4 Sherwood Island Lane, Westport, Connecticut 06880

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.

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $3,899,000, ranging $2,600,000 to $4,625,000.

Within a 15-minute walk, sold in the last year
• 221 Greens Farms Road5 bd · 6 ba · 5,789 sq ft · 0.4 mi away
  $2,995,000$517/sq ft2026-08-05
• 6 Clapboard Hill Road6 bd · 6 ba · 5,607 sq ft · 0.5 mi away
  $4,500,000$802/sq ft2026-08-26
• 10 Tierney Lane5 bd · 8 ba · 7,400 sq ft · 0.7 mi away
  $4,625,000$625/sq ft2026-06-01
• 123 Greens Farms Road4 bd · 5 ba · 5,207 sq ft · 0.7 mi away
  $2,600,000$499/sq ft2026-05-15
• 11 Edgewater Hillside4 bd · 5 ba · 4,693 sq ft · 0.7 mi away
  $3,899,000$830/sq ft2026-07-31

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.

More homes in Westport

Closest in price to this one.

• 47 Charcoal Hill Road4 bed · 6 bath · 10,522 sq ft$10,500,000
• 11 Dogwood Lane6 bed · 8 bath · 9,100 sq ft$10,650,000
• 9 Over Rock Lane6 bed · 9 bath · 9,200 sq ft$9,860,000
• 38 Prospect Road6 bed · 9 bath · 8,623 sq ft$9,200,000
• 14 Owenoke Park5 bed · 7 bath · 6,050 sq ft$11,995,000
• 11 Manitou Court7 bed · 9 bath · 9,415 sq ft$8,995,000

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