261 Winthrop Drive, Cheshire, CT 06410
SOLD
MAY 27, 2026

261 Winthrop Drive
Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,152 sqft (on 0.46 acres)

$440,000

Last Sold: May 27, 2026
3% over list $429K
$382/sqft
Est. Refi. Payment $3,062/mo*
Refinance Your Home

$440,000

Last Sold: May 27, 2026
3% over list $429K
$382/sqft
Est. Refi. Payment $3,062/mo*
Refinance Your Home
3 Beds
2 Baths
1,152 sqft
(on 0.46 acres)

Local Information

  • Map ViewExplore the area around 261 Winthrop Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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. Showings start Saturday 4/11/2026. Room sizes are approximate.
261 Winthrop Drive, Cheshire, CT 06410 is a 3 bedroom, 2 bathroom, 1,152 sqft single-family home built in 1967. It last sold for $440,000 on May 27, 2026 (3% above the $429,000 asking price). It is currently off market. The Trulia Estimate is $441,500, with a rent estimate of $2,746/month.

Home Highlights

Parking
2 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$382/sqft
Listed
93 days ago

Home Details for 261 Winthrop Drive

Interior Features

Interior Details
Basement: Full,Heated,Garage Access,Interior EntryNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Family Room, Kitchen
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1152 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Ceiling Fan(s),Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Sidewalk, Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1152 Square Feet

Property Information

Year Built
Year Built: 1967
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Shingle Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2339190

Price & Status

Price
List Price: $429,000Price Per Sqft: $382/sqft
Status Change & Dates
Off Market Date: Thu Apr 23 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Cheshire
School Information
Elementary School: Per Board of EdJr High / Middle School: DoddHigh School: Cheshire

Building

Building Area
Building Area: 1152 Square Feet

Community

Community Features: Library, Medical Facilities, Park, Playground, Pool, Public Rec Facilities
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.46 acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24161568Attic: Crawl Space, Access Via HatchAttribution Contact: (203) 379-7087Above Grade Unfinished Area: 1152

Additional Information

LibraryMedical FacilitiesParkPlaygroundPoolPublic Rec Facilities
Last check for updates: about 5 hours ago
Listed by Cheryl A. Rosadino, (203) 379-7087
Berkshire Hathaway NE Prop., (203) 272-2828
Bought with: Melinda K. Martinez, (860) 890-0535, Real Broker CT, LLC, (855) 450-0442
Source: Smart MLS, MLS#24161568

Price History for 261 Winthrop Drive

DatePriceEventSource
05/27/2026$440,000Sold
Smart MLS #24161568
05/18/2026$429,000PendingSmart MLS #24161568
04/14/2026$429,000ContingentBerkshire Hathaway HomeServices New England Properties #24161568
04/10/2026$429,000Listed For SaleSmart MLS #24161568
06/30/2022$360,000Sold
Smart MLS #170482358
06/30/2022$325,000ContingentSmart MLS #170482358
05/10/2022$325,000PendingWilliam Raveis Real Estate, Mortgage & Insurance #170482358
05/05/2022$325,000Listed For SaleSmart MLS #170482358

Market trends in Cheshire

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$467K
Sale-to-List Price
101.3%
Price per sq ft
$261
Available listings
61
1MoM
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Property Tax and Assessment

Year2025
Tax$7,332
Assessment$246,540
Home facts updated by county records

Comparable Sales for 261 Winthrop Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Heath Court, Cheshire, CT
0.23
Single-Family Home
$430,000
01/05/26
4
3
2,100
767 Ives Row, Cheshire, CT
0.75
Single-Family Home
$445,000
05/15/26
3
1.5
1,725
202 Mountain Road, Cheshire, CT
0.66
Single-Family Home
$457,000
07/18/25
3
1.5
1,356
248 Mountain Road, Cheshire, CT
0.77
Single-Family Home
$416,100
11/14/25
3
2
1,955
233 Mountain Road, Cheshire, CT
0.70
Single-Family Home
$430,000
08/22/25
3
1.5
2,028
100 Lynwood Dr Extension, Cheshire, CT
0.83
Single-Family Home
$590,000
02/13/26
3
1.5
1,360
264 Timber Lane, Cheshire, CT
0.97
Single-Family Home
$409,000
12/19/25
3
2
1,350

Nearby homes

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Assigned Schools

These are the assigned schools for 261 Winthrop Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Cheshire

At least 102 Trulia users voted on each feature.

