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$499,900 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,554 Sq. Ft.
  • 2 Car Garage
  • Updated 4 hours ago

Next open house:

Open House: 10:00 AM - 12:00 PM

Sunday 7/12 10:00 AM - 12:00 PM

44 Williamsburg Drive,Cheshire, CT 06410

44 Williamsburg DriveCheshireCT06410

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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!

Full Property Details for 44 Williamsburg Dr

General

  • Price: $499,900
  • Taxes: (July 2025-June 2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24190110
  • Updated: 7/9/2026
  • Added to Site: 1 day(s) ago
  • Expected Market Date: 7/12/2026

Interior

  • Number of Rooms: 6
  • Interior Features: Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Wall/Wall Carpet, Hardwood Floor, 11 x 15, Main
  • Bedroom 1: Bedroom - Wall/Wall Carpet, Hardwood Floor, 10 x 11, Main
  • Bedroom 2: Bedroom - Wall/Wall Carpet, Hardwood Floor, 10 x 14, Main
  • Bedroom 3: Bedroom - Wall/Wall Carpet, Hardwood Floor, 11 x 12, Main

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 13 x 22, Main
  • Kitchen: Kitchen - Remodeled, Tile Floor, 13 x 11, Main
  • Dining Room: Dining Room - Hardwood Floor, 14 x 10, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Patio
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 3
  • Parking: Under House Garage, Paved, Driveway

Location

  • County: New Haven
  • Driving Directions: Rte. 70 to Carriage Drive to Williamsburg Dr. House on left.

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Dodd
  • Intermediate School: Per Board of Ed
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,554
  • Above Ground: 1,554 Sq. Ft.
  • Year Built: 1965

Lot Features

  • Lot Size (Acres): 1.14
  • Driveway/Sidewalk: Private, Paved
  • Zoning: R-40
  • Lot Description: In Subdivision, Sloping Lot

Green Features

  • Energy Features: Generator Ready, Thermopane Windows

Financial Considerations

  • Assessment Amount: $249,900
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1085143

Listed by Calcagni Real Estate, Stacey Deangelis

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Listing agent

— 44 Williamsburg Dr —

  • Stacey Deangelis

    Calcagni Real Estate

Agent Contact: (203) 494-7068 Office Contact: (203) 272-1821

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 Williamsburg Dr

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-61 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-81.2 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 Williamsburg Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/09/2026
Listed
$499,900
56.17%
MLS
2/09/2006
Sold
$320,100
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 Williamsburg Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,432
8%
$249,900
—
2023
$6,862
5%
$249,900
34%
2023
$6,559
2%
$186,930
—
2022
$6,415
2%
$186,930
—
2021
$6,303
1%
$186,930
—
2020
$6,210
—
$186,930
—
2019
$6,210
3%
$186,930
1%
2018
$6,058
2%
$185,710
—
2017
$5,932
2%
$185,710
—
2016
$5,792
2%
$185,710
—
2015
$5,699
1%
$185,710
—
2014
$5,618
-1%
$185,710
-10%
2011
$5,671
—
$205,460
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Calcagni Real Estate, Stacey Deangelis

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44 Williamsburg Drive, Cheshire, CT 06410 (MLS# 24190110) is a Single Family property with 4 bedrooms and 2 full bathrooms. 44 Williamsburg Drive is currently listed for $499,900 and was received on July 09, 2026. Want to learn more about 44 Williamsburg Drive? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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