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For sale
    • Price cut: $4.5M (8/3)
    $10,500,000

    4 Sherwood Island Lane, Westport, CT 06880

    7beds
    6,215sqft
    : 
    $65,965/mo
    Get pre-qualified
    Single Family Residence
    Built in 1940
    20.85 Acres Lot
    $-- Zestimate®
    $1,689/sqft
    $-- HOA

    What's special

    Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come. Please see the proposed Master Plan in the attachments prepared by distinguished local architect Mark Finlay, illustrating how a future owner might thoughtfully reimagine and reposition a family compound.
    151 days
    |
    2,436
    |
    100
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Andrew S. Whiteley (203)258-1595,

    Brown Harris Stevens 203-254-1500,

    Wendy Ryan 203-964-7450,

    Brown Harris Stevens

    Source: Smart MLS,MLS#: 24160355MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 7
      • Full bathrooms: 6
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Solarium
      Primary bedroom
      • Features: Bedroom Suite, Built-in Features, Dressing Room, Hardwood Floor
      • Level: Main
      Bedroom
      • Features: Hardwood Floor
      • Level: Main
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Bedroom
      • Features: Hardwood Floor
      • Level: Upper
      Dining room
      • Features: Fireplace, French Doors, Hardwood Floor
      • Level: Main
      Family room
      • Features: Built-in Features, Hardwood Floor
      • Level: Main
      Kitchen
      • Features: Breakfast Bar, Eating Space, Fireplace, Kitchen Island, Pantry, Hardwood Floor
      • Level: Main
      Library
      • Features: Bookcases, Built-in Features, Fireplace, Hardwood Floor
      • Level: Main
      Living room
      • Features: Bay/Bow Window, Fireplace, Hardwood Floor
      • Level: Main
      Media room
      • Level: Upper
      Sun room
      • Features: Wet Bar, French Doors, Hardwood Floor
      • Level: Main
      Heating
      • Hydro Air, Zoned, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water Heater
      Features
      • Sound System, Wired for Data, Sauna, Entrance Foyer, Wired for Sound
      • Basement: Full,Partially Finished
      • Attic: Pull Down Stairs
      • Number of fireplaces: 4
      Interior area
      • Total structure area: 6,215
      • Total interior livable area: 6,215 sqft
      • Finished area above ground: 6,215

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached
      • Attached garage spaces: 2
      Features
      • Has private pool: Yes
      • Pool features: Indoor
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront, River Front, Walk to Water, Beach Access, Water Community, Access
      Lot
      • Size: 20.85 Acres
      • Features: Secluded, Wetlands, Borders Open Space, Level, Landscaped, In Flood Zone
      Details
      • Parcel number: 417967
      • Zoning: AAA

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Foundation: Concrete Perimeter
      • Roof: Slate
      Condition
      • New construction: No
      • Year built: 1940

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public

      Community & HOA

      Community
      • Security: Security System
      • Subdivision: Greens Farms
      HOA
      • Has HOA: No
      Location
      • Region: Westport

      Financial & listing details

      • Price per square foot: $1,689/sqft
      • Tax assessed value: $3,907,000
      • Annual tax amount: $73,686
      • Date on market: 3/26/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/3/2026Price change$10,500,000-30%$1,689/sqft
        Source: Smart MLS #24160355 Report a problem
        3/26/2026Listed for sale$15,000,000$2,414/sqft
        Source: Halstead / Brown Harris Stevens #24160355 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$73,686 +1.3%$3,907,000
        2024$72,748 +1.5%$3,907,000
        2023$71,693 +1.5%$3,907,000
        2022$70,599 $3,907,000
        2021$70,599 +2.9%$3,907,000 -4.8%
        2020$68,611 -0.9%$4,106,000
        2019$69,227 $4,106,000
        2018$69,227 $4,106,000
        2017$69,227 $4,106,000
        2016$69,227 $4,106,000
        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: Greens Farms

        Getting around

        4 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Greens Farms
        • Middle: Bedford
        • High: Staples

        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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