236 Caroline St Orange, VA 22960
Orange AreaEstimated payment $5,681/month
Highlights
- 2.95 Acre Lot
- No HOA
- Forced Air Heating and Cooling System
- 4 Fireplaces
- More Than Two Accessible Exits
About This Home
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.
Listing Agent
(540) 388-2541 pat@licatagroup.com EXP Realty, LLC Brokerage Phone: 5403882541 License #0225260453 Listed on: 06/22/2026
Co-Listing Agent
(540) 388-2541 pat@licatagroup.com EXP Realty, LLC Brokerage Phone: 5403882541 License #0225197494
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $2,840
Year Built
- Built in 1831
Lot Details
- 2.95 Acre Lot
- Property is zoned TAC
Parking
- Driveway
Home Design
- Brick Foundation
- Frame Construction
Interior Spaces
- Property has 4 Levels
- 4 Fireplaces
Bedrooms and Bathrooms
Accessible Home Design
- More Than Two Accessible Exits
Schools
- Orange Elementary School
- Prospect Heights Middle School
- Orange County High School
Utilities
- Forced Air Heating and Cooling System
- Heat Pump System
- Heating System Powered By Owned Propane
- Electric Water Heater
Community Details
- No Home Owners Association
Listing and Financial Details
- Assessor Parcel Number 044A400210001A
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $1,411 | $170,800 | $99,100 | $71,700 |
| 2024 | $1,411 | $170,800 | $99,100 | $71,700 |
| 2023 | $1,411 | $170,800 | $99,100 | $71,700 |
| 2022 | $2,349 | $295,900 | $99,100 | $196,800 |
| 2021 | $2,255 | $313,200 | $99,100 | $214,100 |
| 2020 | $2,255 | $313,200 | $99,100 | $214,100 |
| 2019 | $3,755 | $467,000 | $99,100 | $367,900 |
| 2018 | $3,755 | $467,000 | $99,100 | $367,900 |
| 2017 | $3,755 | $467,000 | $99,100 | $367,900 |
| 2016 | $3,755 | $467,000 | $99,100 | $367,900 |
| 2015 | $4,072 | $565,500 | $109,100 | $456,400 |
| 2014 | $4,072 | $565,500 | $109,100 | $456,400 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 06/22/2026 06/22/26 | For Sale | $999,000 | -- | $265 / Sq Ft |
Source: Bright MLS
MLS Number: VAOR2014482
APN: 044-A4-00-21-0001-A
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Ask me questions while you tour the home.