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$775,000

  • For Sale
  • Active
  • Single Family
  • 7 Beds
  • 3 Full Baths
  • 4,225 Sq. Ft.
  • 2 Car Garage
  • Updated 11 days ago
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PRICE REDUCTION!!! Welcome to your dream home! This completely renovated single-family residence blends modern luxury with classic charm in one of Cheshire's most desirable neighborhoods - everything is new, stylish, and ready for you to enjoy. This light-filled residence features 4-bedrooms and 4-baths which has been beautifully renovated with high-end finishes and a bright open layout. Step into a brand-new living room designed for comfort and style with new flooring, fresh neutral paint and modern recessed lighting. New open-concept kitchen and dining room with modern finishes, ideal for entertaining. The family room shines with a custom fireplace, build-in TV. Upstairs Primary bedroom suite with a brand-new en-suite bathroom, offering spa-like comfort and privacy. Two spacious additional bedrooms upstairs with generous closet space and natural light. The home includes a two-car attached garage and a long private driveway, offering plenty of parking.

Full Property Details for 296 Winthrop Dr

General

  • Price: $775,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24145612
  • Updated: 1/5/2026
  • Added to Site: 26 day(s) ago

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Range, Microwave, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Primary Bathroom: Primary Bath, Upper

Bedrooms

  • Total Bedrooms: 7
  • Primary Suite: Bedroom Suite, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper
  • Bedroom 5: Bedroom, Upper
  • Bedroom 6: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Family Room: Family Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Laundry: Main Level

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Neighborhood: Mixville
  • Driving Directions: GPS

School Information

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

Community

  • Community Name: Mixville

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding, Brick
  • Basement Desc.: Full, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,225
  • Above Ground: 2,920 Sq. Ft.
  • Below Ground: 1,305 Sq. Ft.
  • Year Built: 1969

Lot Features

  • Lot Size (Acres): 0.89
  • Zoning: R-20
  • Lot Description: Corner Lot, Level Lot

Financial Considerations

  • Assessment Amount: $338,730
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2338634
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 296 Winthrop Dr —

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 296 Winthrop Dr

School District:Cheshire School District
NameGradesDistance
Doolittle School
735 Cornwall Avenue, Cheshire, CT 06410
1-61.3 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-81.6 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-122.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 296 Winthrop Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/05/2026
Price Reduced
$775,000
-3.12%
MLS
12/22/2025
Listed
$799,999
—
MLS
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 296 Winthrop Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$10,074
8%
$338,730
—
2023
$9,302
11%
$338,730
41%
2023
$8,412
2%
$239,720
—
2022
$8,227
2%
$239,720
—
2021
$8,083
2%
$239,720
—
2020
$7,963
—
$239,720
—
2019
$7,963
-1%
$239,720
-3%
2018
$8,056
2%
$246,980
—
2017
$7,889
2%
$246,980
—
2016
$7,703
2%
$246,980
—
2015
$7,580
1%
$246,980
—
2014
$7,471
3%
$246,980
-6%
2011
$7,235
—
$262,120
—
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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296 Winthrop Drive, Cheshire, CT 06410 (MLS# 24145612) is a Single Family property with 7 bedrooms and 3 full bathrooms. 296 Winthrop Drive is currently listed for $775,000 and was received on December 22, 2025. This property is listed by Arta Sevrani from our Orange Post Rd Office.Want to learn more about 296 Winthrop 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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