Skip to main content

108 Maple Avenue

Old Saybrook, Connecticut 06475

ACTIVE$1,850,000

Reduced from $2,200,000

Beds
4
Baths
2 | 2
SqFt
3,188
Acres
1.80
Year Built
1965
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
2-Car Garage2 FireplacesVirtual TourPrice Reduced

About This Home

Contemporary coastal elegance meets exceptional privacy along South Cove in Old Saybrook. Set on an extraordinary 1.8-acre parcel, this cedar-sided, 3,188-square-foot residence offers breathtaking water views from nearly every room and a setting that is virtually impossible to recreate. Originally built in 1965 and thoughtfully rebuilt in 1991, the home was designed to capture its spectacular surroundings with vaulted ceilings, expansive windows, and seamless indoor-outdoor living. The living room showcases custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a well-appointed family room and opens to a 300-square-foot enclosed porch, an ideal space for entertaining and relaxation. The main floor primary suite is a private retreat with soaring ceilings, deck access, stunning water views, dual bathrooms, and an impressive 120-square-foot walk-in closet. A formal dining room, additional bedroom, and separate laundry room complete the first floor. Upstairs, two bedrooms share a Jack-and-Jill bath, providing comfort and privacy for family and guests. Set well back from the road, this exceptional property provides the perfect balance of seclusion and convenience. Whether enjoyed as a year-round residence or a legacy waterfront retreat, the setting offers endless opportunities. Properties of this caliber, acreage, and waterfront presence are extraordinarily rare. A true heritage property and a once-in-a-generation op

Key Facts

City/Town
Old Saybrook
Neighborhood
N/A
Property / Style
Single Family · Contemporary
Year Built
1965
Days on Market
39 days
Beds
4
Baths
2 full · 2 half
Living Area
3,188 sq ft
Lot Size
1.80 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$14,813 / Annually

Market Snapshot

The Old Saybrook Market

Single Family · trailing 12 months

Median Days on Market

41

33 active listings

Median $ / Sq Ft

$573

33 active listings

Sale-to-List Ratio

98.9%

127 sales

How this home compares

List Price

$1.85M

vs $1.07M median

72.1% above median

Price / Sq Ft

$580

vs $573 median

In line with median

Days on Market

39 days

vs 41 days median

In line with median

Based on 33 active and 127 closed sales (trailing 12 mo) of single family in Old Saybrook. Source: SmartMLS · As of July 28, 2026.

Location

108 Maple Avenue, Old Saybrook, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,284

per month

  • Principal & Interest$9,433
  • Property Taxes$1,234
  • Insurance$617
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Old Saybrook
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Contemporary
Year Built
1965
New Construction
No/Resale
Living Area
3,188 sq ft

Schools

Elementary
Kathleen E. Goodwin
High
Old Saybrook

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Ceiling FansCentral Air
Fireplaces
2
Laundry
Main Level
Laundry Location
Full laundry room located on main floor
Appliances
Gas CooktopWall OvenRefrigeratorDishwasherWasherDryerWine Chiller
Basement
Crawl SpaceStorageHatchway Access
In-Law Apartment
No
Interior Features
Audio SystemAuto Garage Door OpenerOpen Floor Plan
Additional Rooms
FoyerLaundry Room

Exterior & Lot

Lot Size
1.80 acres
Zoning
AA-2
Garage / Parking
2 garage spaces6 total parking spacesDetached GaragePavedDrivewayPrivateAsphalt
Waterfront Details
Walk to WaterView
Water Source
Private Well
Sewer
Septic
Flood Zone
Yes
Construction
Cedar
Color
Grey
Roof
Asphalt ShingleShingle
Foundation
Concrete
Exterior Features
BalconyShedPorchWrap Around DeckDeckLighting
Lot Description
SecludedCity ViewsInterior LotLevel LotProfessionally LandscapedWater View

Listing & Financials

Property Taxes
$14,813 / Annually
Days on Market
39
MLS #
24185410
MLS Status
Active

Similar Properties

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

Listed By

Jessica Blancato

(860) 888-3277

William Pitt Sotheby's Int'l

(860) 434-2400

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 5:25 AM UTC.