373 Boston Post Road
Madison, Connecticut 06443
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 4,766
- Acres
- 1.59
- Year Built
- 1997
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
35
28 under contract
Median List Price
$1.20M
35 active listings
Median Closed Price
$775,000
225 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per 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
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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.