Claudia Dixon

4 Sherwood Island Lane

Westport, CT
$ 10,500,000 Beds 7 Baths 6.5 Sq 6,215
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 10,500,000
  • City
  • Westport
  • Bedrooms
  • 7
  • Full Bathrooms
  • 6
  • County
  • Fairfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 20.85 Acres
  • Zip
  • 06880
  • Sqr Footage
  • 6,215
  • Year Built
  • 1940
  • Taxes
  • $ 73686
  • Style
  • MLS#
  • 24160355
Listed By: Andrew Whiteley 203-258-1595 with Brown Harris Stevens. - (203) 254-1500
Data Source: Smart MLS

Features

General

Zoning AAA
Neighborhood Greens Farms
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 20.85
Directions Sherwood Island Connector. Before entering Sherwood Island State Park, turn left down private drive to gated driveway.
High School Staples
City Westport
Elementary School Greens Farms
Sq Ft Total 6215
DOM 117
Year Built 1940
Style Colonial
Year Built Source Public Records
Pool Description Indoor Pool

Interior Features

Cooling System Central Air
Total Rooms 14
Basement Description Full,Partially Finished

Exterior Features

Water Source Public Water Connected
Lot Description Secluded,Some Wetlands,Borders Open Space,Level Lot,Professionally Landscaped,Water View
Color White

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Greens Farms Elementary School
Middle School Unknown Middle School
High School Staples High School

Price History

3/26/2026 Listed $15,000,000
8/3/2026 30% - $10,500,000

Property vs Zip Code Average in 06880

Price
AVG $4.45M
$10.5M
Year Built
AVG 1983
1940

In The Neighborhood

Areas That We Cover

4 Sherwood Island Lane Westport, CT is a Single Family Home for sale at $10500000 with 6215 sqft and a lot size of 20.85 Acres Acre(s). 4 Sherwood Island Lane Westport has 7 bedrooms, 6 baths and was built in 1940. The property's zip code is 06880 which is in Westport, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Claudia Dixon

Claudia Dixon

Sales Associate

860-881-7725

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