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153 Middle Beach Road

Madison, Connecticut 06443

ACTIVE$2,150,000
Beds
4
Baths
2
SqFt
2,251
Acres
0.70
Year Built
1928
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Guest House3-Car GarageVirtual Tour

About This Home

Rare opportunity to own a Nantucket-style coastal retreat on coveted Middle Beach Road in Madison. Just moments from East Wharf Beach and downtown, this distinctive property offers timeless shoreline charm, a huge porch, breathtaking tidal marsh views, and glimpses of Long Island Sound from the second floor. Filled with character and reminiscent of a 1920s seaside cottage, the sun-filled main house features iconic fir floors, generous living spaces, and abundant natural light. The spacious 26' x 13' living room is ideal for entertaining, while the private 17' x 10' family room provides a cozy retreat. A first-floor bedroom and adjacent full bath offer flexibility for guests or single-level living. Upstairs are three additional bedrooms, a full bath, and a walk-up attic for storage. Adding exceptional versatility is the detached carriage guest house, built in 2004. This charming space features vaulted ceilings, built-in cabinetry and bookshelves, a trundle bed, a beautifully remodeled full bath, and a delightful kitchen with granite countertops and a breakfast bar.The expansive deck overlooks a stunning tidal marsh and winding serpentine river, creating a spectacular setting for relaxing, entertaining, and enjoying coastal wildlife. Ospreys, egrets, and other shorebirds are frequent visitors.Ideal as a year-round residence, vacation home, investment property, or multi-generational retreat, this exceptional shoreline offering captures the best of Madison's coastal lifestyle.

Key Facts

City/Town
Madison
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1928
Days on Market
53 days
Beds
4
Baths
2 full
Living Area
2,251 sq ft
Lot Size
0.70 acres
Garage / Parking
3 garage · 6 total
Property Taxes
$28,775 / Annually

Market Snapshot

The Madison Market

Single Family · trailing 12 months

Median Days on Market

57

29 active listings

Median $ / Sq Ft

$434

29 active listings

Sale-to-List Ratio

100.0%

223 sales

How this home compares

List Price

$2.15M

vs $1.30M median

65.5% above median

Price / Sq Ft

$955

vs $434 median

2.2× the median

Days on Market

53 days

vs 57 days median

4 days fresher than median

Based on 29 active and 223 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of July 28, 2026.

Location

153 Middle Beach Road, Madison, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,077

per month

  • Principal & Interest$10,962
  • Property Taxes$2,398
  • Insurance$717
  • 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
1928
New Construction
No/Resale
Living Area
2,251 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Daniel Hand

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Window Unit
Laundry
Main Level
Laundry Location
main level
Appliances
Oven/RangeRefrigeratorDishwasherWasherDryer
Basement
Crawl Space
In-Law Apartment
YesDetached
Interior Features
Cable - AvailableOpen Floor Plan

Exterior & Lot

Lot Size
0.70 acres
Zoning
R-4
Garage / Parking
3 garage spaces6 total parking spacesDetached GarageDrivewayCrushed Stone
Waterfront Details
Walk to WaterWater CommunityView
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
Yes
Construction
Clapboard
Color
grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
PorchDeckGuest House
Lot Description
Level LotWater View

Listing & Financials

Property Taxes
$28,775 / Annually
Days on Market
53
MLS #
24164243
MLS Status
Active

Similar Properties

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

Listed By

Sheila Tinn Murphy

(203) 915-7530

Berkshire Hathaway NE Prop.

(203) 245-3100

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:05 AM UTC.