86 Winterhill Road, Madison, CT 06443
OFF MARKET

$729,200

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,330 sqft (on 1.27 acres)

86 Winterhill Road, Madison, CT 06443

Est. Refi. Payment $5,270/mo*
Refinance Your Home
Currently Off Market - Sold Sep 30, 2025 for $703,500

Home Value

Trulia Estimate
$729K
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$17K (+2.4%)
Since last sale
Increased$26K (+3.7%)
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 +104% in the last 10 years
MonthEstimated value
2026
September 2026$730K
August 2026$731K
July 2026$724K
June 2026$727K
May 2026$716K
April 2026$713K
March 2026$718K
February 2026$718K
January 2026$719K
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
96 Winterhill Road, Madison, CT
0.05
Single-Family Home
$715,000
06/04/26
4
2.5
2,950
60 Winterhill Road, Madison, CT
0.11
Single-Family Home
$620,000
11/25/25
4
2.5
1,992
9 Monroe Lane, Madison, CT
0.30
Single-Family Home
$640,000
06/30/26
4
2.5
1,894
37 Pine Drive, Madison, CT
0.25
Single-Family Home
$730,000
12/01/25
4
2.5
2,390
258 Opening Hill Road, Madison, CT
0.37
Single-Family Home
$805,500
06/10/26
4
2.5
2,627
286 Opening Hill Road, Madison, CT
0.36
Single-Family Home
$610,000
03/27/26
4
2.5
1,870
16 Eastwood Road, Madison, CT
0.44
Single-Family Home
$700,000
11/21/25
4
3
2,555
338 Opening Hill Road, Madison, CT
0.53
Single-Family Home
$628,000
10/24/25
4
2.5
1,792

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
96 Winterhill Road, Madison, CT 06443
0.05
$715,000
4
2.5
2,950
Recently Sold
60 Winterhill Road, Madison, CT 06443
0.11
$620,000
4
2.5
1,992
Recently Sold
28 Pine Drive, Madison, CT 06443
0.22
$831,900
3
2
2,376
Off Market
23 Paper Mill Drive, Madison, CT 06443
0.23
$752,700
5
2.5
2,323
Off Market
37 Pine Drive, Madison, CT 06443
0.25
$730,000
4
2.5
2,390
Recently Sold
43 Colonial Road, Madison, CT 06443
0.25
$736,700
4
2.5
2,506
Off Market
31 Pine Drive, Madison, CT 06443
0.30
$912,700
4
2.5
2,804
Off Market
9 Monroe Lane, Madison, CT 06443
0.30
$640,000
4
2.5
1,894
Recently Sold
339 Warpas Road, Madison, CT 06443
0.29
$696,800
3
2
1,889
Off Market
469 Warpas Road, Madison, CT 06443
0.34
$614,300
3
1.5
1,864
Off Market
60 Colonial Road, Madison, CT 06443
0.33
$1,348,300
4
3.5
3,472
Off Market

Local Information

  • Map ViewExplore the area around 86 Winterhill Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1979
1.27 acre lot
2,330 sqft
$313/sqft
2 Car Garage

About this House

Welcome to this charming and spacious 4-bedroom, 2.1-bath Colonial nestled on a beautifully groomed and landscaped lot, offering the perfect blend of classic New England style and thoughtful updates. From the moment you step inside, you'll feel right at home. The heart of the home is the oversized family room with plenty of room to relax, gather, or entertain. It flows seamlessly into the kitchen, where you'll find ample cabinetry, generous counter space, and a casual dining area. Both the kitchen and family room offer direct access to a large deck, ideal for summer barbecues, morning coffee, or simply enjoying the peaceful backyard. Throughout the home, you'll find beautiful hardwood floors, adding warmth and character to every room. Upstairs, the four bedrooms are all generously sized, including a primary suite with a private bath. The current owners have converted the 4th BR into a fabulous closet/dressing room. A bonus room is perfect for whatever your needs may be (guest space, home office, rec room, media room) and laundry is conveniently located on this level. Boiler 2019, roof 2018, 3 split ac units 2023. A short drive to Hammonasset Beach State Park, where you can enjoy miles of shoreline, walking trails, and nature programs, Madison town beaches, and close to downtown Madison, filled with local favorites like RJ Julia Booksellers, cozy cafes, restaurants, and boutique shopping. Easy access to I-95 and the Shore Line East train, making commuting a breeze. Recent upgrades include a shed 2023, minisplit air conditioning 2023 (there is one in the primary bedroom, dining room, and family room), updated electric service to 200 amps 2023, upstairs full bathroom remodel 2023, conversion of 4th bedroom to closet 2023, new well pump 2023. See attachments for complete list of upgrades.
86 Winterhill Road, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,330 sqft single-family home built in 1979. It last sold for $703,500 on Sep 30, 2025 (2% above the $690,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $729,200, with a rent estimate of $4,232/month.
Last check for updates: about 9 hours ago
Listed by Kim Fetera, (203) 430-5660
Coldwell Banker Realty, (203) 239-2553
Bought with: Cathy Lynch, (203) 627-2331, Coldwell Banker Realty, (203) 245-4700
Source: Smart MLS, MLS#24111029

Home Details for 86 Winterhill Road

Interior Features

Interior Details
Basement: Full,Unfinished,Hatchway AccessNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2330 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: Storm Door(s)

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Porch, DeckOther Structures: Shed(s)Foundation: Concrete PerimeterNo 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
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2330 Square Feet

Property Information

Year Built
Year Built: 1979
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1158900

Price & Status

Price
List Price: $690,000
Status Change & Dates
Off Market Date: Tue Jul 22 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdHigh School: Daniel Hand

Agent Information

Buyer Agent
Buyer Company Name: Cathy Lynch & Team

Building

Building Area
Building Area: 2330 Square Feet

Community

Community Features: Library, Medical Facilities, Park, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 1.27 Acres

Energy

Energy Efficiency Features: Doors, Windows

Miscellaneous

BasementMls Number: 24111029Attic: Pull Down StairsAbove Grade Unfinished Area: 2330

Additional Information

LibraryMedical FacilitiesParkShopping/Mall

Price and Tax history

DateEventPrice
Sep 30, 2025
Source: Smart MLS #24111029
Sold
$703,500
Sep 9, 2025
Source: Smart MLS #24111029
Pending
$690,000
Jul 20, 2025
Source: Smart MLS #24111029
Listed For Sale
$690,000
Oct 7, 2022
Source: Smart MLS #170515012
Sold
$615,000
Sep 16, 2022
Source: Smart MLS #170515012
Contingent
$585,000

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

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Frequently asked questions about 86 Winterhill Road

  • What is 86 Winterhill Road estimated to be worth?
    Trulia's estimated value for 86 Winterhill Road in Madison, CT is $729,200.
  • What is the price history for 86 Winterhill Road?
    86 Winterhill Road in Madison, CT last sold for $703,500 in September 2025.
  • 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 86 Winterhill Road have air conditioning?
    Yes, 86 Winterhill Road in Madison, CT has air conditioning.
  • Does 86 Winterhill Road have laundry facilities?
    Yes, 86 Winterhill Road in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Madison, CT

Explore by feature - Air Conditioning

18 rentals with air conditioning in Madison, CT

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24 rentals with a washer/dryer in Madison, CT

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