9 Winding Rd, Madison, CT 06443
OFF MARKET

9 Winding Rd
Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 2,800 sqft (on 1.37 acres)

$642,900

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,403/mo*
Refinance Your Home

$642,900

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,403/mo*
Refinance Your Home
4 Beds
3 Baths
2,800 sqft
(on 1.37 acres)

Local Information

  • Map ViewExplore the area around 9 Winding Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This house is in great condition - solid and sound. Although everything works fine, the kitchen & baths are outdated - pink bath, blue bath & sunshine yellow bath. The kitchen is large & the cabinets have been brightened with paint. Light yellow laminate counters date the space. The trim is dark but the floors are all a beautiful light hardwood. This is so much house and a great opportunity for the smart buyer. 4 Bedrooms, 3 Baths, Central A/C, Hardwood Floors, 2 Car Garage, 2800 SqFt with a 1.3 Acre corner lot in a conveniently located Madison subdivision. This house just needs a family to give it a fresh start. MAKE AN OFFER! If you or anyone you know is interested in viewing this home, I'd be happy to arrange a private showing. For more information on this property and other real estate opportunities, call Judy Moriarty at 203-996-8980, or Wil Aloe at 203-896-1002, Prudential CT Realty, 845 Boston Post Rd, Madison, CT. Updated 6/27/08. Agent licensed in CT.
9 Winding Rd, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,800 sqft single-family home built in 1969. It last sold for $290,000 on Aug 26, 2008. It is currently off market. The Trulia Estimate is $642,900, with a rent estimate of $5,755/month.

Home Highlights

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

Home Details for 9 Winding Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 8Ceiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stucco
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 1.37 acres

Price History for 9 Winding Rd

DatePriceEventSource
08/26/2008$290,000Sold
Smart MLS #M9103103

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$7,124
Assessment$317,600
Home facts updated by county records

Comparable Sales for 9 Winding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
81 Bartlett Drive, Madison, CT
0.32
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
76 Bartlett Drive, Madison, CT
0.30
Single-Family Home
$780,000
04/17/26
5
2.5
3,100
10 Scenic Road, Madison, CT
0.27
Single-Family Home
$685,000
06/16/26
5
3
2,210
98 Bartlett Drive, Madison, CT
0.41
Single-Family Home
$740,000
04/22/26
3
2.5
2,446
93 Deepwood Dr, Madison, CT
0.24
Single-Family Home
$350,000
12/08/25
3
1
1,754
15 Stepping Stone Lane, Madison, CT
0.36
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
71 Deepwood Dr, Madison, CT
0.25
Single-Family Home
$475,000
10/31/25
4
2
1,236
37 Sheffield Lane, Madison, CT
0.41
Single-Family Home
$761,000
08/14/25
4
2.5
2,989
18 Deepwood Drive, Madison, CT
0.43
Single-Family Home
$440,000
12/22/25
3
2
1,975
4 Sheffield Lane, Madison, CT
0.63
Single-Family Home
$730,000
07/03/25
4
2.5
2,312

Nearby homes

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Assigned Schools

These are the assigned schools for 9 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
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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
    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
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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"
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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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Homes for sale near 9 Winding Rd

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Off Market Homes Near 9 Winding Rd

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