509 Boston Post Rd

2,382 Sq. Ft.
$60 / Sq. Ft.
2,382
Sq. Ft.
$60
per Sq. Ft.

Description

Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday Farmer's Market. This home shines with historical moments, yet it is appointed with modern amenities, making...Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday Farmer's Market. This home shines with historical moments, yet it is appointed with modern amenities, making time spent here a delight. Enjoy coffee in the morning in the three season sunroom, a glass of wine and views of the Long Island Sound by the firepit (s'mores anyone?) , afternoon snoozes on the back terrace or cozy up with a book in the library or family room. The 1st floor features the cook's kitchen, elegant dining room, family room, library, sunroom, study, laundry room, and a full bath. You'll find 3 bedrooms and 2 full baths on the second floor. Tucked away, yet close to everything, this home is a wonderful place to hang your hat for the month of August. Truly one of a kind! Simply drop your bags and exhale. No pets or smoking, excellent credit is required.
  1. Listed by Phoebe V Finch • William Pitt Sotheby's Int'l
    P: (617)-645-3907 C: (617)-645-3907 pschreiner@wpsir.com

Property Details for 509 Boston Post Road

Basement Description
Crawl Space
Direct Waterfront
No
Garages Number
0
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Driveway
Swimming Pool
No
LISTING UPDATED: 04/15/2026 08:43 PM

Property Details for 509 Boston Post Road

StatusActive
MLS #24167301
Days on Market3
Rental Incentives-
Costs & Fees-
Available Date08/15/2026
Lease Term-
Furnished-
Property TypeRental
MLS TypeResidential Rental / Single Family Rental
Year Built1740
Lot Size0.71 AC / 30,927 SF
CountyNew Haven County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch
Add your commute

Building Information for 509 Boston Post Road

Building/Complex509 Boston Post RdFloor-Stories-Pet Policy-Pet Policy DetailsNoYear Built1740Building Size-Lot Size0.71 AC / 30,927 SF

Property Information for 509 Boston Post Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Boston Post Road heading south. Entrance across from Cherry Lane. Half moon driveway. Be mindful as you enter. The mailbox is on the far side.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.27757
  • Longitude: -72.6061
  • Pets Allowed: No
  • State: Connecticut
Parking
  • Parking Total Spaces: 2
HOA and Fees
  • Home Owner's Assocation: No
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Walk to Water, View
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • Attic Description: Walk-In
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Laundry Room Info: Main Level
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Kitchen
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Main
  • Room Type: Family Room
Room 4
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Library
Room 5
  • Listing Key: 4F766186882EE9A9E0631A01100ACC1D
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Study
Room 6
  • Room Entry Order: 6
  • Room Features: Full Bath
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Driveway Type: Private, Crushed Stone
  • New Construction Type: No/Resale
  • Smoking Allowed: No
  • Year Built: 1740
  • Year Built Source: Public Records
  • Living Area SQFT Per Public Records: 2382
Lot Information
  • Lot Description: Sloping Lot, Cleared, Professionally Landscaped
  • Parcel Number: 1154704
  • Sq Ft Est Heated Above Grade: 2382.0
  • Sq Ft Total: 2382.0
  • Zoning: R-1
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner
Rental
Rental
  • Rental Duration: One Month

Schools near 509 Boston Post Road

This home is within Madison School District.
Rating
School
Type
Grades
Distance
Public - K to 3
Public - 6 to 8
Public - 9 to 12
Public - 4 to 5
Rating
School
Distance
Kathleen H. Ryerson Elementary School
PublicK to 3

Walter C. Polson Upper Middle School
Public6 to 8

Daniel Hand High School
Public9 to 12

Dr. Robert H. Brown Middle School
Public4 to 5

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.

509 Boston Post Road is available for rent in Madison, CT 06443. This property was listed on April 16, 2026 by William Pitt Sotheby's Int'l, it's currently listed at $12,000. This listing's school district is Madison School District. Nearby schools include Kathleen H. Ryerson Elementary School, Walter C. Polson Upper Middle School and Daniel Hand High School. 509 Boston Post Road is a 3-bed, 3-bath, 2,382 sqft a property built in 1740.

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 owner. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch

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.