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66 Gifford Avenue

Windham, Connecticut 06226

PENDING$269,000
Beds
2
Baths
1
SqFt
1,010
Acres
0.23
Year Built
1952
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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About This Home

There's something special about a home that instantly feels warm and welcoming, and this charming ranch in Windham does exactly that. From the moment you walk inside, sunlight pours through the living room, reflecting beautifully off the hardwood floors and creating a space that simply feels like home. The open layout makes everyday living easy, with a cozy dining area that flows naturally into the eat-in kitchen featuring stainless steel appliances, abundant cabinetry, and plenty of room to cook, gather, and make memories. Both bedrooms offer hardwood flooring, ceiling fans, and generous closet space, creating comfortable retreats at the end of the day. Downstairs, the unfinished basement is ready for your imagination whether you envision a home gym, workshop, recreation room, or additional living space. Outside is where this home truly shines. Relax beneath the covered patio with your morning coffee, listen to the sounds of nature, and enjoy the privacy of the peaceful backyard with various fruit trees. Thoughtfully updated with new kitchen appliances, kitchen flooring, fresh paint, professionally cleaned vents, a new furnace motor, and new water heater, this home offers both comfort and peace of mind! Whether you're just starting out, downsizing, or looking for a place to truly make your own, this inviting ranch is ready to welcome its next chapter.

Key Facts

City/Town
Windham
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1952
Days on Market
61 days
Beds
2
Baths
1 full
Living Area
1,010 sq ft
Lot Size
0.23 acres
Property Taxes
$4,633 / Annually

Market Snapshot

The Windham Market

Single Family · trailing 12 months

Median Days on Market

32

14 active listings

Median $ / Sq Ft

$176

14 active listings

Sale-to-List Ratio

100.8%

165 sales

How this home compares

List Price

$269,000

vs $299,450 median

10.2% below median

Price / Sq Ft

$266

vs $176 median

51.1% above median

Days on Market

61 days

vs 32 days median

29 days longer than median

Based on 14 active and 165 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of July 29, 2026.

Location

66 Gifford Avenue, Windham, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,848

per month

  • Principal & Interest$1,372
  • Property Taxes$386
  • Insurance$90
  • HOA$0

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

Location

City/Town
Windham
Neighborhood
N/A
County
Windham

Residence

Property Type
Single Family
Style
Ranch
Year Built
1952
New Construction
No/Resale
Living Area
1,010 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Windham

Interior

Heating
Hot AirWood/Coal Stove
Heat Fuel
OilWood
Cooling
Ceiling FansWindow Unit
Laundry
Lower Level
Appliances
Electric RangeOven/RangeMicrowaveRange HoodRefrigeratorFreezerIcemakerDishwasherInstant Hot Water TapWasherDryer
Basement
FullUnfinishedInterior AccessConcrete Floor
Interior Features
Cable - Available

Exterior & Lot

Lot Size
0.23 acres
Zoning
R4
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
GuttersLightingCovered Deck
Lot Description
Lightly WoodedSloping Lot

Listing & Financials

Property Taxes
$4,633 / Annually
Days on Market
61
MLS #
24175215
MLS Status
Under Contract - Continue to Show

Similar Properties

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Listed By

Tina Frigeri

(860) 818-3170

KW Legacy Partners

(860) 313-0700

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.