Orange VA Real Estate, Homes for Sale Near Prospect Heights

3 Beds ⋅ 4 Baths ⋅ VAOR2015178 MLS

Welcome to 9599 Woodberry Forest Road! This traditional brick home offers the best of both worlds - convenient in-town living combined with a quiet neighborhood setting with privacy and nature. Step outside in one direction and enjoy mature trees and the sounds of a flowing creek that eventually leads toward the Rapidan River; head the other way and enjoy a stroll through the peaceful neighborhood along Glebe Road. Quality built and meticulously maintained, this 3-bedroom, 3.5-bath home has received numerous recent upgrades and is freshly painted throughout. The kitchen features new quartz countertops, new flooring, a new cooktop, double wall ovens, and oak cabinetry. Bathrooms have been remodeled with updated vanities and flooring, including a walk-in tiled shower in the primary suite. Solid oak hardwood floors, crown molding, and chair rail add warmth and custom craftsmanship throughout. The main level features a gas-log stove and custom gas fireplace, while the partially finished basement offers an additional wood-burning fireplace with an oversized hearth - along with a newly remodeled half bath and plenty of bright unfinished space for storage or future expansion. Above, the large unfinished attic provides exceptional storage and potential for a future recreation or bonus room. Additional features include 400-amp electrical service, central heating and air, 6-inch insulated walls, brick and Hardie siding exterior, and copper gutters. A generously sized screened porch and patio provide excellent outdoor entertaining space. The property also offers a paved driveway, 16-foot-wide garage door accommodating oversized vehicles, a 12x24 brick outbuilding with 100-amp service, and an additional 12x12 shed with electric. Enjoy the convenience of the Town of Orange while remaining within comfortable driving distance of Culpeper and Charlottesville, providing easy access to additional shopping, dining, employment, medical services, and recreation. Beautifully maintained and thoughtfully upgraded, this home offers a unique combination of in-town convenience, neighborhood living, privacy, and natural surroundings.

9599 Woodberry Forest Rd, Orange

$295,000

3 Beds ⋅ 1 Baths ⋅ VAOR2015184 MLS

Nestled in the charming Town of Gordonsville, this delightful farmhouse-style home, built in 1930 and set to undergo major renovations in 2026, offers a perfect blend of classic character and modern comfort. With three spacious bedrooms and a well-appointed full bathroom, this residence is designed for both relaxation and functionality. Step inside to discover a warm and inviting interior featuring luxury vinyl plank flooring that flows seamlessly throughout the traditional floor plan. The family room, conveniently located off the kitchen, creates an ideal space for gatherings and everyday living. The kitchen boasts upgraded countertops and an efficient layout, complete with ample table space for casual dining. Enjoy the convenience of electric stainless steel appliances, including an oven/range and refrigerator, while the main floor laundry hookups add to the home's practicality. The exterior of the property is equally appealing, showcasing durable vinyl siding and an outbuilding that offers additional storage or creative potential. The 0.19-acre lot provides a cozy outdoor space, perfect for gardening or enjoying the fresh air. A community pool nearby invites you to relax and socialize during the warmer months, enhancing the sense of community. Located in the heart of Gordonsville, this home benefits from a vibrant neighborhood atmosphere. Residents enjoy easy access to local parks, where you can take leisurely strolls or engage in outdoor activities. The community is known for its friendly spirit and offers a variety of public services that cater to residents' needs. The neighborhood's welcoming vibe and community events foster connections among residents, making it a wonderful place to call home. With its blend of historical charm and modern updates, this property is a true gem in Gordonsville. Whether you're looking for a peaceful retreat or a lively community, this home offers the best of both worlds. Embrace the opportunity to create lasting memories in a space that feels just right.

113 Cobb St, Gordonsville

$175,000

3 Beds ⋅ 1 Baths ⋅ VAOR2015092 MLS

It's time to stop renting and become a homeowner! This affordable Colonial style home in the heart of the Town of Orange is full of character and charm. Main level bedroom and bathroom, with two additional bedrooms upstairs. Unique features include built in kitchen cabinets and a layout that offers a natural flow. The living room provides a comfortable setting for relaxing or spending time with family and friends. The kitchen connects to the main living area. Oversized lot with large backyard will make this haven a dream come true. Fully fenced property and outbuilding for storage. Roof updated in 2016. The location offers the best of small-town living with everyday convenience and walking distance to shopping and dining. Property has been in the family for years and has been a place of comfort and happiness, where memories have been made and the next chapter is ready to begin for a new family!

