20 Crestview Dr, Madison, CT 06443
Property image
Property image
OFF MARKET

$1,314,300

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 5,210 sqft (on 1.39 acres)

20 Crestview Dr, Madison, CT 06443

Est. Refi. Payment $9,179/mo*
Refinance Your Home
Currently Off Market - Sold Jun 10, 2021 for $800,000

Home Value

Trulia Estimate
$1.31M
Since last month
Increased$16K (+1.2%)
Since last year
Increased$67K (+5.3%)
Since last sale
Increased$520K (+65%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$1.32M
July 2026$1.3M
June 2026$1.34M
May 2026$1.31M
April 2026$1.29M
March 2026$1.27M
February 2026$1.24M
January 2026$1.23M
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
70 High Hill Circle, Madison, CT
0.26
Single-Family Home
$1,325,000
03/29/26
5
4.5
4,760
76 High Hill Circle, Madison, CT
0.28
Single-Family Home
$1,675,000
05/01/26
5
4.5
5,575
25 Williamsburg Circle, Madison, CT
0.58
Single-Family Home
$900,000
04/02/26
4
3.5
3,982
198 Summer Hill Road, Madison, CT
0.40
Single-Family Home
$960,000
07/17/26
4
2.5
3,316
132 Summer Hill Road, Madison, CT
0.41
Single-Family Home
$2,324,000
06/12/26
4
4.5
4,517
89 Summer Hill Road, Madison, CT
0.46
Single-Family Home
$769,000
08/20/26
4
2.5
2,647
50 Overbrook Road, Madison, CT
0.47
Single-Family Home
$930,000
06/19/26
3
3
3,766
82 Concord Drive, Madison, CT
0.67
Single-Family Home
$1,100,000
06/25/26
4
3.5
4,242
40 Harkness Drive, Madison, CT
0.59
Single-Family Home
$735,000
07/02/26
4
2.5
2,657
48 Bar Gate Trail, Killingworth, CT
0.55
Single-Family Home
$699,000
12/19/25
4
2.5
2,882

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
924 Durham Road, Madison, CT 06443
0.15
$674,000
4
2.5
1,992
Off Market
61 High Hill Circle, Madison, CT 06443
0.19
$1,684,900
7
6
6,300
Off Market
70 High Hill Circle, Madison, CT 06443
0.26
$1,325,000
5
4.5
4,760
Recently Sold
939 Durham Road, Madison, CT 06443
0.25
$642,500
3
2
2,204
Off Market
76 High Hill Circle, Madison, CT 06443
0.28
$1,675,000
5
4.5
5,575
Recently Sold
195 Summer Hill Road, Madison, CT 06443
0.26
$791,300
4
2.5
2,511
Off Market
15 Cedarcroft Drive, Madison, CT 06443
0.32
$548,000
3
2
2,204
Off Market
62 Granby Drive, Madison, CT 06443
0.35
$713,500
3
2.5
2,026
Off Market
122 Summer Hill Road, Madison, CT 06443
0.38
$2,362,000
5
4.5
4,900
Off Market
17 Lyle Drive, Madison, CT 06443
0.39
$768,600
4
2.5
2,862
Off Market
65 Granby Drive, Madison, CT 06443
0.40
$645,500
4
2.5
2,280
Off Market
198 Summer Hill Road, Madison, CT 06443
0.40
$960,000
4
2.5
3,316
Recently Sold

Local Information

  • Map ViewExplore the area around 20 Crestview Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1996
Lot Size
1.39 acres
Living Area
5,210 sqft
Price/Sqft
$252
Parking
Garage

About this House

The best of "All" worlds ! Beautifully maintained & updated Colonial PLUS fully equip one bedroom in-law apartment with private entrance PLUS newly built living space in walk out lower level that includes custom bathroom, spacious bedroom, living room & tons of storage.
First floor flow is perfect for today's lifestyle. Spacious & open kitchen with a bright & sunny family room that overlooks your private back yard. Huge multi-layer deck with hot tub will be the hit of all your outdoor gatherings.
Second floor includes three generous bedrooms, and a master bedroom suite with a walk in closet that you'll get lost in!
Bonus room above garage perfect for office, fitness center or just your private retreat.
This home has it all and way too many updates to list but just a few benefits you'll enjoy will be propane cooking & fireplace, quartz kitchen countertop, freshly painted in-law apartment, hardwood floors throughout first floor of main home, multi zone heating/cooling, and so much more. Absolutely move in condition! All of this in the perfect location close to town with over an acre of land in a sought after neighborhood.
20 Crestview Dr, Madison, CT 06443 is a 6 bedroom, 6 bathroom, 5,210 sqft single-family home built in 1996. It last sold for $800,000 on Jun 10, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,314,300, with a rent estimate of $7,950/month.

Home Details for 20 Crestview Dr

Interior Features

Heating & Cooling
Heating: Oil, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Oil
Interior Details
In-law unitNumber of Rooms: 15Types of Rooms: Dining Room, Family Room, Office, Sun Room
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Other
Security
Security System

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleDeckExterior: VinylPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Lot Information

Lot Area: 1.39 acres

Price and Tax history

DateEventPrice
Jun 10, 2021
Source: Smart MLS #170383345
Sold
$800,000
Mar 29, 2021
Source: Real Living Real Estate #170383345
Pending
$800,000
Mar 29, 2021
Source: Smart MLS #170383345
Contingent
$800,000
Mar 26, 2021
Source: Smart MLS #170383345
Listed For Sale
$800,000
Sep 14, 2018
Source: Smart MLS #170090269
Sold
$582,000

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 20 Crestview Dr

  • What is 20 Crestview Dr estimated to be worth?
    Trulia's estimated value for 20 Crestview Dr in Madison, CT is $1,314,300.
  • What is the price history for 20 Crestview Dr?
    20 Crestview Dr in Madison, CT last sold for $800,000 in June 2021.
  • 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 20 Crestview Dr have air conditioning?
    Yes, 20 Crestview Dr in Madison, CT has air conditioning.
  • How big is the lot at 20 Crestview Dr?
    The lot at 20 Crestview Dr in Madison, CT is about 1.4 acres.

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