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$999,000 Just Listed
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Property 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.
Full Property Details
Full Property Details for 236 Caroline St
General
- Price: $999,000
- Taxes: $2,840 (2022)
- Status: Active
- Type: Apartment
- Source: BrightMLSMidAtlantic
- MLS ID: VAOR2014484
- Updated: 6/22/2026
- Added to Site: 7 day(s) ago
Business
- Business Type: Banquet Facility/Lodge, Apartment Building, Bed and
Rooms
Bathrooms
- Restrooms: 6
Parking
- Total Spaces: 12
- Parking Type: Driveway
Location
- County: ORANGE
- Driving 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.
- Historic District: Yes
- City Limits: Yes
School Information
- Elementary School: Orange
- Middle School: Prospect Heights
- High School: Orange County
Heating & Cooling
- Cooling Type: None
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric, Propane - Owned
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Construction: Frame
- Building Size: 6943
- Year Built: 1831
- Year Built Source: Assessor
Unit Information
- # Tenants: Multiple
Lot Features
- Lot Size (Acres): 2.95
- Lot Size (Sq. Ft.): 128,632
- Lot Size Source: Assessor
- Zoning: TAC
- Lot Description: Backs to Trees, Corner, Partly Wooded
Financial Considerations
- Price Per Sq. Ft.: $143.89
- Assessment Year: 2022
- Tax w/Assessment: $313,200
- Tax Amount: $2,840
- Tax Year: 2022
Disclosures and Reports
- Ownership: Fee Simple
Listed by EXP Realty, LLC, Kathleen Annette Ayers and EXP Realty, LLC, Patricia E Licata
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Schools
Schools serving 236 Caroline St
School District:Orange County Public Schools
| Name | Grades | Distance |
|---|---|---|
Orange Elementary School 230 Montevista Avenue, Orange, VA 22960 | PK-5 | 0.6 mi |
Prospect Heights Middle School 202 Dailey Drive, Orange, VA 22960 | 6-8 | 0.3 mi |
Orange Co. High School 201 Selma Road, Orange, VA 22960 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 236 Caroline St
Date
Details
Price
Change
Source
6/22/2026
Listed
$999,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 236 Caroline St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,411
—
$170,800
—
2024
$1,411
—
$170,800
—
2023
$1,411
-40%
$170,800
-42%
2022
$2,349
4%
$295,900
-6%
2021
$2,255
—
$313,200
—
2020
$2,255
-40%
$313,200
-33%
2019
$3,755
—
$467,000
—
2018
$3,755
—
$467,000
—
2017
$3,755
—
$467,000
—
2016
$3,755
-17%
$467,000
-17%
2015
$4,547
—
$565,500
—
2014
$4,547
12%
$565,500
—
2013
$4,072
—
$565,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 236 Caroline St
236 Caroline Street, Orange, VA 22960 (MLS# VAOR2014484) is a Apartment property. 236 Caroline Street is currently listed for $999,000 and was received on June 22, 2026. Want to learn more about 236 Caroline Street? Do you have questions about finding other Apartment real estate for sale in Orange? You can browse all Orange real estate or contact a Coldwell Banker agent to request more information.

