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$649,000
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

$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

$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

$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

$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

$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

$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

$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

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