29 Five Fields Rd, Madison, CT 06443
Property image
Property image
OFF MARKET

29 Five Fields Rd
Madison, CT 06443

  • 5 Beds
  • 3 Baths
  • 3,306 sqft (on 1.04 acres)

$735,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $5,149/mo*
Refinance Your Home

$735,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $5,149/mo*
Refinance Your Home
5 Beds
3 Baths
3,306 sqft
(on 1.04 acres)

Local Information

  • Map ViewExplore the area around 29 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
1.04 acres
Living Area
3,306 sqft
Price/Sqft
$222
Parking
Garage

About this House

Welcome to one of Madison's most desired neighborhoods- Five Fields!This Embankment Colonial has room for everyone and everything.Potential in-law suite with private bedroom, full bath, living room and rec room on first floor. Or, use as work from home space, teen hang out, exercise space- whatever suits your needs, the space is here. As you head up the staircase to the Main floor, you'll notice beautifully restored and refinished wider plank Cherrywood floors, recessed lighting, enormous floor to ceiling (newer) windows pouring in natural light and a cozy gas log fireplace.The Formal dining room has a beautiful bay window overlooking the ample decking and back gardens.Adjacent to both rooms is the recently renovated eat-in kitchen, complete with Granite Island with seating, built-in breakfast nook,Quartzite counters around the perimeter, Marble backsplash and more. Sliders take you out to the one-of-a-kind Antique sunroom. 6 sets of Antique doors open up to richly stained decking that runs the width of the home.Wonderful indoor/outdoor entertaining space!Laundry room/pantry space off the kitchen.Down the hallway, is an updated double sink full bathroom, 3 more bedrooms with great storage and light, and the Master bedroom with a Full bath, walk-in closet, and access to the back deck.Association field across the street,where people can gather and play. Picnics and Holiday Parties are also part of this community as well a short distance to the popular Town Campus sledding hill!
29 Five Fields Rd, Madison, CT 06443 is a 5 bedroom, 3 bathroom, 3,306 sqft single-family home built in 1969. It last sold for $472,000 on Aug 6, 2020. It is currently off market. The Trulia Estimate is $735,400, with a rent estimate of $5,243/month.

Home Details for 29 Five Fields Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Dining Room
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: StoneGardenPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.04 acres

Building

Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Price History for 29 Five Fields Rd

DatePriceEventSource
08/06/2020$472,000Sold
N/A
06/07/2020$465,000Listed For SaleAgent Provided
11/22/2019$480,000ListingRemovedAgent Provided
05/16/2019$480,000PriceChange
Agent Provided
03/20/2019$499,000Listed For SaleAgent Provided
09/17/2014$309,000Sold
Smart MLS #M9148322
06/09/2014$329,600Listed 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$8,384
Assessment$373,800
Home facts updated by county records

Comparable Sales for 29 Five Fields Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
123 Five Fields Road, Madison, CT
0.17
Single-Family Home
$860,000
08/29/25
5
2.5
3,664
221 Duck Hole Road, Madison, CT
0.13
Single-Family Home
$600,000
07/17/26
3
3
2,068
173 Duck Hole Rd, Madison, CT
0.19
Single-Family Home
$261,900
06/22/26
3
2
1,463
31 Meadowbrook Road, Madison, CT
0.60
Single-Family Home
$1,005,000
08/28/25
4
2.5
3,360
26 Flintlock Road, Madison, CT
0.73
Single-Family Home
$775,000
02/09/26
5
3
2,904
4 Van Dyke Lane, Clinton, CT
0.36
Single-Family Home
$459,000
03/06/26
3
2
1,104
29 Flintlock Road, Madison, CT
0.67
Single-Family Home
$711,000
08/21/25
4
1.5
2,458
190 Wildcat Road, Madison, CT
0.50
Single-Family Home
$1,260,444
08/07/26
3
2.5
2,451
318 Horsepond Road, Madison, CT
0.70
Single-Family Home
$725,000
12/22/25
4
2.5
2,622
56 Buttonball Ln, Madison, CT
0.96
Single-Family Home
$735,000
10/30/25
5
2.5
3,230

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Five Fields Rd.
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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
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  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
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  • 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 29 Five Fields Rd

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Off Market Homes Near 29 Five Fields Rd

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Frequently asked questions about 29 Five Fields Rd

  • What is 29 Five Fields Rd estimated to be worth?
    Trulia's estimated value for 29 Five Fields Rd in Madison, CT is $735,400.
  • What is the price history for 29 Five Fields Rd?
    29 Five Fields Rd in Madison, CT last sold for $472,000 in August 2020.
  • 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 29 Five Fields Rd have air conditioning?
    Yes, 29 Five Fields Rd in Madison, CT has air conditioning.
  • Does 29 Five Fields Rd have laundry facilities?
    Yes, 29 Five Fields Rd in Madison, CT has in-unit laundry.