44 Winding Rd, Madison, CT 06443
OFF MARKET

44 Winding Rd
Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 2,204 sqft (on 1.62 acres)

$598,800

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $4,125/mo*
Refinance Your Home

$598,800

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $4,125/mo*
Refinance Your Home
4 Beds
2 Baths
2,204 sqft
(on 1.62 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

A beautiful 1.62 acre setting provides the picturesque backdrop to this terrific home. Enjoy the convenience of one-level living with the added bonus of a partially finished lower level. Hardwood floors grace the main living areas and three of the four bedrooms. From the foyer, French pocket doors open into the living room where a fireplace creates an inviting setting for entertaining. The formal dining room is well-suited for everyday dining as well as special occasions and features a bay window overlooking the property's lush grounds. Meal preparation is a breeze in the updated kitchen which features newer cabinetry, and a skylight for a bright and a skylight for a bright and cheerful space. Off of the kitchen, you'll just love spending time in the year-round sunroom with its own separate heating zone and a woodburning stove. Curl up with a good book by the stove in the winter, or relax with a cool beverage in the warmer months. From the sun room, step out onto the oversized deck which is perfect for hosting a barbecue. There is ample room among four bedrooms and two full baths, with the master bedroom enjoying its own private bath. On the lower level, two finished rooms may be used as a playroom, office, hobby or exercise room. Numerous updates including a newer roof, gutters, driveway, windows and garage doors further enhance this home's outstanding value!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

Home Details for 44 Winding Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 1.62 acres

Price History for 44 Winding Rd

DatePriceEventSource
02/17/2009$310,000Sold
Smart MLS #M9111056
08/31/2008$340,000PriceChange
Agent Provided
07/25/2008$360,000PriceChange
Agent Provided
06/11/2008$399,900Listed For SaleAgent Provided
04/27/1993$170,000Sold
N/A
04/29/1988$199,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$7,052
Assessment$314,400
Home facts updated by county records

Comparable Sales for 44 Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
93 Deepwood Dr, Madison, CT
0.06
Single-Family Home
$350,000
12/08/25
3
1
1,754
71 Deepwood Dr, Madison, CT
0.13
Single-Family Home
$475,000
10/31/25
4
2
1,236
18 Deepwood Drive, Madison, CT
0.37
Single-Family Home
$440,000
12/22/25
3
2
1,975
313 Bradley Corners Road, Madison, CT
0.48
Single-Family Home
$640,000
04/16/26
4
2
1,848
81 Bartlett Drive, Madison, CT
0.45
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
24 Deepwood Drive, Madison, CT
0.35
Single-Family Home
$475,000
09/03/25
3
1.5
1,200
37 Sheffield Lane, Madison, CT
0.23
Single-Family Home
$761,000
08/14/25
4
2.5
2,989
5 Dover Lane, Madison, CT
0.52
Single-Family Home
$670,000
08/21/25
4
2.5
2,096
4 Sheffield Lane, Madison, CT
0.46
Single-Family Home
$730,000
07/03/25
4
2.5
2,312
12 Rustic Lane, Madison, CT
0.69
Single-Family Home
$620,000
05/13/26
4
2
1,849

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Assigned Schools

These are the assigned schools for 44 Winding Rd.
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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

  • 89 % 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
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  • 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
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  • 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
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  • 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
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  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
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  • 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
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  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
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  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
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  • 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
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  • 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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44 Winding Rd, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 2,204 sqft single-family home built in 1968. This property is not currently available for sale. 44 Winding Rd was last sold on Feb 17, 2009 for $310,000. The current Trulia Estimate for 44 Winding Rd is $598,800.