25 Winding Trail
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 3,773
- Acres
- 1.01
- Year Built
- 1999
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Step into the sun-drenched, two-story foyer of this exceptional south-end Colonial. Designed with practicality in mind, you'll notice ample storage space thoughtfully integrated throughout the entire home. The heart of the home is the renovated kitchen, featuring granite counters and an expansive island built for entertaining large parties. It opens directly to a striking family room with soaring vaulted ceilings, custom cabinetry, and a copper-trimmed gas fireplace. Unwind in the cozy, heated sunroom with panoramic views of your backyard oasis, or retreat to the main-floor office behind classic French doors. Gleaming hardwood flooring stretch across the entire first floor, tying together the spacious living and dining areas. Upstairs, four sizable bedrooms offer excellent storage, accompanied by updated bathrooms boasting brand-new showers. The primary suite features a large walk-in closet and a beautifully updated dual-vanity ensuite bath. The entertainment potential multiplies in the walk-out lower level, featuring a massive rec room, custom-crafted wet bar, and a half bath. Walk straight out to your covered patio-complete with a ceiling fan and TV hookup-to overlook the spectacular, reconstructed heated inground pool, featuring a newer liner, pool solar cover, and storage roller. Perfectly positioned near top-tier schools, local retail, and the scenic Farmington Canal Walking Trail.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1999
- Days on Market
- 28 days
- Beds
- 4
- Baths
- 2 full · 2 half
- Living Area
- 3,773 sq ft
- Lot Size
- 1.01 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $14,985 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
Median Days on Market
33
24 active listings
Median $ / Sq Ft
$270
24 active listings
Sale-to-List Ratio
101.6%
238 sales
How this home compares
List Price
$799,000
vs $642,000 median
24.5% above median
Price / Sq Ft
$212
vs $270 median
21.5% below median
Days on Market
28 days
vs 33 days median
5 days fresher than median
Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.
Location
25 Winding Trail, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,074
- Property Taxes$1,249
- Insurance$266
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Cheshire
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1999
- New Construction
- No/Resale
- Living Area
- 3,773 sq ft
- Below Grade
- 800 sq ft
Schools
- Elementary
- Norton
- High
- Cheshire
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- First FloorMud Room
- Appliances
- Electric RangeRefrigeratorDishwasherDisposal
- Basement
- FullHeatedStorageCooledPartially FinishedLiveable SpaceFull With Walk-Out
- In-Law Apartment
- No
- Interior Features
- Auto Garage Door OpenerCentral VacuumSecurity System
- Additional Rooms
- Mud Room
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- R-40
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- HeatedIn Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-HeatedPorch-EnclosedUnderground UtilitiesSidewalkShedPorchUnderground SprinklerPatio
- Lot Description
- Treed
Listing & Financials
- Property Taxes
- $14,985 / Annually
- Days on Market
- 28
- MLS #
- 24187651
- MLS Status
- Under Contract - Continue to Show
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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 7/28/2026. 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 6:10 AM UTC.