$15,000,000

4 Sherwood Island Lane, Westport, CT 06880

  • 7 beds |
  • 7 baths |
  • 6,215 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1940
  • Property Lot Size Icon20.85acre lot
  • Property Parking Icon 2 car garage
  • Property Price Per Square Feet Icon $2,414/sqft
  • Property List Date Icon Listed 1 month ago

Property Description

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.

Listing Status:
Active
Date Added:
March 26, 2026
Data Last Updated:
May 11, 2026 at 8:52PM
Listing Office:
Brown Harris Stevens : (203) 254-1500
Listing Agent:
Andrew Whiteley : (203) 258-1595
MLS ID:
24160355
  • General: Audio SystemCable - Pre-wiredSaunaSecurity System
  • Rooms: FoyerSolarium
  • Appliances: Wall OvenRefrigeratorFreezerDishwasherWasherDryer
  • Basement: FullPartially Finished
  • A/C: Central Air
  • Heating: Hydro AirZonedOil
  • Fireplace: Fireplaces: 4
  • Style: Colonial
  • Pool: Indoor Pool
  • Roofing: Slate
  • County: Fairfield
  • Zoning: AAA417967
  • Water: Public Water Connected
  • Sewer: Septic

This listing courtesy of Andrew Whiteley , Brown Harris Stevens

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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