2 Winding Way, Trumbull, CT 06611
OFF MARKET

2 Winding Way
Trumbull, CT 06611

  • 3 Beds
  • 3 Baths
  • 2,636 sqft

$978,800

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $6,356/mo*
Refinance Your Home

$978,800

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $6,356/mo*
Refinance Your Home
3 Beds
3 Baths
2,636 sqft

Local Information

  • Map ViewExplore the area around 2 Winding Way.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This condo is located at 2 Winding Way, Trumbull, CT. 2 Winding Way is in Trumbull, CT and in ZIP code 06611. This property has 3 bedrooms, 3 bathrooms and approximately 2,636 sqft of floor space. This property was built in 2005.
2 Winding Way, Trumbull, CT 06611 is a 3 bedroom, 3 bathroom, 2,636 sqft condo built in 2005. It last sold for $635,000 on Jan 25, 2021. It is currently off market. The Trulia Estimate is $978,800, with a rent estimate of $3,771/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2 Winding Way

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: CondoArchitecture: Other

Price History for 2 Winding Way

DatePriceEventSource
01/25/2021$635,000Sold
N/A
10/03/2014$715,000Sold
N/A
01/12/2006$779,900Sold
N/A

Market trends in Trumbull

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
74
8MoM
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Property Tax and Assessment

Year2025
Tax$17,141
Assessment$466,480
Home facts updated by county records

Comparable Sales for 2 Winding Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
267 Mayfield Dr, Trumbull, CT
0.54
Condo
$510,000
12/05/25
2
2
1,622
306 Hadley Dr, Trumbull, CT
0.63
Condo
$500,000
08/26/25
2
2
1,767
306 Hadley Drive #306, Trumbull, CT
0.63
Condo
$500,000
08/25/25
2
2
1,767
177 Mayfield Drive #177, Trumbull, CT
0.63
Condo
$540,000
04/06/26
2
2
1,595
267 Mayfield Drive #267, Trumbull, CT
0.63
Condo
$510,000
12/04/25
2
2
1,622
177 Mayfield Dr, Trumbull, CT
0.71
Condo
$540,000
04/10/26
2
2
1,595
283 Mayfield Drive #283, Trumbull, CT
0.69
Condo
$500,000
01/20/26
2
2
1,510
283 Mayfield Dr, Trumbull, CT
0.51
Condo
$500,000
01/22/26
1
2
1,510
84 Cider Mill Lane, Trumbull, CT
0.95
Condo
$551,000
09/24/25
2
2
2,270
71 Cider Mill Lane, Trumbull, CT
0.96
Condo
$565,000
03/05/26
1
2.5
2,660

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Winding Way.
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 Trumbull

At least 234 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 86 % Say parking is easy

  • 85 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 77 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 66 % Say kids play outside

  • 66 % Say it's quiet

  • 65 % Say people would walk alone at night

  • 63 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 37 % Say streets are well-lit

  • 33 % Say there are sidewalks

  • 31 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Emily.stumph
    "The parks are great but there is no safe way to bike between them, you need a car to enjoy Trumbull’s nature "
    0
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  • Mjconstructionpro
    "Yes I do see people walking with their dogs, I love my neighbors. People are so nice… Trumbull is the town for me "
    0
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  • E Rocco
    "not bad. trumbull is nice and close to the merit. i grew up here and wouldn’t change a thing! its a safe and friendly town"
    0
    Flag
  • Xgv8mhqqpg
    "My commute is short with easy access to highway systems. Very little traffic lights and I am only limited by stop signs. Cars are on the road are friendly. "
    0
    Flag
  • Trulia User
    "The area is quiet and family oriented. Neighbors look out for neighbors to keep the peace and order. Nice park with playground area and sports events next to a nice library "
    0
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  • RMV
    "There are many young families and parks all over town. I live around the corner from the entrance of a walking trail that leads into a park that’s great for a hike or recreation. There are not many restaurants on my side of town except a wine bar, but Starbucks and Dunkin Donuts are walking distance."
    11
    Flag
  • Nicole D.
    "dog friendly area. plenty of state parks and trails for the dogs. just watch out for wildlife with the smaller dogs."
    1
    Flag
  • Jnapoli2521
    "I live in Trumbull Town Commons and some dog owners do not pick up after their dog despite the signs "
    2
    Flag
  • Msvindland
    "Town movies, town pools and block parties. They have a wonderful walking trail that my dog and I use frequently and a wonderful dog park. They have the Trumbull mall which is very well maintained and the movie theater that has security"
    5
    Flag
  • Rebeccalore
    "There are a lot of dogs in the neighborhood and they are well cared for. There is also a good dog park near by. "
    1
    Flag
  • Ashley U.
    "My neighborhood is almost perfect. The only problem is that everything is spaced out. The mall is in one direction, the movie theater in another and the small shops and such are all about. It’s quite boring here if you ask me. "
    9
    Flag
  • KMM
    "I’ve grown up/lived here for 25 years. Amazing town to grow up in! School system is great too. People are friendly and it feels like home."
    2
    Flag
  • Bruce S.
    "We have lived here for more than 50 years. I would never want to move. Beautiful year round, near nice beaches, excellent schools, safe neighborhoods and reasonably affordable. "
    6
    Flag
  • Heather Uva
    "Trumbull is very blue collar down to earth people.. we are friendly, nonjudgemental, who work hard, and love our children. It is a pleasure to live here. Trumbull is close to major highway also for quick ride to the major cities around her."
    2
    Flag
  • Olgui L.
    "Great school system. Very safe town. I have lived here for 42 years, have never had any bad experiences. "
    2
    Flag
  • KB
    "It’s a great residential neighborhood, however there aren’t a ton of options for restaurants in the city itself, however it is really close to surrounding towns with plenty of life."
    0
    Flag
  • Mike s.
    "You can get a fair amount of property that you can expand upon. Even though it’s a double yellow I feel safe when my little ones are playing. "
    1
    Flag
  • Adeliofpimenta
    "I love living here because of the neiborhoods are very nice , and quiet my kids can save ride a bike , and enjoy the weather outside with the beautiful parks around ! "
    0
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  • Mike s.
    "The school system is trumbull is amazing. Both of our boys are thriving thanks to TECEC. There are also some private school options which we have taken advantage of and have not been disappointed. "
    0
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  • Lsosa2007
    "This neighborhood is unique because of all the nice people that make it a neighborhood. All the fun things that happen in my neighborhood bring us together."
    1
    Flag
  • Tobiascarling
    "I’ve lived here for eight years and cherish the warm, friendly neighborhood. People are constantly out walking or running, kids playing, and neighbors are chatty."
    0
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  • Loveeherrr
    "It’s a gated community, everyone is friendly . There’s a gym, pool area, cookout area, guest lounge. You need a key to get in and there’s security that do hourly walks through the neighborhood to keep an eye for anything "
    0
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  • Tobiascarling
    "We have a very friendly neighborhood, full of families and empty nesters. I love being close to the Merritt, playgrounds, the Trumbull mall, and the grocery store."
    0
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Homes for sale near 2 Winding Way

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Off Market Homes Near 2 Winding Way

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