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44 Williamsburg Drive

Cheshire, Connecticut 06410

PENDING$499,900
Beds
4
Baths
2
SqFt
1,554
Acres
1.14
Year Built
1965
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Welcome home to this beautifully updated ranch in a highly desirable neighborhood, just minutes from shopping, restaurants, and everyday conveniences. This move-in ready home features hardwood floors throughout and a spacious living room with a classic brick fireplace and Vermont Castings wood-burning insert, creating a warm and inviting gathering space. The dining room flows seamlessly into the living room and remodeled kitchen, offering an ideal layout for everyday living and entertaining, with French doors leading outside. The kitchen features porcelain tile flooring, abundant cabinetry, generous counter space, and a double oven. Four spacious bedrooms provide flexibility for family, guests, or a home office. The primary bedroom offers a large closet and beautifully remodeled private bath, while a second remodeled full bath serves family and guests. Additional features include central air, updated electrical and plumbing, newer copper piping, newer radiators, central vacuum, alarm system, generator hookup, Thermopane windows, vinyl siding, newer solid-core interior doors, public water, and a radon mitigation system. The unfinished lower level offers exceptional storage and future expansion potential. Relax on the beautiful bluestone patio overlooking a large, private backyard framed by mature trees. A two-car garage completes this exceptionally maintained home. Thoughtfully updated inside and out!

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1965
Days on Market
20 days
Beds
4
Baths
2 full
Living Area
1,554 sq ft
Lot Size
1.14 acres
Garage / Parking
2 garage · 3 total
Property Taxes
$7,432 / 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

$499,900

vs $642,000 median

22.1% below median

Price / Sq Ft

$322

vs $271 median

18.8% above median

Days on Market

20 days

vs 31 days median

11 days fresher 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

44 Williamsburg Drive, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,335

per month

  • Principal & Interest$2,549
  • Property Taxes$619
  • Insurance$167
  • 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
Ranch
Year Built
1965
New Construction
No/Resale
Living Area
1,554 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Cheshire

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
Basement
Appliances
Oven/RangeRefrigeratorDishwasher
Basement
FullUnfinished
In-Law Apartment
No
Interior Features
Auto Garage Door OpenerCable - AvailableCentral VacuumSecurity System

Exterior & Lot

Lot Size
1.14 acres
Zoning
R-40
Garage / Parking
2 garage spaces3 total parking spacesUnder House GaragePavedDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Construction
Vinyl Siding
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Patio
Lot Description
In SubdivisionSloping Lot

Listing & Financials

Property Taxes
$7,432 / Annually
Days on Market
20
MLS #
24190110
MLS Status
Under Contract - Continue to Show

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Stacey Deangelis

(203) 494-7068

Calcagni Real Estate

(203) 272-1821

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.