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360 Westford Drive

Fairfield, Connecticut 06890

ACTIVE - NEW$999,900
Beds
4
Baths
2
SqFt
2,044
Acres
0.28
Year Built
1947
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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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

City/Town
Fairfield
Neighborhood
Southport
Property / Style
Single Family · Colonial
Year Built
1947
Days on Market
0 days
Beds
4
Baths
2 full
Living Area
2,044 sq ft
Lot Size
0.28 acres
Property Taxes
$10,209 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,657

per 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

City/Town
Fairfield
Neighborhood
Southport
County
Fairfield

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

Similar Properties

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Listed By

Gina Williams

(203) 856-5942

Preston Gray Real Estate

(475) 269-5100

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.