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For sale
    • Price cut: $26K (7/23)
    $1,299,000

    21 Deepwood Road, Weston, CT 06883

    5beds
    4,436sqft
    : 
    $8,643/mo
    Get pre-qualified
    Single Family Residence
    Built in 1979
    2.14 Acres Lot
    $1,285,400 Zestimate®
    $293/sqft
    $-- HOA

    What's special

    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.
    34 days
    |
    1,281
    |
    70
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Vantagepoint Properties at Real Broker,

    Colby Gee (607)351-1527,

    Real Broker CT 413-231-6114,

    Co-Listing Agent: Michael Spindler 347-419-2250,

    Real Broker CT

    Source: Smart MLS,MLS#: 24190123MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 3
      • Full bathrooms: 3
      Rooms
      • Room types: Bonus Room, Exercise Room
      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, Subzero, Dishwasher, Washer, Dryer, Water Heater
      • Laundry: Lower Level
      Features
      • Basement: Full,Heated,Finished,Garage Access,Walk-Out Access
      • Attic: Pull Down Stairs
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,436
      • Total interior livable area: 4,436 sqft
      • Finished area above ground: 4,436

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached
      • Attached garage spaces: 2
      Features
      • Patio & porch: Deck, Patio
      • Exterior features: Balcony
      • 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
      • Vertical Siding, Cedar
      • Foundation: Block
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1979

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $293/sqft
      • Tax assessed value: $728,210
      • Annual tax amount: $17,404
      • Date on market: 7/9/2026

        Estimated market value

        $1,285,400

        $1.22M - $1.35M

        $7,979/mo

        Price history

        DateEventPrice
        7/23/2026Price change$1,299,000-2%$293/sqft
        Source: Smart MLS #24190123 Report a problem
        7/11/2026Listed for sale$1,325,000+50.6%$299/sqft
        Source: Smart MLS #24190123 Report a problem
        3/2/2026Sold$880,000+16.6%$198/sqft
        Source: Public Record Report a problem
        4/11/2005Sold$755,000$170/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

        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: 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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