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

38 Winding Rd
Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,178 sqft (on 1.97 acres)

$547,200

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $3,850/mo*
Refinance Your Home

$547,200

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $3,850/mo*
Refinance Your Home
3 Beds
2 Baths
1,178 sqft
(on 1.97 acres)

Local Information

  • Map ViewExplore the area around 38 Winding Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1968
Lot Size
1.97 acres
Living Area
1,178 sqft
Price/Sqft
$465
Parking
Garage

About this House

Looking for a property to work from home? Whether you are a contractor, landscaper, boat and/or car enthusiasts, this 3 bedroom, 2 full bath Ranch with a huge barn with office is for you! Situated on an oversized corner lot in a cul-de-sac neighborhood in Madison, CT for only $300,000! At a time when many are working from home, here's your opportunity to have the separation you desire from home and work life. The home offers a large Kitchen with skylight, hardwood floors throughout the main living area and bedrooms. Family room has a fireplace that opens to the Dining room with sliders to a back deck. The 1,272 square foot detached Barn has a garage that's deep with high ceilings suitable for boat, workshop, equipment storage or even a horse stable as horses are allowed on this property. There is also an attached office to the Barn with a separate entrance. Just imagine how this set-up can work for you and make it happen before it's too late!
38 Winding Rd, Madison, CT 06443 is a 3 bedroom, 2 bathroom, 1,178 sqft single-family home built in 1968. It last sold for $306,000 on Feb 1, 2021. It is currently off market. The Trulia Estimate is $547,200, with a rent estimate of $3,556/month.

Home Details for 38 Winding Rd

Interior Features

Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Appliances & Utilities
DishwasherRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylPatioPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached, Garage Detached

Property Information

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

Lot Information

Lot Area: 1.97 acres

Building

Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Price History for 38 Winding Rd

DatePriceEventSource
02/01/2021$306,000Sold
Smart MLS #170347617
01/06/2021$300,000ContingentSmart MLS #170347617
11/10/2020$300,000PendingAgent Provided
10/17/2020$300,000PriceChange
Agent Provided
02/28/2020$315,000PriceChange
Agent Provided
11/07/2019$325,000PriceChange
Agent Provided
09/23/2019$359,900Listed For SaleAgent Provided
07/13/2019$359,900ListingRemovedAgent Provided
03/26/2019$359,900PriceChange
Agent Provided
10/25/2018$389,900Listed For SaleAgent Provided
03/02/2005$450,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$6,794
Assessment$302,900
Home facts updated by county records

Comparable Sales for 38 Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
93 Deepwood Dr, Madison, CT
0.08
Single-Family Home
$350,000
12/08/25
3
1
1,754
71 Deepwood Dr, Madison, CT
0.11
Single-Family Home
$475,000
10/31/25
4
2
1,236
24 Deepwood Drive, Madison, CT
0.32
Single-Family Home
$475,000
09/03/25
3
1.5
1,200
18 Deepwood Drive, Madison, CT
0.34
Single-Family Home
$440,000
12/22/25
3
2
1,975
660 Opening Hill Road, Madison, CT
0.46
Single-Family Home
$490,000
06/25/26
4
2
1,688
313 Bradley Corners Road, Madison, CT
0.47
Single-Family Home
$640,000
04/16/26
4
2
1,848
15 Stepping Stone Lane, Madison, CT
0.49
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
12 Rustic Lane, Madison, CT
0.68
Single-Family Home
$620,000
05/13/26
4
2
1,849
37 Sheffield Lane, Madison, CT
0.24
Single-Family Home
$761,000
08/14/25
4
2.5
2,989
81 Bartlett Drive, Madison, CT
0.45
Single-Family Home
$630,000
12/12/25
4
2.5
2,088

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 38 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
    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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

8 pet-friendly rentals in Madison, CT

Explore by feature - Garage

6 rentals with a garage in Madison, CT

Explore by feature - Air Conditioning

25 rentals with air conditioning in Madison, CT

Explore by feature - Washer/dryer

22 rentals with a washer/dryer in Madison, CT

Homes for sale near 38 Winding Rd

Skip to last item
Skip to first item

Off Market Homes Near 38 Winding Rd

Skip to last item
Skip to first item