50 Overbrook Road, Madison, CT 06443
SOLD
JUN 19, 2026

$936,900

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 3,766 sqft (on 1.88 acres)

50 Overbrook Road, Madison, CT 06443

Est. Refi. Payment $6,750/mo*
Refinance Your Home
Currently Off Market - Sold Jun 19, 2026 for $930,000 (13% above list price)

Home Value

Trulia Estimate
$937K
Since last month
Increased$1K (+0.1%)
Since last year
Increased$137K (+17.1%)
Since last sale
Increased$8K (+0.8%)
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 +114% in the last 10 years
MonthEstimated value
2026
September 2026$938K
August 2026$937K
July 2026$934K
June 2026$931K
May 2026$880K
April 2026$885K
March 2026$788K
February 2026$788K
January 2026$786K
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
370 Opening Hill Road, Madison, CT
0.42
Single-Family Home
$660,000
05/12/26
3
2.5
2,073
70 High Hill Circle, Madison, CT
0.35
Single-Family Home
$1,325,000
03/29/26
5
4.5
4,760
714 Durham Road, Madison, CT
0.72
Single-Family Home
$725,000
10/29/25
3
3.5
3,933
198 Summer Hill Road, Madison, CT
0.81
Single-Family Home
$960,000
07/17/26
4
2.5
3,316
89 Summer Hill Road, Madison, CT
0.58
Single-Family Home
$769,000
08/20/26
4
2.5
2,647
40 Harkness Drive, Madison, CT
0.58
Single-Family Home
$735,000
07/02/26
4
2.5
2,657
96 Winterhill Road, Madison, CT
0.64
Single-Family Home
$715,000
06/04/26
4
2.5
2,950
76 High Hill Circle, Madison, CT
0.40
Single-Family Home
$1,675,000
05/01/26
5
4.5
5,575
86 Winterhill Road, Madison, CT
0.61
Single-Family Home
$703,500
09/30/25
4
2.5
2,330

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
40 Overbrook Road, Madison, CT 06443
0.05
$767,900
4
2.5
2,532
Off Market
81 Colonial Road, Madison, CT 06443
0.19
$747,800
4
2.5
1,986
Off Market
60 Colonial Road, Madison, CT 06443
0.31
$1,348,300
4
3.5
3,472
Off Market
436 Opening Hill Road, Madison, CT 06443
0.30
$369,400
3
1.5
1,144
Off Market
23 Paper Mill Drive, Madison, CT 06443
0.38
$752,700
5
2.5
2,323
Off Market
62 Granby Drive, Madison, CT 06443
0.35
$703,000
3
2.5
2,026
Off Market
70 High Hill Circle, Madison, CT 06443
0.35
$1,325,000
5
4.5
4,760
Recently Sold
441 Opening Hill Road, Madison, CT 06443
0.37
$1,975,000
4
2
3,882
For Sale
43 Colonial Road, Madison, CT 06443
0.40
$736,700
4
2.5
2,506
Off Market
133 Overbrook Road, Madison, CT 06443
0.38
$897,800
3
2.5
2,974
Off Market
370 Opening Hill Road, Madison, CT 06443
0.42
$660,000
3
2.5
2,073
Recently Sold

Local Information

  • Map ViewExplore the area around 50 Overbrook Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1992
1.88 acre lot
3,766 sqft
$247/sqft
2 Car Garage

About this House

Welcome to a beautiful Cape Cod-Contemporary retreat that perfectly blends modern updates with a comfortable, inviting atmosphere. The heart of this home is the stunning chef's kitchen, featuring a large center island with seating for 4, professional gas cooking, high-end appliances, and an incredible amount of pantry and storage space. It flows naturally into the dining room, where a cozy gas fireplace makes the space perfect for hosting everything from holiday dinners to casual weeknight meals. Relax in the living room or head to the family room to enjoy a second gas fireplace and walls of windows that bring the beauty of the private backyard inside. Walk in from your 2 car garage to a mudroom space complete with half bath and dedicated laundry room. The floor plan is designed for easy living, highlighted by a main-level primary suite complete with two walk-in closets with great organization systems and a spacious bathroom featuring double sinks and a beautifully tiled shower. Upstairs, you'll find two oversized bedrooms, both with their own walk-in closets, and a full guest bath. The finished lower level offers additional living space with a bonus room, private office and half bath. There is an abundance of storage in the lower level and throughout the home. Outside, the large AZEK deck leads to a heated in-ground pool, creating a private summer oasis. This home is as reliable as it is beautiful, featuring a new roof (2018), a whole-house Generac generator, a high-end Burnham boiler, and Trane central air. And it is one of the few homes in central Madison with Natural gas! The gas currently runs the generator, gas stove and both gas fireplaces. It's a move-in-ready gem that offers the perfect balance of style, space, and peace of mind.
50 Overbrook Road, Madison, CT 06443 is a 3 bedroom, 4 bathroom, 3,766 sqft single-family home built in 1992. It last sold for $930,000 on Jun 19, 2026 (13% above the $825,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $936,900, with a rent estimate of $6,629/month.
Last check for updates: about 17 hours ago
Listed by Kate Esposito, (203) 215-8824
William Pitt Sotheby's Int'l, (203) 453-2533
Bought with: Michael Martinez, (203) 996-4984, Houlihan Lawrence WD, (203) 787-6888
Source: Smart MLS, MLS#24168571

Home Details for 50 Overbrook Road

Interior Features

Interior Details
Basement: Full,Heated,Cooled,Partially FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3766 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Gas Cooktop, Oven, Microwave, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Fireplace: InsertHas a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckOther Structures: Shed(s)Exterior: Sidewalk, Awning(s), Rain GuttersFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener
Pool
Pool: Heated, Vinyl, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2996 Square FeetFinished Area (below surface): 770 Square Feet

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod,Contemporary
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1159260

Price & Status

Price
List Price: $825,000Price Per Sqft: $247/sqft
Status Change & Dates
Off Market Date: Mon Apr 27 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdJr High / Middle School: Polson Middle SchoolHigh School: Daniel Hand

Building

Building Area
Building Area: 3766 Square Feet

Community

Community Features: Library, Park, Playground, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 1.88 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24168571Attic: Access Via HatchAttribution Contact: (203) 215-8824Above Grade Unfinished Area: 2996Activation Date: Fri Apr 24 2026

Additional Information

LibraryParkPlaygroundShopping/Mall

Price and Tax history

DateEventPrice
Jun 19, 2026
Source: Smart MLS #24168571
Sold
$930,000
Apr 27, 2026
Source: Smart MLS #24168571
Pending
$825,000
Apr 24, 2026
Source: Smart MLS #24168571
Listed For Sale
$825,000
Aug 29, 2003
Source: Smart MLS #M9075469
Sold
$480,000
Jun 2, 1999
Source: N/A
Sold
$318,000

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$716K
$6.67KMoM
Sale-to-List Price
101.8%
0.2%MoM
Price per sq ft
$337
$3MoM
Available listings
59
4MoM

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

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Frequently asked questions about 50 Overbrook Road

  • What is 50 Overbrook Road estimated to be worth?
    Trulia's estimated value for 50 Overbrook Road in Madison, CT is $936,900.
  • What is the price history for 50 Overbrook Road?
    50 Overbrook Road in Madison, CT last sold for $930,000 in June 2026.
  • 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 $716K. That is up $6.67K from the prior month.
  • Does 50 Overbrook Road have air conditioning?
    Yes, 50 Overbrook Road in Madison, CT has air conditioning.
  • Does 50 Overbrook Road have a pool?
    Yes, 50 Overbrook Road in Madison, CT has a pool.

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