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4 Crawford Road

Westport, Connecticut 06880

ACTIVE - NEW$2,799,000
Beds
5
Baths
3 | 1
SqFt
4,471
Acres
1.20
Year Built
1732
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage2 FireplacesVirtual Tour

About This Home

Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth throughout. Original elements reflect the home's storied past, while carefully integrated updates provide exceptional comfort for today's lifestyle. A standout feature is the distinctive pub room with its original wood bar - an unforgettable setting for intimate gatherings, celebrations, or quiet evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, or home office. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. Completing the property is a charming barn with electricity, water, cable, & convenient parking, offering exceptional flexibility as a studio, workshop, recreation space, or a future vision uniquely tailored to the next owner. Just minutes from downtown Westport, award-winning schools, shopping, restaurants, beaches, & the train, this exceptional property presents a rare opportunity to become the next steward of one of Westport's most treasured homes. A truly special place to call home!

Key Facts

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Colonial
Year Built
1732
Days on Market
7 days
Beds
5
Baths
3 full · 1 half
Living Area
4,471 sq ft
Lot Size
1.20 acres
Garage / Parking
2 garage
Property Taxes
$21,245 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

56

71 active listings

Median $ / Sq Ft

$820

71 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$2.80M

vs $4.60M median

39.1% below median

Price / Sq Ft

$626

vs $820 median

23.7% below median

Days on Market

7 days

vs 56 days median

49 days fresher than median

Based on 71 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

4 Crawford Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$16,974

per month

  • Principal & Interest$14,271
  • Property Taxes$1,770
  • Insurance$933
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Westport
Neighborhood
Old Hill
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1732
New Construction
No/Resale
Living Area
4,471 sq ft

Schools

Elementary
Kings Highway
High
Staples

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central AirZoned
Fireplaces
2
Laundry
Main Level
Appliances
Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedSump PumpStorageInterior AccessConcrete FloorFull With Hatchway
In-Law Apartment
No
Interior Features
Auto Garage Door OpenerCable - Available
Additional Rooms
FoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
1.20 acres
Zoning
AAA
Garage / Parking
2 garage spacesDetached Garage
Waterfront Details
Walk to WaterBeach RightsWater Community
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Clapboard
Color
white
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
BarnGuttersStone WallFrench DoorsUnderground SprinklerPatio
Lot Description
Corner LotLightly WoodedDryProfessionally Landscaped

Listing & Financials

Property Taxes
$21,245 / Annually
Days on Market
7
MLS #
24189715
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Barbara Sweeney

(203) 451-6522

Coldwell Banker Realty

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 10:10 AM UTC.