65 Winding Rd, Madison, CT 06443
OFF MARKET

65 Winding Rd
Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,288 sqft (on 0.95 acres)

$442,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $3,123/mo*
Refinance Your Home

$442,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $3,123/mo*
Refinance Your Home
3 Beds
2 Baths
1,288 sqft
(on 0.95 acres)

Home Value

Trulia Estimate
$443K
Since last month
Increased$3K (+0.7%)
Since last year
Decreased$5K (-1.1%)
Since last sale
Increased$259K (+139.8%)
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 +71% in the last 10 years
MonthEstimated value
2026
August 2026$444K
July 2026$441K
June 2026$452K
May 2026$444K
April 2026$429K
March 2026$431K
February 2026$420K
January 2026$422K
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
93 Deepwood Dr, Madison, CT
0.18
Single-Family Home
$350,000
12/08/25
3
1
1,754
71 Deepwood Dr, Madison, CT
0.27
Single-Family Home
$475,000
10/31/25
4
2
1,236
24 Deepwood Drive, Madison, CT
0.48
Single-Family Home
$475,000
09/03/25
3
1.5
1,200
18 Deepwood Drive, Madison, CT
0.50
Single-Family Home
$440,000
12/22/25
3
2
1,975
15 Stepping Stone Lane, Madison, CT
0.54
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
81 Bartlett Drive, Madison, CT
0.35
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
98 Bartlett Drive, Madison, CT
0.43
Single-Family Home
$740,000
04/22/26
3
2.5
2,446
18 St. Francis Woods Road, Madison, CT
0.63
Single-Family Home
$550,000
07/08/26
3
2.5
1,824
10 Scenic Road, Madison, CT
0.44
Single-Family Home
$685,000
06/16/26
5
3
2,210
45 Milano Pond Drive, Madison, CT
0.56
Single-Family Home
$795,000
07/15/26
3
2.5
1,908

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
123 Deepwood Drive, Madison, CT 06443
0.16
$544,200
3
1.5
1,884
Off Market
105 Deepwood Drive, Madison, CT 06443
0.17
$530,100
3
2
1,832
Off Market
101 Winding Road, Madison, CT 06443
0.18
$532,600
4
2
1,848
Off Market
50 Wheatstone Road, Madison, CT 06443
0.20
$1,306,500
4
2.5
4,402
Off Market
62 Bartlett Drive, Madison, CT 06443
0.23
$698,800
3
2.5
2,186
Off Market
22 Silo Hill, Madison, CT 06443
0.31
$1,214,500
5
3.5
3,882
Off Market
76 Bartlett Drive, Madison, CT 06443
0.31
$780,000
5
2.5
3,100
Recently Sold
37 Sheffield Lane, Madison, CT 06443
0.34
$788,000
4
2.5
2,989
Off Market
81 Bartlett Drive, Madison, CT 06443
0.35
$630,000
4
2.5
2,088
Recently Sold
26 Jenda Way, Madison, CT 06443
0.38
$737,000
4
2.5
2,147
Off Market
22 Scenic Road, Madison, CT 06443
0.43
$687,300
4
3
2,628
Off Market
77 Silo Hill, Madison, CT 06443
0.43
$1,300,000
5
3.5
4,783
For Sale

Local Information

  • Map ViewExplore the area around 65 Winding Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1971
Lot Size
0.95 acres
Living Area
1,288 sqft
Price/Sqft
$344

About this House

This single-family home is located at 65 Winding Rd, Madison, CT. 65 Winding Rd is in Madison, CT and in ZIP code 06443. This property has 3 bedrooms, 2 bathrooms and approximately 1,288 sqft of floor space. This property has a lot size of 0.95 acres and was built in 1971.
65 Winding Rd, Madison, CT 06443 is a 3 bedroom, 2 bathroom, 1,288 sqft single-family home built in 1971. It last sold for $185,000 on Nov 30, 1999. It is currently off market. The Trulia Estimate is $442,500, with a rent estimate of $3,632/month.

Home Details for 65 Winding Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Lot Information

Lot Area: 0.95 acres

Price and Tax history

DateEventPrice
Nov 30, 1999
Source: N/A
Sold
$185,000

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

What Locals Say about Madison

At least 57 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say yards are well-kept

  • 89 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 85 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 74 % Say it's quiet

  • 66 % Say neighbors are friendly

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

  • 62 % Say kids play outside

  • 39 % Say there are community events

  • 31 % Say streets are well-lit

  • 29 % Say it's walkable to grocery stores

  • 26 % Say it's walkable to restaurants

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag
  • Ginavan1
    "Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
    0
    Flag
  • Ginavan1
    "Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
    0
    Flag
  • Jv4450
    "I’m just trying my luck with this and it doesn’t look too great for the job and the way the company looks I just have no confidence "
    0
    Flag
  • Trulia User
    "I’ve lived here for 30 years. Home prices continue to go up with the NYC families inching this way causing taxes to get out of control. "
    1
    Flag
  • Diana
    "I see people walking dogs but there is no dog park like in neighboring towns. However, there are many walking trails that you can take your leashed dog to walk in."
    4
    Flag
  • Elizabeth L.
    "Great neighborhood. Great schools. Beautiful town. Great library. Great beaches. New England vibe. Shoreline East train takes you to new Haven with direct connection to NYC. "
    2
    Flag
  • Cassidy W.
    "Great place. Been here for 23 years, wouldn’t change a thing. Very small town. Not a lot of commercial business in Madison, close by in Guilford, very local business oriented. "
    1
    Flag
  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
    Flag
  • Jcimino5
    "Nice community with good school system and organized sports teams. Nice beach and walking trails. Can get a bit crowded in the summer."
    2
    Flag
  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
    Flag
  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
    Flag
  • Bob B
    "Great community. Families partipate in local activities. Safe town. Beautiful town beach properties. Great local shopping and restaurants. School system is top notch and lots of state parks close by. It’s really a picture perfect town. Lived in Madison for 42 years "
    0
    Flag
  • Robuess
    "Its the best town in America hands down. We love the local restaurants and can ride our bikes to the beach. Friendly locals who will stop and ask if you need help. Very fortunate to have lived here for 40 years!!"
    0
    Flag
  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
    Flag
  • Pamelajbrown1234
    "Almost everyone has a dog, we take them everywhere. There is a dog park in town. People walk their dogs all over town and down at Hammonasette State Park. Dogs mostly seem very well trained and socialized"
    7
    Flag
  • Nicole L.
    "There is a real sense of community and people actually care about each other here. Schools are excellent and our beaches make it feel like you're always on vacation. "
    0
    Flag
  • Mike H.
    "I’ve lived here since 1990 and love it! There’s everything here, from great dining and great bookstore, coffee shops and terrific local cinema!"
    0
    Flag
  • David F.
    "Great for young families!"
    0
    Flag
  • Robert S.
    "We have lived in Madison for 15 years. This is a great neighborhood with only 12 houses. It is quiet and private as well as being a friendly and considerate group of folks. Mix of retierees and families with close proximity to many local amenities."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 65 Winding Rd

  • What is 65 Winding Rd estimated to be worth?
    Trulia's estimated value for 65 Winding Rd in Madison, CT is $442,500.
  • What is the price history for 65 Winding Rd?
    65 Winding Rd in Madison, CT last sold for $185,000 in November 1999.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • How big is the lot at 65 Winding Rd?
    The lot at 65 Winding Rd in Madison, CT is about 0.95 acres (41,382 sq ft).

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