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59 Williams Road

Cheshire, Connecticut 06410

PENDING$659,900
Beds
3
Baths
2 | 1
SqFt
2,124
Acres
1.08
Year Built
1993
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Some homes check the boxes. This one checks them all and then pulls you in with something harder to quantify: the feeling that you've found exactly where you're supposed to be. Tucked away on a private rear acre in one of Cheshire's most coveted in-town locations, this beautifully maintained 3-4 bedroom, 2.5-bath colonial offers the rare combination of peaceful seclusion and unbeatable walkability. Stroll to the shops, restaurants, and community life that make Cheshire's town center so beloved - then come home to your own quiet corner of it all. At 2,124 square feet, the layout lives generously with additional flex space in the lower level. The kitchen offers warm, easy-care Corian counters and flows naturally into the living spaces, making everyday life feel effortless and every gathering feel natural. Fresh updates throughout, including a new roof (2024), new deck (2024), and new bedroom carpets (2024) simply settle in and enjoy. Upstairs, the primary suite is a true sanctuary. Walk-in closet offers the kind of storage that actually changes your morning routine, and the additional room, easily styled as a home office, makeup room, dressing room, private reading nook, cozy TV lounge or 4th bedroom is the personal retreat most buyers have always wanted but rarely find. A brand-new tub shower insert completes the suite with a fresh, polished finish. Step outside onto the new deck and into a backyard that feels like your own private escape.

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1993
Days on Market
69 days
Beds
3
Baths
2 full · 1 half
Living Area
2,124 sq ft
Lot Size
1.08 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$9,085 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

Median Days on Market

31

20 active listings

Median $ / Sq Ft

$271

20 active listings

Sale-to-List Ratio

101.6%

239 sales

How this home compares

List Price

$659,900

vs $642,000 median

In line with median

Price / Sq Ft

$311

vs $271 median

14.8% above median

Days on Market

69 days

vs 31 days median

38 days longer than median

Based on 20 active and 239 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 29, 2026.

Location

59 Williams Road, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,342

per month

  • Principal & Interest$3,365
  • Property Taxes$757
  • Insurance$220
  • 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
1993
New Construction
No/Resale
Living Area
2,124 sq ft

Schools

Elementary
Doolittle
High
Cheshire

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Attic FanWindow Unit
Fireplaces
1
Appliances
Oven/RangeRefrigeratorDishwasherDisposal
Basement
FullPartially Finished
Interior Features
Auto Garage Door OpenerCable - Available

Exterior & Lot

Lot Size
1.08 acres
Zoning
R-20
Garage / Parking
2 garage spaces4 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
cream
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedDeck
Lot Description
Interior LotLightly WoodedLevel Lot

Listing & Financials

Property Taxes
$9,085 / Annually
Days on Market
69
MLS #
24175251
MLS Status
Under Contract

Similar Properties

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Listed By

Leanne Delrosso

(203) 915-9588

Lamacchia Realty

(860) 426-6886

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 10:10 AM UTC.