236 Caroline St, Orange, VA 22960
Local realty services provided by:ERA Bill May Realty Company
236 Caroline St,Orange, VA 22960
$999,000
- 7 Beds
- 6 Baths
- 3,765 sq. ft.
- Single family
- Active
Listed by: kathleen ayers, patricia licata
Office: exp realty, llc.
MLS#:VAOR2008380
Source:VA_HRAR
Price summary
- Price:$999,000
- Price per sq. ft.:$265.34
About this home
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 statu
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Home facts
- Year built:1831
- Listing ID #:VAOR2008380
- Added:454 day(s) ago
- Updated:February 19, 2026 at 03:34 PM
Rooms and interior
- Bedrooms:7
- Total bathrooms:6
- Full bathrooms:6
- Living area:3,765 sq. ft.
Heating and cooling
- Cooling:Central AC
- Heating:Electric, Forced Air, Heat Pump, Propane
Structure and exterior
- Year built:1831
- Building area:3,765 sq. ft.
- Lot area:2.95 Acres
Schools
- High school:Orange
- Middle school:Prospect Heights
- Elementary school:Orange
Utilities
- Water:Public Water
- Sewer:Public Sewer
Finances and disclosures
- Price:$999,000
- Price per sq. ft.:$265.34
- Tax amount:$2,840 (2022)
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