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

$953,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,054 sqft (on 40,075.20 acres)

248 Boston Post Rd, Madison, CT 06443

Refinance Your Home
Currently Off Market - Sold Aug 2, 2021 for $710,000

Home Value

Trulia Estimate
$954K
Since last month
Decreased$13K (-1.3%)
Since last year
Increased$23K (+2.5%)
Since last sale
Increased$241K (+34%)
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 increased by +140% in the last 10 years
MonthEstimated value
2026
August 2026$951K
August 2026$951K
July 2026$964K
June 2026$985K
May 2026$948K
April 2026$952K
March 2026$935K
February 2026$910K
January 2026$922K
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
35 Governors Way, Madison, CT
0.13
Single-Family Home
$604,000
05/11/26
4
2
2,520
22 Nathans Lane, Madison, CT
0.32
Single-Family Home
$526,000
03/30/26
3
2
2,582
46A Beach Avenue, Madison, CT
0.37
Single-Family Home
$800,000
06/01/26
3
2
1,504
42 Neck Road, Madison, CT
0.10
Single-Family Home
$520,000
05/22/26
3
1.5
1,288
33 River Edge Farms Road, Madison, CT
0.43
Single-Family Home
$1,750,000
08/31/26
3
2.5
2,416
115 River Edge Farms Road, Madison, CT
0.50
Single-Family Home
$1,300,000
10/20/25
5
2.5
3,077
58 Neck Rd, Madison, CT
0.13
Single-Family Home
$690,000
07/14/26
3
2
1,477
101 Sandelwood Drive, Madison, CT
0.47
Single-Family Home
$530,000
08/07/26
3
2.5
2,196
99 Garnet Park Road, Madison, CT
0.50
Single-Family Home
$1,710,000
08/31/26
4
2.5
2,957
73 Garnet Park Road, Madison, CT
0.38
Single-Family Home
$925,000
07/22/26
3
2
2,166

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
42 Neck Road, Madison, CT 06443
0.10
$520,000
3
1.5
1,288
Recently Sold
236 Boston Post Road, Madison, CT 06443
0.07
$789,500
4
3
2,998
Off Market
61 Governors Way, Madison, CT 06443
0.13
$1,651,500
4
4
6,010
Off Market
Lot #2 Shorelands Drive, Madison, CT 06443
0.12
-
-
-
-
Off Market
Lot #3 Shorelands Drive, Madison, CT 06443
0.13
-
-
-
-
Off Market
35 Governors Way, Madison, CT 06443
0.13
$382,500
4
2
2,520
Foreclosure
18 Kelsey Place, Madison, CT 06443
0.17
$665,000
3
2
1,260
Recently Sold
273 Boston Post Road, Madison, CT 06443
0.14
$1,153,700
5
3.5
3,318
Off Market
9 Shorelands Drive, Madison, CT 06443
0.16
$2,127,900
4
3.5
3,125
Off Market
72 Neck Road, Madison, CT 06443
0.19
$747,100
3
2
1,581
Off Market
18 Lee Way, Madison, CT 06443
0.19
$588,800
2
2.5
858
Off Market
76 Neck Road, Madison, CT 06443
0.21
$749,900
3
2.5
1,459
Off Market

Local Information

  • Map ViewExplore the area around 248 Boston Post Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1709
40,075.2 acre lot
3,054 sqft
$312/sqft

About this House

Old world meets new world in Madison\'s historic Shelley House, circa 1709. Masterful renovation, 3054 SF, 4 BR, 2.1 BA, 4 FP, security system, central air, .92 acres. Flexible floorplan is perfect for home business (home occupation permit required.)
248 Boston Post Rd, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 3,054 sqft single-family home built in 1709. It last sold for $710,000 on Aug 2, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $953,700, with a rent estimate of $4,538/month.

Home Details for 248 Boston Post Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood

Property Information

Year Built
Year Built: 1709
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 40075.20 acres

Price and Tax history

DateEventPrice
Aug 2, 2021
Source: Smart MLS #170384672
Sold
$710,000
Apr 5, 2016
Source: N/A
Sold
$400,000
Feb 18, 2011
Source: Smart MLS #M9120364
Sold
$740,000
Dec 22, 2010
Source: Agent Provided
Pending
$795,000
Sep 2, 2010
Source: Agent Provided
PriceChange
$795,000
Price decreased by 8%

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 248 Boston Post Rd

  • What is 248 Boston Post Rd estimated to be worth?
    Trulia's estimated value for 248 Boston Post Rd in Madison, CT is $953,700.
  • What is the price history for 248 Boston Post Rd?
    248 Boston Post Rd in Madison, CT last sold for $710,000 in August 2021.
  • 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.
  • How big is the lot at 248 Boston Post Rd?
    The lot at 248 Boston Post Rd in Madison, CT is about 0.90 acres (39,204 sq ft).

Explore by feature - Pet Friendly

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