14 Hillside Pl, Madison, CT 06443
OFF MARKET

$1,762,800

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,624 sqft (on 0.42 acres)

14 Hillside Pl, Madison, CT 06443

Est. Refi. Payment $12,351/mo*
Refinance Your Home
Currently Off Market - Sold Jun 17, 1998 for $570,000

Home Value

Trulia Estimate
$1.76M
Since last month
Increased$27K (+1.6%)
Since last year
Increased$60K (+3.5%)
Since last sale
Increased$1M (+209.9%)
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 +99% in the last 10 years
MonthEstimated value
2026
August 2026$1.77M
August 2026$1.76M
July 2026$1.74M
June 2026$1.8M
May 2026$1.74M
April 2026$1.69M
March 2026$1.63M
February 2026$1.61M
January 2026$1.58M
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
14 Waterbury Ave, Madison, CT
0.13
Single-Family Home
$1,787,500
11/14/25
4
3
2,100
35 Hotchkiss Lane, Madison, CT
0.24
Single-Family Home
$1,585,000
03/25/26
3
2.5
2,400
32 Liberty Street, Madison, CT
0.33
Single-Family Home
$1,100,000
10/08/25
3
3
1,188
166 Bishop Lane, Madison, CT
0.42
Single-Family Home
$900,000
11/14/25
3
3
2,968
9 Madrina Lane, Madison, CT
0.58
Single-Family Home
$530,000
10/17/25
3
2
2,159
64 Webster Point Road, Madison, CT
0.35
Single-Family Home
$2,185,000
07/31/26
4
3.5
4,010
123 Liberty Street, Madison, CT
0.16
Single-Family Home
$1,600,000
12/30/25
4
3.5
4,988
7 Linden Lane, Madison, CT
0.60
Single-Family Home
$1,710,000
06/10/26
3
2.5
2,661
39 Madison Avenue, Madison, CT
0.86
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
137 Liberty Street, Madison, CT
0.22
Single-Family Home
$2,200,000
08/06/26
5
5.5
5,543

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
4 Neptune Avenue, Madison, CT 06443
0.08
$1,766,700
3
2.5
2,103
Off Market
73 Liberty Street, Madison, CT 06443
0.16
$1,818,300
5
2.5
2,799
Off Market
123 Liberty Street, Madison, CT 06443
0.16
$1,600,000
4
3.5
4,988
Recently Sold
40 Grove Avenue, Madison, CT 06443
0.19
$2,534,700
4
2.5
2,771
Off Market
7 Barberry Lane, Madison, CT 06443
0.17
$1,690,300
4
2.5
2,226
Off Market
17 Barberry Lane, Madison, CT 06443
0.18
$3,000,000
4
5
4,833
For Sale
61 Liberty Street, Madison, CT 06443
0.20
$1,768,300
3
2.5
2,500
Off Market
1055 Boston Post Road, Madison, CT 06443
0.22
$472,000
3
1
1,454
Off Market
53 Liberty Street, Madison, CT 06443
0.23
$1,317,200
3
2
1,552
Off Market
137 Liberty Street, Madison, CT 06443
0.22
$2,200,000
5
5.5
5,543
Recently Sold
33 N Street, Madison, CT 06443
0.25
$185,100
2
1
629
Off Market
1075 Boston Post Road, Madison, CT 06443
0.24
$1,114,300
4
2.5
2,620
Off Market

Local Information

  • Map ViewExplore the area around 14 Hillside Pl.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1928
0.42 acre lot
2,624 sqft
$672/sqft
Garage

About this House

Summer at the beach in lovely Barberry Farms. Charming, beautifully appointed home in private enclave with central air, formal living and dining, den, sunroom and eat-in kitchen. Steps to private association beach.
14 Hillside Pl, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,624 sqft single-family home built in 1928. It last sold for $570,000 on Jun 17, 1998. More recently, it was listed as a rental in May 2012 with an asking price of $10,000 per month. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,762,800, with a rent estimate of $4,525/month.

Home Details for 14 Hillside Pl

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.42 acres

Price and Tax history

DateEventPrice
May 23, 2012
Source: Agent Provided
Listed For Rent
$10,000
Jun 17, 1998
Source: N/A
Sold
$570,000

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 14 Hillside Pl

  • What is 14 Hillside Pl estimated to be worth?
    Trulia's estimated value for 14 Hillside Pl in Madison, CT is $1,762,800.
  • What is the price history for 14 Hillside Pl?
    14 Hillside Pl in Madison, CT last sold for $570,000 in June 1998.
  • 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.
  • How big is the lot at 14 Hillside Pl?
    The lot at 14 Hillside Pl in Madison, CT is about 0.42 acres (18,295 sq ft).
  • Does 14 Hillside Pl have a garage?
    Yes, 14 Hillside Pl in Madison, CT has a garage.

Explore by feature - Pet Friendly

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