318 Peliso Ave, Orange

$425,000

3 Beds ⋅ 2 Baths ⋅ VAOR2015128 MLS

Nestled in the charming Town of Orange, this delightful all-brick ranch offers a wonderful blend of comfort, character, and functionality. Featuring three spacious bedrooms and two full bathrooms, the thoughtfully designed layout provides easy, one-level living with plenty of room to relax and entertain. The bright, well-appointed kitchen flows seamlessly into a cozy breakfast area, creating an inviting space for casual meals and morning gatherings. A separate dining room and generously sized living room provide additional space for hosting family and friends. Two beautiful brick fireplaces add warmth and character to the home—one in the living room and another in the separate semi-detached addition. The versatile addition offers endless possibilities and could easily serve as a home office, gym, hobby room, or additional storage space. A charming glass-enclosed breezeway connects the spaces and provides a wonderful spot for year-round lounging, relaxing, or entertaining while enjoying views of the surrounding property. Outside, the generous open lot offers a cleared front yard and a peaceful rear yard, providing plenty of space for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. A circular asphalt driveway and attached carport offer ample parking for both residents and guests.The inviting front porch is the perfect place to unwind while taking in panoramic views. Conveniently located near local amenities, this well-loved home offers a peaceful retreat with the space, flexibility, and charm to create lasting memories.

905 Madison Rd N, Orange

$460,000

3 Beds ⋅ 3 Baths ⋅ VAOR2015094 MLS

Welcome to 19406 Briar Patch Drive in Hare Glen Subdivision, just minutes from the charming town of Gordonsville! Situated on a shaded, level corner lot, this classic Colonial offers 2,240 finished square feet, 3 bedrooms, 2.5 baths, and plenty of room to spread out. The home has historically been used as a 4-bedroom residence; however, the septic system is rated for 3 bedrooms. The main level features hardwood flooring throughout and a traditional, functional floor plan with a formal living room and dining room, family room with gas fireplace, breakfast area, kitchen, and half bath. Step outside to the rear deck, offering a great spot for entertaining, grilling, or simply relaxing and enjoying the shaded setting. Upstairs, you’ll find the bedrooms and two full baths, along with recently replaced carpeting. Numerous updates have been completed over the years, including the HVAC system, roof, and granite countertops approximately 10 years old; hardwood flooring (excluding the living room), gas fireplace, dishwasher, and generator plug approximately 3 years old; kitchen exterior door and storm door approximately 6 years old; an upgraded electrical panel; and toilets replaced in January 2026. FiberLync high-speed internet makes working from home a breeze. Enjoy a walkable neighborhood setting that feels private and peaceful while remaining convenient to Gordonsville’s restaurants, breweries, wineries, shopping, and everyday amenities. Route 29 and Charlottesville are an easy drive, with Richmond within reach as well. All appliances convey EXCEPT the kitchen refrigerator. With its spacious floor plan, level corner lot, established neighborhood, and convenient location, this home is ready for its next owner to add their personal touches and make it their own. Come see all that 19406 Briar Patch Drive has to offer!

19406 Briar Patch Dr, Gordonsville

$109,900

2 Beds ⋅ 2 Baths ⋅ VAOR2015104 MLS

NEW HOME! PRICED TO SELL FAST! This 869 sq. ft. 2 BED 2 BATH home is one of the newest models in Madison Run MHP. The split floor plan features Primary bedroom opposite of the 2nd bedroom, 2 baths and additional office space. Recessed lighting, kitchen appliances included. 5x5 decks on the front and rear with white vinyl and black pickets, gravel walkway with stepping stones, custom landscaping. Builder warranty included. Photos are of a rendering, professional photos to come. Ground rent is 400/mo and includes water and sewer.

15398 Knights Ct, Gordonsville

$274,900

3 Beds ⋅ 1 Baths ⋅ VAOR2015068 MLS ⋅ Orange BLDG.

Location, character, convenience, and a home that has been well cared for! Welcome to 255 Montevista Ave, a charming and well-maintained one-level ranch nestled in the established Johnson Village neighborhood in the heart of Orange. This inviting 3-bedroom home offers the ease of single-level living along with the character buyers appreciate, including beautiful original hardwood floors and a bright, welcoming living area. The updated kitchen is a true highlight, featuring granite countertops, custom cabinetry, stainless steel appliances, and a movable butcher-block island that provides excellent workspace and storage. A convenient rear mudroom adds practical everyday living space and includes the washer and dryer. All three bedrooms are comfortably sized, while the fully fenced backyard provides a private place for pets, gardening, entertaining, or simply enjoying the outdoors. A storage shed adds even more utility. Updates include gutters replaced, new floor and painting in the kitchen, updated HVAC condenser, and many more improvements made recently to this house. Perhaps the greatest feature is the location. Orange Elementary School is immediately across the street, while the established neighborhood provides a wonderful sense of community and easy access to the best of small-town Orange. Enjoy the ability to walk to historic Downtown Orange for local restaurants, shops, arts, community events, and the rich history that gives this area its distinctive character. For buyers looking for a home that combines comfortable one-level living, thoughtful updates, outdoor space, an established neighborhood, and an exceptional location, 255 Montevista Ave is a wonderful opportunity to make yourself at home in Orange.

