59 Williams Road
Cheshire, Connecticut 06410
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,124
- Acres
- 1.08
- Year Built
- 1993
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
20
58 under contract
Median List Price
$642,000
20 active listings
Median Closed Price
$555,000
239 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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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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.