353 Boston Post Rd, Madison, CT 06443
OFF MARKET

353 Boston Post Rd
Madison, CT 06443

  • 5 Beds
  • 3 Baths
  • 2,904 sqft (on 17.12 acres)

$1,303,000

Trulia Estimate
as of Jun 26, 2026
Est. Refi. Payment $8,922/mo*
Refinance Your Home

$1,303,000

Trulia Estimate
as of Jun 26, 2026
Est. Refi. Payment $8,922/mo*
Refinance Your Home
5 Beds
3 Baths
2,904 sqft
(on 17.12 acres)

Local Information

  • Map ViewExplore the area around 353 Boston Post Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Barberry Hill Farm- this iconic property is offered for the first time in over a century! This almost eighteen-acre gem sits on the Boston Post Road directly across from the Madison Country Club's 13th & 14th holes, the Madison Surf Club's Lowrey playing fields, the Madison Surf Club beach, and less than 1 mile from the village center with its quaint shops and more. Walk to the beach and ride your bike to the village. The elegant 2,900 square foot, five bedroom, 3 bath colonial was built in 1910 by United States District Court for the Southern District of New York Judge Henry Warren Goddard, who famously presided over the Alger Hiss trial in 1949. The Goddard family has continuously inhabited the property for better than 100 years. The home sits atop one of the highest pieces of ground in southern Madison well set back from the stone wall lined roads. A two bedroom guest cottage, several barns and sheds and a pond complete the property. Currently an active working farm with seasonal farm stand and special events including weddings and Farm dinners, this idyllic setting begs for an imaginative buyer. With 517 feet of frontage on the Post Road and 1,345 feet on pastoral Stony Lane, property ideal for either residential development or as a private family compound or simply to maintain as a working farm. This amazing location can't be duplicated this close to the town & L.I. Sound. Twenty minutes to New Haven, 90 from NYC, approx 1 hr to Providence and Hartford airports.
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
No Info
Outdoor
Patio
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 353 Boston Post Rd

Interior Features

Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 10

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherPatio

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 17.12 acres

Price History for 353 Boston Post Rd

DatePriceEventSource
12/10/2019$5,650,000ListingRemovedAgent Provided
05/01/2019$5,650,000Listed For SaleAgent Provided
06/11/2013$630,000Sold
N/A
10/03/2008$850,000Sold
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$14,535
Assessment$648,000
Home facts updated by county records

Comparable Sales for 353 Boston Post Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
31 Stony Lane Lot 6 Road, Madison, CT
0.05
Single-Family Home
$2,001,250
01/28/26
4
3.5
3,400
35 Governors Way, Madison, CT
0.60
Single-Family Home
$604,000
05/11/26
4
2
2,520
395 Boston Post Road, Madison, CT
0.26
Single-Family Home
$1,400,000
05/01/26
4
5
3,779
43 Burcam Drive, Madison, CT
0.56
Single-Family Home
$941,000
10/01/25
3
3
2,393
108 Sandelwood Drive, Madison, CT
0.59
Single-Family Home
$475,000
09/05/25
3
2
2,640
46 Beach Ave, Madison, CT
0.74
Single-Family Home
$800,000
06/03/26
3
2
2,427
519 Boston Post Road, Madison, CT
0.77
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
22 Nathans Lane, Madison, CT
0.61
Single-Family Home
$526,000
03/30/26
3
2
2,582
513 Boston Post Road, Madison, CT
0.74
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
53 Governors Way, Madison, CT
0.63
Single-Family Home
$1,365,000
08/26/25
4
4
4,145

Nearby homes

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Assigned Schools

These are the assigned schools for 353 Boston Post Rd.
View nearby schools on GreatSchools
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
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  • 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
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  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
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  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
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  • 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"
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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
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  • 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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Homes for sale near 353 Boston Post Rd

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Off Market Homes Near 353 Boston Post Rd

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353 Boston Post Rd, Madison, CT 06443 is a 5 bedroom, 3 bathroom, 2,904 sqft single-family home built in 1910. This property is not currently available for sale. 353 Boston Post Rd was last sold on Jun 11, 2013 for $630,000. The current Trulia Estimate for 353 Boston Post Rd is $1,303,000.