Off Market Aug 2025 for $935K

$1,034,324

Est. refi paymentEst. refi $1,047/mo

•

2,728

sq ft

109 Boston Post Rd, Madison, CT 06443

About this home

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.

Single-familyProperty Type

1854Year Built

1 acresLot Size

$379Est. Price/Sq.Ft.

2 garage spacesParking

Listed by John Hill • Seabury Hill REALTORS

Bought with Anne-Marie Pagli • William Raveis Real Estate

Source:Smart MLS #24106360

Redfin Estimate

$1,034,324

$99K since sold in August 2025$15K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 46.9% higher than the average sale price ($704K) of 6 comparable homes.

SOLD JUN 24, 2026
$515,000
A
4 beds2 baths2,746 sq ft
12 Sportsman's Hill Rd, Madison, CT 06443
SOLD JUN 11, 2026
$1,100,000
B
3 beds3 baths2,694 sq ft
242 Neck Rd, Madison, CT 06443
SOLD AUG 7, 2026
$530,000
C
3 beds2.5 baths2,196 sq ft
101 Sandelwood Dr, Madison, CT 06443
SOLD AUG 17, 2026
$775,000
D
4 beds2 baths2,348 sq ft
170 Mungertown Rd, Madison, CT 06443
SOLD MAR 30, 2026
$526,000
E
3 beds2 baths2,582 sq ft
22 Nathans Ln, Madison, CT 06443
SOLD JUL 10, 2026
$778,000
F
4 beds2.5 baths2,230 sq ft
53 Wellsweep Dr, Madison, CT 06443

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Earn from this home

Sell

$237,869

Est. take-home

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Refinance

Est. cash available

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Rent

$4,170/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.6%

+0.1% MoM

Median sale price

$731K

$26K MoM

Avg. days on market

45d

6 days MoM

Recently sold homes

15 MoM

New listings for sale

$524,000
3 beds2 baths1,288 sq ft
35 Aileen Dr, Madison, CT 06443
$500,000
2 beds2 baths1,280 sq ft
22 Thelbridge St #22, Madison, CT 06443
COMING SOON
$4,499,000
6 beds6.5 baths5,817 sq ft
14 Middle Beach Rd W, Madison, CT 06443
$561,000
3 beds1 bath1,023 sq ft
1466 Durham Rd, Madison, CT 06443
COMING SOON
$1,700,000
3 beds3 baths2,674 sq ft
50 Webster Point Rd, Madison, CT 06443
$3,000,000
4 beds5 baths4,833 sq ft
17 Barberry Ln, Madison, CT 06443
$349,900
2 beds1 bath625 sq ft
66 Wildcat Rd, Madison, CT 06443
$210,000
1 bed0.5 baths732 sq ft
40 East St, Madison, CT 06443
See all

