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For sale
  • $999,000

    236 Caroline St, Orange, VA 22960

    7beds
    --sqft
    : 
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    Single Family Residence
    Built in 1831
    2.95 Acres Lot
    $970,100 Zestimate®
    $--/sqft
    $-- HOA

    What's special

    Private drivewayCurated landscapingAmple parkingSeven bedroomsSix bathrooms
    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.
    20 days
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    370
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    25
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    Zillow last checked:

    Listing updated:

    Listed by:

    Kathleen Ayers 540-395-6488,

    EXP Realty, LLC,

    Listing Team: The Licata Group, Co-Listing Team: The Licata Group,Co-Listing Agent: Patricia E Licata 540-735-7998,

    EXP Realty, LLC

    Source: Bright MLS,MLS#: VAOR2014482MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 6
      • Full bathrooms: 6
      Basement
      • Area: 1820
      Heating
      • Forced Air, Heat Pump, Electric, Propane
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Electric Water Heater
      Features
      • Has basement: No
      • Number of fireplaces: 4
      Interior area
      • Total structure area: 3,765
      • Finished area above ground: 0

      Property

      Parking
      • Parking features: Driveway
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: 2+ Access Exits
      Features
      • Levels: Four
      • Stories: 4
      • Pool features: None
      Lot
      • Size: 2.95 Acres
      Details
      • Additional structures: Above Grade
      • Parcel number: 044A400210001A
      • Zoning: TAC
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Brick/Mortar
      Condition
      • New construction: No
      • Year built: 1831

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Subdivision: None Available
      HOA
      • Has HOA: No
      Location
      • Region: Orange

      Financial & listing details

      • Tax assessed value: $313,200
      • Annual tax amount: $2,840
      • Date on market: 6/22/2026
      • Listing agreement: Exclusive Right To Sell
      • Ownership: Fee Simple

        Estimated market value

        $970,100

        $922,000 - $1.02M

        $3,595/mo

        Price history

        DateEventPrice
        6/22/2026Listed for sale$999,000
        Source: Bright MLS #VAOR2014482 Report a problem
        6/1/2026Listing removed$999,000
        Source: eXp Realty #VAOR2008380 Report a problem
        11/21/2024Listed for sale$999,000
        Source: Bright MLS #VAOR2008380 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$1,584 +12.3%$238,200 +39.5%
        2024$1,411 $170,800
        2023$1,411 -39.9%$170,800 -42.3%
        2022$2,349 +4.2%$295,900
        2021$2,255 $295,900
        2020$2,255 -50.4%$295,900 -36.6%
        2018$4,547 +21.1%$467,000
        2017$3,755 -7.8%$467,000
        2016$4,072 $467,000 -17.4%
        2015$4,072 $565,500
        2014$4,072 $565,500
        2013-- $565,500
        2012-- $565,500 -30%
        2011-- $807,700
        2010-- $807,700 -1.5%
        2009-- $820,200
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 22960

        Getting around

        50 / 100
        Car-Dependent
        24 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Orange
        • Middle: Prospect Heights
        • High: Orange County
        • District: Orange County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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