37 Five Fields Rd, Madison, CT 06443
OFF MARKET

37 Five Fields Rd
Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,100 sqft (on 1.39 acres)

$675,300

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $4,735/mo*
Refinance Your Home

$675,300

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $4,735/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,100 sqft
(on 1.39 acres)

Local Information

  • Map ViewExplore the area around 37 Five Fields Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1969
Lot Size
1.39 acres
Living Area
3,100 sqft
Price/Sqft
$218
Parking
Garage

About this House

Welcome to Five Fields. One of Madison's most cherished neighborhoods. Just minutes to Madison's town Green, gorgeous beaches and all the shoreline has to offer. This charming home has a Large inviting living room with gas fireplace, 4 generously sized bedrooms, 2.5 Totally remodeled baths, and a large bonus room in the lower level with another fireplace. The master suite has a private master bath and large walk in closets. There are beautiful hardwood floors in the main living area and all the bedrooms. The oversized deck and private back yard are great for barbeques and entertaining guest and family. There's a mud room and spacious 2 car garage just off the kitchen with plenty of storage. Newer roof and city water. Come see this wonderful home so close to all that Madison has to offer.
37 Five Fields Rd, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 3,100 sqft single-family home built in 1969. It last sold for $330,000 on Sep 20, 2019. It is currently off market. The Trulia Estimate is $675,300, with a rent estimate of $5,056/month.

Home Details for 37 Five Fields Rd

Interior Features

Heating & Cooling
Heating: Radiant, ElectricCooling System: OtherHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: Split-level

Lot Information

Lot Area: 1.39 acres

Price History for 37 Five Fields Rd

DatePriceEventSource
09/20/2019$330,000Sold
N/A
08/01/2019$339,000PendingAgent Provided
07/16/2019$339,000PriceChange
Agent Provided
06/03/2019$349,000PriceChange
Agent Provided
05/07/2019$359,000PriceChange
Agent Provided
04/23/2019$369,900Listed For SaleAgent Provided
07/03/2018$369,900ListingRemovedAgent Provided
06/18/2018$369,900PriceChange
Agent Provided
05/29/2018$379,900PriceChange
Agent Provided
05/08/2018$389,900PriceChange
Agent Provided
04/26/2018$399,900Listed For SaleAgent Provided
05/25/2012$360,000Sold
N/A
04/12/2012$369,900Listed For SaleAgent Provided

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
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Property Tax and Assessment

Year2025
Tax$7,985
Assessment$356,000
Home facts updated by county records

Comparable Sales for 37 Five Fields Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
221 Duck Hole Road, Madison, CT
0.11
Single-Family Home
$600,000
07/17/26
3
3
2,068
123 Five Fields Road, Madison, CT
0.18
Single-Family Home
$860,000
08/29/25
5
2.5
3,664
173 Duck Hole Rd, Madison, CT
0.20
Single-Family Home
$261,900
06/22/26
3
2
1,463
31 Meadowbrook Road, Madison, CT
0.57
Single-Family Home
$1,005,000
08/28/25
4
2.5
3,360
190 Wildcat Road, Madison, CT
0.48
Single-Family Home
$1,260,444
08/07/26
3
2.5
2,451
4 Van Dyke Lane, Clinton, CT
0.38
Single-Family Home
$459,000
03/06/26
3
2
1,104
318 Horsepond Road, Madison, CT
0.68
Single-Family Home
$725,000
12/22/25
4
2.5
2,622
29 Flintlock Road, Madison, CT
0.65
Single-Family Home
$711,000
08/21/25
4
1.5
2,458
6 Yankee Peddler Path, Madison, CT
0.80
Single-Family Home
$660,000
06/12/26
4
2
2,642
107 Horse Pond Road, Madison, CT
0.54
Single-Family Home
$430,000
06/12/26
3
2
864

Nearby homes

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Assigned Schools

These are the assigned schools for 37 Five Fields Rd.
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
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Apartments for Rent

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Explore by feature - Pet Friendly

8 pet-friendly rentals in Madison, CT

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23 rentals with air conditioning in Madison, CT

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21 rentals with a washer/dryer in Madison, CT

Homes for sale near 37 Five Fields Rd

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Off Market Homes Near 37 Five Fields Rd

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Frequently asked questions about 37 Five Fields Rd

  • What is 37 Five Fields Rd estimated to be worth?
    Trulia's estimated value for 37 Five Fields Rd in Madison, CT is $675,300.
  • What is the price history for 37 Five Fields Rd?
    37 Five Fields Rd in Madison, CT last sold for $330,000 in September 2019.
  • 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 $763K.
  • Does 37 Five Fields Rd have air conditioning?
    Yes, 37 Five Fields Rd in Madison, CT has air conditioning.
  • How big is the lot at 37 Five Fields Rd?
    The lot at 37 Five Fields Rd in Madison, CT is about 1.4 acres.