7 Winding Trl, Middlebury, CT 06762
OFF MARKET

$525,800

Trulia Estimate
  • Studio

7 Winding Trl, Middlebury, CT 06762

Est. Refi. Payment $3,886/mo*
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Home Value

Trulia Estimate
$526K
Since last month
Increased$500 (+0.1%)
Since last year
Decreased$9K (-1.6%)
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 decreased by -4% in the last 10 years
MonthEstimated value
2026
September 2026$525K
August 2026$524K
July 2026$521K
June 2026$526K
May 2026$527K
April 2026$520K
March 2026$512K
February 2026$520K
January 2026$517K
2025

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
38 Avalon Drive, Middlebury, CT
0.14
Single-Family Home
$815,000
07/29/26
3
2.5
3,217
1 Hampshire Court, Middlebury, CT
0.24
Single-Family Home
$800,000
12/16/25
4
3.5
3,711
Lot 41 Somerset Drive, Middlebury, CT
0.30
Single-Family Home
$949,417
09/24/26
3
2.5
2,878
37 Atwood St, Middlebury, CT
0.32
Single-Family Home
$84,500
06/29/26
3
1
1,176
23 Somerset Dr, Middlebury, CT
0.33
Single-Family Home
$899,000
12/18/25
3
3
3,323
111 Dwyer Road, Middlebury, CT
0.76
Single-Family Home
$710,000
12/18/25
3
2.5
3,212
11 Upper Whittemore Road, Middlebury, CT
0.83
Single-Family Home
$461,000
02/11/26
3
1
1,120
6 Pommel Lane #6, Middlebury, CT
0.88
Single-Family Home
$525,000
10/16/25
2
2.5
1,917
245 Upper Whittemore Road, Middlebury, CT
0.97
Single-Family Home
$875,000
06/15/26
3
2.5
2,990
2 Judd Hill Road, Woodbury, CT
1.06
Single-Family Home
$575,000
07/02/26
3
2
1,470

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
34 Avalon Drive, Middlebury, CT 06762
0.13
$785,800
3
3.5
3,374
Off Market
38 Avalon Drive, Middlebury, CT 06762
0.14
$815,000
3
2.5
3,217
Recently Sold
285 Southford Road, Middlebury, CT 06762
0.10
$650,000
3
2
2,007
For Sale
9 Whitehall Court, Middlebury, CT 06762
0.13
$979,900
4
4
4,261
For Sale
400 Long Meadow Road, Middlebury, CT 06762
0.17
$708,800
4
2.5
2,778
Off Market
2 Dogwood Court #2, Middlebury, CT 06762
0.22
$545,000
3
3.5
3,103
Recently Sold
1 Dogwood Court #1, Middlebury, CT 06762
0.23
$597,800
3
3.5
3,477
Off Market
171 Judd Hill Road, Middlebury, CT 06762
0.23
$918,600
5
4
3,700
Off Market
106 Judd Hill Road, Middlebury, CT 06762
0.24
$1,047,100
4
3.5
4,200
Off Market
14 Dogwood Court #14, Middlebury, CT 06762
0.24
$655,700
3
3.5
3,477
Off Market
12 Arrowwood Drive #191, Middlebury, CT 06762
0.26
$605,300
3
2.5
2,485
Off Market
23 Ridgewood Drive #23, Middlebury, CT 06762
0.25
$478,200
2
2.5
1,963
Off Market

Local Information

  • Map ViewExplore the area around 7 Winding Trl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

7 Winding Trl is in Middlebury, CT and in ZIP code 06762.
7 Winding Trl, Middlebury, CT 06762 is a studio property. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $525,800, with a rent estimate of $3,565/month.

Price and Tax history

DateEventPrice
Feb 14, 2024
Source: Smart MLS #170619516
ListingRemoved
Jan 21, 2024
Source: Smart MLS #170619516
Listed For Sale
$479,900

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
9MoM

Around this home

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. "
    3
    Flag
  • 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. "
    1
    Flag
  • 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"
    0
    Flag
  • 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."
    0
    Flag
  • darrenwittko
    "With excellent schools and beautiful parks, Middlebury is the perfect family community. Close to I-84, it's great for commuters too."
    0
    Flag
  • 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,"
    0
    Flag
  • 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."
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 7 Winding Trl

  • What is 7 Winding Trl estimated to be worth?
    Trulia's estimated value for 7 Winding Trl in Middlebury, CT is $525,800.
  • 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.
  • What are the closest schools to 7 Winding Trl?
    The closest schools to 7 Winding Trl in Middlebury, CT are Long Meadow Elementary School (Pre-K, rated 5/10), Memorial Middle School (rated 8/10), Pomperaug Regional High School (rated 8/10).

Apartments for Rent

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Off Market Homes Near 7 Winding Trl

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