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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

eXp Realty, LLC.

540-388-2541

Last updated:

July 15, 2026, 05:12 PM

MLS#

VAOR2014482

Source:

VA HRAR

About This Home

236 Caroline St

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

Home Facts

Single Family

6 Baths

7 Bedrooms

Built in 1831

Subdivision & Development:

NONE

Price Summary

999,000

$265 per Sq. Ft.

MLS #:

VAOR2014482

Last Updated:

July 15, 2026, 05:12 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

7

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

6


Structure

Structure

Building Area:

3,765 Sq. Ft.

Year Built:

1831


Lot

Lot Size (Sq. Ft):

128,502


Finances & Disclosures

Finances

Price:

$999,000

Price per Sq. Ft:

$265 per Sq. Ft.

Source:VA HRAR
The information being provided by Harrisonburg Rockingham Association Of REALTORS® is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Harrisonburg Rockingham Association Of REALTORS® All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.