236 Caroline St
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....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.
- Listed by Kathleen Annette Ayers • EXP Realty, LLCP: (540)-395-6488 kathleen@licatagroup.com
- Listed by Patricia E Licata • EXP Realty, LLCP: (540)-735-7998 pat@licatagroup.com
Property Details for 236 Caroline Street
Tax ID Number
044A400210001A
OwnershipFee Simple
Condo Coop AssociationNo
HOANo
Structure TypeDetached
StyleOther
Levels/Stories4
WaterfrontNo
LISTING UPDATED: 01/09/2026 01:01 AM
Property Details for 236 Caroline Street
| Status | Active |
|---|---|
| MLS # | VAOR2008380 |
| Days on Market | 469 |
| Taxes | $2,840 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Fee Simple |
| Year Built | 1831 |
| Lot Size | 2.95 AC / 128,632 SF |
| County | Orange County |
Location
Listing Courtesy of EXP Realty, LLC
Add your commute
Building Information for 236 Caroline Street
Stories4Year Built1831Building Size-Lot Size2.95 AC / 128,632 SF
Payment Calculator
$5,106 per month
30 year fixed, 6.15% Interest
Principal and Interest
$4,869
Property Taxes
$237
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 236 Caroline Street
Location
Location
- In City Limits: Yes
- School District Name: ORANGE COUNTY PUBLIC SCHOOLS
- School District County ID: 121141052477
- SchoolDistrictSource: Listing Agent
- Elementary School: ORANGE (ORANGE VA)
- ElementarySchoolSource: Listing Agent
- Middle Or Junior School: PROSPECT HEIGHTS (ORANGE VA)
- MiddleSchoolSource: Listing Agent
- High School: ORANGE COUNTY (ORANGE VA)
- HighSchoolSource: Listing Agent
- County: ORANGE
Waterfront / Water Access
Waterfront / Water Access
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
- Property Manager Y/N: No
- Senior Community: No
Taxes and Assessment
Taxes and Assessment
- Tax Year: 2022
- Tax Assessed Value: $313,200
- Year Assessed: 2022
- County Tax: $2,349
- Improvement Assessed Value: $214,100
- City Town Tax: $491
- Land Assessed Value: $99,100
- Clean Green Assessed: No
- Land Use Code: 017
- Agricultural Tax Due: No
- Historic: Yes
- Zoning: TAC
- Tax Lot: 1A
- School Tax: $0
- Automatically Update Tax Values Y/N: Yes
Rooms
All Upper Levels
- # Bedrooms Count All Upper Levels: 5
- # Bathrooms Count All Upper Levels: 4
- # Bathrooms Full All Upper Levels: 4
Upper Level 1
- # Bedrooms Count Upper Level: 3
- # Bathrooms Count Upper Level: 2
- # Bathrooms Full Upper Level: 2
Upper Level 2
- # Bedrooms Count Upper Level: 2
- # Bathrooms Count Upper Level: 2
- # Bathrooms Full Upper Level: 2
All Lower Levels
- # Bedrooms All Lower Levels: 2
- # Bathrooms All Lower Levels: 2
- # Bathrooms Full All Lower Levels: 2
Lower Level 1
- # Bedrooms Lower Level: 2
- # Bathrooms Lower Level: 2
- # Bathrooms Full Lower Level: 2
Rooms
- Stories: Lower 1, Upper 1, Upper 2
Building Info
Building Info
- Total Finished SQFT: .00
- Total Finished SQFT Source: Estimated
- Tax Total Finished SQFT: 3,765.00
- Total SQFT: 3,765.00
- Total SQFT Source: Estimated
- Construction Materials: Frame
- Foundation Details: Brick/Mortar
- Room and Floor: Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Lower Level 1-1, Bedrooms-Lower Level 1-2, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Lower Level 1-1, Bathrooms Full-Lower Level 1-2, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2, Bathrooms Full-Upper Level 2-1, Bathrooms Full-Upper Level 2-2
- # Bathrooms Full: 6
- Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
- Lot Size Source: Assessor
- Parcel ID: 18829352
- Ground Rent Exists: No
Parking
Parking
- Type Of Parking: Driveway
Interior Features
Interior Features
- Fireplace: Yes
- Fireplaces Count: 4
- Accessibility Features: 2+ Access Exits
Exterior Features
Exterior Features
- Spa: No
- Pool: No Pool
- Horse: No
Utilities
Utilities
- Heating: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Forced Air, Heat Pump(s)
- Heating Fuel: Electric, Propane - Owned
- Hot Water: Electric
- Water Source: Public
- Sewer Septic: Public Sewer
Confidential Data
Listing Office
- List Agent AOR: Fredericksburg Area Association of REALTORS
Property History for 236 Caroline Street
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jun 3, 2025 | Listed (Active) BRIGHT #VAOR2008380 | $999,000 | — |
| May 31, 2025 | Expired BRIGHT #VAOR2008380 | — | |
| Nov 21, 2024 | Listed (Active) BRIGHT #VAOR2008380 | $999,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 06/03/2025 | Listed (Active) BRIGHT #VAOR2008380 | $999,000 |
| 05/31/2025 | Expired BRIGHT #VAOR2008380 | — |
| 11/21/2024 | Listed (Active) BRIGHT #VAOR2008380 | $999,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 236 Caroline Street
Taxable ValueLand$99,100Additions$71,700Total$170,800
Tax Record2025$1,411 ($118 / month)
Home Facts
Beds6Baths6Total Finished SqFt7,483 SqFtAbove Grade Finished SqFt5,663 SqFtFinished Basement SqFt1,820 SqFtStories3Lot Size128,633 SqFtStyleSingle Family ResidenceYear Built1831ZoningTAC TOWN ACTICountyORANGEAPN044-A4-00-21-0001-AFireplace TypeHas Fireplace
Schools near 236 Caroline Street
This home is within Orange County Public Schools.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Private - | PK to 8 |
Rating | School | Distance |
|---|---|---|
Orange Elementary School PublicPK to 5 | ||
Prospect Heights Middle School Public6 to 8 | ||
Orange Co. High School Public9 to 12 | ||
Grymes Memorial School PrivatePK to 8 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Listing Courtesy of EXP Realty, LLC
© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 01/09/2026 01:01 AM