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For sale
    • Price cut: $145K (7/29)
    $2,750,000

    220 Painter Hill Road, Roxbury, CT 06783

    4beds
    4,570sqft
    : 
    $16,961/mo
    Get pre-qualified
    Single Family Residence
    Built in 2007
    4.68 Acres Lot
    $-- Zestimate®
    $602/sqft
    $-- HOA

    What's special

    Stylish barThree-story elevatorRestored stone wallsHeated garagePergola-covered carportOversized islandPremium appliances
    Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner. Owner is Agent
    119 days
    |
    999
    |
    73
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Stacey Matthews (203)671-9067,

    W. Raveis Lifestyles Realty 860-868-0511,

    Pels Matthews 203-671-5432

    Source: Smart MLS,MLS#: 24167130MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Laundry, Sitting Room, Wine Cellar
      Primary bedroom
      • Features: High Ceilings, Dressing Room, Walk-In Closet(s), Wall/Wall Carpet
      • Level: Upper
      Bedroom
      • Features: Full Bath, Hardwood Floor, Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Features: High Ceilings, Full Bath, Hardwood Floor, Walk-In Closet(s)
      • Level: Main
      Bedroom
      • Level: Upper
      Office
      • Features: Full Bath
      • Level: Upper
      Heating
      • Heat Pump, Forced Air, Zoned, Electric, Oil, Propane
      Cooling
      • Central Air
      Appliances
      • Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Electric Water Heater
      • Laundry: Main Level, Mud Room
      Features
      • Elevator, Open Floorplan, Entrance Foyer
      • Doors: French Doors
      • Windows: Thermopane Windows
      • Basement: Full,Partially Finished
      • Attic: Pull Down Stairs
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 4,570
      • Total interior livable area: 4,570 sqft
      • Finished area above ground: 3,870
      • Finished area below ground: 700

      Property

      Parking
      • Total spaces: 3
      • Parking features: Carport, Attached, Garage Door Opener
      • Attached garage spaces: 3
      • Has carport: Yes
      Accessibility
      • Accessibility features: Accessible Hallway(s)
      Features
      • Patio & porch: Screened, Porch, Deck, Patio
      • Exterior features: Garden, Stone Wall, Underground Sprinkler
      • Has private pool: Yes
      • Pool features: Gunite, Heated, Salt Water, Lap, In Ground
      • Fencing: Stone
      Lot
      • Size: 4.68 Acres
      • Features: Few Trees, Cleared, Landscaped, Open Lot
      Details
      • Parcel number: 867195
      • Zoning: C
      • Other equipment: Generator, Humidistat

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard, HardiPlank Type
      • Foundation: Concrete Perimeter
      • Roof: Asphalt,Metal
      Condition
      • New construction: No
      • Year built: 2007

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Underground Utilities
      Green energy
      • Energy efficient items: Thermostat, Ridge Vents, Windows

      Community & HOA

      Community
      • Features: Golf, Health Club, Library, Park, Playground, Private School(s), Stables/Riding, Tennis Court(s)
      • Security: Security System
      • Subdivision: Painter Hill
      HOA
      • Has HOA: No
      Location
      • Region: Roxbury

      Financial & listing details

      • Price per square foot: $602/sqft
      • Tax assessed value: $781,830
      • Annual tax amount: $10,164
      • Date on market: 4/15/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/29/2026Price change$2,750,000-5%$602/sqft
        Source: Smart MLS #24167130 Report a problem
        4/15/2026Listed for sale$2,895,000+7.4%$633/sqft
        Source: Smart MLS #24167130 Report a problem
        6/16/2023Listing removed--
        Source: William Raveis Real Estate, Mortgage & Insurance Report a problem
        5/28/2023Price change$2,695,000-3.6%$590/sqft
        Source: Smart MLS #170564145 Report a problem
        4/26/2023Listed for sale$2,795,000+299.3%$612/sqft
        Source: Smart MLS #170564145 Report a problem
        5/20/2021Sold$700,000+7.7%$153/sqft
        Source: Public Record Report a problem
        8/28/2020Sold$650,000-5.1%$142/sqft
        Source: Smart MLS #170097451 Report a problem
        6/3/2020Pending sale$685,000$150/sqft
        Source: Coldwell Banker Realty #170097451 Report a problem
        3/5/2020Listed for sale$685,000-13.8%$150/sqft
        Source: Coldwell Banker Residential Brokerage #170097451 Report a problem
        3/27/2019Listing removed$795,000$174/sqft
        Source: Coldwell Banker Residential Brokerage - Newtown Office #170097451 Report a problem
        2/5/2019Price change$795,000-9.1%$174/sqft
        Source: Coldwell Banker Residential Brokerage - Newtown Office #170097451 Report a problem
        8/5/2018Price change$875,000-5.4%$191/sqft
        Source: Coldwell Banker Residential Brokerage #170097451 Report a problem
        6/20/2018Listed for sale$925,000$202/sqft
        Source: Coldwell Banker Residential Brokerage #170097451 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,164 +3.2%$781,830
        2024$9,851 -0.2%$781,830 -0.2%
        2023$9,872 +14.8%$783,510 +39%
        2022$8,597 +0.8%$563,750 +1.8%
        2021$8,530 -31.5%$553,880 -29.7%
        2020$12,450 -0.3%$787,960
        2019$12,489 $787,960
        2018$12,489 +0.3%$787,960 -10.1%
        2017$12,451 +3.7%$876,810
        2016$12,012 $876,810
        2015$12,012 +2.2%$876,810
        2014$11,749 +0.7%$876,810
        2013$11,662 +4.1%$876,810 -5.3%
        2012$11,205 +1.7%$926,040
        2011$11,020 +4.4%$926,040
        2010$10,557 +4.6%$926,040
        2009$10,094 +6.7%$926,040 +6.7%
        2008$9,456 +372.6%$867,520 +567.6%
        2007$2,001 $129,950
        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
        18 / 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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