321 Boston Post Rd, Madison, CT 06443
Property image
Property image
OFF MARKET

321 Boston Post Rd
Madison, CT 06443

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

$1,898,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $13,156/mo*
Refinance Your Home

$1,898,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $13,156/mo*
Refinance Your Home
5 Beds
6.5 Baths
3,938 sqft
(on 11.10 acres)

Home Value

Trulia Estimate
$1.9M
Since last month
Increased$81K (+4.4%)
Since last year
Increased$179K (+10.4%)
Since last sale
Increased$922K (+94.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -20% in the last 10 years
MonthEstimated value
2026
August 2026$1.9M
July 2026$1.82M
June 2026$2M
May 2026$1.92M
April 2026$1.86M
March 2026$1.82M
February 2026$1.77M
January 2026$1.7M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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 3 Road, Madison, CT
0.09
Single-Family Home
$1,875,000
06/29/26
4
3.5
4,565
31 Stony Lane Lot 6 Road, Madison, CT
0.13
Single-Family Home
$2,001,250
01/28/26
4
3.5
3,400
53 Governors Way, Madison, CT
0.55
Single-Family Home
$1,365,000
08/26/25
4
4
4,145
46 Beach Ave, Madison, CT
0.68
Single-Family Home
$800,000
06/03/26
3
2
2,427
35 Governors Way, Madison, CT
0.52
Single-Family Home
$604,000
05/11/26
4
2
2,520
43 Burcam Drive, Madison, CT
0.64
Single-Family Home
$941,000
10/01/25
3
3
2,393
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
513 Boston Post Road, Madison, CT
0.83
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
31 Stony Lane Lot 3 Road, Madison, CT 06443
0.09
$1,875,000
4
3.5
4,565
Recently Sold
31 Stony Lane Lot 6 Road, Madison, CT 06443
0.13
$2,001,250
4
3.5
3,400
Recently Sold
348 Boston Post Road, Madison, CT 06443
0.19
$1,680,700
3
2.5
2,100
Off Market
287 Boston Post Road, Madison, CT 06443
0.22
$852,400
3
2
2,093
Off Market
374 Boston Post Road, Madison, CT 06443
0.27
$1,540,400
5
3.5
3,060
Off Market
27 Maplewood Lane, Madison, CT 06443
0.26
$768,600
3
2
1,938
Off Market
273 Boston Post Road, Madison, CT 06443
0.28
$1,161,300
5
3.5
3,318
Off Market
23 Esterly Farms Road #23, Madison, CT 06443
0.28
$425,100
2
2.5
1,606
Off Market
9 Neck Road, Madison, CT 06443
0.31
$2,074,200
-
-
-
Off Market
395 Boston Post Road, Madison, CT 06443
0.35
$1,400,000
4
5
3,779
Recently Sold
9 Shorelands Drive, Madison, CT 06443
0.34
$2,127,900
4
3.5
3,125
Off Market
Lot #3 Shorelands Drive, Madison, CT 06443
0.34
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 321 Boston Post Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1806
Lot Size
11.1 acres
Living Area
3,938 sqft
Price/Sqft
$482
Parking
Garage

About this House

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.
321 Boston Post Rd, Madison, CT 06443 is a 5 bedroom, 7 bathroom, 3,938 sqft single-family home built in 1806. It last sold for $975,000 on Feb 10, 2020. It is currently off market. The Trulia Estimate is $1,898,600, with a rent estimate of $6,828/month.

Home Details for 321 Boston Post Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Forced AirAir 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 and Tax history

DateEventPrice
Feb 10, 2020
Source: Smart MLS #170201277
Sold
$975,000
Sep 11, 2019
Source: Agent Provided
PriceChange
$1,250,000
Price decreased by 14%
Jun 21, 2019
Source: Agent Provided
Listed For Sale
$1,450,000
May 26, 2017
Source: Agent Provided
ListingRemoved
$1,750,000
Jan 9, 2017
Source: Agent Provided
PriceChange
$1,750,000
Price decreased by 21%

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 321 Boston Post Rd

  • What is 321 Boston Post Rd estimated to be worth?
    Trulia's estimated value for 321 Boston Post Rd in Madison, CT is $1,898,600.
  • What is the price history for 321 Boston Post Rd?
    321 Boston Post Rd in Madison, CT last sold for $975,000 in February 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 $710K. That is down $53.67K from the prior month.
  • Does 321 Boston Post Rd have air conditioning?
    Yes, 321 Boston Post Rd in Madison, CT has air conditioning.
  • Does 321 Boston Post Rd have a pool?
    Yes, 321 Boston Post Rd in Madison, CT has a pool.

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