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373 Boston Post Road

Madison, Connecticut 06443

COMING SOON - NEW$2,675,000
Beds
4
Baths
4 | 1
SqFt
4,766
Acres
1.59
Year Built
1997
Matt Caiola

Matt Caiola

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2-Car Garage3 Fireplaces

About This Home

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), a powder room and a large veranda ideal for outdoor living. Host 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, laundry room and two other bedrooms that share a snarky bath complete the second floor. The lower level, with private full bath, has a large bonus room which could serve any number of purposes along with a separate ideal office area. 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!

Key Facts

City/Town
Madison
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1997
Days on Market
0 days
Beds
4
Baths
4 full · 1 half
Living Area
4,766 sq ft
Lot Size
1.59 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$31,000 / Annually

Market Snapshot

The Madison Market

Single Family · trailing 12 months

Median Days on Market

55

35 active listings

Median $ / Sq Ft

$388

35 active listings

Sale-to-List Ratio

100.0%

225 sales

How this home compares

List Price

$2.67M

vs $1.20M median

2.2× the median

Price / Sq Ft

$561

vs $388 median

44.6% above median

Days on Market

0 days

vs 55 days median

55 days fresher than median

Based on 35 active and 225 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of September 19, 2026.

Location

373 Boston Post Road, Madison, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$17,641

per month

  • Principal & Interest$14,166
  • Property Taxes$2,583
  • Insurance$892
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Madison
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1997
New Construction
No/Resale
Living Area
4,766 sq ft
Below Grade
624 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hydro AirZoned
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
3
Laundry
Upper Level
Appliances
Gas RangeWall OvenMicrowaveRange HoodSubzeroDishwasherWasherDryer
Basement
FullStoragePartially FinishedLiveable SpaceFull With Hatchway
In-Law Apartment
PossibleLower LevelUpper Level
Interior Features
Auto Garage Door OpenerCable - Available
Additional Rooms
Laundry Room

Exterior & Lot

Lot Size
1.59 acres
Zoning
R1
Garage / Parking
2 garage spaces4 total parking spacesDetached GarageDrivewayPrivateAsphalt
Waterfront Details
View
Water Source
Public Water Connected
Sewer
Septic
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyUnderground UtilitiesPorchStone WallFrench DoorsUnderground Sprinkler
Lot Description
Sloping LotProfessionally Landscaped

Listing & Financials

Property Taxes
$31,000 / Annually
Days on Market
0
MLS #
24207210
MLS Status
Coming Soon

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Margaret Muir

(203) 415-9187

William Pitt Sotheby's Int'l

(203) 245-6700

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/19/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/19/2026 at 9:15 PM UTC.