Agent profile image in chat bubble
Agent profile image in chat header

IDX Support

sales rep | Brivity IDX

Agent profile image in message

236 Caroline St , Orange, VA 22960
$999,000
Est. Payment: $5,233.63/mo
6943 Sqft
2.95 Acres
Status: active | Days on site: 131
Get Pre-Qualified
EXPY8 - 3342180,3021967
By proceeding and clicking the sign up button, you consent to receive calls and texts (SMS/MMS) including marketing and promotional communications, from IDX Support, its affiliates, and agents or vendors acting on their behalf. These communications may be delivered using an automatic telephone dialing system or by using an artificial or prerecorded voice. Message and data rates may apply. To opt out of text messages, reply STOP. Your consent is not required as a condition of any purchase. By continuing, you also agree to our Terms of Use and Privacy Policy.

House 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.

Highlights

Listed by Kathleen Annette Ayers , 5403956488 and Patricia E Licata , 5407357998 EXP Realty, LLC , 5403882541. Bright MLS

Property Type

Commercial Sale

Lot/Acreage
2.95

Year Built

1831

County

Orange

School District

Orange County Public Schools

Listing ID

VAOR2014484

Questions about this listing?

Contact Agent

Interior Features

Water:Public

Exterior Features

Lot:Backs to Trees,Corner,Partly Wooded,Not New Construction,Horse Property: No,In City Limits
Garage Capacity:12
Zoning:TAC
Sewer:Public Sewer
Parking Features:Driveway,4+ Spaces,3+ Spaces,2+ Spaces,1+ Spaces
Principal Interest
$5,234
Taxes
$237

Home Price

$999,000

Loan Details

30 yrs
6.844%

Down Payment

20%
$199,800
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$5,233.63

Principal

Taxes

Principal Taxes HOA Total
Monthly $5,233.63 $236.67 $0.00 $5,470.30
Yearly $62,803.58 $2,840.00 $0.00 $65,643.58
Total $1,884,107.25 $85,200.00 $0.00 $1,969,307.25
Lender profile image
Chico Gordy
Test
GET PRE-QUALIFIED

Never Miss a Property

Be the first to know when a property hits the market.

Current Listings

Last 30 Days
N/A
Nov 2026

Average Price

All Price Ranges
N/A
Nov 2026

Average Days on Market

All Price Ranges
N/A
Nov 2026
Market insight data is pulled from the same city as the listing being viewed (Orange, VA).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Information provided by Bright MLS, and is deemed reliable but not guaranteed accurate.

IDX service by Blueroof 360

Data last updated: 2026-11-13T17:14:43.000Z

© 2026 Bright MLS