44 Williamsburg Drive
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2
- SqFt
- 1,554
- Acres
- 1.14
- Year Built
- 1965
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
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
$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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.