280 Main Street, Westport, Connecticut 06880

About this home

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/primary bedroom suite, thoughtfully added in the 1960s, offers convenient one-level living and adds flexibility to the original floor plan. Upstairs, two roomy bedrooms share a generously sized bathroom that presents an exciting renovation opportunity: the space could be reconfigured to create two en-suite bathrooms, one for each bedroom, adding modern functionality while preserving the home's charm and character. While the house is in need of renovation, its established setting, private grounds, classic details, and highly desirable in-town location make it an exceptional opportunity for those looking to restore, renovate, and make the home their own. For buyers seeking in-town convenience, privacy, and authentic Westport character, this is a special property with tremendous potential.

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 $1,300,000, ranging $969,000 to $1,960,000.

Within a 15-minute walk, sold in the last year
• 7 Wild Rose Road3 bd · 3 ba · 1,805 sq ft · 0.1 mi away
  $1,960,000$1,085/sq ft2026-01-12
• 20 Woods Grove Road4 bd · 2 ba · 1,941 sq ft · 0.3 mi away
  $969,000$499/sq ft2026-08-07
• 2 Evergreen Avenue3 bd · 3 ba · 2,128 sq ft · 0.4 mi away
  $1,721,000$808/sq ft2026-10-01
• 113 Kings Highway North3 bd · 3 ba · 1,549 sq ft · 0.4 mi away
  $1,300,000$839/sq ft2026-03-02
• 5 Edge Hill Trail3 bd · 3 ba · 2,400 sq ft · 0.4 mi away
  $1,050,000$437/sq ft2026-08-24

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.

• 6 Willowbrook Drive4 bed · 3 bath · 2,622 sq ft$1,295,000
• 53 Cross Highway3 bed · 2 bath · 1,400 sq ft$1,000,000
• 183 Wilton Road3 bed · 3 bath · 2,679 sq ft$999,000
• 38 Guyer Road4 bed · 2 bath · 1,665 sq ft$1,399,000
• 4 Woods Grove Road4 bed · 3 bath · 2,133 sq ft$999,000
• 9 Primrose Lane4 bed · 3 bath · 3,343 sq ft$1,399,000

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