Off market dec 2022 for $875K

$1,075,460

Est. refi paymentEst. refi $2,408/mo

•

3,453

sq ft

58 Shepherds Trl, Madison, CT 06443

About this home

Modern luxury awaits at this stunning Madison colonial! Set privately on a 1.54 acre lot, this home provides a spectacular living space, both inside and out. An expansive foyer awaits you upon entering, filled with natural light and beautifully refinished hardwood floors. The dream-come-true chef's kitchen boasts sleek quartzite counter-tops, expansive center island with electric cooktop, double wall ovens, dishwasher, a Sub Zero refrigerator and pantry. The kitchen opens into a spacious family room with a great wood fireplace & doors leading to the private sunroom and outdoor deck. The formal dining room and living room with fireplace provide ample space for this year's holiday gatherings. A private office with glass French doors can be found just off of the living room. Follow the grand staircase to the second level where you'll find the main bedroom suite which offers a walk in closet with custom storage and organizers, and large en-suite bathroom with double sinks, tiled shower, and soaking tub. Three large bedrooms and a full bathroom complete the second level along with bonus space off the kitchen and above the garage, which offers option for 5th bedroom, a guest suite, studio, home office, hang-out space etc. The back yard oasis is perfect for entertaining and features an inground swimming pool, surrounded by stone patio, with charming New England stone walls, mature foliage, and an open, level yard. Come see what Madison has to offer and schedule your showing today!

Single-familyProperty Type

1996Year Built

1.54 acresLot Size

$311Est. Price/Sq.Ft.

3 car garageParking

Listed by Taylor Shapiro • Better Homes and Gardens Real Estate Executive Real Estate

Bought with Hilary Reid • Coldwell Banker Realty

Source:Smart MLS #170533606

Redfin Estimate

$1,075,460

$200K since sold in December 2022$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.1% higher than the average sale price ($1.06M) of 5 comparable homes.

SOLD SEP 1, 2026
$1,250,000
A
4 beds3 baths3,816 sq ft
128 Concord Dr, Madison, CT 06443
SOLD JUL 17, 2026
$960,000
B
4 beds2.5 baths3,316 sq ft
198 Summer Hill Rd, Madison, CT 06443
SOLD JUL 27, 2026
$1,012,500
C
4 beds2.5 baths4,019 sq ft
86 Quail Run, Madison, CT 06443
SOLD JUL 23, 2026
$1,200,000
D
4 beds3.5 baths4,250 sq ft
86 Nursery Ln, Madison, CT 06443
SOLD AUG 18, 2026
$895,000
E
4 beds3.5 baths3,165 sq ft
10 Grace Ln, Killingworth, CT 06419

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

Earn from this home

Sell

$362,644

Est. take-home

List your home with Redfin and save $10,755

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,740/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

101.5%

1.1% MoM

Median sale price

$713K

$86K MoM

Avg. days on market

38d

0 days MoM

Recently sold homes

4 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 baths1,280 sq ft
23 Wilshire Rd Unit A, Madison, CT 06443
See all

