360 Westford Drive
Fairfield, Connecticut 06890
- Beds
- 4
- Baths
- 2
- SqFt
- 2,044
- Acres
- 0.28
- Year Built
- 1947
- Neighborhood
- Southport
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 360 Westford Drive, nestled in the highly sought-after Village of Southport. Privately situated at the end of a quiet cul-de-sac, this charming 4/5-bedroom Colonial offers a wonderful combination of space, flexibility, and privacy. With just a little TLC, this home has unlimited potential. The inviting 1st floor features an open-concept floor plan centered around a large kitchen and spacious family room, creating an ideal setting for everyday living and entertaining. A formal dining room, full bathroom, main level bedroom and a versatile flex room complete the main level, offering endless possibilities for guest accommodations, an office, playroom, laundry, gym, or additional living space. Upstairs, you'll find 2 generously-sized bedrooms, along with a spacious primary bedroom featuring an enormous walk-in closet. An updated Jack-and-Jill bathroom provides convenient access for all 3 bedrooms. Outside, a large deck overlooks a level yard, offering a wonderful space for outdoor dining, entertaining, relaxing, and enjoying the peaceful scenery. Ideally situated for enjoying the best of Southport living, this home is conveniently located 1/2 mile from Metro-North train station and close to the Village Center, Pequot Library, Southport Harbor, and Southport Beach. Enjoy nearby shops, restaurants, cultural attractions, boating, beaches, and recreational opportunities, all while coming home to the privacy and tranquility this home has to offer.
Key Facts
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
118
71 under contract
Median List Price
$1.20M
118 active listings
Median Closed Price
$1.16M
582 sales
Median Days on Market
26
118 active listings
Median $ / Sq Ft
$497
118 active listings
Sale-to-List Ratio
102.5%
582 sales
How this home compares
List Price
$999,900
vs $1.20M median
16.3% below median
Price / Sq Ft
$489
vs $497 median
In line with median
Days on Market
0 days
vs 26 days median
26 days fresher than median
Based on 118 active and 582 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of October 8, 2026.
Location
360 Westford Drive, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$5,473
- Property Taxes$851
- Insurance$333
- 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
- 1947
- New Construction
- No/Resale
- Living Area
- 2,044 sq ft
Schools
- Elementary
- Mill Hill
- High
- Fairfield Ludlowe
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Main Level
- Laundry Location
- Hookups also in the basement
- Appliances
- Gas RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinished
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.28 acres
- Zoning
- A
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedDeck
- Lot Description
- Level LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $10,209 / Annually
- Days on Market
- 0
- MLS #
- 24209334
- MLS Status
- Active
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Co-Listed By
Anthony Cali
Preston Gray Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/8/2026. 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 10/8/2026 at 1:10 PM UTC.