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For sale
  • $288,500

    106 Greenbrier Rd, Chesapeake, VA 23320

    3beds
    1,100sqft
    : 
    $1,818/mo
    Get pre-qualified
    Single Family Residence
    Built in 1955
    0.75 Acres Lot
    $289,400 Zestimate®
    $262/sqft
    $-- HOA

    What's special

    Open concept with character
    Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character. The property is zoned Industrial and the current legal use is residential (nonconforming-grandfathered) Buyers should independently verify requirements with the City of Chesapeake, for any plans for additions or redevelopment or converting to an Airbnb STR.
    44 days
    |
    1,241
    |
    92
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jay Hassell,

    Keller Williams Realty Twn Ctr 757-499-5911,

    Leslie Claire,

    Keller Williams Realty Twn Ctr

    Source: REIN Inc.,MLS#: 10642393MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 1
      • Full bathrooms: 1
      Rooms
      • Room types: 1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, PBR with Bath, Spare Room
      Heating
      • Baseboard, Electric, Zoned
      Cooling
      • Wall/Window Unit(s)
      Appliances
      • Included: Microwave, Electric Range, Refrigerator, Electric Water Heater
      • Laundry: Dryer Hookup, Washer Hookup
      Features
      • Ceiling Fan(s)
      • Flooring: Laminate/LVP, Vinyl, Wood
      • Basement: Crawl Space
      • Attic: Scuttle
      • Number of fireplaces: 1
      • Fireplace features: Wood Burning
      Interior area
      • Total interior livable area: 1,100 sqft

      Property

      Parking
      • Total spaces: 4
      • Parking features: 4 Space
      Accessibility
      • Accessibility features: Curbless Shower, Grip-Accessible Features, Handheld Showerhead, Offset Shower Controls
      Features
      • Stories: 1
      • Patio & porch: Porch
      • Pool features: None
      • Fencing: None
      • Has view: Yes
      • View description: City, Trees/Woods
      • Waterfront features: Not Waterfront
      • Frontage length: .
      Lot
      • Size: 0.75 Acres
      • Features: Corner, Cul-De-Sac
      Details
      • Parcel number: 0370000000830
      • Zoning: M1
      • Special conditions: Owner Agent
      • Other equipment: Pump

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod,Cottage,Ranch
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Roof: Asphalt Shingle
      Condition
      • New construction: No
      • Year built: 1955

      Utilities & green energy

      • Sewer: City/County
      • Water: City/County

      Community & HOA

      Community
      • Subdivision: Greenbrier
      HOA
      • Has HOA: No
      Location
      • Region: Chesapeake

      Financial & listing details

      • Price per square foot: $262/sqft
      • Tax assessed value: $245,700
      • Annual tax amount: $2,482
      • Date on market: 7/2/2026

        Estimated market value

        $289,400

        $275,000 - $304,000

        $2,093/mo

        Price history

        Price history is unavailable.

        Public tax history

        YearProperty taxesTax assessment
        2025$2,482 +8.2%$245,700 +8.2%
        2024$2,293 +16.4%$227,000 +16.4%
        2023$1,971 +3.5%$195,100 +7.6%
        2022$1,905 +11.8%$181,400 +11.8%
        2021$1,704 $162,300 +0.9%
        2020-- $160,900 -21.9%
        2019$2,162 +44%$205,900 +0.2%
        2018$1,502 +3.2%$205,400 +48.3%
        2017$1,454 +0%$138,500
        2016$1,454 +300%$138,500
        2015$364 $138,500
        2014$364 -74.9%$138,500 +0.4%
        2013$1,449 -3.5%$138,000 -3.5%
        2012$1,502 -6.5%$143,000 -6.5%
        2011$1,607 $153,000
        2010$1,607 -6.6%$153,000 -6.6%
        2009$1,720 $163,800
        2008$1,720 -0.6%$163,800 +0.4%
        2007$1,730 -4.5%$163,200
        2006$1,812 +63%$163,200 +88%
        2004$1,111 +9.6%$86,800 +9.6%
        2003$1,014 +6.6%$79,200 +6.6%
        2002$951 +5.1%$74,300 +5.1%
        2001$905 $70,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: Greenbrier East

        Getting around

        61 / 100
        Somewhat Walkable
        0 / 100
        No Nearby Transit
        48 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Greenbrier Primary
        • Middle: Greenbrier Middle
        • High: Indian River

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

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