255 Montevista Ave, Orange

$395,000

3 Beds ⋅ 2 Baths ⋅ VAOR2014404 MLS

Tucked away on a spacious .70-acre lot in the Town of Orange, this rock-solid 1960s home offers that hard-to-find combination of privacy, lush green space, and convenience. Mature surroundings create a peaceful, tucked-away feel, yet you’re just minutes from downtown Orange, schools, shopping, dining, and everyday necessities. Inside, the home blends the character and quality of an established property with thoughtful updates, including a beautifully renovated kitchen, a new roof in 2025, and a new mini-split system in 2026. The partially finished basement adds valuable flexible space—perfect for a den, home office, hobby area, workout space, or guest retreat. Step outside and enjoy a generous yard with plenty of room to garden, entertain, play, or simply relax and take in the natural beauty. It’s a wonderful setting for anyone who wants a little elbow room without giving up the convenience of being in town. The location makes exploring Central Virginia easy! Enjoy convenient access to Charlottesville, Culpeper, Fredericksburg, Routes 29 and I-64, UVA, and the region’s many wineries, breweries, historic destinations, outdoor recreation, and scenic countryside. There’s truly so much to do and so little time! Solid construction, meaningful updates, flexible living space, a beautiful lot, and a central Orange location—this inviting home offers comfort, convenience, and an opportunity to make it your own. (Room Sizes are rounded up; please view floor plans and or interactive floorplan video for more accurate dimensions)

10226 Glebe Rd, Orange

$220,800

VAOR2014954 MLS

Fantastic opportunity to own 5. 810 wooded acres in a convenient Central Virginia location! Situated along Constitution Highway, a main corridor through Orange County, this property offers road frontage, privacy, and excellent access to the surrounding area. Located approximately 10 miles from Route 29, 20 minutes from NGIC, and 25 minutes from Charlottesville, where you’ll find exceptional dining, shopping, healthcare, entertainment, and the University of Virginia. Enjoy all that Central Virginia has to offer with Shenandoah National Park approximately 30 minutes away and numerous local wineries, breweries, historic attractions, and outdoor recreation opportunities just minutes from the property. With no HOA and no known restrictions, this wooded parcel offers a wonderful opportunity to create your own residential homesite. The property may also have subdivision potential; buyers should verify subdivision possibilities, zoning, requirements, and approvals with Orange County. Its proximity to Charlottesville, Shenandoah National Park, the region’s renowned wineries and breweries, and other popular Central Virginia destinations also makes this property an attractive investment opportunity for those considering vacation rental cabins or short-term rental homes (subject to local regulations and approvals). Whether you’re looking to build your dream home, develop multiple homesites, or invest in a property with income-producing potential, this 5.810-acre parcel offers an exceptional combination of privacy, location, accessibility, and long-term value.

Constitution Hwy, Gordonsville

$465,000

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

$199,900

2 Beds ⋅ 1 Baths ⋅ VAOR2014978 MLS

Bring your vision and grab the opportunity for some sweat equity with this 2 bedroom 1 bath home. This property is listed below assessed value! The home is fully livable and all plumbing and electrical is fully operational. The house could use some cosmetic updates, but it does boast a large porch and a newer roof. Outside you will find a fully fenced yard with ready to go chicken coop and two sheds with electricity. The home is on public water and has a shared septic. Owner financing is available.

