395 Boston Post Rd Madison, CT 06443
Estimated payment $9,173/month
Highlights
- Colonial Architecture
- Attic
- Screened Porch
- Walter C. Polson Upper Middle School Rated A
- 1 Fireplace
- Patio
About This Home
Introducing the historic Ebenezer Dudley Home, circa 1828, a beautifully preserved residence set along the iconic stretch of Boston Post Road in the charming shoreline town of Madison, Connecticut. Situated on nearly an acre of picturesque grounds, this special property seamlessly blends early New England character with thoughtful modern updates, offering both historic charm and everyday comfort. During the past five years of ownership, the current homeowners have undertaken extensive improvements and updates throughout the property. Among them are the addition of a spectacular wraparound screened porch with bluestone flooring, a birch board ceiling and wood burning stove, the conversion to natural gas heat and tankless hot water, installation of a new 50-year architectural shingle roof, an updated kitchen, and a beautifully renovated first-floor bathroom, are just a few of the many thoughtful enhancements made to the home. A significant addition completed in 2003 expanded the home's living space to include the kitchen, family room, and a spacious primary bedroom suite designed for modern living. The private primary suite features a generous full bath, a dressing room and walk-in closet, creating a comfortable and elegant retreat. Two additional ensuite bedrooms complete the second floor, along with a large, gracious landing that connects the three bedrooms and enhances the sense of space.
Listing Agent
William Pitt Sotheby's Int'l Brokerage Phone: (203) 641-6837 License #RES.0761609 Listed on: 03/19/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $17,816
Year Built
- Built in 1828
Lot Details
- 40,075 Sq Ft Lot
- Stone Wall
Home Design
- Colonial Architecture
- Concrete Foundation
- Stone Foundation
- Frame Construction
- Asphalt Shingled Roof
- Clap Board Siding
- Vinyl Siding
Interior Spaces
- 3,779 Sq Ft Home
- 1 Fireplace
- French Doors
- Screened Porch
- Unfinished Basement
- Partial Basement
Kitchen
- Built-In Oven
- Electric Cooktop
- Range Hood
- Microwave
- Dishwasher
Bedrooms and Bathrooms
- 4 Bedrooms
- 5 Full Bathrooms
Laundry
- Laundry on upper level
- Electric Dryer
- Washer
Attic
- Pull Down Stairs to Attic
- Unfinished Attic
Home Security
- Smart Locks
- Smart Thermostat
Parking
- 2 Car Garage
- Automatic Garage Door Opener
- Private Driveway
Outdoor Features
- Patio
- Shed
Location
- Property is near golf course and shops
Schools
- Neck River Elementary School
- Daniel Hand High School
Utilities
- Central Air
- Hot Water Heating System
- Gas Available at Street
- Tankless Water Heater
- Hot Water Circulator
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 1155692
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $17,816 | $794,300 | $313,500 | $480,800 |
| 2024 | $17,475 | $794,300 | $313,500 | $480,800 |
| 2023 | $15,186 | $506,700 | $172,900 | $333,800 |
| 2022 | $14,690 | $499,500 | $172,900 | $326,600 |
| 2021 | $14,411 | $499,500 | $172,900 | $326,600 |
| 2020 | $14,164 | $499,600 | $173,000 | $326,600 |
| 2019 | $14,164 | $499,600 | $173,000 | $326,600 |
| 2018 | $13,487 | $481,000 | $143,000 | $338,000 |
| 2017 | $13,131 | $481,000 | $143,000 | $338,000 |
| 2016 | $12,742 | $481,000 | $143,000 | $338,000 |
| 2015 | $12,391 | $481,000 | $143,000 | $338,000 |
| 2014 | $13,468 | $535,100 | $196,100 | $339,000 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 04/06/2026 04/06/26 | Pending | -- | -- | -- | |
| 03/29/2026 03/29/26 | For Sale | $1,450,000 | +106.3% | $384 / Sq Ft | |
| 02/25/2021 02/25/21 | Sold | $703,000 | -5.6% | $210 / Sq Ft | View Prior Sale |
| 01/18/2021 01/18/21 | Pending | -- | -- | -- | |
| 06/03/2020 06/03/20 | For Sale | $745,000 | -- | $223 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $703,000 | None Available | |
| Deed | -- | -- | |
| Quit Claim Deed | -- | -- | |
| Warranty Deed | $765,000 | -- | |
| Warranty Deed | $399,900 | -- | |
| Warranty Deed | $125,000 | -- | |
| Warranty Deed | $125,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $540,000 | Purchase Money Mortgage | |
| Previous Owner | $479,100 | Stand Alone Refi Refinance Of Original Loan | |
| Previous Owner | $66,000 | No Value Available |
Source: SmartMLS
MLS Number: 24158296
APN: MADI-000037-000000-000002
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
- 31 Stony Lane Lot 2 Rd
- 31 Stony Lane Lot 1 Rd
- 31 Stony Lane Lot 3 Rd
- 37 Lantern Hill Rd
- 24 Cherry Ln
- 14 Centre Village Dr
- 30 Meeting House Ln
- 42 Neck Rd
- 58 Neck Rd
- 75 Fairview Dr
- 10 Middle Beach Rd W
- 41 Harbor Ave
- 115 Harbor Ave
- 8 Old Route 79
- 45 Island Ave
- 98 Island Ave
- 46A Beach Ave
- 15 Cambridge Dr
- 178 Mungertown Rd
- 11 Middle Beach Rd
Ask me questions while you tour the home.