64 Webster Point Road
Madison, Connecticut 06443
Reduced from $2,349,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 4,010
- Acres
- 0.34
- Year Built
- 2005
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
NEW PRICE BELOW RECENT APPRAISAL. One house from L.I. Sound on a quiet Webster Point Road cul-de-sac, this 4000+ sf house delivers the ideal shoreline life: deeded beach access, multi-level panoramic water views, walkable distance to the Hammonasset Trail, and a spacious interior perfect for both large gatherings & cozy family life. A double-height foyer opens the house and leads into light-filled rooms with 10' ceilings & hardwood floors throughout the 1st level. The expansive LR is anchored by a handsome wood-burning FP and flows to a formal DR featuring intricate millwork from a historic mansion. The same heirloom millwork frames the dining area of the kitchen, which is fully-equipped to inspire the modern gourmet. The kitchen has access to a large porch perfect for summer entertaining & connects to a heated 2-car garage. Upstairs, the home offers a rare configuration: 2 primary suites - one on the 2nd floor, one on the 3rd - each with private decks to enjoy the water views that are unparalleled for area houses not directly waterfront. Two additional bedrooms on the 2nd floor share a hall bath & laundry room. The 3rd floor includes a finished den/office & storage. Deeded access to a low-tide beach and the sandy Pent Road beach offer endless opportunities to watch the sun rise or set, relax in the salty breeze, sea-fish, or take the canoe out. The bike-and-walking trail to Hammonasset State Park is at road's end.
Key Facts
- City/Town
- Madison
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2005
- Days on Market
- 96 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 4,010 sq ft
- Lot Size
- 0.34 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $33,145 / 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
$2.19M
vs $1.30M median
69.0% above median
Price / Sq Ft
$547
vs $434 median
26.0% above median
Days on Market
96 days
vs 57 days median
39 days longer 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
64 Webster Point Road, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$11,192
- Property Taxes$2,762
- Insurance$732
- 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
- 2005
- New Construction
- No/Resale
- Living Area
- 4,010 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Upper Level
- Laundry Location
- 2nd floor hall
- Appliances
- Gas RangeWall OvenRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- PartialUnfinished
- In-Law Apartment
- Possible
- Interior Features
- Auto Garage Door OpenerCable - Available
- Additional Rooms
- FoyerMud Room
Exterior & Lot
- Lot Size
- 0.34 acres
- Zoning
- R-4
- Garage / Parking
- 2 garage spaces8 total parking spacesAttached GarageOff Street ParkingDrivewayPrivateAsphaltCrushed Stone
- Waterfront Details
- Walk to WaterAccess
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- ShingleWood
- Roof
- Asphalt Shingle
- Foundation
- BlockConcrete
- Exterior Features
- DeckUnderground Sprinkler
- Lot Description
- Level LotProfessionally LandscapedWater View
Listing & Financials
- Property Taxes
- $33,145 / Annually
- Days on Market
- 96
- MLS #
- 24162180
- MLS Status
- Under Contract
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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 7:01 AM UTC.