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$425,000
3 Beds 2 Baths
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

Listing courtesy of RE/MAX Realty Specialists. Contact:

$274,900
3 Beds 1 Baths
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

Listing courtesy of First Decision Realty LLC. Contact:

$395,000
3 Beds 2 Baths
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

Listing courtesy of Montague, Miller & Company. Contact:

$999,000
7 Beds 6 Baths
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

Listing courtesy of EXP Realty, LLC. Contact: 5403882541

$999,000
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

Listing courtesy of EXP Realty, LLC. Contact: 5403882541

$325,000
3 Beds 3 Baths
Step into the charm of small-town living with all the modern updates you've been looking for. Ideally located in the town of Orange, this home offers a blend of historic character and contemporary comfort. Inside, you'll find an updated interior featuring three spacious bedrooms and three full bathrooms, including a bedroom and full bath on the main level. The conditioned cellar space is partially finished with great storage space and offers so many options to finish the space into a gym, craft room, or the ultimate wine cellar and hang out area. With a newer roof (2018), water heater (2021), HVAC (2026) and new laundry and kitchen appliances (2026- with a 2 year warranty), this is your chance to own a home that is move-in ready, but still has room for you to add your creative touch. Whether you're enjoying a short stroll to downtown dining, relaxing on the back deck, or entertaining friends and family, this home offers the perfect balance of space and location at a great updated price. The listing consists of 2 lots totaling over 0.35 acres. Please note that the Town of Orange has an easement that extends from the driveway behind lot 1 and extends to historic Greenock Manor- the mowed lawn past the easement belongs to the Manor. (old plat is in docs- do your due diligence to understand the lot). The easement is not in use, but cannot be permanently changed/adapted. Please do your due diligence. The cellar space is a true cellar and only accessible by the outside entrance. Fireplace is coal burning and has not been used by seller- at time of their purchase, inspector noted the liner is terracotta and intact, but no longer to code for burning coal. Fireplace can be converted.

293 Caroline St, Orange

Listing courtesy of Weichert, REALTORS. Contact: 5403797359

$365,000
4 Beds 3 Baths
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

Listing courtesy of Redfin Corporation. Contact:

$339,900
3 Beds 2 Baths
Back on the market due to no fault of the seller. Welcome home to this beautifully renovated 3-bedroom, 1.5-bath home with proximity to downtown Orange, Gordonsville, Culpeper and Ruckersville. Inside and out, nearly everything is new! New vinyl siding exterior, new luxury vinyl flooring throughout, with ceramic tile in the full bathroom. The kitchen shines with brand-new white cabinetry, gleaming GRANITE COUNTERTOPS, new stainless steel appliances and recessed LED lighting. The entire interior is freshly painted and soon to be move-in-ready! A new HVAC system adding central air offers peace of mind for years to come! The home features both a living room and a separate family room, (Family Room still under construction - but to be completed: the family room finish-out, a new half bath, and a dedicated laundry closet). One of the home’s most charming features is its front-porch view—an aviation enthusiast's dream! Watch skydivers pop out of the sky from the Orange County Airport, a small local airport right across the street that offers a unique, ever-changing backdrop with beautiful sunsets and distant mountain views. You're just minutes from historic downtown Orange, known for its boutique shops, great local dining, and craft beer. A short drive further brings you to Gordonsville, home to even more restaurants, shopping, and wineries. A thoughtfully updated home in a wonderfully convenient location!

19212 Constitution Hwy, Orange

Listing courtesy of Lake Homes Realty, LLC. Contact: 8665253466

$1,250,000
4 Beds 3 Baths
Agricultural Investment: 98-Acre Farm in Orange County, Virginia Located in the productive agricultural heartland of Orange County, Virginia, 15284 Poplar Road presents a compelling opportunity for farmers, timber investors, and agribusiness owners seeking a versatile 98-acre property with significant operational, income, and long-term asset potential. This expansive farm is strategically situated approximately 75 miles from Richmond, Virginia, and 85 miles from Washington, D.C., offering unparalleled logistical advantages for accessing major metropolitan markets and distribution hubs, while retaining the essential rural character of Central Virginia. Productive Land and Timber Resources: The property encompasses approximately 28+ acres of established loblolly pine, representing a valuable, near-term timber resource. This mature stand offers immediate harvest potential, providing a substantial revenue stream for timber operations or a strategic asset for future forest management. The remaining acreage consists of open, gently rolling farmland, characteristic of the region's fertile soils. Orange County's agricultural lands are known for supporting diverse operations, including row crops, forage production, and livestock grazing, with common soil orders like Ultisols indicating suitability for a range of agricultural endeavors . This land offers a robust foundation for various farming practices. Flexible Zoning for Agribusiness and Diversification: Zoned Agricultural, the property benefits from a broad spectrum of matter-of-right uses directly supporting agricultural enterprises and diversification strategies. This includes traditional farming operations, as well as burgeoning opportunities in agritourism, which is a significant and growing economic contributor in Virginia. The zoning also permits short-term rentals and bed and breakfast establishments, offering avenues for supplementary income through farm stays or event hosting. This regulatory flexibility empowers owners to innovate and adapt their business models to market demands. Operational Efficiency and Market Access: The farm's prime location provides critical access to consumer markets and agricultural supply chains. Proximity to Richmond and Washington, D.C., facilitates efficient transport of produce, livestock, or timber, reducing logistical costs and expanding market reach. This strategic positioning is ideal for operations focused on direct-to-consumer sales, farm-to-table initiatives, or large-scale distribution.

15284 Poplar Rd, Orange

Listing courtesy of CENTURY 21 Envision. Contact: 2402327005

$1,995,000
3 Beds 3 Baths
Estate-Style Residence on nearly 10 Acres in the Town of Orange Welcome to this timeless all-brick traditional estate, offering classic elegance and modern comfort on 9 beautifully manicured acres in the heart of Orange, Virginia. This 3-bedroom, 2.5-bathroom residence showcases spacious living areas, fine architectural details, and inviting spaces both indoors and out. A beautiful formal living room sets the tone upon entry, leading to a grand center staircase and dining room, a comfortable family room, and a well-appointed kitchen. Upstairs, you’ll find three generously sized bedrooms, a bright sunroom, and a versatile bonus room on the third floor—ideal for a home office, studio, or guest retreat. The home features two fireplaces, a basement for additional storage or future expansion, and large windows throughout that fill the home with natural light. Enjoy outdoor living on the expansive covered porch overlooking the landscaped grounds, perfect for relaxing or entertaining. A detached 2-car garage and barn provide ample space for vehicles, hobbies, or agricultural use. The current zoning also allows muti-family/condos by-right. Conveniently located within the Town of Orange, this property combines the charm of estate living with close proximity to shops, dining, and schools. Rarely does an opportunity arise to own a property of this stature, blending traditional craftsmanship with the beauty of Virginia countryside living.

590 N Madison Road, Orange

Listing courtesy of Coldwell Banker Elite. Contact: 5403730100

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