45 Island Avenue
Madison, Connecticut 06443
Reduced from $4,000,000
- Beds
- 5
- Baths
- 4 | 2
- SqFt
- 5,657
- Acres
- 1.57
- Year Built
- 2001
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.
Key Facts
- City/Town
- Madison
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2001
- Days on Market
- 140 days
- Beds
- 5
- Baths
- 4 full · 2 half
- Living Area
- 5,657 sq ft
- Lot Size
- 1.57 acres
- Garage / Parking
- 3 garage · 10 total
- Property Taxes
- $32,281 / Annually
Market Snapshot
The Madison Market
Single Family · trailing 12 months
Active Listings
28
38 under contract
Median List Price
$1.25M
28 active listings
Median Closed Price
$745,000
219 sales
Median Days on Market
64
28 active listings
Median $ / Sq Ft
$489
28 active listings
Sale-to-List Ratio
100.0%
219 sales
How this home compares
List Price
$3.50M
vs $1.25M median
2.8× the median
Price / Sq Ft
$618
vs $489 median
26.4% above median
Days on Market
140 days
vs 64 days median
76 days longer than median
Based on 28 active and 219 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of August 31, 2026.
Location
45 Island Avenue, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$17,968
- Property Taxes$2,690
- Insurance$1,165
- 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
- 2001
- New Construction
- No/Resale
- Living Area
- 5,657 sq ft
- Below Grade
- 1,020 sq ft
Schools
- Elementary
- Neck River
- Middle
- Per Board of Ed
- High
- Daniel Hand
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Laundry
- Upper Level
- Laundry Location
- Second Floor Laundry
- Appliances
- Gas CooktopConvection RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullFull With Walk-Out
- In-Law Apartment
- YesOver Garage
- Interior Features
- Cable - Pre-wired
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 1.57 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spaces10 total parking spacesAttached GaragePavedDrivewayPrivateCircularPaved
- Waterfront Details
- Access
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedSpaIn Ground Pool
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BreezewayPorchDeckGarden AreaLightingHot TubPatio
- Lot Description
- SecludedLightly WoodedTreedDryProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $32,281 / Annually
- Days on Market
- 140
- MLS #
- 24166497
- 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 8/31/2026. 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 8/31/2026 at 5:55 PM UTC.