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64 Webster Point Road

Madison, Connecticut 06443

PENDING$2,195,000

Reduced from $2,349,000

Beds
4
Baths
3 | 1
SqFt
4,010
Acres
0.34
Year Built
2005
Matt Caiola

Matt Caiola

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2-Car Garage2 FireplacesPrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,686

per 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

Similar Properties

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

Listed By

Margaret Muir

(203) 415-9187

William Pitt Sotheby's Int'l

(203) 245-6700

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.