18235 Lahore Rd, Orange

$499,000

3 Beds ⋅ 3 Baths ⋅ VAOR2014766 MLS

Welcome to this beautifully renovated all-brick ranch, where timeless quality meets modern comfort. Situated on 2.08 private acres, this move-in-ready home offers 3 bedrooms, 3 full bathrooms, 1,714 finished square feet on the main level plus an additional 1,714-square-foot walkout basement, for a total of 3,428 square feet under roof , an attached two-car garage, and an impressive detached two-car garage. Completely updated from top to bottom, this home has been thoughtfully renovated with attention to both style and function. Step inside to discover an open, inviting floor plan featuring beautiful Peace Oak luxury flooring, fresh paint, updated lighting throughout, and a stunning kitchen with professionally refinished cabinetry, quartz countertops, subway tile backsplash, designer pendant lighting, updated hardware, and modern finishes. All three full bathrooms have been completely remodeled with quality materials and timeless finishes. A rare and highly desirable feature is the laundry hookup on both the main level and in the basement, providing exceptional convenience for everyday living while offering tremendous flexibility should the lower level be finished as an in-law suite, guest quarters, or additional living space. The walkout basement has already been prepared for future expansion with insulated walls, a freshly painted concrete floor, a beautifully finished full bathroom, and abundant storage. Whether you envision a recreation room, home theater, home office, fitness area, or private guest suite, the hard work has already been completed, allowing you to finish the space to meet your own needs. The extensive list of improvements includes: * New plumbing throughout * Updated electrical service with whole-house surge protector * Generator hookup * New water heater * New pressure tank * New interior and exterior lighting * New gutters * Wrapped fascia and soffits for low-maintenance living * New vinyl siding in the gable areas * New garage doors on Main home * Fresh interior and exterior paint * Beautifully updated landscaping and exterior improvements Outdoor living is just as impressive with a spacious covered front and rear porch featuring a freshly coated Benjamin Moore Stonehearth concrete finish, white maintenance-free wrapped columns, and Black Fox accent doors and shutters that complement the classic brick exterior. The private backyard provides the perfect setting for entertaining, relaxing, or enjoying peaceful country evenings. The detached two-car garage has also been extensively updated with a brand-new roof, matching new garage doors, fresh paint, and exterior improvements, making it ideal for vehicles, hobbies, a workshop, or additional storage. Located just minutes from the Town of Orange, Madison , Culpeper this property offers the perfect combination of privacy, quality construction, and modern updates. With virtually every major improvement already completed, this is a home where the next owner can simply move in and enjoy. From the beautifully renovated interior to the extensive infrastructure improvements, this home has been thoughtfully transformed into a truly turnkey property offering exceptional value, flexibility, and peace of mind. This property is shown by appointment only make your appointment today.

9271 Little Skyline Dr, Orange

$399,900

4 Beds ⋅ 4 Baths ⋅ VAOR2014830 MLS ⋅ The Bristow BLDG.

Welcome to 4562 Blue Run Rd! This spacious 4-bedroom, 4-bath home offers the perfect blend of comfort, functionality, and peaceful country living with no HOA. A grand foyer welcomes you into an inviting floor plan featuring a formal dining room and an open-concept kitchen with a center island that flows seamlessly into the great room, making it ideal for everyday living and entertaining. The home features two primary suites, including a main-level primary with a private ensuite bath and an expansive upper-level primary retreat with a vaulted ceiling, sitting area, double vanity, and separate shower. Conveniently located just minutes from Charlottesville, the University of Virginia, shopping, dining, and the area's award-winning wineries, this home offers the best of scenic Virginia living with modern convenience. Don't miss this exceptional opportunity��welcome home!

4562 Blue Run Rd, Somerset

$199,990

2 Beds ⋅ 2 Baths ⋅ VAOR2014794 MLS

Welcome to 145 Bowler Lane in historic and charming Orange, Virginia—this property offers the perfect blend of comfort, space, and rural living. Nestled at the end of a cul-de-sac and with a cozy front porch, the home has abundant natural light, and a warm, welcoming atmosphere. The updated kitchen flows seamlessly into the dining and living areas, making it ideal for everyday living and entertaining. Two bedrooms share an updated full bath. A rear addition includes a half bath and huge utility room which acts as an office, laundry and provides extra storage - it could even be updated/used as a 3rd bedroom. Outside, enjoy the generous yard with plenty of room for gardening, recreation, or simply relaxing while taking in the tranquil surroundings. Recent updates include new HVAC, new HWH, new electrical, new plumbing, new floors, new interior doors, updated kitchen, updated paint, new fixtures and an electric fireplace. Conveniently located just minutes from the Town of Orange with local shops, dining and wineries, this property offers the serenity of rural living without sacrificing convenience.

145 Bowler Ln, Orange

$410,000

3 Beds ⋅ 2 Baths ⋅ VAOR2014760 MLS

Welcome to 10712 Mt. Sharon Rd, where peaceful country living meets modern comfort on nearly 2 private acres in beautiful Orange County. This thoughtfully designed one-level home offers nearly 2,000 square feet of living space with 3 bedrooms, 2 full bathrooms, and an open floor plan that combines spaciousness with everyday functionality. Built in 2023, this home offers the added peace of mind that comes with newer construction, allowing buyers to enjoy their new home without the immediate concerns of replacing major systems, appliances, or the roof. At the heart of the home, the expansive great room is anchored by a stunning floor-to-ceiling stone wood-burning fireplace with custom built-in shelving, creating a warm and inviting gathering space. The well-appointed kitchen is designed for both everyday living and entertaining, featuring an oversized center island, abundant counter space, stainless steel appliances, recessed lighting, and an adjoining dining area large enough to accommodate family gatherings and holiday meals. The spacious primary suite serves as a private retreat, complete with double vanities, built-in storage, an oversized walk-in shower with bench seating, a dedicated dressing area with additional vanity space, and an impressive walk-in closet. Two additional bedrooms provide flexibility for guests, a home office, or hobbies, while the oversized laundry and utility room offers exceptional storage, workspace, and convenient access to the backyard. Outside, enjoy the privacy and tranquility of nearly 2 acres with plenty of room for gardening, recreation, pets, or simply taking in the peaceful surroundings. Located just minutes from the Town of Orange, you'll enjoy the perfect balance of rural living while remaining close to shopping, dining, wineries, parks, and everyday conveniences. If you've been searching for the ease of one-level living, generous interior spaces, the confidence of newer construction, and the serenity of country life, this beautiful home is one you won't want to miss.

