252 Boston Post Road
Madison, Connecticut 06443
- Beds
- 4
- Baths
- 2
- SqFt
- 1,728
- Acres
- 0.76
- Year Built
- 1953
- Neighborhood
- East River
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Experience the best of coastal living in this distinctive property, featuring a beautifully renovated main residence, an income-producing in-law residence, and generous grounds in one of Connecticut's most desirable shoreline communities. Set toward the rear of the .76-acre parcel, comfortably removed from Boston Post Road, the main home enjoys an attractive setting surrounded by lush greenery and magnificent mature trees. The expansive grounds provide a beautiful backdrop for outdoor entertaining, gardening, or simply relaxing in the natural surroundings. Extensively renovated throughout, the main residence combines contemporary style with everyday comfort and convenience. Enjoy a beautifully updated kitchen and bath, attractive new flooring, modern lighting, replacement windows, a new roof, and an updated heating system. These substantial improvements offer the immediate enjoyment of a move-in-ready home without the disruption and expense of a major renovation. A bright breezeway connects the home to its attached one-car garage, providing convenient, sheltered access, while the full basement offers valuable storage and utility space. A separate in-law residence toward the front of the parcel is currently leased for $1,700 per month. This rental income provides a meaningful financial advantage, helping offset ownership expenses while adding versatility and value.
Key Facts
- City/Town
- Madison
- Neighborhood
- East River
- Property / Style
- Single Family · Ranch
- Year Built
- 1953
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,728 sq ft
- Lot Size
- 0.76 acres
- Garage / Parking
- 1 garage · 5 total
- Property Taxes
- $9,185 / Annually
Market Snapshot
The Madison Market
Single Family · trailing 12 months
Active Listings
42
21 under contract
Median List Price
$865,000
42 active listings
Median Closed Price
$778,000
223 sales
Median Days on Market
58
42 active listings
Median $ / Sq Ft
$366
42 active listings
Sale-to-List Ratio
100.0%
223 sales
How this home compares
List Price
$549,900
vs $865,000 median
36.4% below median
Price / Sq Ft
$318
vs $366 median
13.1% below median
Days on Market
0 days
vs 58 days median
58 days fresher than median
Based on 42 active and 223 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of October 25, 2026.
Location
252 Boston Post Road, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$3,022
- Property Taxes$765
- Insurance$183
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Madison
- Neighborhood
- East River
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1953
- New Construction
- No/Resale
- Living Area
- 1,728 sq ft
Schools
- Elementary
- Neck River
- Middle
- Per Board of Ed
- High
- Daniel Hand
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasher
- Basement
- Partial
- In-Law Apartment
- YesFirst FloorSeparate Entry
Exterior & Lot
- Lot Size
- 0.76 acres
- Zoning
- R-2
- Garage / Parking
- 1 garage space5 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivateCircularPavedAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- Breezeway
- Lot Description
- DryLevel LotClearedOpen Lot
Listing & Financials
- Property Taxes
- $9,185 / Annually
- Days on Market
- 0
- MLS #
- 24216244
- MLS Status
- Coming Soon
- Financing
- FHA,VA,CHFA
Similar Properties
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Co-Listed By
Paul Violano
Compass Connecticut, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/25/2026. 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 10/25/2026 at 4:15 PM UTC.