58 Shepherds Trl, Madison, CT 06443
Property image
Property image
OFF MARKET

58 Shepherds Trl
Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,453 sqft (on 1.54 acres)

$1,058,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $7,253/mo*
Refinance Your Home

$1,058,000

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $7,253/mo*
Refinance Your Home
4 Beds
3 Baths
3,453 sqft
(on 1.54 acres)

Local Information

  • Map ViewExplore the area around 58 Shepherds Trl.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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.
58 Shepherds Trl, Madison, CT 06443 is a 4 bedroom, 4 bathroom, 3,453 sqft single-family home built in 1996. It last sold for $875,000 on Dec 29, 2022. It is currently off market. The Trulia Estimate is $1,058,000, with a rent estimate of $7,191/month.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 58 Shepherds Trl

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.54 acres

Price History for 58 Shepherds Trl

DatePriceEventSource
12/29/2022$875,000Sold
Smart MLS #170533606
11/16/2022$849,900ContingentSmart MLS #170533606
11/11/2022$849,900Listed For SaleSmart MLS #170533606
08/21/2020$635,000Sold
Smart MLS #170244216
10/14/2019$674,900Listed For SaleAgent Provided
12/01/1988$120,000Sold
N/A

Market trends in Madison

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
69
4MoM
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Property Tax and Assessment

Year2025
Tax$13,797
Assessment$615,100
Home facts updated by county records

Comparable Sales for 58 Shepherds Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Buck Hill Road, Madison, CT
0.06
Single-Family Home
$690,000
10/24/25
4
2.5
3,999
48 Shepherds Trail, Madison, CT
0.06
Single-Family Home
$775,000
01/16/26
4
2.5
4,879
174 Concord Drive, Madison, CT
0.41
Single-Family Home
$705,000
05/28/26
4
2.5
3,212
197 Concord Drive, Madison, CT
0.31
Single-Family Home
$618,660
12/30/25
3
2.5
2,793
100 Concord Drive, Madison, CT
0.78
Single-Family Home
$860,000
03/02/26
4
3
3,517
25 Madison Hollow, Killingworth, CT
0.47
Single-Family Home
$815,000
06/23/26
3
2.5
3,432
82 Concord Drive, Madison, CT
0.77
Single-Family Home
$1,100,000
06/25/26
4
3.5
4,242
25 Williamsburg Circle, Madison, CT
0.96
Single-Family Home
$900,000
04/02/26
4
3.5
3,982
659 Summer Hill Road, Madison, CT
1.09
Single-Family Home
$960,000
08/29/25
3
2.5
2,558
195 Summer Hill Road, Madison, CT
1.13
Single-Family Home
$650,000
07/28/25
4
2.5
2,511

Nearby homes

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Assigned Schools

These are the assigned schools for 58 Shepherds Trl.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Madison

At least 57 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say yards are well-kept

  • 89 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 85 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 74 % Say it's quiet

  • 66 % Say neighbors are friendly

  • 63 % Say they plan to stay for at least 5 years

  • 62 % Say kids play outside

  • 39 % Say there are community events

  • 31 % Say streets are well-lit

  • 29 % Say it's walkable to grocery stores

  • 26 % Say it's walkable to restaurants

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag
  • Ginavan1
    "Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
    0
    Flag
  • Ginavan1
    "Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
    0
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  • Jv4450
    "I’m just trying my luck with this and it doesn’t look too great for the job and the way the company looks I just have no confidence "
    0
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  • Trulia User
    "I’ve lived here for 30 years. Home prices continue to go up with the NYC families inching this way causing taxes to get out of control. "
    1
    Flag
  • Diana
    "I see people walking dogs but there is no dog park like in neighboring towns. However, there are many walking trails that you can take your leashed dog to walk in."
    4
    Flag
  • Elizabeth L.
    "Great neighborhood. Great schools. Beautiful town. Great library. Great beaches. New England vibe. Shoreline East train takes you to new Haven with direct connection to NYC. "
    2
    Flag
  • Cassidy W.
    "Great place. Been here for 23 years, wouldn’t change a thing. Very small town. Not a lot of commercial business in Madison, close by in Guilford, very local business oriented. "
    1
    Flag
  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
    Flag
  • Jcimino5
    "Nice community with good school system and organized sports teams. Nice beach and walking trails. Can get a bit crowded in the summer."
    2
    Flag
  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
    Flag
  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
    Flag
  • Bob B
    "Great community. Families partipate in local activities. Safe town. Beautiful town beach properties. Great local shopping and restaurants. School system is top notch and lots of state parks close by. It’s really a picture perfect town. Lived in Madison for 42 years "
    0
    Flag
  • Robuess
    "Its the best town in America hands down. We love the local restaurants and can ride our bikes to the beach. Friendly locals who will stop and ask if you need help. Very fortunate to have lived here for 40 years!!"
    0
    Flag
  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
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  • Pamelajbrown1234
    "Almost everyone has a dog, we take them everywhere. There is a dog park in town. People walk their dogs all over town and down at Hammonasette State Park. Dogs mostly seem very well trained and socialized"
    7
    Flag
  • Nicole L.
    "There is a real sense of community and people actually care about each other here. Schools are excellent and our beaches make it feel like you're always on vacation. "
    0
    Flag
  • Mike H.
    "I’ve lived here since 1990 and love it! There’s everything here, from great dining and great bookstore, coffee shops and terrific local cinema!"
    0
    Flag
  • David F.
    "Great for young families!"
    0
    Flag
  • Robert S.
    "We have lived in Madison for 15 years. This is a great neighborhood with only 12 houses. It is quiet and private as well as being a friendly and considerate group of folks. Mix of retierees and families with close proximity to many local amenities."
    0
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Explore by feature - Pet Friendly

7 pet-friendly rentals in Madison, CT

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Homes for sale near 58 Shepherds Trl

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Off Market Homes Near 58 Shepherds Trl

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