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Under contract
  • $4,795,000

    271 Overlook Dr, Greenwich, CT 06830

    5beds
    4,778sqft
    : 
    $31,477/mo
    Get pre-qualified
    Residential, Single Family Residence
    Built in 2011
    0.29 Acres Lot
    $4,749,800 Zestimate®
    $1,004/sqft
    $260/mo HOA

    What's special

    En-suite bedroomNewly redesigned contemporary kitchenHigh ceilingsFantastic vegetable gardenAbundant natural lightGracious formal roomsExceptional closet
    The property you have been waiting for! Chic, sun-filled and turn key, this beautifully appointed five-bedroom home pairs fresh, modern interiors with the warmth and character of a classic Greenwich residence. Tucked into the coveted Milbrook Association, just around the corner from the private Club and minutes from Greenwich Avenue, the train and schools, 271 Overlook offers an exceptional combination of neighborhood charm, in-town convenience and relaxed luxury. High ceilings, hardwood floors and abundant natural light set the tone throughout. Gracious formal rooms give way to a welcoming Great Room with fireplace, a sun-filled breakfast room and newly redesigned contemporary kitchen with direct access to an expansive stone terrace. A walk-in pantry, mudroom and powder room complete the main level. Upstairs, the spectacular primary suite features vaulted ceiling, an exceptional closet and a luxurious bath with radiant heated floors. Three additional light-filled bedrooms provide generous accommodations for family and guests. The finished lower level adds flexible living and entertaining space with a wine cellar, family/playroom, office/gym, second laundry and en-suite bedroom. Outside, the setting is truly enchanting with lovely lawn for play, a shaded terrace and a fantastic vegetable garden. Experience the best of Milbrook, with dedicated security, a neighborhood playground and a welcoming sense of community, plus priority positioning for Club membership. Just steps away, the Milbrook Club offers golf, tennis, paddle, swimming and dining - an exceptional lifestyle in one of Greenwich's most coveted neighborhoods. This is Greenwich living at its best!
    11 days
    2,142
    159

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Ellen Mosher 203-705-9680,

    Houlihan Lawrence

    Source: Greenwich MLS, Inc.,MLS#: 125962MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Heating
      • Natural Gas, Forced Air
      Cooling
      • Central Air
      Appliances
      • Laundry: Laundry Room
      Features
      • Pantry, Central Vacuum
      • Basement: Finished
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 4,778
      • Total interior livable area: 4,778 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage
      • Garage spaces: 2
      Features
      • Patio & porch: Terrace
      Lot
      • Size: 0.29 Acres
      • Features: Level
      Details
      • Parcel number: 13193/S
      • Zoning: R-12
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Residential, Single Family Residence
      Materials
      • Shingle Siding, Stone
      • Roof: Asphalt
      Condition
      • Year built: 2011
      • Major remodel year: 2020

      Utilities & green energy

      • Water: Public

      Community & HOA

      Community
      • Security: Security System
      HOA
      • Has HOA: Yes
      • HOA fee: $3,124 annually
      • HOA name: Milbrook
      Location
      • Region: Greenwich

      Financial & listing details

      • Price per square foot: $1,004/sqft
      • Tax assessed value: $2,055,410
      • Annual tax amount: $21,549
      • Date on market: 9/30/2026
      • Inclusions: Washer/Dryer, All Kitchen Applncs

        Estimated market value

        $4,749,800

        $4.51M - $4.99M

        Not available

        Price history

        DateEventPrice
        10/8/2026Contingent$4,795,000$1,004/sqft
        Source: Greenwich MLS, Inc. #125962 Report a problem
        9/30/2026Listed for sale$4,795,000+88%$1,004/sqft
        Source: Greenwich MLS, Inc. #125962 Report a problem
        8/1/2017Sold$2,550,000-5.4%$534/sqft
        Source: Public Record Report a problem
        6/1/2017Price change$2,695,000-5.4%$564/sqft
        Source: Houlihan Lawrence #99589 Report a problem
        5/22/2017Price change$2,850,000-3.4%$596/sqft
        Source: Houlihan Lawrence #99589 Report a problem
        4/21/2017Listed for sale$2,950,000+218.9%$617/sqft
        Source: Houlihan Lawrence #99589 Report a problem
        12/16/2010Sold$925,000$194/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$19,465 +3.5%$1,574,930
        2024$18,798 +2.6%$1,574,930
        2023$18,326 +0.9%$1,574,930
        2022$18,159 -10.6%$1,574,930 -6.6%
        2021$20,309 +0.2%$1,686,790
        2020$20,275 -1%$1,686,790
        2019$20,478 +2.3%$1,686,790
        2018$20,022 -2.3%$1,686,790 -1%
        2017$20,487 +30.6%$1,704,570 +29.5%
        2015$15,691 +2.6%$1,315,790
        2014$15,296 +2.8%$1,315,790
        2013$14,882 +49.7%$1,315,790 +45.6%
        2012$9,941 +28.7%$903,700 +24.4%
        2011$7,727 -0.1%$726,180 -15.2%
        2010$7,737 +3.4%$855,890
        2009$7,480 +3.5%$855,890
        2008$7,224 $855,890
        2007-- --
        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: 06830

        Getting around

        42 / 100
        Car-Dependent
        32 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Julian Curtiss
        • Middle: Central

        Source: Greenwich MLS, 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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