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

$2,243,200

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 4,919 sqft (on 1.64 acres)

385 Boston Post Rd, Madison, CT 06443

Madison Center
Est. Refi. Payment $15,613/mo*
Refinance Your Home
Currently Off Market - Sold Aug 21, 2020 for $1,495,000

Home Value

Trulia Estimate
$2.24M
Since last month
Increased$8K (+0.3%)
Since last year
Increased$123K (+5.9%)
Since last sale
Increased$734K (+49.1%)
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 +91% in the last 10 years
MonthEstimated value
2026
August 2026$2.23M
July 2026$2.22M
June 2026$2.31M
May 2026$2.25M
April 2026$2.19M
March 2026$2.16M
February 2026$2.11M
January 2026$2.07M
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
0.09
Single-Family Home
$1,400,000
05/01/26
4
5
3,779
31 Stony Lane Lot 3 Road, Madison, CT
0.21
Single-Family Home
$1,875,000
06/29/26
4
3.5
4,565
31 Stony Lane Lot 6 Road, Madison, CT
0.17
Single-Family Home
$2,001,250
01/28/26
4
3.5
3,400
43 Burcam Drive, Madison, CT
0.36
Single-Family Home
$941,000
10/01/25
3
3
2,393
584 Boston Post Road, Madison, CT
0.84
Single-Family Home
$1,525,000
10/01/25
5
5.5
6,278
513 Boston Post Road, Madison, CT
0.53
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
519 Boston Post Road, Madison, CT
0.56
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
10 Middle Beach Road West, Madison, CT
0.86
Single-Family Home
$3,775,000
05/19/26
6
6
6,074
55 Island Avenue, Madison, CT
0.92
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
36 Cedar Lane, Madison, CT
1.10
Single-Family Home
$2,310,000
07/15/26
4
4
3,926

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
395 Boston Post Road, Madison, CT 06443
0.09
$1,400,000
4
5
3,779
Recently Sold
374 Boston Post Road, Madison, CT 06443
0.14
$1,520,400
5
3.5
3,060
Off Market
27 Sterling Park, Madison, CT 06443
0.20
$937,100
3
2.5
2,458
Off Market
31 Stony Lane Lot 6 Road, Madison, CT 06443
0.17
$2,001,250
4
3.5
3,400
Recently Sold
31 Stony Lane Lot 3 Road, Madison, CT 06443
0.21
$1,875,000
4
3.5
4,565
Recently Sold
348 Boston Post Road, Madison, CT 06443
0.24
$1,693,800
3
2.5
2,100
Off Market
30 Overlook Drive, Madison, CT 06443
0.30
$1,248,200
4
2.5
2,855
Off Market
51 Lantern Hill, Madison, CT 06443
0.32
$3,515,500
5
6.5
6,000
Off Market
23 Lantern Hill, Madison, CT 06443
0.32
-
-
-
-
Off Market
37 Lantern Hill, Madison, CT 06443
0.32
$2,089,900
4
4.5
5,400
Off Market
33 Overlook Drive, Madison, CT 06443
0.33
$1,848,400
6
4.5
4,903
Off Market
43 Fort Path Road, Madison, CT 06443
0.35
$503,000
3
1.5
1,346
Recently Sold

Local Information

  • Map ViewExplore the area around 385 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
1997
Lot Size
1.64 acres
Living Area
4,919 sqft
Price/Sqft
$456
Parking
Garage

About this House

Stunning One of a kind, Mediterranean style home located in the desirable and private neighborhood of Leatherman's Hill, conveniently close to Madison town, beaches and train. The property is situated on a cul de sac, with park like grounds and custom designed outside lighting, giving it a serene estate like feeling. The home features luxurious finishes and many architectural details, including coffered ceilings, built- in book shelves, family/media room, high ceilings and sun filled rooms, all leading to the secluded outside oasis. The outdoor sanctuary includes an in ground Gunite pool with a waterfall and hot tub, along with a garden area to use for entertaining or as your own retreat. The home offers an open floor plan with spacious rooms, exquisite detailing and numerous banks of windows, a light filled center hall that has 12 ft ceilings and graceful curving stairway, making this an unparalleled estate. This 5 bedroom, 4.1 bath home, has a 3rd floor bonus room, which provides ample space for family and guests. The master suite has cathedral ceilings, luxurious bath and its own private balcony overlooking the grounds and pool area. There is a 4 car garage with custom designed cedar doors with chrome inlay and a unique storage area all specifically designed for the car enthusiast.
385 Boston Post Rd, Madison, CT 06443 is a 5 bedroom, 5 bathroom, 4,919 sqft single-family home in Madison Center, built in 1997. It last sold for $1,495,000 on Aug 21, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,243,200, with a rent estimate of $7,915/month.

Home Details for 385 Boston Post Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Pantry, Recreation Room, Sun RoomWet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: StuccoGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1997Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.64 acres

Price and Tax history

DateEventPrice
Aug 21, 2020
Source: Smart MLS #170309280
Sold
$1,495,000
Jun 30, 2020
Source: Agent Provided
Pending
$1,495,000
Jun 24, 2020
Source: Agent Provided
Listed For Sale
$1,495,000
Nov 30, 2019
Source: Agent Provided
ListingRemoved
$1,495,000
Sep 11, 2019
Source: Agent Provided
PriceChange
$1,495,000
Price decreased by 6%

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

Neighborhood Overview

Madison Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Madison Center

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say it's dog friendly

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 50 % Say there are community events

  • 50 % Say streets are well-lit

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

LGBTQ Local Legal Protections

Frequently asked questions about 385 Boston Post Rd

  • What is 385 Boston Post Rd estimated to be worth?
    Trulia's estimated value for 385 Boston Post Rd in Madison, CT is $2,243,200.
  • What is the price history for 385 Boston Post Rd?
    385 Boston Post Rd in Madison, CT last sold for $1,495,000 in August 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 385 Boston Post Rd have air conditioning?
    Yes, 385 Boston Post Rd in Madison, CT has air conditioning.
  • Does 385 Boston Post Rd have a pool?
    Yes, 385 Boston Post Rd in Madison, CT has a pool.

Explore by feature - Pet Friendly

8 pet-friendly rentals in Madison, CT

Explore by feature - Air Conditioning

24 rentals with air conditioning in Madison, CT

Explore by feature - Washer/dryer

27 rentals with a washer/dryer in Madison, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 385 Boston Post Rd

Skip to last item
Skip to first item

Homes for sale near 385 Boston Post Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item