Features & Amenities

Interior

  • Total Bedrooms

    7

  • Bathrooms

    6

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Propane, Forced Air, Heat Pump

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Frame

  • Parking

    Driveway

  • Pool

    No

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    2.95

  • Lot Size(square feet)

    128,632

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Other

Price

  • Sales Price

    $999,000

  • Tax Amount

    $2,840

  • Sq. Footage

    3,765

  • Price/SqFt

    $265

HOA

  • Association

    No

Property Resources

  • Horse Property

    NO

School District

  • Elementary School

    ORANGE

  • Middle School

    PROSPECT HEIGHTS

  • High School

    ORANGE COUNTY

Property Features

  • New Construction

    NO

  • Foundation Details

    Brick/Mortar

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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Location

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ORANGE

Elementary School

ORANGE

Middle School

PROSPECT HEIGHTS

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ORANGE COUNTY

Listing Courtesy of Kathleen Annette Ayers, EXP Realty, LLC

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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.

236 CAROLINE STREET

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Paved driveway and concrete walkways.
Outside lights.

First Floor:
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1 ½ Floor:
Mid-level den currently used as an office.

Second Floor;
Master bedroom-with full Jack and Jill vanity, a 2-person shower, and large soaking tub, walk in closet, and sitting room. Also, another gas fireplace is in the master bedroom.
Three other good-sized bedrooms with walk-in closets and full bathrooms are on the second floor

Basement:
Full walk-out basement accompanied by a full eat in kitchen, with gas stove, and gas log fireplace,  a Theatre room / living room, bonus craft/ room,  and bar with a small dining area attached, another gas log fireplace- and this area can be assessed from the first floor inside stairs, or outside doors from the back ground level basement patio.

Garage:
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4 stall shed row barn:
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