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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

$1,150,000
4 Beds 6 Baths
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

Listing courtesy of The Greene Realty Group. Contact: 8882785840

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