10712 Mt Sharon Rd, Orange

$150,000

2 Beds ⋅ 1 Baths ⋅ VAOR2014666 MLS

Price Improvement! Investor special in the heart of historic Gordonsville. Sold as is. Bring your vision and discover the potential this property has to offer in one of Central Virginia's most beloved small towns. Whether you're looking for your next renovation project, an investment opportunity, or the chance to breathe new life into a classic home, this property is ready for its next chapter. Gordonsville, recognized by Southern Living Magazine as "The Best Little Main Street in the State," is known for its inviting downtown filled with locally owned restaurants, charming shops, galleries, and year-round community events. Spend weekends exploring nearby wineries, parks, and scenic countryside, all while enjoying the convenience of being between Charlottesville and Richmond. Opportunities to invest in a location with this much character and potential do not come along often. Come see the possibilities for yourself and imagine what you could create.

409 Park St, Gordonsville

$729,000

3 Beds ⋅ 3 Baths ⋅ VAOR2014476 MLS

Discover the perfect balance of refined modern living and peaceful country charm with this exceptional new ‘To Be Built’ home, beautifully situated on 6.07 acres in the desirable Lake Orange subdivision. Centrally located and positioned along a state-maintained road, this property offers the privacy and space you've been searching for without sacrificing convenience. Designed with today's lifestyle in mind, this thoughtfully crafted home features 3 bedrooms, 2.5 baths, with a home office or study. Offering an open-concept floor plan filled with quality finishes and timeless design elements. The gourmet kitchen serves as the heart of the home, boasting granite countertops, a generous 6-foot center island, upgraded cabinetry, a farmhouse sink, and stainless-steel appliances—perfect for gathering with family and friends. Throughout the home, you'll find durable luxury vinyl plank flooring, 9' ceilings, craftsman-style trim, and carefully selected finishes that create a warm and inviting atmosphere. The spacious primary suite provides a private retreat, complete with a luxurious spa-like bath featuring a ceramic tile shower and elegant glass enclosure. Looking for room to grow? The full unfinished walkout basement includes a rough-in for a future bathroom and offers endless possibilities for additional living space, recreation, or storage. The oversized, insulated, and finished two-car garage is equipped with a Level 2 electric vehicle charger and Wi-Fi-enabled garage door openers with battery backup for added convenience and peace of mind. The exterior is equally impressive with architectural shingles, attractive board-and-batten siding accented by shaker details, a covered concrete front porch, and a covered rear deck where you can relax and enjoy the beauty and tranquility of your surroundings. Buyers may have the opportunity to personalize selections and finishes if contracted early enough in the construction process and builder selections remain available. This is an ideal location for commuters, offering easy access to surrounding communities while allowing you to enjoy all that Orange County has to offer. Orange is rich in history and surrounded by scenic countryside, enjoy our many local vineyards & breweries, explore the 124-acre Lake Orange and other nearby attractions including Lake Anna and the Blue Ridge Mountains. Come home to the space, comfort, and lifestyle you've been dreaming of. Photos are similar and may show optional features. Specifications, finishes, and features are subject to change without notice.

Lot 37 Harbor Dr, 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

$999,000

VAOR2014484 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 six 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

$369,999

4 Beds ⋅ 3 Baths ⋅ VAOR2014540 MLS

HUGE $10K PRICE IMPROVEMENT -- UNIQUE OPPORTUNITY TO ASSUME A 5.25% RATE (UNTIL APRIL 2031) VA LOAN IF APPROVED WITH THE CURRENT LENDER! SELLER WILL ALLOW NON-VA ELIGIBLE BUYERS TO ASSUME THIS LOAN! Step back in time without sacrificing modern comfort in this beautifully restored circa 1878 National Folk Farmhouse, perfectly blending historic charm with today's conveniences. This fully renovated 2,112 square foot 4-bedroom, 2.5-bath home showcases timeless character alongside extensive updates throughout. The heart of the home is the stunning new kitchen featuring granite countertops, a farmhouse sink, stainless steel appliances, and abundant workspace for cooking and entertaining. Spacious living areas, updated baths, and thoughtfully preserved architectural details create a warm and inviting atmosphere. Outside, you'll find a private backyard retreat complete with extensive hardscaping, a brick patio, tranquil koi pond, pergola, privacy fencing, and an expansive concrete driveway. A storage shed provides additional space for tools and equipment. RV enthusiasts will appreciate the dedicated 30-amp RV outlet along with convenient exterior 120-volt outlets. Major improvements include a new roof (May 2026), heat pumps installed in 2013 and 2017, and a water heater replaced in 2016. Solar panels are available for purchase separately if desired by the buyer; otherwise, they will be removed prior to closing. Experience the perfect combination of historic elegance, modern upgrades, and exceptional outdoor living at this one-of-a-kind Gordonsville property.

