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$799,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2 Partial Baths
  • 3,773 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago

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Open House: 11:00 AM - 1:00 PM

Sunday 7/5 11:00 AM - 1:00 PM

25 Winding Trail,Cheshire, CT 06410

25 Winding TrailCheshireCT06410

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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.

Full Property Details for 25 Winding Trail

General

  • Price: $799,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24187651
  • Updated: 7/3/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Mud Room
  • Interior Features: Auto Garage Door Opener, Central Vacuum, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Range, Refrigerator, Dishwasher, Disposal

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 2
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Walk-In Closet, Wall/Wall Carpet, Upper
  • Bedroom 1: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 2: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 3: Bedroom - Walk-In Closet, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Vaulted Ceiling, Built-Ins, Ceiling Fan, Gas Log Fireplace, Hardwood Floor, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Granite Counters, Island, Sliders, Hardwood Floor, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, Main
  • Office: Office - 9 ft+ Ceilings, French Doors, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - 9 ft+ Ceilings, Built-Ins, Wet Bar, Half Bath, Sliders, Wall/Wal, Lower
  • Rec Room: 9 ft+ Ceilings, Built-Ins, Wet Bar, Half Bath, Sliders, Wall/Wall Carpet, Lower
  • Laundry: Lower Level

Additional Information

  • Pool: Yes
  • Pool Description: Heated, In Ground Pool

Exterior

  • Exterior Features: Porch-Heated, Porch-Enclosed, Underground Utilities, Sidewalk, Shed, Porch, Underground Sprinkler, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Driving Directions: North Brooksvale Rd (Rte 42) to Towpath Ln to Winding Trail

School Information

  • Elementary School: Norton
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Ceiling Fans, Central Air
  • Heating Type: Hot Air, Zoned, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Storage, Cooled, Partially Finished, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,773
  • Above Ground: 2,973 Sq. Ft.
  • Below Ground: 800 Sq. Ft.
  • Year Built: 1999

Lot Features

  • Lot Size (Acres): 1.01
  • Zoning: R-40
  • Lot Description: Treed

Financial Considerations

  • Assessment Amount: $503,860
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2100394

Listed by Higgins Group Real Estate, Adriana's Team of Higgins Group Real Estate, Paola Dominguez

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Listing agent

— 25 Winding Trail —

  • Paola Dominguez

    Higgins Group Real Estate

Agent Contact: (203) 561-8824 Office Contact: (203) 301-4844

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 25 Winding Trail

School District:Cheshire School District
NameGradesDistance
Norton School
414 North Brooksvale Road, Cheshire, CT 06410
1-60.3 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-82.4 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 25 Winding Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/03/2026
Listed
$799,000
4.31%
MLS
12/06/2023
Sold
$766,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 25 Winding Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,985
8%
$503,860
—
2023
$13,836
10%
$503,860
41%
2023
$12,559
2%
$357,910
—
2022
$12,283
2%
$357,910
—
2021
$12,069
2%
$357,910
—
2020
$11,890
—
$357,910
—
2019
$11,890
-4%
$357,910
-5%
2018
$12,340
2%
$378,300
—
2017
$12,083
1%
$378,300
-1%
2016
$11,912
2%
$381,930
—
2015
$11,721
1%
$381,930
—
2014
$11,553
6%
$381,930
-3%
2011
$10,860
—
$393,490
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 25 Winding Trail

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Higgins Group Real Estate, Adriana's Team of Higgins Group Real Estate, Paola Dominguez

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25 Winding Trail, Cheshire, CT 06410 (MLS# 24187651) is a Single Family property with 4 bedrooms, 2 full bathrooms and 2 partial bathrooms. 25 Winding Trail is currently listed for $799,000 and was received on July 03, 2026. Want to learn more about 25 Winding Trail? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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