109 Boston Post Rd

Madison, CT 06443

$935,570
Last Sold Price
3
Beds
2,728 Sq. Ft.
$343 / Sq. Ft.
2,728
Sq. Ft.
$343
per Sq. Ft.
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Closed 8/14/25Virtual Tour
Closed 8/14/25Virtual Tour
a front view of a house with a yard

Description

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...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.
  1. Listed by John Hill • Seabury Hill REALTORS
    P: (203)-675-3942 C: (203)-675-3942 jack@seaburyhill.com

Property Details for 109 Boston Post Road

Basement Description
Full, Unfinished
Direct Waterfront
No
Expected Active Date
06-26-2025
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Detached Garage, Off Street Parking, Driveway
Swimming Pool
No
LISTING UPDATED: 08/16/2025 05:49 AM

Property Details for 109 Boston Post Road

StatusClosed
MLS #24106360
Days on Market18
Taxes$14,194 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1854
Lot Size1.00 AC / 43,560 SF
CountyNew Haven County
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Location

Listing Courtesy of Seabury Hill REALTORS, John Hill

Sold By William Raveis Real Estate, Anne-Marie Pagli

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Building Information for 109 Boston Post Road

Stories-Year Built1854Building Size-Lot Size1.00 AC / 43,560 SF

Payment Calculator

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$5,743 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,560

Property Taxes

$1,183

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 109 Boston Post Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 109 Boston Post Road between Wildwood Avenue & Green Acres Drive
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.284992
  • Longitude: -72.637371
  • Neighborhood Amenities: Park, Shopping/Mall, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $14,194
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Gutters, Garden Area, Lighting, Underground Sprinkler
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Finished, Walk-up
  • Cooling System: Central Air
  • Heat Type: Baseboard, Radiator
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Laundry Room Info: Lower Level
  • Laundry Room Location: Basement laundry
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Length: 16.8
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.0
Room 2
  • Room Entry Order: 2
  • Room Length: 17.5
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.8
Room 3
  • Room Entry Order: 3
  • Room Length: 15.1
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 15.1
Room 4
  • Room Entry Order: 4
  • Room Length: 15.8
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 12.9
Room 5
  • Listing Key: 384180D5BA58398AE0631A01100AA29F
  • Room Entry Order: 5
  • Room Length: 12.2
  • Room Level: Main
  • Room Type: Den
  • Room Width: 13.4
Room 6
  • Room Entry Order: 6
  • Room Length: 15.11
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 24.8
Room 7
  • Room Entry Order: 7
  • Room Length: 15.8
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.1
Room 8
  • Room Entry Order: 8
  • Room Length: 10.5
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.5
Room 9
  • Listing Key: 384180D5BA58398AE0631A01100AA29F
  • Room Entry Order: 9
  • Room Length: 9.5
  • Room Level: Upper
  • Room Type: Loft
  • Room Width: 29.5
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Driveway Type: Crushed Stone
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete, Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1854
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 2728
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped
  • Parcel Number: 1156415
  • Sq Ft Est Heated Above Grade: 2728.0
  • Sq Ft Total: 2728.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Other
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 109 Boston Post Road

DateEvent & SourcePriceAppreciation
Aug 14, 2025

Closed (Public Record)

Public Record #1910985198

$935,570

+5.5% / yr

Jun 28, 2021

Closed (Public Record)

Public Record #1465627015

$750,000

+5.7% / yr

Aug 14, 1992

Closed (Public Record)

Public Record #92241434

$151,166—
DateEvent & SourcePrice
08/14/2025

Closed (Public Record)

Public Record #1910985198

$935,570

+5.5% / yr

06/28/2021

Closed (Public Record)

Public Record #1465627015

$750,000

+5.7% / yr

08/14/1992

Closed (Public Record)

Public Record #92241434

$151,166

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 109 Boston Post Road

Taxable ValueLand$190,600Additions$442,200Total$632,800
Tax Record2024$14,194 ($1,183 / month)
Home Facts
Beds3Baths3Total Finished SqFt2,728 SqFtAbove Grade Finished SqFt2,728 SqFtStories2Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1854ZoningR-2CountyNEW HAVENAPNMADI M:44 B:33

Schools near 109 Boston Post Road

This home is within Madison School District.
Rating
School
Type
Grades
Distance
J. Milton Jeffrey Elementary School
Public - K to 3
Walter C. Polson Upper Middle School
Public - 6 to 8
Daniel Hand High School
Public - 9 to 12
Island Avenue Elementary School
Public - K to 4
Rating
School
Distance
J. Milton Jeffrey Elementary School
PublicK to 3

Walter C. Polson Upper Middle School
Public6 to 8

Daniel Hand High School
Public9 to 12

Island Avenue Elementary School
PublicK to 4

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Seabury Hill REALTORS, John Hill

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.