153 Middle Beach Road
Madison, Connecticut 06443
- Beds
- 4
- Baths
- 2
- SqFt
- 2,251
- Acres
- 0.70
- Year Built
- 1928
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
29
47 under contract
Median List Price
$1.30M
29 active listings
Median Closed Price
$729,000
223 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 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.