500a Knighting Rd, Gordonsville

$365,000

4 Beds ⋅ 3 Baths ⋅ VAOR2014478 MLS

Live upstairs and let the lower level help offset your mortgage! 189 Newton Street offers something increasingly hard to find—a beautifully updated home paired with a fully separate 1-bedroom, 1-bath apartment, creating exceptional flexibility for rental income, multigenerational living, extended family, long-term guests, or a private work-from-home setup. The main residence features 3 spacious bedrooms and 2 full bathrooms, combining timeless character with thoughtful modern updates. High ceilings, gleaming hardwood floors, recessed lighting, and replacement windows create bright and inviting living spaces. The remodeled kitchen is equally impressive with granite countertops, stainless steel appliances, a farmhouse sink, soft-close cabinetry and drawers, and tile flooring. What truly sets this property apart is the separate lower-level apartment. With 1 bedroom, 1 full bathroom, its own living space, kitchen, private entrance, and separate laundry, it functions independently from the main residence. Rent the lower level to help offset your monthly housing costs, keep it available as a private suite for extended family or guests, or take advantage of the additional space for your own needs. For buyers looking for a home that can potentially generate income, this is a feature that can make a meaningful difference in the cost of homeownership. Set on a generous corner lot with a spacious yard, the property also offers separate laundry areas for each level and numerous recent improvements, including a freshly painted exterior, a new air handler installed in 2025, and a smart Ecobee thermostat. Whether you're a homeowner looking for a creative way to offset your mortgage, an investor seeking income potential, or a household needing a true multigenerational living arrangement, 189 Newton Street offers a level of versatility most traditional single-family homes simply can't match. One property, two distinct living spaces, and countless possibilities.

189 Newton St, Orange

$749,000

5 Beds ⋅ 3 Baths ⋅ VAOR2014406 MLS

Offered for the first time, 252 Boxley Lane presents a rare opportunity to own a truly distinctive custom residence designed and built by its original owners. Nestled on 2.37 private acres in beautiful Orange County, this one-of-a-kind property combines exceptional craftsmanship, thoughtful design, and timeless character in a setting that offers both privacy and convenience. Boasting 3,788 square feet of living space, this expansive home features 5 bedrooms and 3 full baths, providing ample room for entertaining and guests. Designed with the ease of primarily one-level living in mind, the home’s unique floor plan showcases spacious rooms, abundant natural light, and architectural details that are seldom found in today’s homes. Multiple fireplaces create warm and inviting gathering spaces throughout the residence, while one of the home’s most remarkable features—a custom Japanese-style sunken soaking tub—offers a tranquil retreat and serves as a testament to the originality and vision of its creators. Arrive via the paved driveway and enjoy the convenience of the attached two-car garage. The picturesque 2.37-acre homesite provides a peaceful backdrop with mature landscaping, open space, and room to enjoy the beauty of the surrounding countryside. Lovingly cared for by the same family since its construction, this exceptional home reflects decades of pride of ownership, thoughtful maintenance, a level of quality, individuality, and pride of ownership that is increasingly difficult to find. For buyers seeking something beyond the ordinary, 252 Boxley Lane is a rare and unforgettable offering—a custom-designed home with a story, character, and charm all its own.

252 Boxley Ln, Orange

$264,000

2 Beds ⋅ 2 Baths ⋅ VAOR2014322 MLS

Welcome to 20322 Gum Tree Road—a charming country retreat nestled on 3.49 private acres. This well-maintained 2-bedroom, 1.5-bath home offers comfortable living space, perfect for those seeking peaceful rural living with modern conveniences. Inside, you'll find a warm and inviting living a cozy fireplace, creating the perfect gathering space during cooler months. The functional floor plan maximizes every square foot, while the kitchen comes fully equipped with all appliances conveying, making this home move-in ready. Outside, the property offers plenty of room to enjoy nature, garden, or simply relax and take in the surrounding countryside. Multiple sheds provide abundant storage for tools, equipment, hobbies, or workshop space, adding exceptional versatility to the property. Whether you're looking for a full-time residence, weekend getaway, or investment opportunity, this delightful home combines comfort and acreage in a beautiful Orange County setting. Don't miss the opportunity to own this charming property with acreage, outbuildings, and all the essentials for country living.

