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For sale
    • Price cut: $100K (8/21)
    $1,695,000

    25 Highmeadow Lane, Roxbury, CT 06783

    4beds
    4,310sqft
    : 
    $9,822/mo
    Get pre-qualified
    Single Family Residence
    Built in 1986
    17.31 Acres Lot
    $-- Zestimate®
    $393/sqft
    $-- HOA

    What's special

    Beautifully appointed colonialClassic barn with apartmentExpansive groundsGated entranceHeated gunite saltwater poolTwo baths upstairsLots of storage
    Imagine yourself at this private Litchfield County estate where open land, views, and timeless New England charm come together. Set on over 17 acres, this exceptional property offers the rare combination of privacy, recreation, and versatility, featuring a beautifully appointed Colonial, classic barn with apartment, heated gunite saltwater pool, and expansive grounds just 90 minutes from Manhattan. The sun-filled eat-in kitchen has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic family room with vaulted ceilings, dining room, living room, large office/den/library, laundry room, and powder room. Four bedrooms and two baths upstairs, including a spacious primary suite with walk-in closets and dressing area. The lower level has lots to offer with another half bath, gym/workout area, lots of storage and access to the 2-car garage. Drive through the gated entrance to find a parklike setting with stone walls, a brook, a pond, walking & riding trails. Stroll over to the heated, gunite, midnight blue PebbleTec saltwater pool, and the New England barn with hay loft and 930 sq ft apartment w/bedroom, bath and kitchen (making the full property 5 BD, 4 BA). Multi-stall barn and several other outbuildings offer flexibility for equestrian pursuits, collector storage, creative studios, wellness uses, and income potential. Separate 3-Bay detached garage (great for car collectors!), a whole-property generator, and so much more.
    110 days
    |
    914
    |
    36
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    The Rick Distel Team at Compass,

    William K. Bolls (646)285-8197,

    Compass Connecticut, LLC 203-293-9715,

    Co-Listing Agent: Rick Distel 646-417-2720,

    Compass Connecticut, LLC

    Source: Smart MLS,MLS#: 24171982MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 2
      • 1/2 bathrooms: 2
      Primary bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Dining room
      • Level: Main
      Family room
      • Features: Sliders
      • Level: Main
      Kitchen
      • Features: Skylight, Sliders
      • Level: Main
      Living room
      • Level: Main
      Office
      • Level: Lower
      Rec play room
      • Level: Lower
      Study
      • Level: Main
      Heating
      • Heat Pump, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Gas Range, Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater
      Features
      • Basement: Full,Partially Finished
      • Attic: Pull Down Stairs
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,310
      • Total interior livable area: 4,310 sqft
      • Finished area above ground: 3,810
      • Finished area below ground: 500

      Property

      Parking
      • Total spaces: 2
      • Parking features: Barn, Attached
      • Attached garage spaces: 2
      Features
      • Patio & porch: Deck
      • Exterior features: Awning(s), Fruit Trees, Garden
      • Has private pool: Yes
      • Pool features: Gunite, Heated, In Ground
      Lot
      • Size: 17.31 Acres
      • Features: Wetlands, Farm, Level, Sloped, Open Lot
      Details
      • Additional structures: Shed(s), Barn(s), Stable(s)
      • Parcel number: 866518
      • Zoning: C
      • Horses can be raised: Yes
      • Horse amenities: Paddocks

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Slab
      • Roof: Wood
      Condition
      • New construction: No
      • Year built: 1986

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Golf, Lake, Library, Park, Private School(s), Shopping/Mall, Stables/Riding, Tennis Court(s)
      HOA
      • Has HOA: No
      Location
      • Region: Roxbury

      Financial & listing details

      • Price per square foot: $393/sqft
      • Tax assessed value: $1,238,930
      • Annual tax amount: $16,106
      • Date on market: 5/4/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/21/2026Price change$1,695,000-5.6%$393/sqft
        Source: Smart MLS #24171982 Report a problem
        5/7/2026Listed for sale$1,795,000+116.3%$416/sqft
        Source: Smart MLS #24171982 Report a problem
        11/18/2020Sold$829,900$193/sqft
        Source: Public Record Report a problem
        9/17/2020Pending sale$829,900$193/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        8/28/2020Price change$829,900-6.6%$193/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        7/29/2020Price change$889,000-1.2%$206/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        6/26/2020Price change$899,900-7.7%$209/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        5/20/2020Price change$975,000-1%$226/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        2/25/2020Price change$985,000-1.5%$229/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        1/31/2020Price change$999,900-4.8%$232/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        10/16/2019Price change$1,050,000-4.5%$244/sqft
        Source: Aspen Realty Group #170234250 Report a problem
        8/27/2019Price change$1,100,000-8.3%$255/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        7/29/2019Price change$1,200,000-0.8%$278/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        6/28/2019Price change$1,210,000-1.2%$281/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        6/3/2019Price change$1,225,000-2%$284/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        5/10/2019Price change$1,250,000-1.2%$290/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        4/12/2019Price change$1,265,000-0.8%$294/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        3/4/2019Price change$1,274,900-1.2%$296/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        1/24/2019Listed for sale$1,290,000+7.5%$299/sqft
        Source: Silver and Oak Realty #170234250 Report a problem
        12/1/2017Listing removed$1,200,000$278/sqft
        Source: William Pitt Sotheby's International Realty #L10139311 Report a problem
        12/14/2016Price change$1,200,000-14%$278/sqft
        Source: William Pitt Sotheby's International Realty #L10139311 Report a problem
        11/11/2016Price change$1,395,000-7%$324/sqft
        Source: William Pitt Sotheby's International Realty #L10139311 Report a problem
        8/24/2016Price change$1,500,000-11%$348/sqft
        Source: William Pitt Sotheby's International Realty #L10139311 Report a problem
        5/29/2016Listed for sale$1,685,000$391/sqft
        Source: William Pitt Sotheby's International Realty #L10139311 Report a problem
        3/1/2015Listing removed$1,685,000+34.8%$391/sqft
        Source: Klemm Real Estate Inc #L148904 Report a problem
        4/2/2002Sold$1,250,000+762.1%$290/sqft
        Source: Public Record Report a problem
        1/10/1995Sold$145,000$34/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$16,106 +5.8%$1,238,930 +2.6%
        2024$15,220 $1,207,920
        2023$15,220 -2%$1,207,920 +18.6%
        2022$15,537 +2.5%$1,018,790 +3.5%
        2021$15,158 -8.3%$984,300 -5.9%
        2020$16,521 -0.3%$1,045,630
        2019$16,573 +1.1%$1,045,630 +1.1%
        2018$16,390 +5.1%$1,034,080 -5.9%
        2017$15,597 +3.6%$1,098,370
        2016$15,048 $1,098,370
        2015$15,048 +2.2%$1,098,370
        2014$14,718 +0.8%$1,098,370
        2013$14,608 +5.7%$1,098,370 -3.8%
        2012$13,818 +1.7%$1,141,980
        2011$13,590 +4.4%$1,141,980
        2010$13,019 +4.6%$1,141,980
        2009$12,448 -0.3%$1,141,980 -0.3%
        2008$12,486 -7.7%$1,145,480 +30.4%
        2007$13,527 $878,390
        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.
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        Climate risks

        Neighborhood: 06783

        Getting around

        0 / 100
        Car-Dependent
        5 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Booth Free

        Source: Smart 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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