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MLS: #VAOR2014482, Listed By: Kathleen Annette Ayers, EXP Realty, LLC, Source:Bright MLS

236 Caroline Street

ORANGE, VA 22960
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Bed 7

Bed

Bath 6

Bath

Acres2.95

Acres(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $999,000

AD Id : 85752616

MLS Id : VAOR2014482

Beds : 7

Lot Size : 2.95 Acres

Year Built : 1831

County : ORANGE

Subdivision: None Available

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Feature Features

  • Bedroom Information

    Total beds: 7

    Bathroom Information

    Total Baths: 6 Full Baths: 6
  • Interior Features

    Appliances: Electric Water Heater
  • Heating & Cooling

    Has Heating: Yes Heating: Electric, Propane, Forced Air, Heat Pump Has Cooling: Yes Cooling: Central Air, Electric

  • Building Information

    Year Built: 1831 Building Area Total: 3765 Construction Materials: Frame Pool Features: None Private Pool: No

  • Lot Information

    Lot Size Acres: 2.95 Lot Size Source: Assessor Lot Size Square Feet: 128632

    Property Information

    Subdivision: NONE AVAILABLE Source Property Type: Residential Postal Code Plus 4: 1541 Property SubType: Single Family Residence Levels: Three Or More Property Age: 195

  • Listing Price Information

    Listing Price: $999000

  • Tax Information

    Parcel Number: 044A400210001A Tax Year: 2022 Annual Tax: $2840

  • Parking Information

    Driveway

  • School Information

    Elementary School: ORANGE
    Junior High School: PROSPECT HEIGHTS
    Senior High School: ORANGE COUNTY
  • Location Information

    Direction: 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. WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
25014 Constitution, Orange, VA, 22960 $1,685,000 4 3 2,481 2,481 SqFt
TBD Mount Pisgah Church.., Orange, VA, 22960 $129,000 3 1 --
Clover Lane Elderberry .., Orange, VA, 22960 $449,990 3 3 2,470 2,470 SqFt
Clover Lane Alexandrite.., Orange, VA, 22960 $404,990 3 2 1,799 1,799 SqFt
Clover Lane Lapis Plan, Orange, VA, 22960 $414,990 3 3 2,187 2,187 SqFt
15109 Poplar Court, Orange, VA, 22960 $439,500 4 2 2,072 2,072 SqFt
7313 Oakwood Drive, Orange, VA, 22960 $1,098,000 4 3 1,964 1,964 SqFt
7206 Old Dickersons Road, Orange, VA, 22960 $389,900 3 2 1,352 1,352 SqFt
6808 John Taylor Lane, Orange, VA, 22960 $1,375,000 5 3 3,600 3,600 SqFt
6616 Summerview Court, Orange, VA, 22960 $2,195,000 7 5 7,029 7,029 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 06/24/2026 @ 00:52

MLS: VAOR2014482 LISTED BY: Kathleen Annette Ayers, EXP Realty, LLC 540-395-6488 SOURCE: Bright MLS

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