Property details
About 236 Caroline St
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 statu
Highlights
Summary
- Full Bathrooms: 6
- Basement: No
- Total Bedroom Count: 7
- Attached Garage: No
- Architectural Style: Other
- Heating: Electric, Forced Air, Heat Pump, Propane
- Cooling: Central Air
- List Price: $999,000
- Annual Tax Amount: $1,410
- Tax Year: 2023
- Directions: From 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.
- Year Built: 1831
- Lot Size: 2.95 Acres
- MLS Number: VAOR2008380
- MLS Name: CharlottesvilleVA
- Office Name: EXP Realty, LLC
- Office Phone: (540) 388-2541
- Office Email: esther@yourtechsavvybroker.com
- Listing Agent: Kathleen Ayers
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Last updated on: 7/18/2025, 7:45:38 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $170,800 | $1,410 |
| 2022 | $295,900 | $2,349 |
| 2021 | $313,200 | $2,255 |
| 2020 | $313,200 | $2,255 |
| 2019 | $467,000 | $3,754 |
| 2018 | $467,000 | $3,754 |
| 2017 | $467,000 | $3,754 |
History based on county public records data.
Nearby schools
4
Orange Elementary School
Public District PK-5
0.7 mi
•230 Montevista Ave
7
Gordon-Barbour Elementary School
Public District PK-5
8.2 mi
•500 W Baker St
4
Lightfoot Elementary School
Public District 3-5
8.7 mi
•11360 Zachary Taylor Hwy
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $42,647. Most Orange, VA residents have annual incomes less than $<35k. Residents typically live in single, no kids family. Typical level of education for residents in this area is high school diploma.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
NASCAR
Monster Trucks
Hunting
Where do the neighbors shop?
Bass Pro Shops
Wal-Mart
Academy Sports & Outdoors
Where do the neighbors go to eat?
Hardee's
Jimmy Johns
Applebees
What do the neighbors drive?
GMC
Chevrolet
Ram
What do the neighbors listen to?
Classic Country- Country
New Country
Frequently asked questions
About 236 Caroline St
The listing price of 236 Caroline St property is $999,000.
The property 236 Caroline St is a house located in Orange, Virginia, 22960.
Active Listing: 236 Caroline St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 236 Caroline St are: Orange Elementary School (GreatSchools Rating 4/10), Gordon-Barbour Elementary School (GreatSchools Rating 7/10), Lightfoot Elementary School (GreatSchools Rating 4/10), Prospect Heights Middle School (GreatSchools Rating 3/10), William H. Wetsel Middle School (GreatSchools Rating 3/10), Louisa County Middle School (GreatSchools Rating 6/10), Orange County High School (GreatSchools Rating 5/10), Madison County High School (GreatSchools Rating 5/10), William Monroe High School (GreatSchools Rating 6/10).
According to the records, the last property tax for 2023 is $1,410 (source: MLS/based on county public records data).
The property at 236 Caroline St has 7 bedrooms and 6 bathrooms.
The year of construction for 236 Caroline St is 1831.
This home is located at 236 Caroline St in Orange, VA and zip code 22960. Features: 7 bedrooms, 6 bathrooms. It has been listed on Rocket Homes since November 21, 2024 and is currently priced at $999,000.
While more than 3 listings in Orange, VA in June 2025 were sold above asking price, there were more than 2 listings sold at asking price, and more than 5 were sold below. Between May and June 2025, Orange, VA real estate market has seen increase in the number of listings by 13.6%. In June 2025, listings were on the market for 135 days. During the same period, the median list price in this real estate market was $430,000.