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4 Sherwood Island Lane

Westport, CT 06880
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Bed 7

Bed

Bath 7

Bath

SqFt6,215

Sqft

Acres20.85

Acres(Lot)

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 col lection 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.

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Detail Ic Property Details

Property Type : Residential

Price : $15,000,000

AD Id : 76515487

MLS Id : 24160355

Beds : 7

Lot Size : 20.85 Acres

Living Area Size : 6,215

Year Built : 1940

Garage : 2

County : Fairfield

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Feature Features

  • Bedroom Information

    Total beds: 7

    Bathroom Information

    Total Baths: 7 Full Baths: 6 Half Baths: 1

    Room Information

    Rooms Total: 14 Has Basement: Yes Basement: Full, Partially Finished
  • Interior Features

    Sound System, Sauna, Entrance Foyer Appliances: Dishwasher, Dryer, Freezer, Refrigerator, Oven, Washer
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Zoned Has Cooling: Yes Cooling: Central Air Water front: 1

  • Building Information

    Year Built: 1940 Building Area Total: 6215 Construction Materials: Shingle Siding, Frame Pool Features: Indoor, Outdoor Pool Private Pool: No Water front Features: River Front, Beach Access View: Water

  • Lot Information

    Lot Size Acres: 20.85 Lot Description: Level, Waterfront

  • Listing Price Information

    Listing Price: $15000000

  • Tax Information

    Parcel Number: 417967 Annual Tax: $73686

  • Parking Information

    Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Greens Farms
    Junior High School: Bedford
    Senior High School: Staples
  • Location Information

    Direction: Sherwood Island Connector. Before entering Sherwood Island State Park, turn left down private drive to gated driveway. WaterSource: Public Security Features: Security System
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Clapboard Hill Road #NE.., Westport, CT, 06880 $7,926,000 6 7 7,200 7,200 SqFt
10 Grist Mill Lane, Westport, CT, 06880 $1,689,000 3 3 2,138 2,138 SqFt
28 Bulkley Avenue, Westport, CT, 06880 $2,500,000 5 5 3,917 3,917 SqFt
359 Greens Farms Road, Westport, CT, 06880 $5,499,000 6 8 7,748 7,748 SqFt
69 Beachside Avenue, Westport, CT, 06880 $7,350,000 6 7 6,585 6,585 SqFt
36 Maple Avenue, Westport, CT, 06880 $5,199,000 6 7 2,448 2,448 SqFt
61 Clapboard Hill Road, Westport, CT, 06880 $3,850,000 4 4 3,418 3,418 SqFt
11 Beachside Common, Westport, CT, 06880 $22,825,000 8 10 9,439 9,439 SqFt
25 Old Road, Westport, CT, 06880 $2,200,000 5 5 4,474 4,474 SqFt
11 Clapboard Hill Road, Westport, CT, 06880 $3,995,000 6 8 5,628 5,628 SqFt

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 06/22/2026 @ 12:19

MLS: 24160355 LISTED BY: Andrew Whiteley, Brown Harris Stevens SOURCE: SmartMLS

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