Provided by Redfin

Sale history for 58 Shepherds Trl

Date

Event

Price

SMARTMLS #170584304

Jul 26, 2023

Rental Removed

$3,800

$1/sq ft

Jul 21, 2023

Listed for Rent

$3,800

$1/sq ft

Smart MLS #170533606

Dec 29, 2022

Sold

$875,000

$253/sq ft

Nov 16, 2022

Pending

—

Nov 13, 2022

Contingent

—

Nov 11, 2022

Listed

$849,900

$246/sq ft

Smart MLS #170244216

Aug 21, 2020

Sold

$635,000

$184/sq ft

Jul 11, 2020

Relisted

—

Jul 10, 2020

Listing Removed

—

Jul 5, 2020

Contingent

—

Jun 27, 2020

Relisted

—

Jun 27, 2020

Listing Removed

—

Jun 10, 2020

Contingent

—

Apr 13, 2020

Relisted

—

Apr 11, 2020

Relisted

—

Apr 10, 2020

Listing Removed

—

Apr 10, 2020

Listing Removed

—

Jan 11, 2020

Relisted

—

Jan 10, 2020

Listing Removed

—

Oct 14, 2019

Listed

$674,900

$195/sq ft

This impressive 4-bedroom custom built meticulously maintained Center Hall Colonial is an elegant home with upscale beauty and comfort. High ceilings plus multiple vaulted ceilings, custom trim work, 2 fireplaces and an abundance of Palladian windows and French doors that lead to the outside, 4 season sunroom and library/music room make this home special. The large, bright kitchen with oversized granite island and loads of cabinets is a natural gathering spot perfect for entertaining. The light-filled family room and formal living room accentuated by beautifully appointed fireplaces contribute to cozy New England winters. Both the home and backyard oasis with in-ground pool are a sanctuary where you will never tire observing the endless flutter of hummingbirds, wildlife and sights and sounds of nature. A pool house with changing room and half bath provides convenience to guests relaxing and cooling off in the crystal-clear water of the in-ground pool. The inviting master bedroom suite features a spacious walk in closet and a roomy spa-like bath with Jacuzzi tub and large walk in shower with tiled seat. The additional 3 bedrooms are generous in size and like all rooms in this home have plenty of natural light. A huge unfinished bonus room with vaulted ceilings can be accessed from both a finished staircase in the kitchen and direct access from the master providing additional potential living space and storage. Be sure to check out the virtual tour of this beautiful Home.

Public Records

Dec 1, 1988

Sold

$120,000

$35/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$12,740 (+1.9%)

$113,700 + $311,400

$425,100

2022

$12,502 (+1.9%)

$113,700 + $311,400

$425,100

2021

$12,264 (+1.8%)

$113,700 + $311,400

$425,100

2020

$12,052

$113,700 + $311,400

$425,100

2019

$12,052 (−2.6%)

$113,700 + $311,400

$425,100

2018

$12,371 (+2.7%)

$126,100 + $315,100

$441,200

2017

$12,045 (+3.1%)

$126,100 + $315,100

$441,200

2016

$11,687 (+5.2%)

$126,100 + $315,100

$441,200

2014

$11,105 (−7.2%)

$126,100 + $315,100

$441,200

2010

$11,967

$142,700 + $444,200

$586,900

Tax history for 58 Shepherds Trl

Year

Property tax

Land + Additions

Assessment*

2023

$12,740 (+1.9%)

$113,700 + $311,400

$425,100

2022

$12,502 (+1.9%)

$113,700 + $311,400

$425,100

2021

$12,264 (+1.8%)

$113,700 + $311,400

$425,100

2020

$12,052

$113,700 + $311,400

$425,100

2019

$12,052 (−2.6%)

$113,700 + $311,400

$425,100

2018

$12,371 (+2.7%)

$126,100 + $315,100

$441,200

2017

$12,045 (+3.1%)

$126,100 + $315,100

$441,200

2016

$11,687 (+5.2%)

$126,100 + $315,100

$441,200

2014

$11,105 (−7.2%)

$126,100 + $315,100

$441,200

2010

$11,967

$142,700 + $444,200

$586,900

*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

1.54 Acres

Year renovated

—

Sq. Ft.

3,453

Year built

1996

Style

Single Family Residential

County

New Haven County

APN

1160535

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
Garages Number: 3

Interior

Interior Information
Total Rooms: 10
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Central Vacuum, Open Floor Plan
Appliances, Electric Outlet(s), Lighting, Thermostat(s)
Fireplaces Total: 2
Cooling System: Central Air
Appliances Included: Electric Cooktop, Oven/Range, Microwave, Refrigerator, Dishwasher

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 2

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Bonus Room
Room Count: 1
Basement Description: Full, Unfinished
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Deck, Gutters, Lighting, Porch-Enclosed

Lot Information
Lot Description: Level Lot

Pool Information
Swimming Pool
Pool Description: Pool House, In Ground Pool

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

Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 3453
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $425,100

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: 50 Gallon Tank
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Thermopane Windows

Location

School Information
High School: Daniel Hand
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Health Club, Medical Facilities, Park, Shopping/Mall
Directions: N Branford Rd to Buck Hill Rd to Shepherds Trl
County: New Haven

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,453
Stories: 2.0
Lot Size: 1.54 acres
Style: Single Family Residential
Year Built: 1996
Year Renovated: —
County: New Haven County
APN: 1160535

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

K - 12
Preschool & daycare

Dr. Robert H. Brown Middle School

Public 4-5 • Assigned • 1.0mi

10/10

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 4.1mi

10/10

Daniel Hand High School

Public 9-12 • Assigned • 4.3mi

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

69% 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

$1.02M – $1.24M

Reach more buyers when you sell with Redfin. Save up to $10,755 in fees. 3 minutes to get started.

