109 Boston Post Road, Madison, CT 06443
OFF MARKET

$975,200

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,728 sqft (on 1 acre)

109 Boston Post Road, Madison, CT 06443

Est. Refi. Payment $7,144/mo*
Refinance Your Home
Currently Off Market - Sold Aug 14, 2025 for $935,570

Home Value

Trulia Estimate
$975K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$39K (+4.2%)
Since last sale
Increased$43K (+4.6%)
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 increased by +55% in the last 10 years
MonthEstimated value
2026
September 2026$979K
August 2026$974K
July 2026$966K
June 2026$968K
May 2026$956K
April 2026$951K
March 2026$959K
February 2026$959K
January 2026$962K
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
108 Boston Post Road, Madison, CT
0.03
Single-Family Home
$535,000
02/13/26
3
2
1,700
41 Allison Drive, Madison, CT
0.42
Single-Family Home
$1,225,000
02/18/26
3
2.5
3,609
22 Nathans Lane, Madison, CT
0.38
Single-Family Home
$526,000
03/30/26
3
2
2,582
70 Wildwood Avenue, Madison, CT
0.34
Single-Family Home
$695,000
03/31/26
3
3
1,916
40 Green Acres Drive, Madison, CT
0.15
Single-Family Home
$537,500
10/07/25
3
1.5
1,864
19 Green Acres Drive, Madison, CT
0.11
Single-Family Home
$660,000
05/04/26
4
2
1,903
101 Sandelwood Drive, Madison, CT
0.40
Single-Family Home
$530,000
08/07/26
3
2.5
2,196
33 River Edge Farms Road, Madison, CT
0.68
Single-Family Home
$1,750,000
08/31/26
3
2.5
2,416
99 Garnet Park Road, Madison, CT
0.49
Single-Family Home
$1,710,000
08/31/26
4
2.5
2,957
73 Garnet Park Road, Madison, CT
0.47
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
108 Boston Post Road, Madison, CT 06443
0.03
$535,000
3
2
1,700
Recently Sold
19 Green Acres Drive, Madison, CT 06443
0.11
$660,000
4
2
1,903
Recently Sold
40 Green Acres Drive, Madison, CT 06443
0.15
$559,000
3
1.5
1,864
Off Market
94 Boston Post Road, Madison, CT 06443
0.12
$677,600
2
2.5
1,668
Off Market
96 Boston Post Road, Madison, CT 06443
0.14
$795,800
4
2.5
2,296
Off Market
52 Sandlewood Drive, Madison, CT 06443
0.21
$679,700
3
2.5
2,438
Off Market
30 Sandlewood Drive, Madison, CT 06443
0.23
$782,000
4
2.5
2,836
Off Market
67 Boston Post Road #8, Madison, CT 06443
0.21
$587,500
2
2.5
1,816
Recently Sold
67 Boston Post Road #13, Madison, CT 06443
0.21
$722,100
2
2
2,057
Off Market
56 Sandlewood Drive, Madison, CT 06443
0.25
$799,400
4
2.5
3,212
Off Market
45 Sandlewood Drive, Madison, CT 06443
0.25
$556,900
3
2
1,992
Off Market

Local Information

  • Map ViewExplore the area around 109 Boston Post Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1854
1 acre lot
2,728 sqft
$357/sqft
Garage

About this House

Built in 1854 for the Chittenden family, this historic Madison home sits on a beautifully landscaped, level one-acre lot and blends classic New England charm with modern upgrades. The main residence features three bedrooms on the second floor, plus a finished third-floor loft that serves as a fourth bedroom, office, or playroom. A highlight is the detached oversized garage with a connected studio suite and full bath-ideal as a guest house, gym, studio, or office. The interior has been meticulously restored, including windows, doors, and moldings, with fully updated HVAC, plumbing, and electrical systems. The formal living room includes hardwood floors, wood-burning fireplaces, and custom built-ins. The dramatic dining room boasts vaulted ceilings, exposed beams, a stone fireplace, and wide-plank floors. A sunlit kitchen features garden views on three sides, granite counters, stainless appliances, and opens to a deck overlooking the yard. A den with built-ins, family room, and full bath complete the first floor. Upstairs, the primary suite has vaulted ceilings with skylights, carpet, and a spa-style bath with sauna shower. Two additional bedrooms with hardwood floors share a tiled bath with claw-foot tub. A bonus room offers flex space. The finished third-floor loft adds even more. Just minutes from beaches, shops, dining, trails, trains, and highways-this is a rare chance to own a piece of Madison history with space to live, create, and entertain.
109 Boston Post Road, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,728 sqft single-family home built in 1854. It last sold for $935,570 on Aug 14, 2025 (6% below the $995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $975,200, with a rent estimate of $4,492/month.
Last check for updates: about 9 hours ago
Listed by John Hill, (203) 675-3942
Seabury Hill REALTORS, (203) 562-1220
Bought with: Anne-Marie Pagli, (203) 687-7702, William Raveis Real Estate, (203) 318-3570
Source: Smart MLS, MLS#24106360

Home Details for 109 Boston Post Road

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Kitchen, Living Room, Loft
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2728 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Electric Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Radiator,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckExterior: Rain Gutters, Garden, Lighting, Underground SprinklerFoundation: Concrete Perimeter, StoneGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Off Street,Driveway,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2728 Square Feet

Property Information

Year Built
Year Built: 1854
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1156415

Price & Status

Price
List Price: $995,000
Status Change & Dates
Off Market Date: Fri Aug 08 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 2728 Square Feet

Community

Community Features: Park, Shopping/Mall, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 1 Acres

Miscellaneous

BasementMls Number: 24106360Attic: Finished, Walk-upAbove Grade Unfinished Area: 2728

Additional Information

ParkShopping/MallTennis Court(s)

Price and Tax history

DateEventPrice
Aug 14, 2025
Source: Smart MLS #24106360
Sold
$935,570
Aug 8, 2025
Source: Smart MLS #24106360
Pending
$995,000
Jun 26, 2025
Source: Smart MLS #24106360
Listed For Sale
$995,000
Jun 28, 2021
Source: Smart MLS #170383751
Sold
$750,000
Jun 9, 2021
Source: William Raveis Real Estate, Mortgage & Insurance #170383751
Pending
$749,900

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$716K
$6.67KMoM
Sale-to-List Price
101.8%
0.2%MoM
Price per sq ft
$337
$3MoM
Available listings
59
4MoM

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

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Frequently asked questions about 109 Boston Post Road

  • What is 109 Boston Post Road estimated to be worth?
    Trulia's estimated value for 109 Boston Post Road in Madison, CT is $975,200.
  • What is the price history for 109 Boston Post Road?
    109 Boston Post Road in Madison, CT last sold for $935,570 in August 2025.
  • 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 $716K. That is up $6.67K from the prior month.
  • Does 109 Boston Post Road have air conditioning?
    Yes, 109 Boston Post Road in Madison, CT has air conditioning.
  • Does 109 Boston Post Road have laundry facilities?
    Yes, 109 Boston Post Road in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

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