66 Gifford Avenue
Windham, Connecticut 06226
- Beds
- 2
- Baths
- 1
- SqFt
- 1,010
- Acres
- 0.23
- Year Built
- 1952
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
14
39 under contract
Median List Price
$299,450
14 active listings
Median Closed Price
$271,000
165 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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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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.