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For sale
    • $1,249,000

    21 Deepwood Road, Weston, CT 06883

    5beds
    4,336sqft
    : 
    $8,724/mo
    Get pre-qualified
    Single Family Residence
    Built in 1979
    2.14 Acres Lot
    $-- Zestimate®
    $288/sqft
    $-- HOA

    What's special

    Two picturesque acresQuiet cul-de-sacPrivate retreatTwo luxurious primary suitesEnhancing comfort and efficiency
    Nestled at the end of a quiet cul-de-sac on two picturesque acres, this extraordinary five-bedroom, three full bath residence offers a rare combination of timeless elegance and peaceful seclusion. Overlooking a gently flowing brook, the property is surrounded by natural beauty, creating a private retreat just minutes from the vibrant shops, acclaimed restaurants, beaches, and Metro-North train station in neighboring Westport. Designed for both everyday living and effortless entertaining, the home features two luxurious primary suites, including one on the main level and a second upstairs with its own private balcony overlooking the tranquil landscape. The sleek kitchen is beautifully appointed with new countertops, while the bathrooms offer sophisticated, contemporary finishes. Brand-new Andersen windows throughout bathe the home in natural light while enhancing comfort and efficiency. Offering an exceptional balance of privacy, convenience, and refined living, this is a rare opportunity to own a truly special home in sought-after Weston.
    19 days
    2,135
    122

    Zillow last checked:

    Listing updated:

    Listed by:

    Vantagepoint Properties at Real Broker,

    Michael Spindler (347)419-2250,

    Real Broker CT 413-231-6114

    Source: Smart MLS,MLS#: 24202535MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 3
      • Full bathrooms: 3
      Primary bedroom
      • Features: Bedroom Suite, Full Bath
      • Level: Main
      Primary bedroom
      • Features: Balcony/Deck, Bedroom Suite, Full Bath, Sliders, Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Dining room
      • Features: Sliders, Hardwood Floor
      • Level: Main
      Family room
      • Features: Dry Bar, Fireplace, Patio/Terrace
      • Level: Lower
      Kitchen
      • Level: Main
      Living room
      • Features: High Ceilings, Balcony/Deck, Fireplace
      • Level: Main
      Rec play room
      • Features: Engineered Wood Floor
      • Level: Main
      Heating
      • Hot Water, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Cooktop, Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Main Level, Upper Level
      Features
      • Open Floorplan, Smart Thermostat
      • Windows: Thermopane Windows
      • Basement: Full,Heated,Finished,Garage Access,Walk-Out Access
      • Attic: Pull Down Stairs
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,336
      • Total interior livable area: 4,336 sqft
      • Finished area above ground: 4,336

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached
      • Attached garage spaces: 2
      Features
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront, Brook
      Lot
      • Size: 2.14 Acres
      • Features: Cul-De-Sac, In Flood Zone
      Details
      • Parcel number: 404619
      • Zoning: R

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Cedar
      • Foundation: Block
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1979

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      Green energy
      • Energy efficient items: Windows

      Community & HOA

      Community
      • Subdivision: Lower Weston
      HOA
      • Has HOA: No
      Location
      • Region: Weston

      Financial & listing details

      • Price per square foot: $288/sqft
      • Tax assessed value: $728,210
      • Annual tax amount: $17,404
      • Date on market: 8/28/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/28/2026Listed for sale$1,249,000-3.8%$288/sqft
        Source: Smart MLS #24202535 Report a problem
        8/27/2026Listing removed$1,299,000$300/sqft
        Source: Smart MLS #24190123 Report a problem
        7/23/2026Price change$1,299,000-2%$300/sqft
        Source: Smart MLS #24190123 Report a problem
        7/11/2026Listed for sale$1,325,000+50.6%$306/sqft
        Source: Smart MLS #24190123 Report a problem
        3/2/2026Sold$880,000+16.6%$203/sqft
        Source: Public Record Report a problem
        4/11/2005Sold$755,000$174/sqft
        Source: Smart MLS #98223946 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$17,404 +1.8%$728,210
        2024$17,091 +5.8%$728,210 +49%
        2023$16,152 +0.3%$488,570
        2022$16,108 +0.1%$488,570
        2021$16,084 +1.7%$488,570
        2020$15,815 $488,570
        2019$15,815 +0.1%$488,570 -9.1%
        2018$15,797 +1.7%$537,500
        2017$15,539 +1.2%$537,500
        2016$15,351 -0.4%$537,500
        2015$15,410 +1.5%$537,500
        2014$15,179 +3.6%$537,500 -12.4%
        2013$14,654 -0.5%$613,400
        2012$14,734 +0.3%$613,400
        2011$14,685 +0.3%$613,400
        2010$14,636 +1.1%$613,400
        2009$14,482 +7.9%$613,400 +9.9%
        2008$13,417 +2.8%$557,900
        2007$13,049 +2.8%$557,900
        2006$12,692 +3.2%$557,900
        2005$12,302 +8.9%$557,900
        2004$11,297 -4.7%$557,900 +17.7%
        2003$11,853 +11.5%$474,110
        2001$10,630 +5.6%$474,110 +0%
        2000$10,065 +13.2%$474,100 +28.2%
        1997$8,892 $369,740
        Find assessor info on the county website

        Monthly payment

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        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.
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        Climate risks

        Neighborhood: 06883

        Getting around

        1 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Hurlbutt
        • Middle: Weston
        • High: Weston

        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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