  • 95 % Say car is needed

  • 94 % Say parking is easy

  • 85 % Say yards are well-kept

  • 85 % Say it's dog friendly

  • 84 % Say there's wildlife

  • 81 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 73 % Say people would walk alone at night

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say kids play outside

  • 62 % Say neighbors are friendly

  • 58 % Say there are sidewalks

  • 58 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 37 % Say there are community events

  • 35 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Beautiful respectful peaceful people and neighborhood grate community. Clean and organized and has such a great atmosphere and very family orientated "
    0
    Flag
  • Joshua Wendell
    "It’s easy to get to the highway. Though in some parts of town it can take time to get through and make your way towards where you’re going. "
    0
    Flag
  • Reneechoquette
    "Great for trick of treating, close to the rail trail for biking, walking, running, or walking the dog! "
    1
    Flag
  • Ctbondlynx
    "Yes dog friendly. Dog parks are near by. And plentiful. Many dogs in the Cheshire neighborhoods. Dogs"
    0
    Flag
  • Reneechoquette
    "Safe, quiet, friendly, and lots of kids in this neighborhood (great for trick or treating!) Thr elementary school and rail trail (for waking and biking) are all in walking distance. "
    0
    Flag
  • Hollie.barclay
    "Amazing school district and great for kids growing up. We drive a vehicle for all our needs and only use a bike for rec purposes. We have walked on a few occasions but not often. "
    1
    Flag
  • Reneechoquette
    "My commute is into Hartford and there is public transportation into the city. The drive otherwise is about 45 min. "
    0
    Flag
  • Taylor D.
    "Lights of hope, relay for life, town sports and community outreach programs. Fairs and festivals in the fall with small business promotion"
    0
    Flag
  • Russell P.
    "about half an hour, I don't work in town. traffic can get pretty bad going south on the highway. back roads offer a good alternative, drivers I. the area tend to be slow though. "
    0
    Flag
  • Sheena N.
    "Cheshire is a nice quiet town. Not too much to do, not many restaurants or shopping centers, but close enough to everything where you don’t really mind. "
    0
    Flag
  • Janemarques08
    "That there are plenty of walking trails and sufficient sidewalks to safely walk your dog, whether it’s early morning or late at night. Totally safe neighborhood. "
    2
    Flag
  • Sheena N.
    "Close to 84 and 691. Not too far from Merritt or 91. Route 10 can be congested at times, but mostly everything is easy to get to"
    0
    Flag
  • Stephanie B. P.
    "Dogs are usually seen walking on leashes. Most are friendly and owners greet each other allowing them to engage. "
    1
    Flag
  • Mary
    "On my neighborhood street almost everyone has well behaved dogs. The neighbors clean up after their dogs. The street is perfect walking dogs- less traffic and extra wide roads. "
    0
    Flag
  • Janemarques08
    "I’ve lived her for two years. I know most of my neighbors. I feel good knowing that my children attend top “A”rated schools and that we live in a safe neighborhood. "
    5
    Flag
  • Nelson_sheena
    "The school system in Cheshire is great. They have tons of fun family activities. The community seems safe as well. Kids ride bikes on the trails and always people are walking their dogs. "
    1
    Flag
  • Nelson_sheena
    "Route 10 can be a little crowded during rush hour, but its not bad. The roads are clear and cleaned. "
    0
    Flag
  • Sjhickok01
    "great safe place, lots of kids, lots of great wildlife. most people walk their dogs 2-3 times a day...almost everyone is friendly. Beautiful area due to all of the different trees and plants. Beautiful holiday lights and halloween is always a favorite. lots of festivals during the spring/summer season."
    0
    Flag
  • janemarques08
    "We have movie night with popcorn near my neighborhood. Lots of group support and activities for the children. "
    1
    Flag
  • Jcasner
    "Safe great schools, best fire department and good police department. Great parks overall one of the best towns in CT. "
    1
    Flag
  • Alyss L.
    "Lots of families with kids and a closed loop street. I also grew up here (1985+) and the town has barely changed. Love that I can raise my kids here now."
    2
    Flag
  • Sara c.
    "My neighborhood is amazing! It is very quiet and and neighbors are friendly. We have easy access to all major highways."
    1
    Flag
  • Nelson_sheena
    "Dogs are always walking all around the neighborhood. Dog friendly for sure. I see more pits and retrievers than any other dog breed"
    1
    Flag
  • Dorothy R.
    "I am retired so I don't have a commute. Family member does and has described it as usually uneventful."
    0
    Flag
  • Emily M. G.
    "Great neighborhood in a great town, I feel safe. I’ve lived and grew up here for 23 years and I would live in cheshire as an adult"
    2
    Flag
  • Nelson_sheena
    "Quiet, farm land, lots to do. Good restaurants and lots to do with the kids. Lots of shops, banks, pretty scenery"
    0
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  • Emily M. G.
    "It’s a small, nice, and safe neighborhood. I’ve lived in the same house my whole life. It’s right next to mixville, I love walking around my neighborhood, everyone’s very nice."
    0
    Flag
  • Nelson_sheena
    "Cheshire is a quiet well kept town. The condos I live in are quiet and everyone is respectful. Lots of wildlife too"
    0
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  • adsinsight
    "Live near by, wish I lived here! Great place to raise a family and enjoy life's simple pleasures. Community is very close.. "
    0
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Apartments for Rent

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Homes for sale near 261 Winthrop Drive

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Off Market Homes Near 261 Winthrop Drive

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.