Provided by Redfin

Sale history for 109 Boston Post Rd

Date

Event

Price

Smart MLS #24106360

Aug 14, 2025

Sold

$935,570

$343/sq ft

Aug 8, 2025

Pending

—

Jul 14, 2025

Contingent

—

Jun 26, 2025

Listed

$995,000

$365/sq ft

Jun 24, 2025

Coming Soon

$995,000

$365/sq ft

Smart MLS #170383751

Jun 28, 2021

Sold

$750,000

$275/sq ft

Apr 27, 2021

Contingent

—

Apr 23, 2021

Relisted

—

Apr 21, 2021

Contingent

—

Apr 8, 2021

Listed

$749,900

$275/sq ft

Mar 30, 2021

Coming Soon

$749,900

$275/sq ft

Open House Cancelled on May 1st! Historic Federal Colonial located between Guilford/Madison for easy access to shore, train to NY or New Have/Yale. Minutes to shops and dining. R2 Zone in Historic East River area. Main house boast "stellar" condition with eat in updated kitchen, Family room and DR both with FPL, Library/Den with built-in book shelves, full bath and formal Parlor to use as you need...formal space, potential first flr BR, main level office? Second floor enjoy MBR suite with full bath and front and back stair cases to 2more BR and another full bath or use the space as 2BR and sitting room -you decide. Third floor currently used as guest BR, has been home office, play room and can be all you need. State of the art detached home office/studio 20x16 with half bath and own septic in rear of house attached to stunning garage 30x28 with walls of glass, both have heat and AC for studio use, home business and perhaps a guest cottage/in-law. Newer mechanicals and peaceful private yard and gardens. In-ground sprinkler system, skylights have "rain"sensor to close them, central vac. Good bye city life! Welcome to Madison, its beaches, its train station, shops and dining. Artists, writers, performing arts enthusiasts this studio/garage is perfect for you! Attorney, accountant, therapist, daycare and so much more can be operated from detached space while you live in main home with great Rte1 exposure for marketing/name recognition. Historic John Newton Chittenden House!

Nothing but the best was done to ensure a safe, sound and secure living environment when these owners gutted and renovated this home. New, new, new electric, plumbing, fixtures, furnace, central vac, fresh air system stainless steal chimney flue, windows, roof, gardens, driveway and so much more. It has been continually and lovingly cared for and most recently the home office/studio with half bath and its own septic was added to garage and both it and garage enjoy split air heating and cooling. Fireplaces (2) are currently capped- easy to convert to city gas (that is what they had hoped to do and never completed). Skylights have "rain sensors" to close automatically and are UV light protected.

Smart MLS #170173976

Aug 27, 2019

Listing Removed

—

Mar 28, 2019

Listed

$725,000

$266/sq ft

Smart MLS #170103050

Feb 1, 2019

Listing Removed

—

Dec 16, 2018

Price Changed

$729,000

$267/sq ft

Sep 17, 2018

Price Changed

$749,000

$275/sq ft

Jul 20, 2018

Listed

$775,000

$284/sq ft

Smart MLS #170012913

Nov 30, 2017

Listing Removed

—

Sep 8, 2017

Listed

$775,000

$284/sq ft

Smart MLS #N10223640

Sep 8, 2017

Listing Removed

—

May 22, 2017

Listed

$795,000

$291/sq ft

Smart MLS #N10177405

Oct 27, 2016

Listing Removed

—

Oct 21, 2016

Listed

$800,000

$293/sq ft

Smart MLS #N10159333

Oct 21, 2016

Listing Removed

—

Aug 12, 2016

Listed

$800,000

$293/sq ft

Smart MLS #N10078995

Dec 31, 2015

Listing Removed

—

Sep 11, 2015

Listed

$939,000

$344/sq ft

Smart MLS #N354704

Sep 11, 2015

Listing Removed

—

Sep 11, 2014

Listed

$939,000

$344/sq ft

Smart MLS #M9139379

Jun 19, 2013

Listing Removed

—

Mar 15, 2013

Listed

$739,900

$271/sq ft

Smart MLS #M9115192

Dec 5, 2009

Listing Removed

—

Mar 5, 2009

Listed

$859,900

$315/sq ft

Public Records

Aug 14, 1992

Sold

$151,166

$55/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$12,719 (+1.9%)

$119,300 + $305,100

$424,400

2022

$12,482 (+1.9%)

$119,300 + $305,100

$424,400

2021

$12,244 (+1.8%)

$119,300 + $305,100

$424,400

2020

$12,032

$119,300 + $305,100

$424,400

2019

$12,032 (+11.9%)

$119,300 + $305,100

$424,400

2018

$10,751 (+2.7%)

$110,600 + $272,800

$383,400

2017

$10,467 (+3.1%)

$110,600 + $272,800

$383,400

2016

$10,156 (+12.0%)

$110,600 + $272,800

$383,400

2014

$9,064 (+40.4%)

$110,600 + $249,500

$360,100

2010

$6,458

$106,100 + $210,600

$316,700

Tax history for 109 Boston Post Rd

Year

Property tax

Land + Additions

Assessment*

2023

$12,719 (+1.9%)

$119,300 + $305,100

$424,400

2022

$12,482 (+1.9%)

$119,300 + $305,100

$424,400

2021

$12,244 (+1.8%)

