Skip to main content

252 Boston Post Road

Madison, Connecticut 06443

COMING SOON - NEW$549,900
Beds
4
Baths
2
SqFt
1,728
Acres
0.76
Year Built
1953
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
1-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,970

per 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

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

Listed By

Mick Marsden

(860) 334-1379

Compass Connecticut, LLC

(860) 767-5390

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.