101 Winding Road, Madison, CT 06443
OFF MARKET

101 Winding Road
Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,848 sqft (on 1.46 acres)

$540,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $3,740/mo*
Refinance Your Home

$540,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $3,740/mo*
Refinance Your Home
4 Beds
2 Baths
1,848 sqft
(on 1.46 acres)

Local Information

  • Map ViewExplore the area around 101 Winding Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This captivating raised ranch is set back from the road on a quiet cul-de-sac and offers 4 bedrooms, 2 full baths, and 1,848 sq ft of finished space. Once inside you will find refinished hardwood floors, crown molding, and a large bay window that allows for lots of natural light. The dining room and kitchen lead to a spacious and private deck which overlooks the fenced in backyard. The delightful kitchen has cherry flooring, newer stainless steel appliances, all granite countertops, and a built-in island for dining. The living room is spacious and has plenty of room to entertain family and friends. The primary bedroom has direct access to a remodeled full bath. Two additional bedrooms can be found on the main floor and have built-in book shelves and hardwood flooring. On the lower level you will find an oversized family room with a fireplace and wood stove insert, hardwood floors, a slider, and additional built-ins. A fourth bedroom on the lower level is perfect for a home office or in-law bedroom. The house also boasts an attached two car garage. Lovely outdoor spaces, sited on 1.46 acres, surrounded by mature trees and perennials. The fully fenced in backyard offers a private and peaceful setting. Schedule your showing today!
101 Winding Road, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 1,848 sqft single-family home built in 1971. It last sold for $440,000 on Nov 3, 2023 (1% above the $435,000 asking price). More recently, it was listed as a rental in July 2020 with an asking price of $2,450 per month. That rental listing was removed on July 22, 2020. It is currently off market. The Trulia Estimate is $540,100, with a rent estimate of $4,551/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 101 Winding Road

Interior Features

Interior Details
Basement: Partial,Partially Finished,Heated,Interior Entry,Garage AccessNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1848 Square Feet
Appliances & Utilities
Utilities: Underground Utilities, Cable AvailableAppliances: Electric Cooktop, Oven/Range, Microwave, Range Hood, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Attic Fan,Central Air,Whole House FanHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Levels, Entrance, & Accessibility
Accessibility: Bath Grab Bars, Multiple Entries/Exits

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PorchFencing: PartialOther Structures: Shed(s)Exterior: Garden, Rain Gutters, Lighting, Stone WallFoundation: Concrete Perimeter, RaisedGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Paved,Garage Door Opener,Private,Asphalt
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1848 Square Feet

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Cedar, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1159654

Price & Status

Price
List Price: $435,000
Status Change & Dates
Off Market Date: Mon Oct 02 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 1848 Square Feet

Community

Community Features: Basketball Court, Golf, Health Club, Library, Park, Playground, Public Rec Facilities, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 1.46 Acres

Miscellaneous

BasementMls Number: 170580927Attic: Pull Down Stairs, Access Via HatchAbove Grade Unfinished Area: 1848

Additional Information

Basketball CourtGolfHealth ClubLibraryParkPlaygroundPublic Rec FacilitiesShopping/Mall
Last check for updates: about 9 hours ago
Listed by Emily Lovejoy, (203) 710-0202
William Raveis Real Estate, (203) 453-0391
Bought with: Toby Knapik, (203) 859-4055, Dow Della Valle, (203) 481-0000
Source: Smart MLS, MLS#170580927

Price History for 101 Winding Road

DatePriceEventSource
11/03/2023$440,000Sold
Smart MLS #170580927
09/12/2023$435,000PendingWilliam Raveis Real Estate, Mortgage & Insurance #170580927
09/12/2023$435,000ContingentSmart MLS #170580927
09/05/2023$435,000Listed For SaleSmart MLS #170580927
08/06/2023ListingRemovedWilliam Raveis Real Estate, Mortgage & Insurance
07/12/2023$449,000PendingWilliam Raveis Real Estate, Mortgage & Insurance #170580927
07/12/2023$449,000ContingentSmart MLS #170580927
07/07/2023$449,000Listed For SaleSmart MLS #170580927
11/12/2022ListingRemovedWilliam Raveis Real Estate, Mortgage & Insurance
11/02/2022$449,900PriceChange
Smart MLS #170525658
10/21/2022$459,000Listed For SaleSmart MLS #170525658
02/17/2021$365,000Sold
Smart MLS #170329106
01/14/2021$379,900PendingBerkshire Hathaway HomeServices New England Properties #170329106
01/06/2021$379,900ContingentSmart MLS #170329106
12/02/2020$379,900PendingAgent Provided
12/02/2020$379,900ContingentSmart MLS #170329106
10/30/2020$379,900PendingToActiveAgent Provided
10/29/2020$379,900PendingAgent Provided
09/23/2020$379,900PriceChange
Agent Provided
08/24/2020$390,000Listed For SaleAgent Provided
07/22/2020$2,450ListingRemovedN/A
07/19/2020$2,450Listed For RentN/A
01/23/2020$2,200ListingRemovedN/A
12/31/2019$2,200Listed For RentN/A
09/29/1995$166,500Sold
N/A

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$6,130
Assessment$273,300
Home facts updated by county records

Comparable Sales for 101 Winding Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Dover Lane, Madison, CT
0.44
Single-Family Home
$670,000
08/21/25
4
2.5
2,096
81 Bartlett Drive, Madison, CT
0.47
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
313 Bradley Corners Road, Madison, CT
0.61
Single-Family Home
$640,000
04/16/26
4
2
1,848
18 Deepwood Drive, Madison, CT
0.61
Single-Family Home
$440,000
12/22/25
3
2
1,975
15 Stepping Stone Lane, Madison, CT
0.71
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
24 Deepwood Drive, Madison, CT
0.58
Single-Family Home
$475,000
09/03/25
3
1.5
1,200
660 Opening Hill Road, Madison, CT
0.72
Single-Family Home
$490,000
06/25/26
4
2
1,688
12 Rustic Lane, Madison, CT
0.79
Single-Family Home
$620,000
05/13/26
4
2
1,849

Nearby homes

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Assigned Schools

These are the assigned schools for 101 Winding Road.
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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

  • 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
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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
    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
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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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Explore by feature - Pet Friendly

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Homes for sale near 101 Winding Road

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Off Market Homes Near 101 Winding Road

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.