Off market feb 2021 for $306K

$533,014

Est. refi paymentEst. refi $2,398/mo

•

1,178

sq ft

38 Winding Rd, Madison, CT 06443

About this home

Looking for a property to work from home? Whether you are a contractor, landscaper, boat and/or car enthusiasts, this 3 bedroom, 2 full bath Ranch with a huge barn with office is for you! Situated on an oversized corner lot in a cul-de-sac neighborhood in Madison, CT for only $300,000! At a time when many are working from home, here's your opportunity to have the separation you desire from home and work life. The home offers a large Kitchen with skylight, hardwood floors throughout the main living area and bedrooms. Family room has a fireplace that opens to the Dining room with sliders to a back deck. The 1,272 square foot detached Barn has a garage that's deep with high ceilings suitable for boat, workshop, equipment storage or even a horse stable as horses are allowed on this property. There is also an attached office to the Barn with a separate entrance. Just imagine how this set-up can work for you and make it happen before it's too late!

Single-familyProperty Type

1968Year Built

1.97 acresLot Size

$452Est. Price/Sq.Ft.

3 car garageParking

Listed by Linda Toscano • Compass Connecticut, LLC

Bought with Fay Abrahamsson • CT Realty Exchange, LLC

Source:Smart MLS #170347617

Redfin Estimate

$533,014

$227K since sold in February 2021$5,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.7% higher than the average sale price ($514K) 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 MAY 13, 2026
$620,000
C
4 beds2 baths1,849 sq ft
12 Rustic Ln, Madison, CT 06443
SOLD SEP 25, 2026
$572,320
D
3 beds2 baths1,362 sq ft
51 Foxwood Rd S, Guilford, CT 06437
SOLD SEP 28, 2026
$599,000
E
3 beds2 baths1,760 sq ft
831 Nut Plains Rd, Guilford, CT 06437
SOLD JAN 13, 2026
$411,500
F
4 beds2 baths1,848 sq ft
313 Bradley Corners Rd, Madison, CT 06443

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Earn from this home

Sell

$283,334

Est. take-home

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Refinance

Est. cash available

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Rent

$2,815/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
NEW 33 HRS AGO
$569,900
4 beds2.5 baths1,804 sq ft
41 Bradley Corners Rd, Madison, CT 06443
NEW 35 HRS AGO
$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 SUN, 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 SUN, 1PM TO 3PM
$1,200,000
3 beds2.5 baths2,531 sq ft
56 River Edge Farms Rd, Madison, CT 06443
OPEN SUN, 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 38 Winding Rd

Date

Event

Price

Smart MLS #170347617

Feb 1, 2021

Sold

$306,000

$260/sq ft

Nov 10, 2020

Contingent

—

Oct 17, 2020

Listed

$300,000

$255/sq ft

Smart MLS #170285702

Oct 1, 2020

Listing Removed

—

Apr 1, 2020

Listed

$315,000

$267/sq ft

Smart MLS #170237512

Mar 31, 2020

Listing Removed

—

Feb 28, 2020

Price Changed

$315,000

$267/sq ft

Dec 31, 2019

Listing Removed

—

Nov 7, 2019

Price Changed

$325,000

$276/sq ft

Sep 23, 2019

Listed

$359,900

$306/sq ft

Smart MLS #170134580

Jul 13, 2019

Listing Removed

—

Mar 26, 2019

Price Changed

$359,900

$306/sq ft

Oct 25, 2018

Listed

$389,900

$331/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$5,907 (+1.9%)

$96,700 + $100,400

$197,100

2022

$5,797 (+2.0%)

$96,700 + $100,400

$197,100

2021

$5,686 (+1.8%)

$96,700 + $100,400

$197,100

2020

$5,588

$96,700 + $100,400

$197,100

2019

$5,588 (+0.3%)

$96,700 + $100,400

$197,100

2018

$5,574 (+2.7%)

$99,500 + $99,300

$198,800

2017

$5,427 (+3.1%)

$99,500 + $99,300

$198,800

2016

$5,266 (+5.2%)

$99,500 + $99,300

$198,800

2014

$5,004 (−8.7%)

