4 Bradley Street, Westport, Connecticut 06880

About this home

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four additional bedrooms are ample in scale - one en-suite, with a Jack-and-Jill bath connecting two others - while a full bath and a dedicated office complete the first level. Outdoors, an expansive terrace invites al fresco dining and entertaining above a manicured, secluded yard set on a coveted corner lot. Beyond the door: sunrise strolls to the water, sunsets over the boardwalk, Longshore Club, downtown shops, dining, and the library, plus a straightforward Manhattan commute via Saugatuck Metro-North. Homes in this enclave seldom surface.

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 $3,750,000, ranging $2,825,000 to $5,300,000.

Within a 15-minute walk, sold in the last year
• 312 Compo Road South4 bd · 4 ba · 3,215 sq ft
  $3,750,000$1,166/sq ft2026-06-18
• 5 Bradley Street4 bd · 4 ba · 3,366 sq ft
  $2,825,000$839/sq ft2025-09-05
• 15 Roosevelt Road4 bd · 5 ba · 3,562 sq ft · 0.2 mi away
  $5,300,000$1,487/sq ft2026-08-10
• 5 Compo Hill Avenue3 bd · 3 ba · 2,554 sq ft · 0.4 mi away
  $3,000,000$1,174/sq ft2025-09-12
• 4 Buena Vista Drive5 bd · 5 ba · 3,929 sq ft · 0.4 mi away
  $3,875,000$986/sq ft2025-11-14

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.

• 2019-03-13$1,500,000Single Family
• 2008-10-03$1,500,000Single Family
• 2005-04-29$1,787,500

More homes in Westport

Closest in price to this one.

• 166 Long Lots Road4 bed · 5 bath · 5,629 sq ft$2,995,000
• 36 East Main Street6 bed · 6 bath · 4,922 sq ft$2,999,000
• 30 Saint Johns Place5 bed · 4 bath · 3,999 sq ft$2,895,000
• 2 Half Mile Common4 bed · 5 bath · 5,039 sq ft$3,100,000
• 27 Bauer Pl Extension5 bed · 6 bath · 4,529 sq ft$2,850,000
• 4 Crawford Road5 bed · 4 bath · 4,471 sq ft$2,799,000

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