usm white logo

236 Caroline StreetOrange, VA 22960Price: $999,000

  • Price: $999,000
  • 45 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Active
236 Caroline Street Orange VA 22960236 Caroline Street Orange VA 22960236 Caroline Street Orange VA 22960
QR Code
  • 2.95Acreage
  • 1831Year Built
  • OrangeUsmArea
  • 144Price Per Square Foot
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.
Listed by Kathleen Annette Ayers of EXP Realty,LLC

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

More Info

Location Information

  • UsmAreaOrange

Parking

  • Parking TypesDriveway

Basic Information

  • Date Listed06/22/2026

Location

  • Address236 Caroline Street
  • Building Number236
  • CountyOrange
  • DirectionsFrom I-95, Take exit 130B toward Culpeper. Drive about 14 miles, left on onto Constitution Hwy (VA-20) toward Orange/Charlottesville. Go for 22.3 mi. Left on Caroline Street, Go for 102 ft. home is on the right.
  • In City Limits YNYes
  • StateVA
  • TownOrange
  • Zip22960

Amenities

  • Accessibility Amenities2+ Access Exits

Other

  • Historic YNYes
  • View Count1

Basic Information

  • Broker NameEXP Realty, LLC
  • List Price$999,000
  • MLS NumberVAOR2014484
  • MLS Property TypeCommercial Sale
  • Price Per Square Foot144
  • StatusACT

Property

  • Acreage2.95
  • Business TypeBanquet Facility/Lodge, Apartment Building, Bed and Breakfast, Flex, Professional, Recreation, Other
  • Lot DescriptionBacks to Trees, Corner, Partly Wooded
  • Lot Size SourceAssessor
  • Lot Size Square Feet128,632
  • New Construction YNN
  • Property SubTypeSpecial Purpose
  • ZoningTAC

Tax Information

  • Assessment Year2022
  • Tax Assessment Amount$313,200
  • Tax Year2022
  • Taxes$2,840
  • Total Taxes Payment FrequencyAnnually

Building

  • Building Area SourceAssessor
  • Building Area Total6943
  • Construction MaterialsFrame
  • Total Garage And Parking Spaces12
  • Total Restrooms6
  • Year Built1831

Utilities

  • CoolingNone
  • Cooling FuelElectric
  • Heat SystemHeat Pump(s)
  • Heating FuelElectric, Propane - Owned
  • Heating YNYes
  • SewerPublic Sewer
  • Water HeaterElectric
  • Water SourcePublic

Ask A Question

Do not fill in this field:

I agree to receive marketing and customer service calls and text messages from Railey Vacations. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated August 5, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Railey Vacations. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.