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

Nearby similar homes

$559,900

3 beds1 bath1,077 sq ft

6 Bower Rd, Madison, CT 06443

New cedar siding • Roof replaced • 1.03 acre lot

$999,000

5 beds5.5 baths3,832 sq ft

1209 Durham Rd, Madison, CT 06443

4 acre compound • Guest house • In home gym

$748,500

4 beds2.5 baths2,572 sq ft

3 Little Hollow Rd, Madison, CT 06443

Wide plank flooring • New light fixtures • New roof

$675,000

3 beds3 baths2,138 sq ft

343 Horse Pond Rd, Madison, CT 06443

Updated kitchen • Detached garage • Hot tub

$575,000

3 beds2 baths1,143 sq ft

179 Route 81, Killingworth, CT 06419

2.9 beautiful acres • Raised ranch house • Two car garage

$834,900

4 beds2.5 baths3,016 sq ft

26 Overlook Farms Rd, Killingworth, CT 06419

Private acres • Walk-out basement • Mature trees

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 baths1,280 sq ft

23 Wilshire Rd Unit A, Madison, CT 06443

Private backyard • Inviting living room • Fireplace

Home values near 58 Shepherds Trl

Data from public records.

Address	Redfin Estimate
33 Shepherds Trl, Madison, CT 3 Beds \| 2.5 Baths \| 1927 Sq. Ft.	$757,567
24 Shepherds Trl, Madison, CT 4 Beds \| 2.5 Baths \| 2974 Sq. Ft.	$909,501
48 Shepherds Trl, Madison, CT 4 Beds \| 2.5 Baths \| 4879 Sq. Ft.	$960,691
3 Doe Ln, Madison, CT 3 Beds \| 2.5 Baths \| 3696 Sq. Ft.	$817,428
24 Buck Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3504 Sq. Ft.	—
13 Buck Hill Rd, Madison, CT 4 Beds \| 3 Baths \| 3256 Sq. Ft.	$1,032,522
34 Buck Hill Rd, Madison, CT 4 Beds \| 3.5 Baths \| 4124 Sq. Ft.	$1,184,289

Address	Redfin Estimate
16 Shepherds Trl, Madison, CT 5 Beds \| 3.5 Baths \| 3849 Sq. Ft.	$1,145,927
52 Shepherds Trl, Madison, CT 3 Beds \| 2 Baths \| 2085 Sq. Ft.	$706,741
10 Doe Ln, Madison, CT 3 Beds \| 3 Baths \| 3718 Sq. Ft.	$899,102
5 Buck Hill Rd, Madison, CT 4 Beds \| 4 Baths \| 4018 Sq. Ft.	$1,023,438
4 Doe Ln, Madison, CT 4 Beds \| 2.5 Baths \| 3671 Sq. Ft.	$904,101
21 Buck Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3963 Sq. Ft.	$1,212,605
52 Buck Hill Rd, Madison, CT 4 Beds \| 3 Baths \| 3278 Sq. Ft.	$1,073,463

Address	Redfin Estimate
38 Shepherds Trl, Madison, CT 4 Beds \| 2.5 Baths \| 2920 Sq. Ft.	$852,348
46 Shepherds Trl, Madison, CT 3 Beds \| 2.5 Baths \| 2350 Sq. Ft.	$720,457
9 Doe Ln, Madison, CT 4 Beds \| 2.5 Baths \| 3245 Sq. Ft.	$1,062,504
14 Buck Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3664 Sq. Ft.	$838,679
27 Buck Hill Rd, Madison, CT 4 Beds \| 3 Baths \| 3508 Sq. Ft.	$950,460
42 Buck Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 3999 Sq. Ft.	$949,126
17 Buck Hill Rd, Madison, CT 5 Beds \| 4 Baths \| 5069 Sq. Ft.	$1,067,902

Property information provided by Smart MLS when last listed in 2023. This data may not match . Learn more.

More real estate resources

Zip Codes
Minor Civil Divisions
Cities
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