16 Island Way, Westport, Connecticut 06880

About this home

Imagine starting your day with a walk to a private beach, an afternoon on the water, and dinner just minutes away in vibrant Saugatuck. This beautifully furnished home offers the lifestyle that makes Westport one of Connecticut's most coveted coastal communities. Walk or bike to three private association beaches with Adirondack chairs, picnic areas, kayak racks, and grills, then enjoy the nearby amenities of Longshore Club Park, including golf, tennis, sailing, swimming, and waterfront dining. Just minutes from the train, Main Street boutiques, and acclaimed restaurants, the location offers the perfect blend of seaside tranquility and everyday convenience. Inside, sun-filled living spaces feature soaring ceilings, custom millwork, rich hardwood floors, and wood-burning fireplaces that create a warm yet sophisticated atmosphere. The chef's kitchen is appointed with professional-grade appliances, an oversized marble island, and generous space for entertaining. Upstairs, four spacious bedrooms, including a serene primary suite with a spa-inspired bath, provide a peaceful retreat after a day by the water. Thoughtfully designed indoor and outdoor living spaces complete this exceptional opportunity to experience the very best of Westport living. Available September 10, 2026 to June 30, 2027

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

Availability, Pets & Lease

Schools

Interior

Building & Exterior

Lot & Land

What's nearby

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

Recent comparable rentals

The 5 closest recent leases to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded lease 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 rentals — median $22,000/mo, ranging $13,000/mo to $49,000/mo.

Within a 15-minute walk, leased in the last year
• 108 Harbor Road5 bd · 3 ba · 2,783 sq ft · 0.1 mi away
  $13,000/mo2025-09-02
• 14 Cockenoe Drive4 bd · 6 ba · 3,627 sq ft · 0.2 mi away
  $49,000/mo2026-03-24
• 3 Nassau Road5 bd · 4 ba · 2,944 sq ft · 0.4 mi away
  $25,000/mo2025-09-09
• 6 Plover Lane4 bd · 6 ba · 3,540 sq ft · 0.5 mi away
  $15,500/mo2026-06-01
• 52 Shorehaven Road3 bd · 3 ba · 3,131 sq ft · 0.6 mi away
  $22,000/mo2026-03-03

Listing & sale history

Every time this exact home has come to market in the MLS data this site tracks. Where a sale closed, the recorded sale price is shown; "asking" marks a price the home was listed at rather than what it sold for.

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.

Recorded sales

Deed transfers on file with the Westport land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

• 2018-01-12$1,500,000Single Family
• 2009-08-10$1,300,000Single Family
• 2005-07-01$1,500,000

More rentals in Westport

Closest in price to this one.

• 19 Bluewater Hill3 bed · 3 bath · 3,066 sq ft$15,000/mo
• 2 Drumlin Road4 bed · 3 bath · 2,528 sq ft$15,000/mo
• 6 Abbotts Lane2 bed · 3 bath · 3,656 sq ft$15,000/mo
• 15 Timber Lane5 bed · 5 bath · 4,605 sq ft$15,500/mo
• 20 Joann Circle5 bed · 4 bath · 3,392 sq ft$14,000/mo
• 222 Compo Road South4 bed · 5 bath · 4,449 sq ft$13,500/mo

← Back to all Stamford listings