20322 Gum Tree Rd, Orange

$299,000

2 Beds ⋅ 1 Baths ⋅ VAOR2014132 MLS

Welcome home to this charming 2-bedroom, 1-bath home offering comfort, character, and convenience in the heart of the charming town of Orange. Filled with natural sunlight, this inviting home features beautiful hardwood floors and a thoughtfully designed layout perfect for everyday living. The spacious bathroom includes double sinks, a full tub/shower combination, and convenient laundry space complete with washer and dryer. The kitchen is both functional and welcoming, showcasing warm oak cabinetry, stainless steel & black appliances, a center island with bar seating - ideal for casual dining or entertaining. Step directly from the kitchen onto the rear covered deck, creating the perfect spot to relax or enjoy outdoor gatherings. The mostly unfinished walkout basement provides abundant storage space and endless potential for future expansion or customization. Large rear yard, partially fenced and ready for outdoor play and barbecues! Remodeled in 2005, this home combines modern updates with timeless charm. Enjoy in-town convenience with easy access to schools, shopping, restaurants, and local entertainment. Come experience all that the beautiful town of Orange has to offer!

358 Williams Dr, Orange

$60,000

VAOR2013948 MLS

Conveniently located near to The Town of Orange, close to everything and ready to build your dream home. Two lots included in sale: Lot 64 and 65. You can either build a duplex or a single family home. Lots were cleaned up 2020, everything you see is just weeds no big trees to tear down. Property is located on a quiet cul-de-sac within walking distance to school.

129 Bowler Ln, Orange

$1,100,000

4 Beds ⋅ 6 Baths ⋅ VAOR2013928 MLS

NEW ROOF June 2026. Estate House located in the bucolic setting of the foothills of the Piedmont area in the Blue Ridge Mountains of Orange Virginia, representing the pleasant aspects of the countryside and life you could be living in and enjoying. Stunning views 5,100 square foot Manor House 4 bedrooms with walk-in closets in each bedroom 6 full baths-4 on the second floor in each bedroom Also, 1 on the first level And the last bathroom in the full walk out basement 3 gas fireplaces-one on each level. New 80-gallon high efficiency hot water heater installed last year. 4 heat pumps total. 3 were replaced 2 years ago-one in the master bedroom, one on the second level, and one on the first level. The other heat pump is in the garage. 35 KW generator. 400 Amp Service Paved driveway and concrete walkways. Outside lights. First Floor: There’s a formal dining room, a formal living room, large den, kitchen with teat-in table area, as well as an island sitting bar area. This floor can be accessed by the front door, and a door directly from the garage, or the back deck. A gas fireplace is in the den. 1 ½ Floor: Mid-level den currently used as an office. Second Floor; Master bedroom-with full Jack and Jill vanity, a 2-person shower, and large soaking tub, walk in closet, and sitting room. Also, another gas fireplace is in the master bedroom. Three other good-sized bedrooms with walk-in closets and full bathrooms are on the second floor Basement: Full walk-out basement accompanied by a full eat in kitchen, with gas stove, and gas log fireplace, a Theatre room / living room, bonus craft/ room, and bar with a small dining area attached, another gas log fireplace- and this area can be assessed from the first floor inside stairs, or outside doors from the back ground level basement patio. Garage: 3 car garage with oversized doors, insulated, drywalled, and painted. The floors have been painted. 4 stall shed row barn: The barn is located on lot 1, and just uphill from a year-round stream for animal grazing. It could also be easily made into a pond. Property was divided into 2 tracts this year with each track being 6.646 acres. House and run in shed are on lot 1. Offered at 1.2 million. CAN ALSO BE DIVIDED INTO A 3 ACRE TRACT AND A 10 ACRE TRACT. Two different ways to divide. Lot 2: 6.646acres will be sold separately. It will have a right of way access easement for access and utilities to the lot, as shown on the plat. Recent 4 bedroom soil work done. Property is in land use. All weather stream also on this property. Offered at $250,000 Up for sale also is 9442 Little Skyline: As an accessory structure / carriage house, to be sold as a separate transaction. It is currently operating as a successful AirBnb on the top floor. The bottom level is a garage. Offered at $200,000 Surrounding area: Woodberry Forest School (2 mi), Montpelier ( 8 mi), Town of Orange (3 mi), Charlottesville & UVA (30 mi), The Inn at Willow Grove is 2 blocks away as the crow flies:):), Madison at the Mills (3 mi), Skydive Orange (8 mi), Fredericksburg (35 mi), Fairfax County (65 mi) , and Washington DC (87 mi)!

