4 Crawford Road
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 4,471
- Acres
- 1.20
- Year Built
- 1732
- Neighborhood
- Old Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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
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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.