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

57 Winding Rd
Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,526 sqft (on 0.95 acres)

$556,900

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $3,853/mo*
Refinance Your Home

$556,900

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $3,853/mo*
Refinance Your Home
4 Beds
2 Baths
1,526 sqft
(on 0.95 acres)

Local Information

  • Map ViewExplore the area around 57 Winding Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Completely updated, 4 br, turn-key ranch--too many updates to mention. Walk out basement/flat rear yard in neighborhood--Must see to fully appreciate. New mechanicals, 200 AMPs, Generator hook up
57 Winding Rd, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 1,526 sqft single-family home built in 1970. It last sold for $305,000 on Nov 14, 2014. It is currently off market. The Trulia Estimate is $556,900, with a rent estimate of $4,243/month.

Home Highlights

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

Home Details for 57 Winding Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Dining Room, Family Room, Master BathCeiling Fan
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.95 acres

Price History for 57 Winding Rd

DatePriceEventSource
11/14/2014$305,000Sold
Smart MLS #N353822
08/28/2014$314,000Listed For SaleAgent Provided
11/15/2012$265,000Sold
Smart MLS #M9137633
10/04/2012$265,000PendingAgent Provided
09/04/2012$265,000PriceChange
Agent Provided
08/12/2012$254,900PriceChange
Agent Provided
06/05/2012$265,000PriceChange
Agent Provided
05/07/2012$275,000PriceChange
Agent Provided
05/01/2012$282,000PriceChange
Agent Provided
04/21/2012$275,000PriceChange
Agent Provided
04/12/2012$282,000PriceChange
Agent Provided
03/24/2012$295,000PriceChange
Agent Provided
02/24/2012$282,000Listed For SaleAgent Provided
12/21/2011$325,000ListingRemovedAgent Provided
12/17/2011$325,000Listed For SaleAgent Provided
10/14/2011$150,000Sold
Smart MLS #M9128328
09/28/2011$199,000PriceChange
Agent Provided
07/02/2011$299,000PriceChange
Agent Provided
05/19/2011$325,000Listed For SaleAgent Provided

Market trends in Madison

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
69
4MoM
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Property Tax and Assessment

Year2025
Tax$6,379
Assessment$284,400
Home facts updated by county records

Comparable Sales for 57 Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Deepwood Dr, Madison, CT
0.24
Single-Family Home
$475,000
10/31/25
4
2
1,236
93 Deepwood Dr, Madison, CT
0.16
Single-Family Home
$350,000
12/08/25
3
1
1,754
18 Deepwood Drive, Madison, CT
0.48
Single-Family Home
$440,000
12/22/25
3
2
1,975
24 Deepwood Drive, Madison, CT
0.45
Single-Family Home
$475,000
09/03/25
3
1.5
1,200
15 Stepping Stone Lane, Madison, CT
0.52
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
81 Bartlett Drive, Madison, CT
0.36
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
10 Scenic Road, Madison, CT
0.42
Single-Family Home
$685,000
06/16/26
5
3
2,210
660 Opening Hill Road, Madison, CT
0.59
Single-Family Home
$490,000
06/25/26
4
2
1,688
76 Bartlett Drive, Madison, CT
0.32
Single-Family Home
$780,000
04/17/26
5
2.5
3,100
313 Bradley Corners Road, Madison, CT
0.58
Single-Family Home
$640,000
04/16/26
4
2
1,848

Nearby homes

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Assigned Schools

These are the assigned schools for 57 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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Explore by feature - Pet Friendly

8 pet-friendly rentals in Madison, CT

Explore by feature - Garage

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Explore by feature - Air Conditioning

22 rentals with air conditioning in Madison, CT

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Homes for sale near 57 Winding Rd

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Off Market Homes Near 57 Winding Rd

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