3 Winding Trl, Middlebury, CT 06762
SOLD
JUL 17, 2026

$561,200

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,403 sqft

3 Winding Trl, Middlebury, CT 06762

Est. Refi. Payment $4,040/mo*
Refinance Your Home
Currently Off Market - Sold Jul 17, 2026 for $559,900

Home Value

Trulia Estimate
$561K
Since last month
Increased$49K (+9.6%)
Since last year
Increased$46K (+9%)
Since last sale
Increased$2K (+0.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +46% in the last 10 years
MonthEstimated value
2026
August 2026$562K
August 2026$562K
July 2026$513K
June 2026$523K
May 2026$523K
April 2026$522K
March 2026$509K
February 2026$509K
January 2026$518K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.00
Condo
$554,000
06/23/26
3
3
2,403
0.00
Condo
$575,000
07/09/26
3
3
2,090
0.00
Condo
$569,900
08/05/26
3
3
1,808
0.35
Condo
$565,000
01/14/26
3
2.5
2,680
0.30
Condo
$559,900
07/16/26
3
2.5
3,179
0.38
Condo
$569,900
07/29/26
3
2.5
2,428
0.22
Condo
$545,000
02/26/26
3
3.5
3,103
0.28
Condo
$554,000
06/22/26
3
3.5
2,879
0.23
Condo
$575,000
11/06/25
3
3.5
3,477

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0.13
$782,700
3
3.5
3,374
Off Market
0.14
$815,000
3
2.5
3,217
Recently Sold
0.13
$979,900
4
4
4,261
For Sale
0.17
$704,600
4
2.5
2,778
Off Market
0.22
$545,000
3
3.5
3,103
Recently Sold
0.23
$596,500
3
3.5
3,477
Off Market
0.23
$917,900
5
4
3,700
Off Market
0.24
$1,061,300
4
3.5
4,200
Off Market
0.24
$657,500
3
3.5
3,477
Off Market
0.26
$639,100
3
2.5
2,485
Off Market
0.25
$485,500
2
2.5
1,963
Off Market
0.25
$563,700
3
2.5
2,122
Off Market

Local Information

  • Map ViewExplore the area around 3 Winding Trl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 2007
2,403 sqft
$233/sqft
Garage

About this House

This condo is located at 3 Winding Trl, Middlebury, CT. 3 Winding Trl is in Middlebury, CT and in ZIP code 06762. This property has 3 bedrooms, 3 bathrooms and approximately 2,403 sqft of floor space. The last sold price per dimension was $233/sqft. This property was built in 2007.
3 Winding Trl, Middlebury, CT 06762 is a 3 bedroom, 3 bathroom, 2,403 sqft condo built in 2007. It last sold for $559,900 on Jul 17, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $561,200, with a rent estimate of $3,454/month.

Home Details for 3 Winding Trl

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: CondoArchitecture: Other

Price & Status

Price
Price Per Sqft: $233/sqft

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Jul 17, 2026
Source: N/A
Sold
$559,900
Nov 5, 2019
Source: N/A
Sold
$335,000

Market trends in Middlebury

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
36
9
MoM

What Locals Say about Middlebury

At least 21 Trulia users voted on each feature.
  • 94 % Say yards are well-kept

  • 93 % Say parking is easy

  • 86 % Say car is needed

  • 82 % Say there's holiday spirit

  • 78 % Say there's wildlife

  • 72 % Say it's quiet

  • 63 % Say it's dog friendly

  • 58 % Say people would walk alone at night

  • 52 % Say kids play outside

  • 48 % Say they plan to stay for at least 5 years

  • 47 % Say neighbors are friendly

  • 45 % Say it's walkable to restaurants

  • 36 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 34 % Say there are community events

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Ginacea313@gmail.com
    "It’s a beautiful community with little to no crime. There is a crystal clear lake and a small amusement park. Additionally, there are plenty of hiking trails. Autumn is quite amazing here, with many vibrant colors. "
  • Ginacea313@gmail.com
    "Middlebury is a beautiful town. It is truly a New England gem. Lake Quassapaug is clean and the MRA is well kept. Summers are heavenly here. "
  • Plandusky
    "Region 15 public schools are some of the best in the state. Middlebury, Southbury public schools. Safe neighborhoods lived here 27 years and could have left the car unlocked the whole time"
  • Cadecres
    "I’ve lived here 11 years now and everyone is friendly and thoughtful. This town is a hidden gem, just far enough away from the bustle yet close enough not to be isolated."
  • darrenwittko
    "With excellent schools and beautiful parks, Middlebury is the perfect family community. Close to I-84, it's great for commuters too."
  • Donathom1114
    "This is an excellent community for families. Top notch schools with excellent family activities. Private community with walking trails and child and pet friendly streets. Wonderful neighbors and pride of home ownership,"
  • castaway45
    "I grew up here, moved here when I was 9. Many fond memories. Great place to walk and for recreation, and for kids to play, points were neighbors, community spirit, natural setting."
  • Rtfa50
    "Great neighborhood for a family with children. Close proximity to I-84 both east and westbound. Excellent area for biking, hiking and walking. Easy access to neighboring towns such as Woodbury, Southbury and easy commute for professionals working in both Waterbury or Danbury. "
  • Hallie
    "I have lived here for 10 years and would not live anywhere else. The schools are fantastic, the parks beautiful, and the town beach perfect. Everywhere you look are flowers, towering oaks, and wonderful jogging paths. This is quintessential New England."

LGBTQ Local Legal Protections

Frequently asked questions about 3 Winding Trl

  • What is 3 Winding Trl estimated to be worth?
    Trulia's estimated value for 3 Winding Trl in Middlebury, CT is $561,200.
  • What is the price history for 3 Winding Trl?
    3 Winding Trl in Middlebury, CT last sold for $559,900 in July 2026.
  • Is Middlebury a buyer's or seller's market?
    Middlebury is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Middlebury?
    Residents describe Middlebury, CT as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Middlebury, CT.

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