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$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

$339,000
3 Beds 3 Baths
Welcome to 293 Caroline Street in Orange, VA. 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, providing flexibility for family, guests, or a home office. 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 charm, location, and modern living. Don't miss your chance, come see this one in person! 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 easement is not in use, but cannot be permanently changed/adapted. Please do your due diligence. 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

$379,000
4 Beds 3 Baths
Discover the perfect blend of charm, flexibility, and investment potential at 189 Newton Street. Situated on a spacious corner lot with a large yard, this well-maintained home offers a unique opportunity with a fully separate lower-level 1-bedroom, 1-bath apartment—ideal for rental income, multigenerational living, guests, or a private home office setup. The beautifully remodeled upper level features 3 bedrooms and 2 full bathrooms, showcasing high ceilings, recessed lighting, replacement windows, and hardwood floors in excellent condition throughout. The updated kitchen is designed for both style and functionality, featuring stainless steel appliances, granite countertops, a farmhouse sink, soft-close drawers and cabinetry, and tile flooring. The bright and inviting living spaces combine classic character with modern updates, creating a move-in-ready home that feels both spacious and welcoming. Other recent improvements include a freshly painted exterior, a smart Ecobee thermostat, and an air handler replaced in 2025 for added peace of mind. The home also offers two separate laundry areas, providing convenience and flexibility for both owners and tenants. Whether you're looking for a primary residence with supplemental rental income or a versatile property for multigenerational living, this home delivers exceptional value, character, and opportunity. Don't miss the chance to own a property that offers both comfortable living and income-producing potential.

189 Newton St, Orange

Listing courtesy of Redfin Corporation. Contact:

$349,900
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

$319,900
4 Beds 1 Baths
Nestled in a serene setting, this charming Cape Cod-style residence exudes warmth and character, offering a perfect blend of classic design and modern comforts. Built in 1940, this home has been thoughtfully maintained, showcasing its timeless appeal while providing a cozy retreat for those who appreciate quality living. Step inside to discover a spacious layout that invites you to unwind. The interior features an entry-level bedroom, ideal for guests or as a private office space, ensuring versatility in how you choose to live. The rich wood flooring throughout adds a touch of elegance, creating a seamless flow from room to room. Natural light pours in through double-hung, insulated vinyl-clad windows, enhancing the inviting atmosphere and providing energy efficiency. The heart of the home is a well-appointed kitchen, equipped with modern appliances, including a washer and dryer for your convenience. This space is perfect for culinary enthusiasts, offering ample room for meal preparation and entertaining. The open layout encourages gatherings, making it easy to connect with loved ones while enjoying the comforts of home. The property boasts four generously sized bedrooms, providing plenty of space for relaxation and personalization. The full bathroom is designed with functionality in mind, ensuring comfort for all who reside here. Outside, the expansive 0.46-acre lot offers a canvas for your outdoor dreams, whether it's creating a lush garden, setting up a cozy patio for al fresco dining, or simply enjoying the tranquility of your surroundings. The off-street parking adds to the convenience, making it easy for you and your guests to come and go. This residence is not just a home; it's a lifestyle. Experience the charm of a classic Cape Cod while enjoying the modern amenities that make everyday living a pleasure. With its inviting ambiance and thoughtful features, this property is ready to welcome you home. Embrace the opportunity to create lasting memories in a space that truly feels like your own. BRAND NEW ROOF! Bring us an offer!

194 Morton St, Orange

Listing courtesy of Cowan Realty, Inc.. Contact: 5408403137

$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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