321 Boston Post Rd, Madison, CT 06443
OFF MARKET

321 Boston Post Rd
Madison, CT 06443

  • 5 Beds
  • 6.5 Baths
  • 3,938 sqft (on 11.10 acres)

$1,929,300

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $13,235/mo*
Refinance Your Home

$1,929,300

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $13,235/mo*
Refinance Your Home
5 Beds
6.5 Baths
3,938 sqft
(on 11.10 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome to one of Madison's truly magnificent properties. Built in 1806 this 4000+ square foot home is situated on 11 private acres, just west of the town center. Entering from the wraparound porch (a large portion screened-in) reveals the expansive main floor, all rooms featuring hardwood floors, ornate molding and woodwork, custom cabinetry, fireplaces, and other stylistic embellishments. Consider the butler's pantry, with its own Sub-Zero refrigerator drawers, dishwasher, and wall oven. Or the casual bar area known as "The Pub." The enormous kitchen is equipped with a professional-grade Viking gas range, 36" Sub-Zero fridge, and separate double-door freezers. The adjacent sitting area with gas fireplace and dining area add even more character. Highlighting the second floor is a gracious master bedroom and bath opening onto a private deck. Two additional bedrooms each have full baths. The third floor encompasses two bedrooms, full bath, and storage areas. The lower level includes a large entertainment area, home gym and full bath. Another fabulous world awaits outdoors, whether on the covered veranda off the kitchen, the rose garden, or the bluestone patio that boasts an incredible outdoor kitchen. Steps away is the pool area with a fully equipped pool house.
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
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 321 Boston Post Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Forced Air, OtherAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Interior Details
Number of Rooms: 13
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Other

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1806
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Lot Information

Lot Area: 11.10 acres

Price History for 321 Boston Post Rd

DatePriceEventSource
02/10/2020$975,000Sold
Smart MLS #170201277
09/11/2019$1,250,000PriceChange
Agent Provided
06/21/2019$1,450,000Listed For SaleAgent Provided
05/26/2017$1,750,000ListingRemovedAgent Provided
01/09/2017$1,750,000PriceChange
Agent Provided
09/03/2016$2,225,000PriceChange
Agent Provided
06/10/2016$2,599,000Listed For SaleAgent Provided
07/28/1999$625,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$22,078
Assessment$984,300
Home facts updated by county records

Comparable Sales for 321 Boston Post Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
395 Boston Post Road, Madison, CT
0.35
Single-Family Home
$1,400,000
05/01/26
4
5
3,779
31 Stony Lane Lot 6 Road, Madison, CT
0.13
Single-Family Home
$2,001,250
01/28/26
4
3.5
3,400
50 Whedon Lane, Madison, CT
0.40
Single-Family Home
$1,667,000
06/17/25
3
3
2,724
53 Governors Way, Madison, CT
0.55
Single-Family Home
$1,365,000
08/26/25
4
4
4,145
61 Governors Way, Madison, CT
0.54
Single-Family Home
$1,585,000
08/22/25
4
4
6,010
114 Neck Road, Madison, CT
0.75
Single-Family Home
$972,000
06/20/25
4
2.5
3,068
43 Burcam Drive, Madison, CT
0.64
Single-Family Home
$941,000
10/01/25
3
3
2,393
16 Rockledge Drive, Madison, CT
0.66
Single-Family Home
$1,225,000
06/19/25
4
3
2,340
20 Cherry Lane, Madison, CT
0.80
Single-Family Home
$1,453,000
08/29/25
5
3.5
2,647
115 River Edge Farms Road, Madison, CT
0.90
Single-Family Home
$1,300,000
10/20/25
5
2.5
3,077

Nearby homes

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Assigned Schools

These are the assigned schools for 321 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 56 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 89 % 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

  • 13 % 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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321 Boston Post Rd, Madison, CT 06443 is a 5 bedroom, 7 bathroom, 3,938 sqft single-family home built in 1806. This property is not currently available for sale. 321 Boston Post Rd was last sold on Feb 10, 2020 for $975,000. The current Trulia Estimate for 321 Boston Post Rd is $1,929,300.