Google street view image for 33 Shepherds Trl, Madison, CT 06443

Local rules require you to be signed in to see more photos.

Sold

$757,567

Est. refi paymentEst. refi $2,868/mo

•

2.5 ba

•

1,927

sq ft

33 Shepherds Trl, Madison, CT 06443

About this home

1990 Built and feels like brand new! Many updates & upgrades to this comfortable and inviting home loc in premier madison n'hood. Remod kitchen, remod and updated baths,re-fin wood flrs, fresh paint & carp, brand new roof. Open sunday 10/17 1 - 3 p.M.

Single-familyProperty Type

1990Year Built

1.42 acresLot Size

$393Est. Price/Sq.Ft.

2 car garageParking

Source:Public Records

Redfin Estimate

$757,567

$293K since sold in December 2010$1,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.8% higher than the average sale price ($654K) of 6 comparable homes.

SOLD AUG 10, 2026
$700,000
A
4 beds2.5 baths2,057 sq ft
476 Summer Hill Rd, Madison, CT 06443
SOLD JUL 15, 2026
$795,000
B
3 beds2.5 baths1,908 sq ft
45 Milano Pond Dr, Madison, CT 06443
SOLD JUN 30, 2026
$634,500
C
3 beds2.5 baths1,848 sq ft
15 Cornfield Ln, Madison, CT 06443
SOLD MAY 12, 2026
$660,000
D
3 beds2.5 baths2,073 sq ft
370 Opening Hill Rd, Madison, CT 06443
SOLD OCT 15, 2026
$660,000
E
4 beds2.5 baths2,536 sq ft
320 Summer Hill Rd, Madison, CT 06443
SOLD OCT 8, 2026
$475,000
F
3 beds2.5 baths1,824 sq ft
18 Saint Francis Woods Rd, Madison, CT 06443

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$711,998

Est. take-home

List your home with Redfin and save $7,576

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,587/mo

Redfin rental estimate

List your home for rent

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
$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 33 Shepherds Trl

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2023

$7,675 (+1.9%)

$113,500 + $142,600

$256,100

2022

$7,532 (+1.9%)

$113,500 + $142,600

$256,100

2021

$7,388 (+1.8%)

$113,500 + $142,600

$256,100

2020

$7,260

$113,500 + $142,600

$256,100

2019

$7,260 (−5.8%)

$113,500 + $142,600

$256,100

2018

$7,703 (+2.7%)

$123,700 + $151,000

$274,700

2017

$7,499 (+3.1%)

$123,700 + $151,000

$274,700

2016

$7,277 (+5.3%)

$123,700 + $151,000

$274,700

2014

$6,914 (+1.8%)

$123,700 + $151,000

$274,700

2010

$6,790

$140,700 + $192,300

$333,000

Tax history for 33 Shepherds Trl

Year

Property tax

Land + Additions

Assessment*

2023

$7,675 (+1.9%)

$113,500 + $142,600

$256,100

2022

$7,532 (+1.9%)

$113,500 + $142,600

$256,100

2021

$7,388 (+1.8%)

$113,500 + $142,600

$256,100

2020

$7,260

$113,500 + $142,600

$256,100

2019

$7,260 (−5.8%)

$113,500 + $142,600

$256,100

2018

$7,703 (+2.7%)

$123,700 + $151,000

$274,700

2017

$7,499 (+3.1%)

$123,700 + $151,000

$274,700

2016

$7,277 (+5.3%)

$123,700 + $151,000

$274,700

2014

$6,914 (+1.8%)

$123,700 + $151,000

$274,700

2010

$6,790

$140,700 + $192,300

$333,000

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.42 Acres

Year renovated

—

Sq. Ft.

1,927

Year built

1990

Style

Single Family Residential

County

New Haven County

APN

1160546

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Around this home

Schools

K - 12
Preschool & daycare

Kathleen H. Ryerson Elementary School

Public K-3 • Assigned • 1.1mi

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 4.2mi

10/10

Daniel Hand High School

Public 9-12 • Assigned • 4.4mi

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

5/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 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

$720,000 – $872,000

Reach more buyers when you sell with Redfin. Save up to $7,576 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$1,295,000

