NOMADEReal Estate

$799,000

ActiveJust Listed3 days ago

25 Winding Trail

Cheshire, Connecticut, 06410 · New Haven County

4

Beds

4

Baths

3,773

Sq Ft

1999

Built

MLS # 24187651

Price / Sq Ft

$212

Property Type

Single Family For Sale

Lot Size

1.01

Class

Property

About This Property

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.

Property Details

25 Winding Trail, Cheshire Connecticut 06410 — Single Family For Sale listed at $799,000.

At a Glance

4

Bedrooms

4

Bathrooms

3,773

Sq Ft

1.01

Lot Size

--

Garage

1999

Year Built

The Details

Property TypeSingle Family For Sale
NeighborhoodNew Haven
Address25 Winding Trail
MLS Number24187651
Year Built1999
Square Footage3,773
Lot Size1.01
Bedrooms4
Bathrooms4
Water SourcePublic Water Connected

Property Details

Other Details

Appliances IncludedElectric Range,Refrigerator,Dishwasher,Disposal
Lockbox LocationFront Door
Parcel Number2100394
Rooms AdditionalMud Room
ZoningR-40

Financial

Assessed Value503860
Mil Rate Total29.74
Property Tax14985
Tax YearJuly 2025-June 2026

Property Features

Attic DescriptionStorage Space,Pull-Down Stairs
Attic YN1
Basement DescriptionFull,Heated,Storage,Cooled,Partially Finished,Liveable Space,Full With Walk-Out
Cooling SystemCeiling Fans,Central Air
Exterior FeaturesPorch-Heated,Porch-Enclosed,Underground Utilities,Sidewalk,Shed,Porch,Underground Sprinkler,Patio
Exterior SidingVinyl Siding
Fireplaces Total1
Foundation TypeConcrete
Fuel Tank LocationIn Basement
Garage ParkingAttached Garage
Garages Number2
Heat Fuel TypeOil
Heat TypeHot Air,Zoned
Hot Water DescriptionElectric,Domestic
Interior FeaturesAuto Garage Door Opener,Central Vacuum,Security System
Laundry Room InfoLower Level
Laundry Room LocationFirst Floor, Mud Room
Pool DescriptionHeated,In Ground Pool
Roof InformationAsphalt Shingle
Swimming Pool YN1

All Photos (39)

MARKET CONTEXTCheshire
Town Median+65% vs list
$485,000
Cheshire, CT
Mill Rate
33.93
New Haven County
NYC Commute
130 min
Metro-North express
Schools
A
3 graded
LOADING COMP CLOUD…

This listing is +65% vs the Cheshire median. Verify against same-school-district comps before competing offers.

Contact Paola Dominguez

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Affordability Calculator

$799,000

Down Payment$159,800
Loan Amount$639,200
Principal & Interest$4,040/mo
Property Tax$799/mo
Insurance$100/mo
Est. Monthly$4,939/mo

Listing Agent

P

Paola Dominguez

Higgins Group Real Estate

Quick Facts

StatusActive
TypeSingle Family For Sale
ClassProperty
MLS #24187651
Last Updated2026-07-05