25 Winding Trail Cheshire, CT $ 799,000
25 Winding Trail
$ 799,000
Open House 7/5 11am - 1pm
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25 Winding Trail

Cheshire, CT, 06410
$ 799,000
Bedrooms4 Baths2.2 Sq 3,773

Monthly Estimate*

$ 5,045

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Single Family Home for sale in Cheshire, CT

for $799,000 with 4 bedrooms and 2 full baths, 2 half baths. This 3,773 square foot home was built in 1999 on a lot size of 1.01.

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.

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Open House

7/5/2026 11:00 AM - 1:00 PM
25 Winding Trail Cheshire, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Coming Soon

Price

$ 799,000

Bedrooms

4

Full Bath

2

Half Bath

2

Property Type

Single Family

Taxes

$ 14,985

Style

Lot Size

1.01

Year Built

1999

Town/City

Cheshire

MLS | Web ID

24187651

Features
General
Zoning R-40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1.01
Directions North Brooksvale Rd (Rte 42) to Towpath Ln to Winding Trail
High School Cheshire
City Cheshire
Elementary School Norton
Sq Ft Total 3773
Year Built 1999
Style Colonial
Year Built Source Public Records
Pool Description Heated In Ground Pool
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Interior
Cooling System Ceiling Fans Central Air
Total Rooms 10
Basement Description Full Heated Storage Cooled Partially Finished Liveable Space Full With Walk-Out
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Exterior
Water Source Public Water Connected
Lot Description Treed
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* Excluded Features
List By
Paola Dominguez

Listing Agent

Higgins Group Real Estate

Broker

paola@adrianaandcompany.com

Email

Affordability Calculator

$6,294
Per Month
80%
20%
0%
Monthly Principal & Interest
$5,045
Monthly Property Taxes
$1,249
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3042859 Elementary School
1232875 Middle School
Cheshire High School High School
Pricing History
DatePricePrice ChangeDescription
6/30/2026$799,000 Listed Price

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25 Winding Trail, Cheshire, CT, 06410 is a Single Family Home for sale at $799,000 with 3,773 sqft and a lot size of 1.01. 25 Winding Trail has 4 bedrooms, 2.2 baths, and was built in 1999. The property's zip code is 06410 which is in Cheshire, CT