27 Winding Rd, Madison, CT 06443
Property image
Property image
OFF MARKET

$636,100

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,152 sqft (on 0.95 acres)

27 Winding Rd, Madison, CT 06443

Est. Refi. Payment $4,505/mo*
Refinance Your Home
Currently Off Market - Sold Aug 17, 2021 for $449,000

Home Value

Trulia Estimate
$636K
Since last month
Decreased$5K (-0.8%)
Since last year
Increased$19K (+3%)
Since last sale
Increased$187K (+41.7%)
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 +86% in the last 10 years
MonthEstimated value
2026
August 2026$636K
August 2026$636K
July 2026$641K
June 2026$649K
May 2026$627K
April 2026$621K
March 2026$608K
February 2026$596K
January 2026$595K
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
18 Deepwood Drive, Madison, CT
0.42
Single-Family Home
$440,000
12/22/25
3
2
1,975
93 Deepwood Dr, Madison, CT
0.17
Single-Family Home
$350,000
12/08/25
3
1
1,754
10 Scenic Road, Madison, CT
0.33
Single-Family Home
$685,000
06/16/26
5
3
2,210
81 Bartlett Drive, Madison, CT
0.35
Single-Family Home
$630,000
12/12/25
4
2.5
2,088
71 Deepwood Dr, Madison, CT
0.20
Single-Family Home
$475,000
10/31/25
4
2
1,236
98 Bartlett Drive, Madison, CT
0.45
Single-Family Home
$740,000
04/22/26
3
2.5
2,446
15 Stepping Stone Lane, Madison, CT
0.43
Single-Family Home
$525,000
05/28/26
4
1.5
1,346
76 Bartlett Drive, Madison, CT
0.33
Single-Family Home
$780,000
04/17/26
5
2.5
3,100
18 Saint Francis Woods Road, Madison, CT
0.76
Single-Family Home
$550,000
07/08/26
3
2.5
1,824
45 Milano Pond Drive, Madison, CT
0.68
Single-Family Home
$795,000
07/15/26
3
2.5
1,908

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
105 Deepwood Drive, Madison, CT 06443
0.20
$525,700
3
2
1,832
Off Market
62 Bartlett Drive, Madison, CT 06443
0.25
$692,600
3
2.5
2,186
Off Market
123 Deepwood Drive, Madison, CT 06443
0.23
$536,800
3
1.5
1,884
Off Market
50 Wheatstone Road, Madison, CT 06443
0.28
$1,293,900
4
2.5
4,402
Off Market
101 Winding Road, Madison, CT 06443
0.29
$525,400
4
2
1,848
Off Market
76 Bartlett Drive, Madison, CT 06443
0.33
$780,000
5
2.5
3,100
Recently Sold
81 Bartlett Drive, Madison, CT 06443
0.35
$630,000
4
2.5
2,088
Recently Sold
22 Scenic Road, Madison, CT 06443
0.31
$678,400
4
3
2,628
Off Market
10 Scenic Road, Madison, CT 06443
0.33
$685,000
5
3
2,210
Recently Sold
37 Sheffield Lane, Madison, CT 06443
0.34
$793,300
4
2.5
2,989
Off Market
22 Silo Hill, Madison, CT 06443
0.42
$1,200,300
5
3.5
3,882
Off Market
579 Opening Hill Road, Madison, CT 06443
0.38
$810,000
5
3.5
2,380
Off Market

Local Information

  • Map ViewExplore the area around 27 Winding Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
0.95 acre lot
2,152 sqft
$296/sqft
Garage

About this House

So many new big ticket items, you'll be able to move in with major peace of mind. Central Air, furnace, FIFTY gallon hot water heater, and 330 gallon oil tank, along with the fridge and stove - all new. This hot water heater has a refresh rate that will never leave you in a cold shower, all in your newly remodeled full bath. You'll be the owner of the house that everyone loves to gather at. Starting in your beautifully updated eat in kitchen, or maybe the dining room with two large openings to the kitchen - giving a very connected feel. Maybe you'll be in the large family room with a nice fire to create the perfect ambiance. There's a full bath plumbed and waiting to be finished just off the kitchen to bring the total full baths to 3. All of this with 3 great sized bedrooms, a huge laundry room, a large shed with a roll up door and a carport. Plenty of storage space, entertainment space, updates, this house has it all. There's just too much to list, so make your appointment and make your offer!
27 Winding Rd, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,152 sqft single-family home built in 1968. It last sold for $449,000 on Aug 17, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $636,100, with a rent estimate of $4,126/month.

Home Details for 27 Winding Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.95 acres

Price and Tax history

DateEventPrice
Aug 17, 2021
Source: Smart MLS #170413006
Sold
$449,000
Jun 26, 2021
Source: William Raveis Real Estate, Mortgage & Insurance #170413006
Pending
$449,000
Jun 22, 2021
Source: William Raveis Real Estate, Mortgage & Insurance #170413006
Listed For Sale
$449,000
Nov 5, 2020
Source: Agent Provided
ListingRemoved
$419,000
Oct 30, 2020
Source: Agent Provided
Listed For Sale
$419,000

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 27 Winding Rd

  • What is 27 Winding Rd estimated to be worth?
    Trulia's estimated value for 27 Winding Rd in Madison, CT is $636,100.
  • What is the price history for 27 Winding Rd?
    27 Winding Rd in Madison, CT last sold for $449,000 in August 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 27 Winding Rd have air conditioning?
    Yes, 27 Winding Rd in Madison, CT has air conditioning.
  • Does 27 Winding Rd have laundry facilities?
    Yes, 27 Winding Rd in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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