Google street view image for 95 Winding Rd, Madison, CT 06443

Off market nov 1992 for $156K

$553,573

Est. refi paymentEst. refi $1,012/mo

•

2 ba

•

1,554

sq ft

95 Winding Rd, Madison, CT 06443

About this home

95 Winding Rd is a 1,554 square foot house on a 0.98 acre lot with 4 bedrooms and 2 bathrooms. - it last sold on November 05, 1992 for $156,400. Based on Redfin's Madison data, we estimate the home's value is $553,573.

Single-familyProperty Type

1971Year Built

0.98 acresLot Size

$356Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$553,573

$397K since sold in November 1992$1,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.3% higher than the average sale price ($526K) of 6 comparable homes.

SOLD SEP 16, 2026
$405,000
A
4 beds2 baths1,698 sq ft
44 Winding Rd, Madison, CT 06443
SOLD OCT 8, 2026
$475,000
B
3 beds2.5 baths1,824 sq ft
18 Saint Francis Woods Rd, Madison, CT 06443
SOLD JUN 29, 2026
$675,000
C
4 beds2.5 baths2,460 sq ft
200 Whitethorn Dr, Guilford, CT 06437
SOLD APR 29, 2026
$614,000
D
4 beds2.5 baths1,818 sq ft
40 Deerfield Dr, Guilford, CT 06437
SOLD SEP 2, 2026
$460,000
E
4 beds2.5 baths2,024 sq ft
53 Summer Hill Rd, Madison, CT 06443
SOLD MAY 28, 2026
$525,000
F
4 beds1.5 baths1,346 sq ft
15 Stepping Stone Ln, Madison, CT 06443

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Earn from this home

Sell

$519,713

Est. take-home

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Refinance

Est. cash available

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Rent

$3,193/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

102.7%

+0.4% MoM

Median sale price

$799K

$6K MoM

Avg. days on market

38d

5 days MoM

Recently sold homes

2 MoM

New listings for sale

$1,779,000
3 beds2.5 baths2,566 sq ft
16 North Ave, Madison, CT 06443
$499,900
3 beds2 baths1,994 sq ft
8 Stephanie Ct, Madison, CT 06443
OPEN SUN, 12PM TO 1:30PM
$499,900
3 beds3 baths1,944 sq ft
25 Samantha Ln, Madison, CT 06443
COMING SOON
$1,299,000
5 beds3.5 baths4,723 sq ft
37 Silo Hl, Madison, CT 06443
$549,900
4 beds2 baths1,728 sq ft
252 Boston Post Rd, Madison, CT 06443
$275,000
2 beds1 bath751 sq ft
59 EAST St, Madison, CT 06434
$550,000
2 beds2 baths1,316 sq ft
91 Neck Rd, Madison, CT 06443
$550,000
2 beds2 baths1,280 sq ft
23 Wilshire Rd Unit A, Madison, CT 06443
$665,000
3 beds2.5 baths2,237 sq ft
3 Poole Rd, Madison, CT 06443
See all

Provided by Redfin

Sale history for 95 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,147 (+1.9%)

$93,100 + $112,000

$205,100

2022

$6,032 (+1.9%)

$93,100 + $112,000

$205,100

2021

$5,917 (+1.8%)

$93,100 + $112,000

$205,100

2020

$5,815

$93,100 + $112,000

$205,100

2019

$5,815 (−2.6%)

$93,100 + $112,000

$205,100

2018

$5,970 (+2.7%)

$96,200 + $116,700

$212,900

2017

$5,812 (+3.0%)

$96,200 + $116,700

$212,900

2016

$5,640 (+5.2%)

$96,200 + $116,700

$212,900

2014

$5,359 (+8.4%)

$96,200 + $116,700

$212,900

2010

$4,943

$133,900 + $108,500

$242,400

Tax history for 95 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,147 (+1.9%)

$93,100 + $112,000

$205,100

2022

$6,032 (+1.9%)

$93,100 + $112,000

$205,100

2021

$5,917 (+1.8%)

$93,100 + $112,000

$205,100

2020

$5,815

$93,100 + $112,000

$205,100

2019

$5,815 (−2.6%)

