


236 Caroline St, Orange, VA, 22960
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.
Getting Around
Schools
Construction
Condition
- Year built: 1831
Materials
- Foundation: Brick/Mortar
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Other
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Electric Water Heater
Basement
- Area: 1820
Bedrooms & Bathrooms
- Bedrooms: 7
- Bathrooms: 6
- Full bathrooms: 6
Features
- Number of fireplaces: 4
- Fireplace: Yes
- Finished area above ground: 0
Heating & Cooling
- Heating features: Forced Air,Heat Pump,Electric,Propane
- Cooling features: Central Air,Electric
Interior Area
- Total structure area: 3,765
Property
Accessibility
- Accessibility features: 2+ Access Exits
Details
- Parcel number: 044A400210001A
- Zoning: TAC
- Special condition: Standard
Features
- Levels: Four
- Stories: 4
- Pool features: None
Lot
- Lot size: 2.95 Acres
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Strong Wind
- Drought
- Earthquake
- Hail
- Hurricane
- Inland Flooding
- Lightning
- Winter Weather
How This Home’s Risks Compare
FEMA Declared Disasters Across Virginia Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $5,051 | $60,612 |
| Home Insurance * | $354 | $4,248 |
| Property Taxes | $549 | $6,588 |
| Electricity | $202 | $2,433 |
| Total | $6,156 | $73,872 |
Income You'd Need if You Spent...
Virginia FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
No zestimate history available
Price History
| Date | Event | Price |
|---|---|---|
| 2024-11-21 | Listed for sale | $999,000 |
