Coming Soon
4 beds4,766 sqft
373 Boston Post Rd, Madison, CT 06443
Est: $16,406/moGet pre-approved
Single FamilyProperty Type
1.59 acresLot Size
1997Year Built
$561/sq ftPrice per sq ft
4 carsParking Spaces

Description

Set back and sited high on a hill overlooking 1.6 aces of estate-like grounds with seasonal views of Long Island Sound and Madison Country Club's 18-hole golf course, this residence was constructed by one of the town's most esteemed builders as his own home, and it shows in every detail. Nine-foot ceilings and abundant light define the first floor, which includes a living/dining room and elegant den, each with a woodburning fireplace, an office (currently a playroom), and a powder room. The living...Set back and sited high on a hill overlooking 1.6 aces of estate-like grounds with seasonal views of Long Island Sound and Madison Country Club's 18-hole golf course, this residence was constructed by one of the town's most esteemed builders as his own home, and it shows in every detail. Nine-foot ceilings and abundant light define the first floor, which includes a living/dining room and elegant den, each with a woodburning fireplace, an office (currently a playroom), and a powder room. The living room opens to large veranda ideal for outdoor living and Fourth of July parties overlooking Madison's annual fireworks display. A spectacular top of the line kitchen has double ovens, A Sub-Zero refrigerator, counter and table seating, as well as an inviting sitting area. Upstairs, the vaulted primary suite offers a sitting area with yet another fireplace, two enormous walk-in closets sure to please, and a fabulous bathroom with double vanity, walk-in shower, and soaking tub. A bedroom with ensuite bath, a laundry room, and two other bedrooms that share a family bath complete the second floor. The finished lower level adds plenty of additional living space, a full bath, and a multi-purpose bonus room. A two-story carriage style garage has space for an office/studio above. Just minutes from Madison's center and the Surf Club, this is a very special, move-in ready property. Be prepared to act quickly!
  • Listed by: Margaret Muir 203.415.9187 mmuir@wpsir.com • William Pitt Sotheby's Int'l
Last updated: 09/19/2026 07:18 PM • Source: SMARTMLS, MLS#: 24207210

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Margaret Muir
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Payment Calculator

$16,406 per month

30 year fixed, 6.71% Interest

Principal and Interest

$13,823

Property Taxes

$2,583

HOA Dues

$0

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Property Information for 373 Boston Post Road

Property Details
  • Taxes: $31,000 / year
  • MLS Type: Residential
  • Basement Description: Full, Storage, Partially Finished, Liveable Space, Full With Hatchway
  • Direct Waterfront: No
  • Expected Active Date: 09-25-2026
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Detached Garage, Driveway
  • Swimming Pool: No
  • Expected On Market Date: 09-25-2026
Building Information
  • Year Built: 1997
  • Lot Size: 1.59 AC / 69,260 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Boston Post Road (Route 1) to #373, sits atop the hill
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.279211
  • Longitude: -72.616456
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Library, Medical Facilities, Shopping/Mall
  • State: Connecticut
Parking
  • Parking Total Spaces: 4
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $31,000
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Underground Utilities, Porch, Stone Wall, French Doors, Underground Sprinkler
  • Waterfront Description: View
Interior Features
  • Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hydro Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Home Automation: Security System, Thermostat(s)
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Laundry Room Info: Upper Level
  • Rooms Additional: Laundry Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Fireplace,French Doors,Hardwood Floor
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 17.0
Room 2
  • Room Entry Order: 10
  • Room Features: Wall/Wall Carpet
  • Room Length: 23.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 24.0
Room 3
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,French Doors,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 11.0
Room 4
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Fireplace,French Doors,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 15.0
Room 5
  • Listing Key: 5B84D2E434A9EB38E0631A01100A9E28
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Built-Ins,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 10.0
Room 6
  • Room Entry Order: 5
  • Room Features: Built-Ins,Dining Area,Island,Pantry,Hardwood Floor
  • Room Length: 25.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 18.0
Room 7
  • Room Entry Order: 6
  • Room Features: 2 Story Window(s),Balcony/Deck,Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 25.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 21.0
Room 8
  • Room Entry Order: 7
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 24.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 9
  • Listing Key: 5B84D2E434A9EB38E0631A01100A9E28
  • Room Entry Order: 8
  • Room Features: Built-Ins,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 10
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Construction Description: Frame
  • Driveway Type: Private, Asphalt
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1997
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level, Upper Level
  • In Law Apartment: Possible
  • Sq Ft Description: Per Vision Appraisal
  • Sq Ft Est Heated Below Grade: 624
Lot Information
  • Lot Description: Sloping Lot, Professionally Landscaped
  • Parcel Number: 1155668
  • Sq Ft Est Heated Above Grade: 4142.0
  • Sq Ft Total: 4766.0
  • Zoning: R1
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Electric, Tankless Hotwater
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 373 Boston Post Road

DateEvent & SourcePriceAppreciation
Nov 1, 1995

Closed (Public Record)

Public Record #92239955

$150,000
DateEvent & SourcePrice
11/01/1995

Closed (Public Record)

Public Record #92239955

$150,000

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

Public Records for 373 Boston Post Road

Taxable ValueLand$480,700Additions$863,900Total$1,344,600
Tax Record2025$30,159 ($2,513 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt4,142 SqFtAbove Grade Finished SqFt4,142 SqFtStories2Lot Size69,260 SqFtStyleSingle Family ResidenceYear Built1997Year Renovated1997ZoningR-1CountySOUTH CENTRAL CONNECTICUAPNMADI M:36 B:37-1

Schools near 373 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 - K to 3
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

Kathleen H. Ryerson Elementary School
PublicK to 3

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.

Similar Homes

373 Boston Post Road is a single family home Coming Soon in Madison, CT 06443. This property is currently priced at $2,675,000. This listing's school district is Madison School District. Nearby schools include J. Milton Jeffrey Elementary School, Walter C. Polson Upper Middle School and Daniel Hand High School. 373 Boston Post Road is a 4-bed, 5-bath, 4,766 sqft single family home built in 1997.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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, Margaret Muir

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.