$99,500 + $99,300

$198,800

2010

$5,483

$149,100 + $119,800

$268,900

Tax history for 38 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,907 (+1.9%)

$96,700 + $100,400

$197,100

2022

$5,797 (+2.0%)

$96,700 + $100,400

$197,100

2021

$5,686 (+1.8%)

$96,700 + $100,400

$197,100

2020

$5,588

$96,700 + $100,400

$197,100

2019

$5,588 (+0.3%)

$96,700 + $100,400

$197,100

2018

$5,574 (+2.7%)

$99,500 + $99,300

$198,800

2017

$5,427 (+3.1%)

$99,500 + $99,300

$198,800

2016

$5,266 (+5.2%)

$99,500 + $99,300

$198,800

2014

$5,004 (−8.7%)

$99,500 + $99,300

$198,800

2010

$5,483

$149,100 + $119,800

$268,900

*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

Stories

Lot width

—

Lot depth

—

Lot size

1.97 Acres

Year renovated

—

Sq. Ft.

1,178

Year built

1968

Style

Single Family Residential

County

New Haven County

APN

1159706

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage, Barn
Garages Number: 3

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 7
Laundry Room Info: Lower Level
In-Law Apartment: No
Appliances Included: Gas Range, Refrigerator, Dishwasher

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 3

Room Information
Rooms Additional: Workshop
Basement Description: Full, Unfinished, Garage Access

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Barn, Deck, Shed

Lot Information
Lot Description: On Cul-De-Sac, Corner Lot, Level Lot, Lightly Wooded

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: white

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1178
Driveway Type: Circular, Asphalt

Financial

Assessments Information
Assessed Value: $197,100

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Energy Features: Storm Windows

Location

School Information
Middle Jr High School: Brown
Intermediate School: Per Board of Ed
High School: Daniel Hand
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Golf Course, Health Club, Library, Playground/Tot Lot, Public Pool, Shopping/Mall, Tennis Courts
Directions: Opening Hill Road to Woodsvale. Right on Winding Road. Home is at the corner of Winding and Cornish Woods Road.
County: New Haven

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,178
Stories: 1.0
Lot Size: 1.97 acres
Style: Single Family Residential
Year Built: 1968
Year Renovated: —
County: New Haven County
APN: 1159706

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

Kathleen H. Ryerson Elementary School

Public K-3 • Assigned • 1.0mi

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, 18 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

$507,000 – $613,000

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Nearby similar homes

NEW 33 HRS AGO

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NEW CONSTRUCTION

$2,215,000

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3D & VIDEO TOUR

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$1,825,000

5 beds7 baths5,414 sq ft

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New listings for sale in 06443

$799,000

3 beds1 bath1,084 sq ft

7 Highlands Ter, Madison, CT 06443

NEW 33 HRS AGO

$569,900

4 beds2.5 baths1,804 sq ft

41 Bradley Corners Rd, Madison, CT 06443

NEW 35 HRS AGO

$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 SUN, 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 SUN, 1PM TO 3PM

$1,200,000

3 beds2.5 baths2,531 sq ft

56 River Edge Farms Rd, Madison, CT 06443

OPEN SUN, 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

Home values near 38 Winding Rd

Data from public records.

Address	Redfin Estimate
62 Winding Road, Madison, CT 4 Beds \| 3 Baths \| 2042 Sq. Ft.	$662,498
44 Winding Road, Madison, CT 4 Beds \| 2 Baths \| 1698 Sq. Ft.	$474,439

Address	Redfin Estimate
48 Winding Road, Madison, CT 4 Beds \| 2 Baths \| 1338 Sq. Ft.	$624,443
53 Winding Road, Madison, CT 4 Beds \| 1.5 Baths \| 1288 Sq. Ft.	$599,715

Address	Redfin Estimate
54 Winding Road, Madison, CT 3 Beds \| 1.5 Baths \| 1250 Sq. Ft.	$499,019
45 Winding Road, Madison, CT 4 Beds \| 2 Baths \| 2080 Sq. Ft.	$630,308

Property information provided by Smart MLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06443, CT

Sale history for 38 Winding Rd

Tax history for 38 Winding Rd

Public record

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 38 Winding Rd

More real estate resources