sets the stage for unforgettable movie nights, while the loft space currently serves as a home office—offering flexibility for your lifestyle needs. Outside is where this property truly shines. Designed for relaxation and recreation, the wraparound deck, outdoor kitchen, patio with firepit, and picnic area by the water invite you to savor every moment. Spend your afternoons fishing, swimming, or sunbathing from your private dock, surrounded by peaceful lake views and the gentle sounds of nature. Whether you’re searching for a full-time residence or a weekend retreat, 1206 Eastover Parkway delivers the ultimate lake lifestyle—modern, refreshed, and ready for your next chapter. For added peace of mind, a one year Choice Home Warranty will convey to the new owner. Nestled in a private, secure, gated community, Lake of the Woods is a paradise of possibilities. With two lakes, a golf course, an equestrian center, fire and rescue services, and even a church within its bounds, this community offers a diverse range of activities. From boating, water skiing, kayaking, and golfing to the simple joy of soaking in mesmerizing views from the clubhouse, deck, yard, or beaches, there's something for everyone. Engage your interests by joining over 60 clubs and organizations, or perhaps indulge in a game of bridge or contribute your talents as a volunteer. Lake of the Woods truly caters to your lifestyle. Located in Orange County, enjoy the added advantage of low real estate taxes. With home prices spanning from $300,000+ to over $1,800,000, Lake of the Woods is the ideal haven for both full-time residents and weekenders. Don't just take my word for it – come and see for yourself! Allow me to guide you through a tour of Lake of the Woods, showcasing the very essence of what makes this community so special. Experience firsthand the captivating charm of Lake of the Woods!

1206 Eastover Pkwy, Locust Grove

108 Wilderness Dr, Locust Grove
$529,900
4 Beds ⋅ 3 Baths ⋅ VAOR2012410 MLS
**Upgraded Gourmet Kitchen** **All Bathrooms Upgraded** **All Flooring Upgraded or Refinished**. **Newer Roof** **Smart Home Google Lighting** **$15,000 of Fresh Landscaping**. **Fresh Paint and Wallpaper** Discover a truly unique gem in the serene Lake of the Woods community in Locust Grove, Virginia, where quiet elegance meets modern living. This exceptional property welcomes you with an open floor plan that effortlessly draws you in, blending spaciousness with subtle sophistication. The main living areas boast refinished hardwood floors that gleam with timeless charm, while the main-level master is a single bedroom suite features newer, luxurious flooring for added comfort. Smart lighting and switches complement the home's features. The heart of the home is a chef’s dream, showcasing a fully upgraded kitchen with sleek new counters, a stylish backsplash, and custom cabinetry that exudes quality. A state-of-the-art gourmet range and hood, paired with an upgraded kitchen island, create a space as functional as it is beautiful—perfect for gatherings or entertaining guests. All bathrooms have undergone major renovations, featuring high-end finishes that elevate everyday living with a touch of spa-like luxury. Step outside to fresh, meticulously designed landscaping that enhances the home’s curb appeal, inviting you to explore further. The large rear deck is an entertainer’s delight, ideal for hosting unforgettable gatherings, while the screened porch—accessible from both the living room and primary bedroom—offers a tranquil retreat for savoring morning coffee or unwinding in the evening breeze. Just a short stroll away, one of Lake of the Woods’ many pristine beaches awaits, perfect for adventures or quiet relaxation. Beyond the property, embrace the vibrant Lake of the Woods lifestyle, complete with resort-style amenities including boating areas, a premier golf course, tennis courts, a sparkling community pool, a lively clubhouse, and a beloved bar and grill where community thrives. This home is more than a residence—it’s a sanctuary of elegance, comfort, and friendly charm, designed for those who seek a distinctive property in an extraordinary setting.

108 Wilderness Dr, Locust Grove

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