$119,300 + $305,100

$424,400

2020

$12,032

$119,300 + $305,100

$424,400

2019

$12,032 (+11.9%)

$119,300 + $305,100

$424,400

2018

$10,751 (+2.7%)

$110,600 + $272,800

$383,400

2017

$10,467 (+3.1%)

$110,600 + $272,800

$383,400

2016

$10,156 (+12.0%)

$110,600 + $272,800

$383,400

2014

$9,064 (+40.4%)

$110,600 + $249,500

$360,100

2010

$6,458

$106,100 + $210,600

$316,700

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1 Acre

Year renovated

—

Sq. Ft.

2,728

Year built

1854

Style

Single Family Residential

County

New Haven County

APN

1156415

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage, Off Street Parking, Driveway
Garages Number: 2

Parking Information
Parking Total Spaces: 4

Interior

Virtual Tour Information

Interior Information
Total Rooms: 10
Laundry Room Location: Basement laundry
Laundry Room Info: Lower Level
Interior Features: Auto Garage Door Opener, Cable - Available
In-Law Apartment: Possible
In-Law Access: Detached
Fireplaces Total: 2
Cooling System: Central Air
Appliances Included: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3

Bedroom Information
Beds Total: 3

Room Information
Basement Description: Full, Unfinished
Has Attic
Attic Description: Finished, Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Wood
Exterior Features: Deck, Gutters, Garden Area, Lighting, Underground Sprinkler

Lot Information
Lot Description: Level Lot, Professionally Landscaped

Building Information
Foundation Type: Concrete, Stone
Construction Description: Frame
Color: White

Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2728
Driveway Type: Crushed Stone

Financial

Assessments Information
Assessed Value: $632,800

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Other
Heat Type: Baseboard, Radiator
Heat Fuel Type: Natural Gas

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Park, Shopping/Mall, Tennis Courts
Directions: 109 Boston Post Road between Wildwood Avenue & Green Acres Drive
County: New Haven

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 2,728
Stories: 2.0
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1854
Year Renovated: —
County: New Haven County
APN: 1156415

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools
Places
Transit

J. Milton Jeffrey Elementary School

Public K-3 • Assigned • 1.3mi

10/10

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 1.2mi

9/10

Daniel Hand High School

Public 9-12 • Assigned • 1.0mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

6/10 Wind Factor

72% chance of strong winds in next 30 years

5/10 Air Factor

5 unhealthy days expected this year, 8 days in 30 years

Provided by First Street

Historical weather

Madison, CT • 06443

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$983,000 – $1.19M

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New listings for sale in 06443

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COMING SOON

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COMING SOON

$1,700,000

3 beds3 baths2,674 sq ft

50 Webster Point Rd, Madison, CT 06443

$3,000,000

4 beds5 baths4,833 sq ft

17 Barberry Ln, Madison, CT 06443

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1 bed0.5 baths732 sq ft

40 East St, Madison, CT 06443

Home values near 109 Boston Post Rd

Data from public records.

Address	Redfin Estimate
90 Boston Post Rd, Madison, CT 3 Beds \| 2 Baths \| 2034 Sq. Ft.	$641,621
104 Boston Post Rd, Madison, CT 3 Beds \| 1.5 Baths \| 1960 Sq. Ft.	$613,271

Address	Redfin Estimate
94 Boston Post Rd, Madison, CT 2 Beds \| 2.5 Baths \| 1668 Sq. Ft.	$727,766
98 Boston Post Rd, Madison, CT 3 Beds \| 2.5 Baths \| 2332 Sq. Ft.	$740,471

Address	Redfin Estimate
115 Boston Post Rd, Madison, CT 3 Beds \| 2.5 Baths \| 3536 Sq. Ft.	$909,699
96 Boston Post Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2296 Sq. Ft.	$799,142

Property information provided by Smart MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06443, CT

Sale history for 109 Boston Post Rd

Tax history for 109 Boston Post Rd

Public record

Property details

Around this home

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06443

Home values near 109 Boston Post Rd

More real estate resources