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$429,000

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,152 Sq. Ft.
  • 2 Car Garage
  • Updated 8 days ago
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Beautifully maintained and fully updated 3-bedroom, 2 full bath ranch located in Cheshire. This move-in ready home features laminate flooring throughout the main level, with cathedral ceilings and an open-concept layout that allows for abundance of natural light. The eat-in kitchen is equipped with quartz countertops, stainless steel appliances, and a center island that provides additional prep space and seating-ideal for entertaining. A slider off the kitchen leads to a private, spacious backyard. The inviting family room showcases a cozy stone fireplace, creating a warm and welcoming atmosphere. The primary bedroom includes a private full bath, while two additional bedrooms offer flexibility, with one ideal for a nursery or home office. Laundry is conveniently located on the main level. The lower level offers great potential for future finishing to suit your needs .It is partially sheet rocked and heated. Additional updates include a new roof (2024), most windows have been replaced, with the exception of the living room picture window. Come see and make this your home. City water, City sewer.

Full Property Details for 261 Winthrop Dr

General

  • Price: $429,000
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24161568
  • Updated: 5/18/2026
  • Added to Site: 46 day(s) ago

Interior

  • Number of Rooms: 7
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Primary Bathroom: Primary Bath - Stall, Main
  • Full Bath: Cathedral Ceiling, Tub w/Shower, Tile Floor, Main

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Cathedral Ceiling, Full Bath, Stall Shower, Tile Floor, 16 x 13.5, Main
  • Bedroom 1: Bedroom - Cathedral Ceiling, Ceiling Fan, Vinyl Floor, 12 x 11, Main
  • Bedroom 2: Bedroom - Cathedral Ceiling, Ceiling Fan, Vinyl Floor, 7 x 12, Main

Other Rooms

  • Family Room: Family Room - Cathedral Ceiling, Fireplace, Vinyl Floor, 19 x 11, Main
  • Kitchen: Kitchen - Cathedral Ceiling, Quartz Counters, Eating Space, Island, Sliders, Vinyl Floor, 18 x 10, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Sidewalk, Gutters
  • Color: blue

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Under House Garage

Location

  • County: New Haven
  • Driving Directions: GPS Friendly

School Information

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

Heating & Cooling

  • Cooling Type: Ceiling Fans, Window Unit
  • Heating Type: Baseboard, Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

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

Structural Information

  • Architectural Style: Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Wood
  • Basement Desc.: Full, Heated, Garage Access, Interior Access
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,152
  • Above Ground: 1,152 Sq. Ft.
  • Year Built: 1967

Lot Features

  • Lot Size (Acres): 0.46
  • Zoning: R-20
  • Lot Description: Lightly Wooded, Sloping Lot

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Annual Sewer Fee: $490
  • Assessment Amount: $246,540
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2339190

Listed by Berkshire Hathaway NE Prop., Cheryl Rosadino

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Listing agent

— 261 Winthrop Dr —

  • Cheryl Rosadino

    Berkshire Hathaway NE Prop.

Agent Contact: (203) 379-7087 Office Contact: (203) 272-2828

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 261 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 ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 261 Winthrop Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/10/2026
Listed
$429,000
19.17%
MLS
6/30/2022
Sold
$360,000
—
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 261 Winthrop Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,332
8%
$246,540
—
2023
$6,770
33%
$246,540
69%
2023
$5,106
2%
$145,520
—
2022
$4,994
2%
$145,520
—
2021
$4,907
2%
$145,520
—
2020
$4,834
—
$145,520
—
2019
$4,834
—
$145,520
-2%
2018
$4,826
2%
$147,950
—
2017
$4,726
2%
$147,950
—
2016
$4,615
2%
$147,950
—
2015
$4,541
1%
$147,950
—
2014
$4,475
-9%
$147,950
-17%
2011
$4,919
—
$178,210
—
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Berkshire Hathaway NE Prop., Cheryl Rosadino

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261 Winthrop Drive, Cheshire, CT 06410 (MLS# 24161568) is a Single Family property with 3 bedrooms and 2 full bathrooms. 261 Winthrop Drive is currently listed for $429,000 and was received on April 10, 2026. Want to learn more about 261 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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