4 Sherwood Island Lane

Westport, CT 06880 Directions
$15,000,000
  • 7Bed
  • 6/1Baths
  • 6,215Sqft
  • 20.85Acres
  • 1940Built
  • $2,414Price/Sqft

Property Highlights

  • Elementary: Greens Farms
  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Greens Farms
  • Days on Market: 28
  • MLS: 24160355

Property Highlights

  • Elementary: Greens Farms
  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Greens Farms
  • Days on Market: 28
  • MLS: 24160355

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...

Property Highlights

  • Elementary: Greens Farms
  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Greens Farms
  • Days on Market: 28
  • MLS: 24160355

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.

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.

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  • Additional Information
    • Attic Description: Pull-Down Stairs
    • Average Days On Market: 23
    • Basement Description: Full, Partially Finished
    • Days On Market: 28
    • Elementary School: Greens Farms
    • Garage: Attached Garage
    • Garage Count: 2
    • Has Pool?: Yes
    • High School: Staples
    • Is Occupied?: Owner
    • Is Waterfront?: Yes
    • Junior High School: Bedford
    • Living Area SqFt: 6,215
    • Neighborhood: Greens Farms
    • Property Tax: $73,686
    • Sewer: Septic
    • Style: Colonial
    • Tax Amount: $73,686
    • Tax Year: July 2025-June 2026
    • Type: Single Family For Sale
    • Year Built: 1940
    • Year Built Details: Public Records
    • Zoning: AAA
  • Amenities
    • Cable - Pre-wired
    • Sauna
    • Security System
  • Interior/Exterior Features
    • Air Conditioning: Central Air
    • Appliances Included: Wall Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer
    • Attic: Yes
    • Beds: 7
    • Cooling: Central Air
    • Exterior Siding: Shingle
    • Fireplaces: 4
    • Full Baths: 6
    • Furnace Type: Oil
    • Half Baths: 1
    • Heat: Oil
    • Heat Fuel: Oil
    • Hot Water: Oil, Domestic
    • Pool Description: Indoor Pool
    • Roof: Slate
    • Rooms: 14
William Pitt / Julia B. Fee Sotheby's International Realty

Westport Brokerage

199 Post Road East
Westport, CT 06880

Listing Courtesy of Andrew Whiteley of Brown Harris Stevens.

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