Is a car needed in Madison, CT?

As of early 2026, 92% of users say car is needed

Is parking easy in Madison, CT?

As of early 2026, 91% of users say parking is easy

Are yards well-kept in Madison, CT?

As of early 2026, 90% of users say yards are well-kept

Is Madison, CT dog-friendly?

As of early 2026, 89% of users say it's dog friendly

Is there wildlife in Madison, CT?

As of early 2026, 88% of users say there's wildlife

Does Madison, CT show holiday spirit?

As of early 2026, 85% of users say there's holiday spirit

Would people walk alone at night in Madison, CT?

As of early 2026, 78% of users say people would walk alone at night

Is Madison, CT quiet?

As of early 2026, 74% of users say it's quiet

Are neighbors friendly in Madison, CT?

As of early 2026, 66% of users say neighbors are friendly

Do residents of Madison, CT plan to stay at least 5 years?

As of early 2026, 63% of users say they plan to stay for at least 5 years

Do kids play outside in Madison, CT?

As of early 2026, 62% of users say kids play outside

Are there community events in Madison, CT?

As of early 2026, 39% of users say there are community events

Are the streets well-lit in Madison, CT?

As of early 2026, 31% of users say streets are well-lit

Is Madison, CT walkable to grocery stores?

As of early 2026, 29% of users say it's walkable to grocery stores

Is Madison, CT walkable to restaurants?

As of early 2026, 26% of users say it's walkable to restaurants

Does Madison, CT have sidewalks?

As of early 2026, 12% of users say there are sidewalks

FOR SALE

NEW - 2 HRS AGO

1.62 ACRES

44 Winding Road
Madison, CT 06443

4 Beds
2 Baths
1,698 sqft (on 1.62 acres)

$400,000

Est. Mortgage $2,835/mo*

Get Pre-Qualified

$400,000

Est. Mortgage $2,835/mo*

Get Pre-Qualified

4 Beds

2 Baths

1,698 sqft

(on 1.62 acres)

Home Highlights

Parking

2 Car Garage

Climate Control

Heating only

Price/Sqft

$236

Listed

Less than a day ago

Local Information

Map ViewExplore the area around 44 Winding Road.
Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

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.

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

Days on Market
Days on Market: <1 day on Trulia

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: $236
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Active

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

Agent Information
Listing Agent Listing ID: 24197194

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

Last check for updates: about 2 hours ago

Listing courtesy of Mark Mermelstein, (347) 634-2123

eXp Realty, (347) 634-2123

Source: Smart MLS, MLS#24197194

Also Listed on Smart MLS, eXp Realty.

Market trends in Madison

Last updated June 2026

Avg. sale price

$763K

Sale-to-List Price

100.7%

Price per sq ft

$327

Available listings

2MoM

Price History for 44 Winding Road

Date	Price	Event	Source
08/06/2026	$400,000	Listed For Sale	Smart MLS #24197194

02/17/2009	$310,000	Sold	Smart MLS #M9111056
Recording Date 02/17/2009 County Transfer Tax N/A Total Transfer Tax N/A
08/31/2008	$340,000	PriceChange	Agent Provided
Price Change $20,000 (-6%)
07/25/2008	$360,000	PriceChange	Agent Provided
Price Change $39,900 (-10%)
06/11/2008	$399,900	Listed For Sale	Agent Provided

04/27/1993	$170,000	Sold	N/A
Recording Date 04/27/1993 County Transfer Tax N/A Total Transfer Tax N/A
04/29/1988	$199,000	Sold	N/A
Recording Date 04/29/1988 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$7,052
Assessment	$314,400

Home facts updated by county records

Comparable Sales for 44 Winding Road

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
24 Deepwood Drive, Madison, CT	0.36	Single-Family Home	$475,000	09/03/25	3	1.5	1,200
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
37 Sheffield Lane, Madison, CT	0.26	Single-Family Home	$761,000	08/14/25	4	2.5	2,989

Nearby homes

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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 44 Winding Road.

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
Resident
6mo ago
"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
Resident
2y ago
"Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
0
Flag
Ginavan1
Resident
2y ago
"Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
0
Flag
Jv4450
Visitor
2y ago
"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
Resident
5y ago
"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
Resident
5y ago
"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.
Resident
5y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
0
Flag
Junedday1
Resident
7y ago
"I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
3
Flag
Bob B
Resident
7y ago
"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
Resident
7y ago
"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.
Resident
7y ago
"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
Resident
7y ago
"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.
Resident
8y ago
"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.
Resident
8y ago
"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.
11y ago
"Great for young families!"
0
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Robert S.
11y ago
"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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LGBTQ Local Legal Protections

Mark Mermelstein, eXp Realty, (347) 634-2123

Agent Phone: (347) 634-2123

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.

44 Winding Road, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 1,698 sqft single-family home built in 1968. This property is currently available for sale and was listed by Smart MLS on Aug 6, 2026. The MLS # for this home is MLS# 24197194.

44 Winding Road
Madison, CT 06443

$400,000