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236 Caroline St
For Sale $999,000
$999,000
- Units
- Unknown Sq Ft
- 128,632 Sq Ft
- Unknown Cap Rate
Description
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.
Amenities
Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt
Property Details
| List Price | $999,000 |
| Property Type | Special Purpose |
| Usable Sqft | Unknown |
| Number of Stories | 0 stories |
| Parking Spots | 0 spots |
| Year Built | 1831 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| APN # | 044A400210001A |
| MLS # | VAOR2008382 |
| Property ID | 321074723 |
| Lot Sqft | 128,632 |
| Zoning | TAC |
| Days on Market | 395 |
| Original List Price | Unknown |
| Date Updated | November 03, 2025 |
| Date Created | November 20, 2024 |
Financials not available online. Please inquire with your agent for more details.
Listing Provided By
Kathleen Annette Ayers an agent of EXP Realty, LLC. Lic #0225260453
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Data last updated: December 20, 2025.
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Robert Crawford
REAL ESTATE AGENT