About this home
Privately nestled in Westport's coveted Old Hill neighborhood, this distinctive five-bedroom New England residence blends timeless character with thoughtful modern updates. Sun-filled interiors, beautifully scaled rooms, and original architectural details create warmth and authenticity throughout. The chef's kitchen is designed for both everyday living and entertaining, while the stunning, light-filled family room with fireplace offers a welcoming gathering space overlooking the beautifully landscaped grounds. A true standout is the inviting pub room with its original wood bar - an exceptional setting for entertaining, celebrations, or relaxed evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, home office or gym. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. A charming barn with electricity, water, cable, and convenient parking adds exceptional flexibility as a studio, workshop, recreation space, or future vision. Just minutes from downtown Westport, award-winning schools, beaches, shopping, dining, and the train, 4 Crawford Road offers a rare opportunity to own a home with genuine character, exceptional privacy, and a wonderful sense of place. A truly special Westport residence that brings together character, comfort, and an exceptional setting.
Flood risk: check the FEMA flood map for this address.
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Building & Exterior
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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
Real streets from OpenStreetMap; distances are straight-line from the property, not driving routes.
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 $1,625,000, ranging $1,475,000 to $2,780,000.
- $2,780,000$512/sq ft2025-10-31
- $1,600,000$419/sq ft2025-10-10
- $1,625,000$318/sq ft2026-06-03
- $1,475,000$410/sq ft2025-12-19
- $1,810,000$542/sq ft2025-12-18
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.
- 2022-06-14$2,076,500Single Family
- 2005-05-18$1,850,000
More homes in Westport
Closest in price to this one.