Google street view image for 86 Winding Rd, Madison, CT 06443

Off market nov 1991 for $197K

$700,695

Est. refi paymentEst. refi $1,481/mo

•

3.5 ba

•

2,358

sq ft

86 Winding Rd, Madison, CT 06443

About this home

86 Winding Rd is a 2,358 square foot house on a 0.95 acre lot with 4 bedrooms and 3.5 bathrooms. - it last sold on November 27, 1991 for $197,000. Based on Redfin's Madison data, we estimate the home's value is $700,695.

Single-familyProperty Type

1971Year Built

0.95 acresLot Size

$297Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$700,695

$504K since sold in November 1991$15K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.3% higher than the average sale price ($659K) of 6 comparable homes.

SOLD JUN 16, 2026
$685,000
A
5 beds3 baths2,210 sq ft
10 Scenic Rd, Madison, CT 06443
SOLD JUN 29, 2026
$675,000
B
4 beds2.5 baths2,460 sq ft
200 Whitethorn Dr, Guilford, CT 06437
SOLD SEP 2, 2026
$460,000
C
4 beds2.5 baths2,024 sq ft
53 Summer Hill Rd, Madison, CT 06443
SOLD AUG 20, 2026
$769,000
D
4 beds2.5 baths2,647 sq ft
89 Summer Hill Rd, Madison, CT 06443
SOLD JUL 2, 2026
$735,000
E
4 beds2.5 baths2,657 sq ft
40 Harkness Dr, Madison, CT 06443
SOLD DEC 12, 2025
$630,000
F
4 beds2.5 baths2,088 sq ft
81 Bartlett Dr, Madison, CT 06443

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Earn from this home

Sell

$658,390

Est. take-home

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Est. cash available

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Rent

$4,200/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated September 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

$799,000
3 beds1 bath1,084 sq ft
7 Highlands Ter, Madison, CT 06443
$569,900
4 beds2.5 baths1,804 sq ft
41 Bradley Corners Rd, Madison, CT 06443
$850,000
7 beds3.5 baths3,428 sq ft
69 Bradley Corners Rd, Madison, CT 06443
$1,125,000
4 beds2.5 baths3,504 sq ft
24 Buck Hill Rd, Madison, CT 06443
OPEN TODAY, 12PM TO 2PM
$1,225,000
4 beds2.5 baths3,254 sq ft
22 Kingsbridge Way #22, Madison, CT 06443
COMING SOON
$599,000
3 beds2 baths1,794 sq ft
16 Tamarac Dr, Madison, CT 06443
OPEN TODAY, 1PM TO 3PM
$1,200,000
3 beds2.5 baths2,531 sq ft
56 River Edge Farms Rd, Madison, CT 06443
OPEN TODAY, 1:30PM TO 3PM
$599,900
4 beds1.5 baths1,884 sq ft
14 Bower Rd, Madison, CT 06443
$2,495,000
3 beds2.5 baths2,494 sq ft
31 Neptune Ave, Madison, CT 06443
See all

Provided by Redfin

Sale history for 86 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,905 (+1.9%)

$92,100 + $138,300

$230,400

2022

$6,776 (+1.9%)

$92,100 + $138,300

$230,400

2021

$6,647 (+1.8%)

$92,100 + $138,300

$230,400

2020

$6,532 (+1.0%)

$92,100 + $138,300

$230,400

2019

$6,469 (−0.9%)

$92,100 + $136,100

$228,200

2018

$6,525 (+2.7%)

$95,800 + $136,900

$232,700

2017

$6,353 (+3.1%)

$95,800 + $136,900

$232,700

2016

$6,164 (+5.2%)

$95,800 + $136,900

$232,700

2014

$5,857 (−1.9%)

$95,800 + $136,900

$232,700

2010

$5,968

$133,600 + $159,100

$292,700

Tax history for 86 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,905 (+1.9%)

$92,100 + $138,300

$230,400

2022

$6,776 (+1.9%)

$92,100 + $138,300

$230,400

2021

$6,647 (+1.8%)

$92,100 + $138,300

$230,400

2020

$6,532 (+1.0%)

$92,100 + $138,300

$230,400

2019

$6,469 (−0.9%)

$92,100 + $136,100

$228,200

2018

$6,525 (+2.7%)

$95,800 + $136,900

$232,700

2017

$6,353 (+3.1%)

$95,800 + $136,900

$232,700

2016

$6,164 (+5.2%)

$95,800 + $136,900

$232,700

2014

$5,857 (−1.9%)

$95,800 + $136,900

$232,700

2010

$5,968

$133,600 + $159,100

$292,700

*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: 3
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 8

Exterior

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

Property Information
Living Sq. Ft: 2,358
Gross Sq. Ft: 4,440
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 41,382
Municipality Name: MADISON
Acres: 0.95
Zoning Code: RU-1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,358
Stories: 2.0
Lot Size: 0.95 acres
Style: Single Family Residential
Year Built: 1971
Year Renovated: —
County: New Haven County
APN: 1159663

Home facts updated by county records on Jul 13, 2023

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 • 3.4mi

9/10

Daniel Hand High School

Public 9-12 • Assigned • 3.5mi

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

$666,000 – $806,000

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Nearby similar homes

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New listings for sale in 06443

$799,000

3 beds1 bath1,084 sq ft

7 Highlands Ter, Madison, CT 06443

$569,900

4 beds2.5 baths1,804 sq ft

41 Bradley Corners Rd, Madison, CT 06443

$850,000

7 beds3.5 baths3,428 sq ft

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$1,125,000

4 beds2.5 baths3,504 sq ft

24 Buck Hill Rd, Madison, CT 06443

OPEN TODAY, 12PM TO 2PM

$1,225,000

4 beds2.5 baths3,254 sq ft

22 Kingsbridge Way #22, Madison, CT 06443

COMING SOON

$599,000

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OPEN TODAY, 1PM TO 3PM

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56 River Edge Farms Rd, Madison, CT 06443

OPEN TODAY, 1:30PM TO 3PM

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4 beds1.5 baths1,884 sq ft

14 Bower Rd, Madison, CT 06443

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Home values near 86 Winding Rd

Data from public records.

Address	Redfin Estimate
62 Winding Rd, Madison, CT 4 Beds \| 3 Baths \| 2042 Sq. Ft.	$662,498
127 Winding Rd, Madison, CT 4 Beds \| 1.5 Baths \| 1340 Sq. Ft.	$659,320

Address	Redfin Estimate
54 Winding Rd, Madison, CT 3 Beds \| 1.5 Baths \| 1250 Sq. Ft.	$499,019
96 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2104 Sq. Ft.	$644,108

Address	Redfin Estimate
130 Winding Rd, Madison, CT 4 Beds \| 2.5 Baths \| 1994 Sq. Ft.	$609,864
122 Winding Rd, Madison, CT 4 Beds \| 2 Baths \| 1558 Sq. Ft.	$540,688

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About this home

Redfin Estimate

Earn from this home

Market trends in 06443, CT

Sale history for 86 Winding Rd

Tax history for 86 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 86 Winding Rd

More real estate resources