About This Home

This 7-bedroom, 6-bathroom single family at 236 CAROLINE Street in Orange, VA is listed for $999,000. Built in 1831, on a 2.95 acres lot.

Key Features

  • Built in 1831
  • 2.95 acre lot
  • 4 stories
  • Fireplace

Property Details

4 stories
6 full
1831

Amenities

FireplaceA/C
Listing 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 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.

Monthly Cost Estimate

$5,343/mo

20% down · 6.5% · 30 years

Principal$722
Interest$4,329
Insurance$291

Estimates only. Actual payments may vary.

Location

236 CAROLINE Street

Orange, VA 22960

NONE AVAILABLE

Property Details

Construction

Frame

Parking

Driveway

Heating

Heat Pump (Heating)Forced Air

Cooling

Central Air

Questions & Answers

This 7-bedroom, 6-bathroom single family at 236 CAROLINE Street is listed at $999,000. The estimated monthly payment is $5,342 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1831, 2.95 acre lot, 4 stories, Fireplace.

This property is listed by Kathleen Annette Ayers and can be reached at 5403956488.

KA

Kathleen Annette Ayers

License 0225260453

Agent at EXP REALTY LLC

(540) 395-6488
Agent website

Listed by EXP REALTY LLC · Broker phone: (866) 825-7169 · View on Broker Site · Broker website

MLS# VAOR2014482· Source: Bright MLS· 85 days on PropertySimple

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

236 CAROLINE Street, Orange, VA 22960

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