144 Windsor Ct, Madison, CT 06443
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Property image
OFF MARKET

144 Windsor Ct
Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 3,800 sqft (on 0.58 acres)

$1,222,300

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $8,368/mo*
Refinance Your Home

$1,222,300

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $8,368/mo*
Refinance Your Home
4 Beds
2 Baths
3,800 sqft
(on 0.58 acres)

Local Information

  • Map ViewExplore the area around 144 Windsor Ct.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Enjoy gracious entertaining and comfortable family living in this finely appointed Colonial located in Madisons highly soughtafter Highgate community A keen sense of style and sophistication is evident from the moment one approaches this exceptional home set on 58 beautifully landscaped acres in an established cul de sac neighborhood of fine homes Casual elegance abounds throughout the home which affords nearly 3800 square feet of living space plus the added bonus of a finished lower level With four bedrooms two full and two half baths there is ample room for a growing family Hardwood floors high ceilings and an abundance of windows lend a bright and airy atmosphere to the homes open floor plan while soft hues enhance the tasteful dcor The versatile layout gives plenty of options for entertaining and leisure The formal dining room is accented with tray ceiling picture frame moldings and bay window Pocket French doors open to a gracious living room boasting custom builtins surrounding a charming window seat A den with bay window is ideal as a private study The heart of the home lies in the wonderful open Great room and kitchen A perfect spot for relaxing with family and friends or spending a quiet evening at home the Great room is anchored by a handsome fireplace flanked by tall windows Theeatin kitchen leaves nothing to be desired among a center island with breakfast bar granite countersdouble ovens gas stove wine cooler and an enormous pantry French doors open to a screened porch with a beautiful mahogany floor and builtin speakers A delightful patio extends the living space to the outdoors For leisure and recreation the beautifully finished lower level has something for everyone It is complete with a living room with builtins play room with shelved closets for games and toys French doors to an exercise room a seperate billiard room a lovely half bath and great storage space A convenient upper level laundry room and attached two car garage round out this distinguis
144 Windsor Ct, Madison, CT 06443 is a 4 bedroom, 2 bathroom, 3,800 sqft single-family home built in 2002. It last sold for $729,000 on May 14, 2010. It is currently off market. The Trulia Estimate is $1,222,300, with a rent estimate of $4,555/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 144 Windsor Ct

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.58 acres

Price History for 144 Windsor Ct

DatePriceEventSource
01/11/2011$749,000ListingRemovedAgent Provided
08/27/2010$749,000Listed For SaleAgent Provided
05/14/2010$729,000Sold
Smart MLS #M9120431
01/30/2010$749,000Listed For SaleAgent Provided
02/09/2004$670,000Sold
N/A
08/26/2002$584,750Sold
Smart MLS #M9069325

Market trends in Madison

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
69
4MoM
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Property Tax and Assessment

Year2025
Tax$12,969
Assessment$578,200
Home facts updated by county records

Comparable Sales for 144 Windsor Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
743 Green Hill Road, Madison, CT
0.35
Single-Family Home
$650,000
04/24/26
4
3.5
2,523
696 Green Hill Road, Madison, CT
0.45
Single-Family Home
$888,000
04/24/26
4
2.5
2,857
24 Grouse Lane, Madison, CT
0.53
Single-Family Home
$770,000
07/31/25
3
2
2,356
691 Green Hill Road, Madison, CT
0.48
Single-Family Home
$590,000
10/01/25
3
1.5
1,663
0 Tamarack Lane Lot 23, Guilford, CT
0.72
Single-Family Home
$757,229
03/02/26
3
2.5
2,075
0 Tamarack Lane Lot 19, Guilford, CT
0.72
Single-Family Home
$715,666
04/15/26
3
2.5
1,708
0 Tamarack Lane Lot 12, Guilford, CT
0.72
Single-Family Home
$795,014
07/21/25
3
2.5
2,200
0 Tamarack Lane Lot 20, Guilford, CT
0.72
Single-Family Home
$795,399
09/10/25
3
2.5
2,200
15 Buttonball Lane, Madison, CT
0.76
Single-Family Home
$900,000
11/17/25
4
3
2,576
85 Fawn Brook Circle, Madison, CT
0.71
Single-Family Home
$1,030,000
06/18/26
4
2.5
2,976

Nearby homes

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Assigned Schools

These are the assigned schools for 144 Windsor Ct.
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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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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

7 pet-friendly rentals in Madison, CT

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Homes for sale near 144 Windsor Ct

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Off Market Homes Near 144 Windsor Ct

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