101 Webb Avenue, Stamford, Connecticut 06902

About this home

Discover this inviting, solidly built, and legally certified three-family home in 'The Cove', one of Stamford's most sought-after coastal neighborhoods! Cherished by the same family for more than six decades, this multi-generational property offers exceptional flexibility-perfect for an owner occupant, an investor, or anyone seeking versatile living arrangements. The main level features a very spacious 3BR/2BTH + den, while the 2nd floor offers both a 2BR/1BTH unit and a 1BR/1BTH unit. Each residence includes generously sized rooms, beautiful wood floors and separate gas & electric meters (the 1BR unit is all electric). The basement provides additional space for an office, workshop, or storage. A rare bonus, the detached oversized three-car garage is perfect for business equipment,winter boat storage, hobby gear, or extra vehicles. Behind the garage, a peaceful grassy area offers the opportunity to create your own garden sanctuary. Recent updates include newer roofs on both the home(2022)and the garage(2021). And the location is unbeatable-a short walk to the beach at Cove Island Park, marina/harbor, and skating rink, with downtown Stamford, the train station, and I-95 just minutes away! Homes like this don't come around often!

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

Energy

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 $940,000, ranging $738,000 to $1,050,000.

Within a 15-minute walk, sold in the last year
• 37 Waterbury Avenue7 bd · 6 ba · 3,972 sq ft · 0.3 mi away
  $940,000$236/sq ft2026-08-26
• 22 Palmer Avenue5 bd · 4 ba · 4,005 sq ft · 0.4 mi away
  $912,000$227/sq ft2025-09-19
• 10 Elmwood Street9 bd · 6 ba · 3,350 sq ft · 0.6 mi away
  $1,050,000$313/sq ft2025-09-02
• 85 Avery Street6 bd · 2 ba · 2,688 sq ft · 0.6 mi away
  $738,000$274/sq ft2025-08-14
• 88 Horton Street6 bd · 2 ba · 2,728 sq ft · 0.7 mi away
  $985,000$361/sq ft2025-08-01

Public record

From the Stamford 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 Stamford

Closest in price to this one.

• 19 Davenport Street9 bed · 3 bath · 2,090 sq ft$999,000
• 604 Fairfield Avenue6 bed · 2 bath · 2,378 sq ft$999,000
• 29 Cowan Avenue6 bed · 3 bath · 2,850 sq ft$989,000
• 34 Raymond Street5 bed · 2 bath · 3,044 sq ft$985,000
• 511 Fairfield Avenue6 bed · 4 bath · 3,200 sq ft$975,000
• 21 Culloden Road7 bed · 3 bath · 2,463 sq ft$965,999

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