21 Princess Dr, Madison, CT 06443
OFF MARKET

21 Princess Dr
Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 2,076 sqft (on 1.09 acres)

$628,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $4,406/mo*
Refinance Your Home

$628,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $4,406/mo*
Refinance Your Home
4 Beds
3 Baths
2,076 sqft
(on 1.09 acres)

Home Value

Trulia Estimate
$629K
Since last month
Decreased$7K (-1.1%)
Since last year
Increased$13K (+2.2%)
Since last sale
Increased$365K (+140.3%)
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$625K
July 2026$631K
June 2026$639K
May 2026$633K
April 2026$610K
March 2026$594K
February 2026$574K
January 2026$585K
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
1353 Durham Road, Madison, CT
0.05
Single-Family Home
$597,104
06/25/26
3
2.5
2,022
42 Lake Drive, Madison, CT
0.81
Single-Family Home
$454,000
08/28/25
4
2.5
2,036
26 Farm View Drive, Madison, CT
0.72
Single-Family Home
$630,000
02/19/26
4
2
1,573
15 Cornfield Lane, Madison, CT
0.78
Single-Family Home
$634,500
06/30/26
3
2.5
1,848
476 Summer Hill Road, Madison, CT
1.01
Single-Family Home
$700,000
08/10/26
4
2.5
2,057
76 Squires Road, Madison, CT
0.97
Single-Family Home
$472,500
12/15/25
5
3
2,652
1543 Durham Road, Madison, CT
0.85
Single-Family Home
$437,000
02/26/26
3
2.5
3,711
69 Squires Road, Madison, CT
1.00
Single-Family Home
$738,000
06/26/26
3
3
2,025
735 Opening Hill Road, Madison, CT
0.96
Single-Family Home
$664,600
01/30/26
4
2
2,028
659 Summer Hill Road, Madison, CT
0.76
Single-Family Home
$960,000
08/29/25
3
2.5
2,558

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
1353 Durham Road, Madison, CT 06443
0.05
$597,104
3
2.5
2,022
Recently Sold
51 Princess Drive, Madison, CT 06443
0.13
$613,400
4
2.5
2,100
Off Market
160 Princess Drive, Madison, CT 06443
0.20
$671,000
4
2.5
2,455
Off Market
35 White Cedar Drive, Madison, CT 06443
0.21
$785,700
4
2.5
2,150
Off Market
20 Northwood Road, Madison, CT 06443
0.28
$865,100
4
2.5
3,575
Off Market
22 Northwood Road, Madison, CT 06443
0.32
$965,100
4
2.5
3,765
Off Market
20 Hidden Springs Road, Madison, CT 06443
0.35
$1,131,600
5
3.5
4,881
Off Market
68 White Cedar Drive, Madison, CT 06443
0.38
$723,600
3
2.5
2,030
Off Market
24 Pond View Lane, Madison, CT 06443
0.45
$742,000
4
2.5
2,426
Off Market
1466 Durham Road, Madison, CT 06443
0.50
$561,000
3
1
1,023
For Sale
1467 Durham Road, Madison, CT 06443
0.50
$517,600
4
2.5
1,611
Off Market
1474 Durham Road, Madison, CT 06443
0.57
$666,900
4
3.5
2,740
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
1.09 acres
Living Area
2,076 sqft
Price/Sqft
$303

About this House

This single-family home is located at 21 Princess Dr, Madison, CT. 21 Princess Dr is in Madison, CT and in ZIP code 06443. This property has 4 bedrooms, 3 bathrooms and approximately 2,076 sqft of floor space. This property has a lot size of 1.09 acres and was built in 1965.
21 Princess Dr, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,076 sqft single-family home built in 1965. It last sold for $259,900 on Jul 24, 1987. It is currently off market. The Trulia Estimate is $628,500, with a rent estimate of $4,549/month.

Home Details for 21 Princess Dr

Interior Features

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

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.09 acres

Price and Tax history

DateEventPrice
Jul 24, 1987
Source: N/A
Sold
$259,900

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 Princess Dr

  • What is 21 Princess Dr estimated to be worth?
    Trulia's estimated value for 21 Princess Dr in Madison, CT is $628,500.
  • What is the price history for 21 Princess Dr?
    21 Princess Dr in Madison, CT last sold for $259,900 in July 1987.
  • 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 Princess Dr?
    The lot at 21 Princess Dr in Madison, CT is about 1.1 acres.

Explore by feature - Pet Friendly

10 pet-friendly rentals in Madison, CT

Explore by feature - Garage

9 rentals with a garage in Madison, CT

Explore by feature - Air Conditioning

25 rentals with air conditioning in Madison, CT

Explore by feature - Washer/dryer

29 rentals with a washer/dryer in Madison, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 21 Princess Dr

Skip to last item
Skip to first item

Homes for sale near 21 Princess Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item