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

50 Overbrook Road
Madison, CT 06443

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

$930,000

Last Sold: Jun 19, 2026
13% over list $825K
$247/sqft
Est. Refi. Payment $6,507/mo*
Refinance Your Home

$930,000

Last Sold: Jun 19, 2026
13% over list $825K
$247/sqft
Est. Refi. Payment $6,507/mo*
Refinance Your Home
3 Beds
3 Baths
3,766 sqft
(on 1.88 acres)

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

Property Type
Single-Family Home
Year Built
1992
Lot Size
1.88 acres
Living Area
3,766 sqft
Price/Sqft
$247/sqft
Parking
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). It is currently off market. The Trulia Estimate is $930,600, with a rent estimate of $6,197/month.

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
Last check for updates: about 4 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

Price History for 50 Overbrook Road

DatePriceEventSource
06/19/2026$930,000Sold
Smart MLS #24168571
04/27/2026$825,000PendingSmart MLS #24168571
04/24/2026$825,000Listed For SaleSmart MLS #24168571
08/29/2003$480,000Sold
Smart MLS #M9075469
06/02/1999$318,000Sold
N/A
11/30/1994$262,000Sold
N/A

Market trends in Madison

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$763K
Sale-to-List Price
100.7%
Price per sq ft
$327
Available listings
71
2MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$10,392
Assessment$463,300
Home facts updated by county records

Comparable Sales for 50 Overbrook Road

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
23 Paper Mill Drive, Madison, CT
0.38
Single-Family Home
$725,000
08/25/25
5
2.5
2,323
70 High Hill Circle, Madison, CT
0.35
Single-Family Home
$1,325,000
03/29/26
5
4.5
4,760
479 Opening Hill Road, Madison, CT
0.47
Single-Family Home
$1,200,000
08/15/25
4
2.5
4,437
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
40 Harkness Drive, Madison, CT
0.58
Single-Family Home
$735,000
07/02/26
4
2.5
2,657
31 Pine Drive, Madison, CT
0.80
Single-Family Home
$875,000
08/01/25
4
2.5
2,804
96 Winterhill Road, Madison, CT
0.64
Single-Family Home
$715,000
06/04/26
4
2.5
2,950

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 50 Overbrook Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

6 pet-friendly rentals in Madison, CT

Explore by feature - Garage

Explore by feature - Air Conditioning

19 rentals with air conditioning in Madison, CT

Explore by feature - Washer/dryer

14 rentals with a washer/dryer in Madison, CT

Homes for sale near 50 Overbrook Road

Skip to last item
Skip to first item

Off Market Homes Near 50 Overbrook Road

Skip to last item
Skip to first item
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.