44 Winding Road, Madison, CT 06443
SOLD
SEP 16, 2026

$405,000

Last sold price
  • 4 Beds
  • 2 Baths
  • 1,698 sqft (on 1.62 acres)

44 Winding Road, Madison, CT 06443

Est. Refi. Payment $2,960/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2026 for $405,000 (1% above list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
660 Opening Hill Road, Madison, CT
0.50
Single-Family Home
$490,000
06/25/26
4
2
1,688
18 Deepwood Drive, Madison, CT
0.38
Single-Family Home
$440,000
12/22/25
3
2
1,975
313 Bradley Corners Road, Madison, CT
0.50
Single-Family Home
$640,000
04/16/26
4
2
1,848
15 Stepping Stone Lane, Madison, CT
0.51
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
81 Bartlett Drive, Madison, CT
0.43
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
12 Rustic Lane, Madison, CT
0.71
Single-Family Home
$620,000
05/13/26
4
2
1,849
10 Scenic Road, Madison, CT
0.38
Single-Family Home
$685,000
06/16/26
5
3
2,210

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
105 Deepwood Drive, Madison, CT 06443
0.12
$515,400
3
2
1,832
Off Market
123 Deepwood Drive, Madison, CT 06443
0.16
$523,300
3
1.5
1,884
Off Market
101 Winding Road, Madison, CT 06443
0.25
$514,000
4
2
1,848
Off Market
37 Sheffield Lane, Madison, CT 06443
0.25
$790,700
4
2.5
2,989
Off Market
50 Wheatstone Road, Madison, CT 06443
0.31
$1,271,800
4
2.5
4,402
Off Market
62 Bartlett Drive, Madison, CT 06443
0.32
$678,500
3
2.5
2,186
Off Market
22 Scenic Road, Madison, CT 06443
0.35
$669,000
4
3
2,628
Off Market
76 Bartlett Drive, Madison, CT 06443
0.40
$780,000
5
2.5
3,100
Recently Sold
24 Deepwood Drive, Madison, CT 06443
0.36
$493,100
3
1.5
1,200
Off Market
10 Scenic Road, Madison, CT 06443
0.38
$685,000
5
3
2,210
Recently Sold
22 Silo Hill, Madison, CT 06443
0.43
$1,175,000
5
3.5
3,882
Off Market

Local Information

  • Map ViewExplore the area around 44 Winding Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
1.62 acre lot
1,698 sqft
$239/sqft
2 Car Garage

About this House

Situated on 1.62 acres, this 4-bedroom, 2-bath ranch offers endless potential for investors, contractors, or buyers looking to create their dream home. The expansive backyard, once used as a sports field, provides an incredible amount of usable outdoor space that's rarely found. Inside, you'll find hardwood floors in many rooms, a spacious living room with a fireplace, a 2-car attached garage, and a bright sunroom/family room just off the kitchen featuring walls of windows overlooking the backyard. The home does require significant updating and repairs, but the layout, lot, and location provide an exceptional opportunity to add value. Conveniently located close to downtown shops, restaurants, and commuter routes.
44 Winding Road, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 1,698 sqft single-family home built in 1968. It last sold for $405,000 on Sep 16, 2026 (1% above the $400,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $3,543/month.
Last check for updates: about 15 hours ago
Listed by Mark Mermelstein, (347) 634-2123
eXp Realty, (866) 828-3951
Bought with: Mark Mermelstein, (347) 634-2123, eXp Realty, (866) 828-3951
Source: Smart MLS, MLS#24197194

Home Details for 44 Winding Road

Interior Features

Interior Details
Basement: FullNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1698 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Water HeaterRefrigerator
Heating & Cooling
Heating: Baseboard,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: ShingleFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1698 Square Feet

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1159705

Price & Status

Price
List Price: $400,000Price Per Sqft: $239/sqft
Status Change & Dates
Off Market Date: Fri Aug 14 2026Possession 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: 1698 Square Feet

HOA

No HOA

Lot Information

Lot Area: 1.62 Acres

Miscellaneous

BasementMls Number: 24197194Attic: Access Via HatchAttribution Contact: (347) 634-2123Above Grade Unfinished Area: 1698

Price and Tax history

DateEventPrice
Sep 16, 2026
Source: Smart MLS #24197194
Sold
$405,000
Aug 16, 2026
Source: eXp Realty #24197194
Contingent
$400,000
Aug 16, 2026
Source: Smart MLS #24197194
Pending
$400,000
Aug 6, 2026
Source: Smart MLS #24197194
Listed For Sale
$400,000
Feb 17, 2009
Source: Smart MLS #M9111056
Sold
$310,000

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$716K
$6.67KMoM
Sale-to-List Price
101.8%
0.2%MoM
Price per sq ft
$337
$3MoM
Available listings
59
4MoM

Around this home

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

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Frequently asked questions about 44 Winding Road

  • What is the price history for 44 Winding Road?
    44 Winding Road in Madison, CT last sold for $405,000 in September 2026.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $716K. That is up $6.67K from the prior month.
  • What do residents say about Madison?
    Residents describe Madison, CT as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Madison, CT.
  • How big is the lot at 44 Winding Road?
    The lot at 44 Winding Road in Madison, CT is about 1.6 acres.
  • Does 44 Winding Road have a garage?
    Yes, 44 Winding Road in Madison, CT has an attached garage.

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