27 Shepherds Trl, Madison, CT 06443
OFF MARKET

$998,300

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 3,500 sqft (on 1.96 acres)

27 Shepherds Trl, Madison, CT 06443

Est. Refi. Payment $7,027/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2020 for $570,000

Home Value

Trulia Estimate
$998K
Since last month
Increased$13K (+1.3%)
Since last year
Increased$53K (+5.6%)
Since last sale
Increased$428K (+75.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +78% in the last 10 years
MonthEstimated value
2026
August 2026$998K
August 2026$996K
July 2026$985K
June 2026$1M
May 2026$983K
April 2026$960K
March 2026$940K
February 2026$924K
January 2026$916K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Buck Hill Road, Madison, CT
0.29
Single-Family Home
$690,000
10/24/25
4
2.5
3,999
48 Shepherds Trail, Madison, CT
0.23
Single-Family Home
$775,000
01/16/26
4
2.5
4,879
476 Summer Hill Road, Madison, CT
0.18
Single-Family Home
$700,000
08/10/26
4
2.5
2,057
197 Concord Drive, Madison, CT
0.51
Single-Family Home
$618,660
12/30/25
3
2.5
2,793
174 Concord Drive, Madison, CT
0.64
Single-Family Home
$705,000
05/28/26
4
2.5
3,212
86 Nursery Lane, Madison, CT
0.73
Single-Family Home
$1,200,000
07/23/26
4
3.5
4,250
128 Concord Drive, Madison, CT
0.86
Single-Family Home
$1,250,000
09/01/26
4
3
3,816
25 Madison Hollow, Killingworth, CT
0.71
Single-Family Home
$815,000
06/23/26
3
2.5
3,432
100 Concord Drive, Madison, CT
1.00
Single-Family Home
$860,000
03/02/26
4
3
3,517
1353 Durham Road, Madison, CT
1.10
Single-Family Home
$597,104
06/25/26
3
2.5
2,022

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
661 Old Toll, Madison, CT 06443
0.05
$416,200
2
1
1,331
Off Market
476 Summer Hill Road, Madison, CT 06443
0.18
$700,000
4
2.5
2,057
Recently Sold
48 Shepherds Trail, Madison, CT 06443
0.23
$775,000
4
2.5
4,879
Recently Sold
44 Buck Hill Road, Madison, CT 06443
0.27
$1,015,100
4
2.5
4,448
Off Market
42 Buck Hill Road, Madison, CT 06443
0.29
$716,500
4
2.5
3,999
Off Market
426 Summer Hill Road, Madison, CT 06443
0.31
$778,800
4
2.5
2,830
Off Market
17 Buck Hill Road, Madison, CT 06443
0.30
$945,100
5
4
5,069
Off Market
546 Summer Hill Road, Madison, CT 06443
0.37
$1,481,600
4
3.5
6,267
Off Market
51 Buck Hill Road, Madison, CT 06443
0.42
$1,808,400
5
6
4,994
Off Market
398 Summer Hill Road, Madison, CT 06443
0.47
$990,800
4
2.5
3,470
Off Market
197 Concord Drive, Madison, CT 06443
0.51
$618,660
3
2.5
2,793
Recently Sold
35 Georgetown Circle, Madison, CT 06443
0.50
$1,145,900
4
2.5
3,004
Off Market

Local Information

  • Map ViewExplore the area around 27 Shepherds Trl.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2016
1.96 acre lot
3,500 sqft
$285/sqft
Garage

About this House

Custom built colonial with attention to detail in every room. Newer home privately nestled in a residential community. The nearly 3000 square foot home features hardwood floors in every room. There are 9 foot ceilings and a custom designed kitchen with granite. The stainless steel oven, microwave, gas cooktop and center island are some of the features. The family room with wood fireplace is open to the kitchen. The sliders lead to a custom built stone patio with built-in grill and custom pizza oven. The nearly 2 acres allows room for an in-ground pool. The upper level offers 4 spacious bedrooms plus an office. The master suite with tray ceiling, walk-in closet and custom designed master bath will please all buyers. This home offers features you will not find in most homes. Put this home on your list!
27 Shepherds Trl, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 3,500 sqft single-family home built in 2016. It last sold for $570,000 on Dec 18, 2020. More recently, it was listed as a rental in December 2018 with an asking price of $4,000 per month. That rental listing was removed on December 29, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $998,300, with a rent estimate of $5,303/month.

Home Details for 27 Shepherds Trl

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, OfficeCeiling Fan
Heating & Cooling
Heating: Forced Air, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other, Vinyl
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.96 acres

Price and Tax history

DateEventPrice
Dec 18, 2020
Source: Smart MLS #170349549
Sold
$570,000
Oct 24, 2020
Source: Agent Provided
PriceChange
$599,900
Price decreased by 14%
Oct 6, 2020
Source: N/A
PendingToActive
$699,900
Jul 29, 2020
Source: N/A
Pending
$699,900
Jul 25, 2020
Source: N/A
Listed For Sale
$699,900

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Shepherds Trl

  • What is 27 Shepherds Trl estimated to be worth?
    Trulia's estimated value for 27 Shepherds Trl in Madison, CT is $998,300.
  • What is the price history for 27 Shepherds Trl?
    27 Shepherds Trl in Madison, CT last sold for $570,000 in December 2020.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • Does 27 Shepherds Trl have air conditioning?
    Yes, 27 Shepherds Trl in Madison, CT has air conditioning.
  • Does 27 Shepherds Trl have laundry facilities?
    Yes, 27 Shepherds Trl in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

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