Google street view image for 127 Winding Rd, Madison, CT 06443

SOLD

$642,857

Est. refi paymentEst. refi $1,798/mo

•

1.5 ba

•

1,340

sq ft

127 Winding Rd, Madison, CT 06443

About this home

Pristine move-in condition! Newer rmdld kit&bth's,huge fr & large deck overlooking spacious yard,patio area too! 3Br up,one down - or office! Great quiet neighborhood. Contingency cla. Showings begin 5/11

Single-familyProperty Type

1971Year Built

1.03 acresLot Size

$480Est. Price/Sq.Ft.

2 car garageParking

Source:Public Records

Redfin Estimate

$642,857

$368K since sold in September 2002$9,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.2% lower than the average sale price ($724K) of 6 comparable homes.

SOLD JUN 29, 2026
$850,100
A
4 beds2.5 baths1,954 sq ft
217 Stonehedge Ln, Guilford, CT 06437
SOLD JUN 29, 2026
$675,000
B
4 beds2.5 baths2,460 sq ft
200 Whitethorn Dr, Guilford, CT 06437
SOLD JUN 26, 2026
$738,000
C
3 beds3 baths2,025 sq ft
69 Squires Rd, Madison, CT 06443
SOLD AUG 10, 2026
$700,000
D
4 beds2.5 baths2,057 sq ft
476 Summer Hill Rd, Madison, CT 06443
SOLD MAR 27, 2026
$610,000
E
4 beds2.5 baths1,870 sq ft
286 Opening Hill Rd, Madison, CT 06443
SOLD AUG 20, 2026
$769,000
F
4 beds2.5 baths2,647 sq ft
89 Summer Hill Rd, Madison, CT 06443

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Earn from this home

Sell

$603,872

Est. take-home

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Refinance

Est. cash available

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Rent

$2,884/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.0%

+1.3% MoM

Median sale price

$795K

$70K MoM

Avg. days on market

44d

2 days MoM

Recently sold homes

15 MoM

New listings for sale

COMING SOON
$500,000
2 beds2 baths1,280 sq ft
14 Hampshire Rd #14, Madison, CT 06443
COMING SOON
$699,000
4 beds2 baths2,750 sq ft
38 Church Ln, Madison, CT 06443
OPEN SUN, 11AM TO 1PM
$579,900
3 beds1 bath1,077 sq ft
6 Bower Rd, Madison, CT 06443
$5,000,000
3 beds3 baths3,109 sq ft
Madison, CT 06443
COMING SOON
$700,000
3 beds2.5 baths2,124 sq ft
67 Blakeman Rd, Madison, CT 06443
$524,000
3 beds2 baths1,288 sq ft
35 Aileen Dr, Madison, CT 06443
$500,000
2 beds2 baths1,280 sq ft
22 Thelbridge St #22, Madison, CT 06443
COMING SOON
$4,499,000
6 beds6.5 baths5,817 sq ft
14 Middle Beach Rd W, Madison, CT 06443
$3,000,000
4 beds5 baths4,833 sq ft
17 Barberry Ln, Madison, CT 06443
See all

Provided by Redfin

Sale history for 127 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,808 (+1.9%)

$93,900 + $99,900

$193,800

2022

$5,700 (+1.9%)

$93,900 + $99,900

$193,800

2021

$5,591 (+1.8%)

$93,900 + $99,900

$193,800

2020

$5,494

$93,900 + $99,900

$193,800

2019

$5,494 (+1.9%)

$93,900 + $99,900

$193,800

2018

$5,389 (+2.7%)

$96,000 + $96,200

$192,200

2017

$5,247 (+3.1%)

$96,000 + $96,200

$192,200

2016

$5,091 (+5.2%)

$96,000 + $96,200

$192,200

2014

$4,838 (+1.6%)

$96,000 + $96,200

$192,200

2010

$4,763

$134,800 + $98,800

$233,600

Tax history for 127 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,808 (+1.9%)

$93,900 + $99,900

$193,800

2022

$5,700 (+1.9%)

$93,900 + $99,900

$193,800

2021

$5,591 (+1.8%)

$93,900 + $99,900

$193,800

2020

$5,494

$93,900 + $99,900

$193,800

2019

$5,494 (+1.9%)

$93,900 + $99,900

$193,800

2018

$5,389 (+2.7%)

$96,000 + $96,200

$192,200

2017

$5,247 (+3.1%)

$96,000 + $96,200

$192,200

2016

$5,091 (+5.2%)

$96,000 + $96,200

$192,200

2014

$4,838 (+1.6%)

$96,000 + $96,200

$192,200

2010

$4,763

$134,800 + $98,800

$233,600

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

1.03 Acres

Year renovated

—

Sq. Ft.

1,340

Year built

1971

Style

Single Family Residential

County

New Haven County

APN

1159659

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Around this home

Schools

Kathleen H. Ryerson Elementary School

Public K-3 • Assigned • 1.2mi

10/10

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 3.5mi

9/10

Daniel Hand High School

Public 9-12 • Assigned • 3.6mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 94° expected this year, 17 days in 30 years

6/10 Wind Factor

70% chance of strong winds in next 30 years

5/10 Air Factor

5 unhealthy days expected this year, 8 days in 30 years

Provided by First Street

Historical weather

Madison, CT • 06443

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

8.9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$611,000 – $740,000

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Nearby similar homes

OPEN SUN, 11AM TO 1PM

$579,900

3 beds1 bath1,077 sq ft

6 Bower Rd, Madison, CT 06443

$1,249,900

4 beds4 baths5,267 sq ft

625 State St, Guilford, CT 06437

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4 beds2 baths1,505 sq ft

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NEW CONSTRUCTION

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23 Sheep Pasture Rd, Madison, CT 06443

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1 bed1 bath806 sq ft

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New listings for sale in 06443

COMING SOON

$500,000

2 beds2 baths1,280 sq ft

14 Hampshire Rd #14, Madison, CT 06443

COMING SOON

$699,000

4 beds2 baths2,750 sq ft

38 Church Ln, Madison, CT 06443

OPEN SUN, 11AM TO 1PM

$579,900

3 beds1 bath1,077 sq ft

6 Bower Rd, Madison, CT 06443

$5,000,000

3 beds3 baths3,109 sq ft

Madison, CT 06443

COMING SOON

$700,000

3 beds2.5 baths2,124 sq ft

67 Blakeman Rd, Madison, CT 06443

$524,000

3 beds2 baths1,288 sq ft

35 Aileen Dr, Madison, CT 06443

$500,000

2 beds2 baths1,280 sq ft

22 Thelbridge St #22, Madison, CT 06443

COMING SOON

$4,499,000

6 beds6.5 baths5,817 sq ft

14 Middle Beach Rd W, Madison, CT 06443

$3,000,000

4 beds5 baths4,833 sq ft

17 Barberry Ln, Madison, CT 06443

Home values near 127 Winding Rd

Data from public records.

Address	Redfin Estimate
62 Winding Rd, Madison, CT 4 Beds \| 3 Baths \| 2042 Sq. Ft.	$641,061
54 Winding Rd, Madison, CT 3 Beds \| 1.5 Baths \| 1250 Sq. Ft.	$500,063

Address	Redfin Estimate
86 Winding Rd, Madison, CT 4 Beds \| 3.5 Baths \| 2358 Sq. Ft.	$668,766
130 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 1994 Sq. Ft.	$610,278

Address	Redfin Estimate
48 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 1338 Sq. Ft.	$621,022
96 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2104 Sq. Ft.	$645,075

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