9471 Little Skyline Dr, Orange

$257,000

VAOR2012394 MLS

1.04 vacant lot in the town of Gordonsville. This is a level parcel which has been selectively cleared and is bordered on 3 sides by public road frontage making it ideal for subdivision and development. Beautiful rural setting on town sewer and water. The town of Gordonsville was recently featured in an article in Southern Living Magazine, the title read: "15 Things To Do In Gordonsville, VA. Make The Trip and You Might Stay Forever." Charming Main Street, Gordonsville features gorgeous historical architecture, art galleries, dining and shopping as well as plenty to explore for the wine enthusiast and history buff! There is a major grocery store in town, a library and a new community park under construction which will include tennis and pickleball courts, fitness trails and a playground. The community pool has just been completed in 2025. ( See park design overview in pictures and schematic plans in documents section.) Gordonsville has a municipal airport located just 2 miles northeast of the town. Prime location, just a 25 minute commute to Charlottesville, 1 hour to Richmond, 1 hour to Fredericksburg and 2 hours to D.C.

East St, Gordonsville

$499,900

3 Beds ⋅ 2 Baths ⋅ VAOR2012346 MLS

Pleasant Valley Estates offers a rare living experience for those seeking tranquility, space, and natural beauty. Our new neighborhood features expansive 2 to 4-acre homesites, providing the perfect canvas for your modern new home. It is set in a peaceful, wooded location, ensuring privacy and a sense of seclusion, while still being conveniently close to all the amenities you need including grocery stores, restaurants and other recreational amenities like Lake Anna. It’s the ideal location for those seeking a spacious homesite near employment hubs of Fredericksburg or Culpeper without the hustle and bustle of in town living. - The Chesapeake is one of several thoughtfully designed floorplans available within this community. The Chesapeake features 3-bedrooms and 2-baths on the main level living with unfinished basement. The open Kitchen and family room space provide a perfect space to entertain. The master suite features two walk-in closets, dual vanities and a step-in shower. Bedrooms 2 and 3 share a full bath and are sized right for a growing family or guests. With options of extensions to the family room, a morning room, a sitting room or finished basement, this home can accommodate most any living situation. There is even an optional second floor with a studio space, bedroom and full bath. This base price starts at 1912 sq. ft. on the main level with an unfinished basement. **PLEASE NOTE: The list price reflects the base price only. Final pricing will be determined by the buyer’s personalized interior selections and upgrades chosen at the design studio. Home designs, features, and prices are subject to change without notice. Renderings and photos shown may feature optional features that are not included in the base house. One of several thoughtfully designed floorplans available within this community. This listing is for available homesites, and photos shown represent sample floor plan options that can be built. For details on available floor plans, lot compatibility, and community features and upgrades, please schedule an appointment with our Community Sales Manager. Please call the showing contact listed below to schedule an appointment! Appointment is required as sales office is located offsite.

LOT 3 Tatum Rd, Unionville

$140,000

VAOR2010454 MLS

Location! Location! Location! Located just outside of the Town of Orange limits with state road frontage along Rt 15 south of the town of Orange. Entrance in place, and driveway cut in! Looking for some acreage for privacy, seclusion - this 6.538 acres offers an all wooded parcel with quick access to town amenities. Parcel currently has division rights, verify with County Zoning for particulars.

James Madison Hwy, Orange

$445,999

3 Beds ⋅ 3 Baths ⋅ VAOR2008714 MLS

ASK ABOUT SPECIAL FINANCING! $0 down payment USDA financing eligible! This Lapis by Richmond American is ready now!! There's a lot to love about the Lapis floor plan! The charming front porch leads to an inviting, open layout. Walking through the front door to the left is a adaptable flex room and open oak stairs and beyond that is the main living space. The kitchen with a center island and large walk-in pantry flows into a dining room and a great room with an Allusion electric fireplace, completed by a center-meet sliding door – perfect for future outdoor living. Upstairs, the primary suite offers a full private bath and a generously sized walk-in closet. Adjacent are two additional bedrooms, each with their own walk-in closets and a convenient loft for extra living space. Curated finishes round out this home such as Blanco Maple quartz countertops, Aristokraft White cabinets, 7” Kenwood LVP floors on the main level, and sleek matte black light and plumbing fixtures. Welcome to Round Hill Meadows in Orange! Residents will appreciate the small-town charm as well as the conveniences of being close to routes 15, 522 and 3, award-winning wineries, Lake Anna State Park, Lake Orange and the Rapidan River nearby for fishing, swimming, kayaking and boating! Model is OPEN but visitors are encouraged to call ahead to be guaranteed a dedicated appointment.

611 Clover Ln, Orange

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