1089 Boston Post Rd, Madison, CT 06443
OFF MARKET

1089 Boston Post Rd
Madison, CT 06443

  • 7 Beds
  • 7.5 Baths
  • 9,960 sqft (on 5.83 acres)

$2,577,700

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $17,508/mo*
Refinance Your Home

$2,577,700

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $17,508/mo*
Refinance Your Home
7 Beds
7.5 Baths
9,960 sqft
(on 5.83 acres)

Local Information

  • Map ViewExplore the area around 1089 Boston Post Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

A RARE OPPORTUNITY TO OWN AN EXCEPTIONAL ESTATE. This family home is situated on 5.83 acres and features 7 bedrooms, 6 full bathrooms, 3 half bathrooms, a media room, 2 offices (one with 1/2 bath), a full walk-up attic and a basement (with 10' ceilings) that is the footprint of the home. A portion of the first floor could be converted into an in-law or nanny suite very easily. Situated on over 5 acres of land, this stunning home was built in 2005 with every comfort in mind. The gracious 2 story family room is the "hub" of the "U" shaped home. There are 10' ceilings, radiant heat throughout the kitchen and living room, the fireplace was custom and houses 2 gas fireplaces (one on 1st floor, one on 2nd floor), there are 7 zones of heat and a 3 car heated garage. The grounds host a Rissolo tennis court, a gunite pool with an infinity spa surrounded by blue stone. If you enjoy entertaining family, friends or business associates, this unique Madison property, which is less than 500 yards to the Long Island Sound, the Hammonasset State Park, and only steps to the new Shoreline Greenway Trail, may be for you. Enjoy swimming, tennis or relaxing on a well manicured private 1 acre yard. Finally, as an added bonus, there is an 1150SF 3 bedroom income producing rental cottage (annual lease is currently in place). The sophisticated buyer will appreciate this unique investment opportunity, while living in a one of a kind peaceful, beautiful setting.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

Home Details for 1089 Boston Post Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OtherAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
AtticNumber of Rooms: 14Types of Rooms: Library
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Other

Exterior Features

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

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 5.83 acres

Price History for 1089 Boston Post Rd

DatePriceEventSource
07/17/2018$1,699,000ListingRemovedAgent Provided
05/03/2018$1,699,000PriceChange
Agent Provided
01/17/2017$1,999,000Listed For SaleAgent Provided
12/08/2016$2,499,000ListingRemovedAgent Provided
08/10/2016$315,000Sold
N/A
06/03/2016$2,499,000PriceChange
Agent Provided
05/18/2016$2,899,000PriceChange
Agent Provided
02/01/2016$2,450,000Listed For SaleAgent Provided
12/15/2015$2,599,000ListingRemovedAgent Provided
05/14/2015$2,599,000PriceChange
Agent Provided
06/10/2014$2,999,000PriceChange
Agent Provided
02/14/2014$3,300,000Listed For SaleAgent Provided
11/17/2003$800,000Sold
N/A

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$46,782
Assessment$2,085,700
Home facts updated by county records

Comparable Sales for 1089 Boston Post Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
123 Liberty Street, Madison, CT
0.19
Single-Family Home
$1,600,000
12/30/25
4
3.5
4,988
15 Saxon Road, Madison, CT
0.16
Single-Family Home
$855,000
07/25/25
4
3
2,896
166 Bishop Lane, Madison, CT
0.08
Single-Family Home
$900,000
11/14/25
3
3
2,968
40 Hull Road, Madison, CT
0.44
Single-Family Home
$825,000
05/14/26
4
3
3,462
12 Stanton Court, Madison, CT
0.44
Single-Family Home
$1,360,000
10/27/25
4
3.5
5,219
37 Lovers Lane, Madison, CT
0.58
Single-Family Home
$1,100,000
06/15/26
5
4.5
3,194
16 Forest Hills Drive, Madison, CT
0.59
Single-Family Home
$815,000
03/26/26
5
3
3,992
23 Forest Hills Drive, Madison, CT
0.62
Single-Family Home
$745,000
10/20/25
5
3.5
2,564
14 Horseshoe Lane, Madison, CT
0.51
Single-Family Home
$715,200
11/10/25
3
2.5
2,283
79 Acorn Road, Madison, CT
0.60
Single-Family Home
$645,000
05/27/26
3
2.5
2,352

Nearby homes

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Assigned Schools

These are the assigned schools for 1089 Boston Post 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
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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
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  • 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

6 pet-friendly rentals in Madison, CT

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6 rentals with a garage in Madison, CT

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22 rentals with air conditioning in Madison, CT

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22 rentals with a washer/dryer in Madison, CT

Homes for sale near 1089 Boston Post Rd

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Off Market Homes Near 1089 Boston Post Rd

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1089 Boston Post Rd, Madison, CT 06443 is a 7 bedroom, 9 bathroom, 9,960 sqft single-family home built in 2005. This property is not currently available for sale. 1089 Boston Post Rd was last sold on Aug 10, 2016 for $315,000. The current Trulia Estimate for 1089 Boston Post Rd is $2,577,700.