96 Winding Rd, Madison, CT 06443
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Property image
OFF MARKET

96 Winding Rd
Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,104 sqft (on 0.98 acres)

$642,900

Trulia Estimate
as of Jul 28, 2026
Est. Refi. Payment $4,521/mo*
Refinance Your Home

$642,900

Trulia Estimate
as of Jul 28, 2026
Est. Refi. Payment $4,521/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,104 sqft
(on 0.98 acres)

Local Information

  • Map ViewExplore the area around 96 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
0.98 acres
Living Area
2,104 sqft
Price/Sqft
$306
Parking
Garage

About this House

This single-family home is located at 96 Winding Rd, Madison, CT. 96 Winding Rd is in Madison, CT and in ZIP code 06443. This property has 4 bedrooms, 3 bathrooms and approximately 2,104 sqft of floor space. This property has a lot size of 0.98 acres and was built in 1971.
96 Winding Rd, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,104 sqft single-family home built in 1971. It last sold for $322,000 on Jun 30, 2010. It is currently off market. The Trulia Estimate is $642,900, with a rent estimate of $5,111/month.

Home Details for 96 Winding Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining Room, Family Room, Master BathCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodLawnPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Lot Information

Lot Area: 0.98 acres

Price History for 96 Winding Rd

DatePriceEventSource
06/30/2010$322,000Sold
Smart MLS #G546834
04/22/2010$339,900PriceChange
Agent Provided
03/15/2010$349,900PriceChange
Agent Provided
12/03/2009$375,000PriceChange
Agent Provided
07/17/2009$399,000PriceChange
Agent Provided
06/25/2009$425,000Listed For SaleAgent Provided
11/08/1988$232,000Sold
N/A

Market trends in Madison

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$763K
Sale-to-List Price
100.7%
Price per sq ft
$327
Available listings
71
2MoM
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Property Tax and Assessment

Year2025
Tax$7,171
Assessment$319,700
Home facts updated by county records

Comparable Sales for 96 Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
93 Deepwood Dr, Madison, CT
0.21
Single-Family Home
$350,000
12/08/25
3
1
1,754
81 Bartlett Drive, Madison, CT
0.44
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
71 Deepwood Dr, Madison, CT
0.33
Single-Family Home
$475,000
10/31/25
4
2
1,236
5 Dover Lane, Madison, CT
0.46
Single-Family Home
$670,000
08/21/25
4
2.5
2,096
18 Deepwood Drive, Madison, CT
0.57
Single-Family Home
$440,000
12/22/25
3
2
1,975
18 St. Francis Woods Road, Madison, CT
0.49
Single-Family Home
$550,000
07/08/26
3
2.5
1,824
45 Milano Pond Drive, Madison, CT
0.44
Single-Family Home
$795,000
07/15/26
3
2.5
1,908
10 Scenic Road, Madison, CT
0.57
Single-Family Home
$685,000
06/16/26
5
3
2,210
76 Bartlett Drive, Madison, CT
0.39
Single-Family Home
$780,000
04/17/26
5
2.5
3,100
98 Bartlett Drive, Madison, CT
0.50
Single-Family Home
$740,000
04/22/26
3
2.5
2,446

Nearby homes

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Assigned Schools

These are the assigned schools for 96 Winding Rd.
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 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
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  • 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
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  • David F.
    "Great for young families!"
    0
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  • 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
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16 rentals with air conditioning in Madison, CT

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Homes for sale near 96 Winding Rd

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Off Market Homes Near 96 Winding Rd

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