Home / Listings / Westport
Active · For Sale
$10,500,000

4 Sherwood Island Lane, Westport, Connecticut 06880

7 beds 7 baths 6,215 sq ft Single Family For Sale Built 1940

About this home

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.

Status
Active
Type
Single Family For Sale
Price
$10,500,000
Beds
7
Baths
7
Interior
6,215 sq ft
Lot
20.85 ac
Year Built
1940
MLS #
24160355
ZIP
06880
Days on Market
124
Heat
Oil · Hydro Air, Zoned
Cooling
Central Air
Water
Public Water Connected
Sewer
Septic
Parking
Attached Garage (2-car)
Flood Zone
Yes

Flood risk: check the FEMA flood map for this address.

Schools

Elementary
Greens Farms
Middle / Jr High
Bedford
High School
Staples

Taxes

Property tax
$73,686 (July 2025-June 2026)
Assessed value
$3,907,000

Interior

Appliances
Wall Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer
Basement
Full, Partially Finished
Attic
Pull-Down Stairs
Fireplaces
4
Total rooms
14

Building & Exterior

Style
Colonial
Roof
Slate
Siding
Shingle
Foundation
Concrete
Pool
Indoor Pool
New construction
No/Resale

Lot & Land

Zoning
AAA
Lot
Secluded, Some Wetlands, Borders Open Space, Level Lot, Professionally Landscaped, Water View
Waterfront
L. I. Sound Frontage, River, Walk to Water, Beach Rights, Water Community, View, Access
Direct waterfront
Yes

Public record

From the Westport assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Year built1940
Living area8,067 sq ft
Total rooms14
Lot size17 acres
Stories2
HeatHydroAir
ExteriorWood Shingle
Assessed value$3,907,000
Town appraisal$5,581,500
Last recorded sale2019
Listing courtesy of Brown Harris Stevens — Andrew Whiteley · (203) 254-1500

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