27 Rayfield Road, Westport, Connecticut 06880

About this home

Storybook charm meets comfortable living in this enchanting 3 bedroom, 4 bath home. Located at the end of a quiet block you will find exposed beams, character-rich details, and a warm, inviting atmosphere create a home that feels truly special. Thoughtfully designed spaces blend timeless charm with everyday functionality, offering room to gather, relax, and entertain. A spacious deck extends the living space outdoors, perfect for morning coffee, al fresco dining, or enjoying the surrounding setting. Each bedroom provides its own sense of retreat, while four full baths add exceptional convenience. From its distinctive architectural details to its cozy, welcoming feel, this is a home with personality and a true sense of place. Convenient central location close to trains and the beach.

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

HOA & Fees

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 $2,750,000, ranging $931,500 to $3,150,000.

Within a 15-minute walk, sold in the last year
• 11 Dogwood Lane4 bd · 3 ba · 3,156 sq ft · 0.2 mi away
  $2,337,500$740/sq ft2025-11-06
• 6 Over Rock Lane5 bd · 5 ba · 3,561 sq ft · 0.4 mi away
  $3,150,000$884/sq ft2025-12-03
• 23 Harborview Road4 bd · 4 ba · 3,674 sq ft · 0.6 mi away
  $2,750,000$748/sq ft2026-05-08
• 4 Budner Lane4 bd · 3 ba · 3,015 sq ft · 0.6 mi away
  $2,825,000$936/sq ft2025-10-17
Within about a mile and a half, sold in the last 2 years
• 30 Park Lane4 bd · 3 ba · 2,615 sq ft · 0.1 mi away
  $931,500$356/sq ft2024-11-18

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.

• 2015-06-04$1,210,000Single Family

More homes in Westport

Closest in price to this one.

• 5 Northfield Drive4 bed · 4 bath · 3,174 sq ft$1,890,000
• 2 Drumlin Road4 bed · 3 bath · 2,315 sq ft$1,895,000
• 36 Lyons Plain Road4 bed · 4 bath · 3,514 sq ft$1,899,000
• 4 Lookout Lane4 bed · 4 bath · 2,301 sq ft$1,699,000
• 40 Pequot Trail4 bed · 4 bath · 4,572 sq ft$1,695,000
• 5 Aspetuck Lane6 bed · 4 bath · 3,240 sq ft$1,650,000

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