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 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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
58
40 under contract
Median List Price
$5.00M
58 active listings
Median Closed Price
$2.42M
306 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per 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
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
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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 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.