$93,100 + $112,000

$205,100

2018

$5,970 (+2.7%)

$96,200 + $116,700

$212,900

2017

$5,812 (+3.0%)

$96,200 + $116,700

$212,900

2016

$5,640 (+5.2%)

$96,200 + $116,700

$212,900

2014

$5,359 (+8.4%)

$96,200 + $116,700

$212,900

2010

$4,943

$133,900 + $108,500

$242,400

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

Property details

Interior

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 7

Exterior

Exterior Information
Building Style Type: Ranch
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 1,554
Gross Sq. Ft: 3,470
# of Stories: 1

Lot Information
# of Buildings: 1
Land Sq. Ft: 42,689
Municipality Name: MADISON
Acres: 0.98
Zoning Code: RU-1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 1,554
Stories: 1.0
Lot Size: 0.98 acres
Style: Single Family Residential
Year Built: 1971
Year Renovated: —
County: New Haven County
APN: 1159653

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

K - 12
Preschool & daycare

Kathleen H. Ryerson Elementary School

Public K-3 • Assigned • 1.3mi

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 3.5mi

10/10

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

4/10 Air Factor

5 unhealthy days expected this year, 7 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

$526,000 – $637,000

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New listings for sale in 06443

$1,779,000

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Deeded beach rights • 0.23 acre lot • 2 garage spots

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OPEN SUN, 12PM TO 1:30PM

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252 Boston Post Rd, Madison, CT 06443

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New furnace • Security system • 6,969 sq ft lot

$550,000

2 beds2 baths1,280 sq ft

23 Wilshire Rd Unit A, Madison, CT 06443

Private backyard • Inviting living room • Fireplace

$665,000

3 beds2.5 baths2,237 sq ft

3 Poole Rd, Madison, CT 06443

Private sanctuary • Wooded grounds • Flexible floor plan

Home values near 95 Winding Rd

Data from public records.

Address	Redfin Estimate
62 Winding Rd, Madison, CT 4 Beds \| 3 Baths \| 2042 Sq. Ft.	$661,184
127 Winding Rd, Madison, CT 4 Beds \| 1.5 Baths \| 1340 Sq. Ft.	$646,190
101 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 1848 Sq. Ft.	$592,432
121 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 1800 Sq. Ft.	$794,191
105 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3176 Sq. Ft.	$744,694
36 Silo Hl, Madison, CT 4 Beds \| 3.5 Baths \| 3656 Sq. Ft.	$1,091,181
19 Wheatstone Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3616 Sq. Ft.	$1,086,260

Address	Redfin Estimate
86 Winding Rd, Madison, CT 4 Beds \| 3.5 Baths \| 2358 Sq. Ft.	$701,300
96 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2104 Sq. Ft.	$645,179
89 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 2382 Sq. Ft.	$606,213
115 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 1552 Sq. Ft.	$549,823
65 Winding Rd, Madison, CT 4 Beds \| 1.5 Baths \| 1288 Sq. Ft.	$490,875
9 Wheatstone Rd, Madison, CT 4 Beds \| 3 Baths \| 4425 Sq. Ft.	$1,095,972
28 Wheatstone Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3319 Sq. Ft.	$963,174

Address	Redfin Estimate
130 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 1994 Sq. Ft.	$607,319
122 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 1558 Sq. Ft.	$540,680
85 Winding Rd, Madison, CT 3 Beds \| 2.5 Baths \| 2462 Sq. Ft.	$789,769
109 Winding Rd, Madison, CT 5 Beds \| 2.5 Baths \| 1522 Sq. Ft.	$429,101
40 Silo Hl, Madison, CT 4 Beds \| 2.5 Baths \| 3685 Sq. Ft.	$1,035,058
40 Wheatstone Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3255 Sq. Ft.	$1,096,134
15 Wheatstone Rd, Madison, CT 4 Beds \| 3.5 Baths \| 3949 Sq. Ft.	$1,154,411

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About this home

Redfin Estimate

Earn from this home

Market trends in 06443, CT

Sale history for 95 Winding Rd

Tax history for 95 Winding Rd

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06443

Home values near 95 Winding Rd

More real estate resources