21 Squires Rd, Madison, CT 06443
OFF MARKET

21 Squires Rd
Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,816 sqft (on 2.12 acres)

$584,400

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $4,104/mo*
Refinance Your Home

$584,400

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $4,104/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,816 sqft
(on 2.12 acres)

Home Value

Trulia Estimate
$584K
Since last month
Increased$7K (+1.3%)
Since last year
Increased$31K (+5.5%)
Since last sale
Increased$235K (+67.1%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$585K
July 2026$577K
June 2026$592K
May 2026$574K
April 2026$553K
March 2026$531K
February 2026$512K
January 2026$511K
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
313 Bradley Corners Road, Madison, CT
0.14
Single-Family Home
$640,000
04/16/26
4
2
1,848
12 Rustic Lane, Madison, CT
0.16
Single-Family Home
$620,000
05/13/26
4
2
1,849
69 Squires Road, Madison, CT
0.21
Single-Family Home
$738,000
06/26/26
3
3
2,025
76 Squires Road, Madison, CT
0.26
Single-Family Home
$472,500
12/15/25
5
3
2,652
660 Opening Hill Road, Madison, CT
0.49
Single-Family Home
$490,000
06/25/26
4
2
1,688
18 Deepwood Drive, Madison, CT
0.45
Single-Family Home
$440,000
12/22/25
3
2
1,975
5 Dover Lane, Madison, CT
0.36
Single-Family Home
$670,000
08/21/25
4
2.5
2,096
735 Opening Hill Road, Madison, CT
0.35
Single-Family Home
$664,600
01/30/26
4
2
2,028
93 Deepwood Dr, Madison, CT
0.49
Single-Family Home
$350,000
12/08/25
3
1
1,754
24 Deepwood Drive, Madison, CT
0.44
Single-Family Home
$475,000
09/03/25
3
1.5
1,200

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
37 Squires Road, Madison, CT 06443
0.08
$771,600
3
3.5
2,636
Off Market
4 Sheffield Lane, Madison, CT 06443
0.13
$759,200
4
2.5
2,312
Off Market
313 Bradley Corners Road, Madison, CT 06443
0.14
$640,000
4
2
1,848
Recently Sold
12 Rustic Lane, Madison, CT 06443
0.16
$620,000
4
2
1,849
Recently Sold
57 Squires Road, Madison, CT 06443
0.18
$636,700
4
2.5
2,324
Off Market
69 Squires Road, Madison, CT 06443
0.21
$738,000
3
3
2,025
Recently Sold
76 Squires Road, Madison, CT 06443
0.26
$472,500
5
3
2,652
Recently Sold
88 Hickory Lane, Madison, CT 06443
0.30
$1,455,800
4
4
5,780
Off Market
37 Sheffield Lane, Madison, CT 06443
0.32
$788,000
4
2.5
2,989
Off Market
83 Squires Road, Madison, CT 06443
0.28
$624,100
3
1.5
2,200
Off Market
5 Dover Lane, Madison, CT 06443
0.36
$693,500
4
2.5
2,096
Off Market
735 Opening Hill Road, Madison, CT 06443
0.35
$664,600
4
2
2,028
Recently Sold

Local Information

  • Map ViewExplore the area around 21 Squires Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1970
Lot Size
2.12 acres
Living Area
1,816 sqft
Price/Sqft
$322
Parking
Garage

About this House

Welcome home to this charming Dutch Colonial with over 2 acres with 3 bedrooms, 2.5 baths hardwood floors, wood burning fireplace, newer windows, 2 car garage with a gorgeous lot with stonewalls in this quiet desirable neighborhood in Madison You'll appreciate the size of the large front to back living room perfect for entertaining or just add a few logs to the fireplace and just sit back with a good book With the eat-in kitchen prepare your holiday meals and serve in your formal dining room. Another option for entertaining is the family room that offers a slider to your deck where you can entertain your guests looking out over the expansive backyard enjoying nature at its best. Close to grocery shopping at Roberts Food center (great prepared foods and meats, hiking trails, Chatfield Hollow, Hammonasset Beach State Park, 10 minutes to I-95 and close to Madison center and all the town has to offer. Pack you picnic to enjoy the sandy Madison Town Beach and let's not forget the great Madison Schools You've arrived
21 Squires Rd, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 1,816 sqft single-family home built in 1970. It last sold for $350,000 on Jan 25, 2022. It is currently off market. The Trulia Estimate is $584,400, with a rent estimate of $4,486/month.

Home Details for 21 Squires Rd

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1970Year Updated: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 2.12 acres

Price and Tax history

DateEventPrice
Jan 25, 2022
Source: Smart MLS #170453445
Sold
$350,000
Dec 21, 2021
Source: Smart MLS #170453445
Contingent
$364,900
Dec 11, 2021
Source: Berkshire Hathaway HomeServices New England Properties #170453445
Pending
$364,900
Dec 11, 2021
Source: Smart MLS #170453445
PendingToActive
$364,900
Dec 2, 2021
Source: Smart MLS #170453445
Contingent
$364,900

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 21 Squires Rd

  • What is 21 Squires Rd estimated to be worth?
    Trulia's estimated value for 21 Squires Rd in Madison, CT is $584,400.
  • What is the price history for 21 Squires Rd?
    21 Squires Rd in Madison, CT last sold for $350,000 in January 2022.
  • 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 21 Squires Rd?
    The lot at 21 Squires Rd in Madison, CT is about 2.1 acres.
  • Does 21 Squires Rd have a garage?
    Yes, 21 Squires Rd in Madison, CT has a garage.

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