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25 Winding Trail

Cheshire, Connecticut 06410

PENDING$799,000
Beds
4
Baths
2 | 2
SqFt
3,773
Acres
1.01
Year Built
1999
Matt Caiola

Matt Caiola

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Pool2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,589

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Paola Dominguez

(203) 561-8824

Higgins Group Real Estate

(203) 301-4844

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.