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236 Caroline St

ORANGE, VA 22960
  • $999,000
  • STATUS: Active
  • ON SITE: 426 Days
  • MLS #: VAOR2008380
UPDATED: 20 min ago
$999,000
  • 7
    BEDS
  • 2.95
    ACRES
  • 6
    BATHS
  • 0
    1/2 BATHS
Neighborhood:
Type:
Single-Family Home
Built:
1831
Area:

School Information

Elementary School:
Middle School:
High School:

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 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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Listing information © 2026 Charlottesville Area Association of Realtors Multiple Listing Service. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS or Kline & Co Real Estate. Data last updated 2026-01-22T18:12:33.863.
www.klineandcorealestate.com/homes/158115947
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236 Caroline St ORANGE, VA 22960

  • Price: $999,000
  • Status: Active
  • On Site: 426 Days
  • Updated: 20 min ago
  • MLS #: VAOR2008380
7
Beds
6
Baths
0
½ Baths
2.95
Acres
1831
Built
Neighborhood:
None
Area:
Orange
Elementary School:
Orange
Middle School:
Prospect Heights
High School:
Orange
Property 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 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
Exterior Features

Architectural Style Other Foundation Details Brick / Mortar Garage YN No Pool Features None

Interior Features

Above Grade Finished Area 0 Above Grade Unfinished Area 1945 Basement YN No Below Grade Unfinished Area 1820 Cooling Central Air Cooling YN Yes Fireplace Features Multiple Fireplace YN Yes Heating Electric Forced Air Heat Pump Propane Heating YN Yes Levels Three Or More Multi / Split Quad- Level

Property Features

Association YN No Building Area Total 3765 Lease Amount Frequency Monthly Lease Considered YN No New Construction YN No Possession Close Of Escrow Property Attached YN No Property Sub Type Detached Property Sub Type Additional Detached Sale Or Lease Indicator For Sale Sewer Public Sewer Tax Annual Amount 2840 Tax Year 2022 Water Source Public

Listing provided courtesy of EXP Realty, LLC: .


Listing information © 2026 Charlottesville Area Association of Realtors Multiple Listing Service. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS or Kline & Co Real Estate. Data last updated 2026-01-22T18:12:33.863.
 
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