4 beds4 baths5,979 sq ft

460 White Birch Dr, Guilford, CT 06437

Chef's kitchen • Separate music room • Finished lower level

$515,000

4 beds1.5 baths1,890 sq ft

201 Emanuel Church Rd, Killingworth, CT 06419

Front bay window • New deck • Updated windows

$795,000

4 beds2.5 baths2,572 sq ft

3 Little Hollow Rd, Madison, CT 06443

Wide plank flooring • New light fixtures • New roof

$559,900

3 beds1 bath1,077 sq ft

6 Bower Rd, Madison, CT 06443

New cedar siding • Roof replaced • 1.03 acre lot

$834,900

4 beds2.5 baths3,016 sq ft

26 Overlook Farms Rd, Killingworth, CT 06419

Private acres • Walk-out basement • Mature trees

$999,000

5 beds5.5 baths3,832 sq ft

1209 Durham Rd, Madison, CT 06443

4 acre compound • Guest house • In home gym

New listings for sale in 06443

$1,779,000

3 beds2.5 baths2,566 sq ft

16 North Ave, Madison, CT 06443

Deeded beach rights • 0.23 acre lot • 2 garage spots

$499,900

3 beds2 baths1,994 sq ft

8 Stephanie Ct, Madison, CT 06443

Quiet cul-de-sac • Updated kitchen • Walkout access

$499,900

3 beds3 baths1,944 sq ft

25 Samantha Ln, Madison, CT 06443

Cul-de-sac setting • Open floor plan • Center island

COMING SOON

$1,299,000

5 beds3.5 baths4,723 sq ft

37 Silo Hl, Madison, CT 06443

Eat-in kitchen • Granite counters • Large deck

$549,900

4 beds2 baths1,728 sq ft

252 Boston Post Rd, Madison, CT 06443

Generous grounds • Lush greenery • Updated kitchen

$275,000

2 beds1 bath751 sq ft

59 EAST St, Madison, CT 06434

Finished porch • Remodeled kitchen • Quarts countertops

$550,000

2 beds2 baths1,316 sq ft

91 Neck Rd, Madison, CT 06443

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 33 Shepherds Trl

Data from public records.

Address	Redfin Estimate
29 Shepherds Trail, Madison, CT 3 Beds \| 2.5 Baths \| 2690 Sq. Ft.	$794,890
25 Shepherds Trail, Madison, CT 7 Beds \| 3.5 Baths \| 4803 Sq. Ft.	$837,275
38 Shepherds Trail, Madison, CT 4 Beds \| 2.5 Baths \| 2920 Sq. Ft.	$852,348
46 Shepherds Trail, Madison, CT 3 Beds \| 2.5 Baths \| 2350 Sq. Ft.	$720,457
487 Summer Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 3319 Sq. Ft.	$1,028,164
9 Doe Lane, Madison, CT 4 Beds \| 2.5 Baths \| 3245 Sq. Ft.	$1,062,504
24 Buck Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 3504 Sq. Ft.	—

Address	Redfin Estimate
15 Shepherds Trail, Madison, CT 5 Beds \| 3 Baths \| 3954 Sq. Ft.	$930,484
16 Shepherds Trail, Madison, CT 5 Beds \| 3.5 Baths \| 3849 Sq. Ft.	$1,145,927
24 Shepherds Trail, Madison, CT 4 Beds \| 2.5 Baths \| 2974 Sq. Ft.	$909,501
48 Shepherds Trail, Madison, CT 4 Beds \| 2.5 Baths \| 4879 Sq. Ft.	$960,691
473 Summer Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 2616 Sq. Ft.	$879,444
3 Doe Lane, Madison, CT 3 Beds \| 2.5 Baths \| 3696 Sq. Ft.	$817,428
4 Doe Lane, Madison, CT 4 Beds \| 2.5 Baths \| 3671 Sq. Ft.	$904,101

Address	Redfin Estimate
5 Shepherds Trail, Madison, CT 4 Beds \| 2.5 Baths \| 2432 Sq. Ft.	$800,341
58 Shepherds Trail, Madison, CT 4 Beds \| 3 Baths \| 3453 Sq. Ft.	$1,075,460
52 Shepherds Trail, Madison, CT 3 Beds \| 2 Baths \| 2085 Sq. Ft.	$706,741
27 Shepherds Trail, Madison, CT 4 Beds \| 2.5 Baths \| 2963 Sq. Ft.	$1,033,407
10 Doe Lane, Madison, CT 3 Beds \| 3 Baths \| 3718 Sq. Ft.	$899,102
14 Buck Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 3664 Sq. Ft.	$838,679
506 Summer Hill Road, Madison, CT 5 Beds \| 3 Baths \| 2952 Sq. Ft.	$744,280

More real estate resources

Zip Codes
Cities
Minor Civil Divisions
Popular Searches

07935 homes for sale
07940 homes for sale
07960 homes for sale
07928 homes for sale
07932 homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Bloomfield Township homes for sale
Livingston Township homes for sale
West Orange Township homes for sale
Millburn Township homes for sale
Wayne Township homes for sale

Houses for rent in Madison	Agents near me	Summit, NJ homes for sale	Madison Housing Market
Houses for sale near me	Jersey City, NJ homes for sale	Ridgewood, NJ homes for sale
Land for sale near me	Montclair, NJ homes for sale	Fort Lee, NJ homes for sale
Open Houses near me	Hoboken, NJ homes for sale	Madison Property Records
Condos for sale near me	Princeton, NJ homes for sale	CT New Listings

Montclair homes for sale
Summit homes for sale
New York homes for sale