44 Williamsburg Drive Cheshire, CT $ 499,900
44 Williamsburg Drive
$ 499,900
Open House 7/12 10am - 12pm
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44 Williamsburg Drive

Cheshire, CT, 06410
$ 499,900
Bedrooms4 Baths2.0 Sq 1,554

Monthly Estimate*

$ 3,156

44 Williamsburg Drive, Cheshire, CT 06410 - Image 1

Single Family Home for sale in Cheshire, CT

for $499,900 with 4 bedrooms and 2 full baths. This 1,554 square foot home was built in 1965 on a lot size of 1.14.

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!

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Open House

7/12/2026 10:00 AM - 12:00 PM
44 Williamsburg Drive Cheshire, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Coming Soon

Price

$ 499,900

Bedrooms

4

Full Bath

2

Property Type

Single Family

Taxes

$ 7,432

Style

Lot Size

1.14

Year Built

1965

Town/City

Cheshire

MLS | Web ID

24190110

Features
General
Zoning R-40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1.14
Directions Rte. 70 to Carriage Drive to Williamsburg Dr. House on left.
High School Cheshire
City Cheshire
Elementary School Per Board of Ed
Sq Ft Total 1554
Year Built 1965
Style Ranch
Year Built Source Public Records
Energy Features Generator Ready Thermopane Windows
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Interior
Cooling System Central Air
Total Rooms 6
Basement Description Full Unfinished
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Exterior
Water Source Public Water Connected
Lot Description In Subdivision Sloping Lot
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* Excluded Features
List By
Stacey Deangelis

Listing Agent

Calcagni Real Estate

Broker

stacey_deangelis@calcagni.com

Email

Affordability Calculator

$3,776
Per Month
84%
16%
0%
Monthly Principal & Interest
$3,156
Monthly Property Taxes
$619
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3041960 Elementary School
1232875 Middle School
Cheshire High School High School
Pricing History
DatePricePrice ChangeDescription
7/9/2026$499,900 Listed Price

Map


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44 Williamsburg Drive, Cheshire, CT, 06410 is a Single Family Home for sale at $499,900 with 1,554 sqft and a lot size of 1.14. 44 Williamsburg Drive has 4 bedrooms, 2.0 baths, and was built in 1965. The property's zip code is 06410 which is in Cheshire, CT