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163 Windsor Road

Fairfield, Connecticut 06824

ACTIVE$829,000
Beds
4
Baths
1 | 1
SqFt
1,891
Acres
0.22
Year Built
1959
Matt Caiola

Matt Caiola

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About This Home

Welcome to 163 Windsor Road, a beautifully updated home set on a double cul-de-sac in Fairfield's desirable University Area. A welcoming foyer opens to a bright main living space with vaulted ceilings, exposed beams, recessed lighting, hardwood floors, and a warm sense of character throughout. The open-concept living room, dining area, and renovated kitchen create an easy flow for everyday living and entertaining. The kitchen features white cabinetry, quartz countertops, a center island, coffee bar, with modern finishes. Just beyond the main living area, the cozy den offers a rare expansion of the floor plan and opens directly to the deck, creating an easy connection outdoors for barbecues and al fresco dining. The second floor is home to three bedrooms and a full bathroom. From there, the lower level extends across two additional floors, adding flexibility with a mudroom that provides access to the attached garage, an office or potential fourth bedroom, laundry, and a spacious room ideal for a playroom, media room, or gym. Set on a fenced corner lot in a friendly neighborhood setting, the property offers the ease of being able to walk to Osborn Hill Elementary and nearby Black Rock Turnpike eateries, with parks, shopping, commuter routes, downtown Fairfield, train, beaches, and the best of the University Area lifestyle just a short drive away. Move-in ready with modern updates, natural gas, future expansion potential, and true neighborhood appeal.

Key Facts

City/Town
Fairfield
Neighborhood
University
Property / Style
Single Family · Split Level
Year Built
1959
Days on Market
19 days
Beds
4
Baths
1 full · 1 half
Living Area
1,891 sq ft
Lot Size
0.22 acres
Garage / Parking
1 garage
Property Taxes
$8,909 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

Median Days on Market

33

89 active listings

Median $ / Sq Ft

$500

89 active listings

Sale-to-List Ratio

101.9%

571 sales

How this home compares

List Price

$829,000

vs $1.57M median

47.4% below median

Price / Sq Ft

$438

vs $500 median

12.4% below median

Days on Market

19 days

vs 33 days median

14 days fresher than median

Based on 89 active and 571 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of July 28, 2026.

Location

163 Windsor Road, Fairfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,245

per month

  • Principal & Interest$4,227
  • Property Taxes$742
  • Insurance$276
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Fairfield
Neighborhood
University
County
Fairfield

Residence

Property Type
Single Family
Style
Split Level
Year Built
1959
New Construction
No/Resale
Living Area
1,891 sq ft
Below Grade
604 sq ft

Schools

Elementary
Osborn Hill
High
Fairfield Ludlowe

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Ceiling FansSplit System
Laundry
Lower Level
Appliances
Gas RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullHeatedSump PumpStorageFully FinishedInterior AccessLiveable Space

Exterior & Lot

Lot Size
0.22 acres
Zoning
A
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
SidewalkDeckGuttersPatio
Lot Description
Fence - FullCorner LotLevel LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$8,909 / Annually
Days on Market
19
MLS #
24190167
MLS Status
Active

Similar Properties

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Listed By

Shoshana Snyder

(203) 321-3502

Compass Connecticut, LLC

(203) 255-6841

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 5:15 AM UTC.