236 Caroline St, Orange, VA 22960
Local realty services provided by:Better Homes and Gardens Real Estate Community Realty
236 Caroline St,Orange, VA 22960
$999,000
- 7 Beds
- 6 Baths
- - sq. ft.
- Single family
- Active
Listed by: kathleen annette ayers, patricia e licata
Office: exp realty, llc.
MLS#:VAOR2008380
Source:BRIGHTMLS
Price summary
- Price:$999,000
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 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....
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Home facts
- Year built:1831
- Listing ID #:VAOR2008380
- Added:494 day(s) ago
- Updated:March 31, 2026 at 01:32 PM
Rooms and interior
- Bedrooms:7
- Total bathrooms:6
- Full bathrooms:6
Heating and cooling
- Cooling:Central A/C
- Heating:Electric, Forced Air, Heat Pump(s), Propane - Owned
Structure and exterior
- Year built:1831
- Lot area:2.95 Acres
- Construction Materials:Frame
- Foundation Description:Brick/Mortar
- Levels:4 Story
Schools
- High school:ORANGE COUNTY
- Middle school:PROSPECT HEIGHTS
- Elementary school:ORANGE
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$999,000
- Tax amount:$2,840 (2022)
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