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4 Crawford Road

Westport, Connecticut 06880

ACTIVE - NEW$2,595,000
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 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.

Key Facts

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Colonial
Year Built
1732
Days on Market
0 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

76

58 active listings

Median $ / Sq Ft

$827

58 active listings

Sale-to-List Ratio

100.0%

306 sales

How this home compares

List Price

$2.60M

vs $5.00M median

48.0% below median

Price / Sq Ft

$580

vs $827 median

29.9% below median

Days on Market

0 days

vs 76 days median

76 days fresher than median

Based on 58 active and 306 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of August 31, 2026.

Location

4 Crawford Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,976

per month

  • Principal & Interest$13,341
  • Property Taxes$1,770
  • Insurance$865
  • 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
0
MLS #
24203288
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

(203) 227-8424

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/31/2026. 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 8/31/2026 at 7:16 PM UTC.