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

  • Price: $999,000
  • Est. Mortgage of $/month
  • 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.
  • $999,000List Price
  • 7Bedrooms
  • 6Bathrooms
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.
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

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More Info

Location Information

  • Date Listed06/22/2026
  • ZoningTAC
  • UsmAreaOrange

School Information

  • Junior HighProspect Heights
  • High SchoolOrange County
  • Elementary SchoolOrange

Building

  • High School DistrictOrange County Public Schools
  • Broker NameEXP Realty, LLC
  • Building Number236
  • In City Limits YNYes
  • 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.
  • Lower Levels Total Baths2
  • Lower Level1 Total Baths2
  • Lower Level1 Full Baths2
  • Lower Level1 Bedrooms2
  • Lower Levels Total Bedrooms2
  • Lower Levels Total Full Baths2
  • Upper Level2 Total Baths2
  • Upper Levels Total Full Baths4
  • Upper Levels Total Bedrooms5
  • Upper Levels Total Baths4
  • Upper Level2 Full Baths2
  • Upper Level1 Bedrooms3
  • Upper Level1 Full Baths2
  • Upper Level2 Bedrooms2
  • Upper Level1 Total Baths2
  • Story ListLower 1, Upper 1, Upper 2
  • Structure Design TypeDetached
  • Construction MaterialsFrame
  • Property StyleOther
  • Bedrooms7
  • Full Bath6
  • Bathroom6
  • Levels4
  • Fireplace YNYes
  • Fireplace4

Basic Information

  • MLS NumberVAOR2014482
  • Ownership InterestFee Simple
  • List Price$999,000
  • Acreage2.95
  • Year Built1831
  • MLS Property TypeResidential
  • StatusACT

Location

  • Address236 Caroline Street
  • Area Total3,765
  • SubdivisionNone Available
  • TownOrange
  • StateVA
  • Zip22960
  • CountyOrange

Utilities

  • Water SourcePublic
  • SewerPublic Sewer
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterElectric
  • Heating FuelElectric, Propane - Owned
  • Heat SystemForced Air, Heat Pump(s)

Other

  • View Count1

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Assessment Amount313200
  • Tax Year2022
  • Taxes$2,840
  • Assessment Year2022
  • City Town Tax$491

Parking

  • Parking TypesDriveway

Property

  • New Construction YNN

Interior

  • Heating YNYes
  • CoolingCentral A/C

Exterior

  • FoundationBrick/Mortar

Property Information

  • Lot Size Square Feet128,632
  • Above Grade Unfinished Area1945
  • Below Grade Area Total1,820
  • Below Grade Unfinished Area1820

Amenities

  • PoolNo Pool
  • Accessibility Amenities2+ Access Exits
  • Other AmenitiesFireplace

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.

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