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95 Middletown Avenue

Old Saybrook, Connecticut 06475

PENDING$1,049,900

Reduced from $1,099,900

Beds
4
Baths
2
SqFt
1,566
Acres
0.15
Year Built
1926
Matt Caiola

Matt Caiola

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About This Home

95 Middletown Avenue offers a rare opportunity to enjoy four season living in the heart of Saybrook Manor, one of Old Saybrook's most sought after shoreline communities. Renovated in 2022 with thoughtful attention to comfort and design, this beautifully updated home combines timeless coastal character with modern amenities and sweeping views of the Oyster River & Long Island Sound. With approx. 1,600 sq ft. of living space, the home features a reverse floor plan designed to maximize natural light and take advantage of the water views. The main living spaces feel bright and open, w/ hardwood floors, updated finishes, and open layout. A spacious deck with full panoramic views provides the perfect setting for morning coffee, outdoor dining, or relaxing while overlooking the water & shoreline. The home includes four bedrooms and two full bathrooms, offering flexibility for guests, remote work, or year round living. The updated kitchen opens comfortably into the living/dining areas, creating an inviting atmosphere. Modern conveniences including central air and mini split. The property includes a rare two car garage along w/ 400 square foot barn full of charm and potential perfect for a studio, workshop, gym, storage. An outdoor shower after a day at the beach. Residents enjoy a private beach exclusive to the community steps away! This home does not require flood ins adding long term value. Just minutes from marinas, restaurants, shopping the location is best CT shoreline living.

Key Facts

City/Town
Old Saybrook
Neighborhood
Saybrook Manor
Property / Style
Single Family · Colonial
Year Built
1926
Days on Market
68 days
Beds
4
Baths
2 full
Living Area
1,566 sq ft
Lot Size
0.15 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$6,257 / Annually
HOA Fee
$321 / 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

$1.05M

vs $1.07M median

In line with median

Price / Sq Ft

$670

vs $573 median

16.9% above median

Days on Market

68 days

vs 41 days median

27 days longer than 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

95 Middletown Avenue, Old Saybrook, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,251

per month

  • Principal & Interest$5,353
  • Property Taxes$521
  • Insurance$350
  • HOA$27

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

Location

City/Town
Old Saybrook
Neighborhood
Saybrook Manor
County
Middlesex

Residence

Property Type
Single Family
Style
Colonial
Year Built
1926
New Construction
No/Resale
Living Area
1,566 sq ft
Below Grade
150 sq ft

Schools

Elementary
Per Board of Ed
High
Old Saybrook

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Ceiling FansCentral AirSplit System
Laundry
Lower Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullGarage Access
Interior Features
Auto Garage Door OpenerOpen Floor Plan

Exterior & Lot

Lot Size
0.15 acres
Zoning
A
Garage / Parking
2 garage spaces6 total parking spacesAttached GarageDrivewayPrivate
Waterfront Details
Walk to WaterBeach RightsViewAccess
Water Source
Public Water In Street
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyShedCovered Deck
Lot Description
Water View

HOA / Association

Fee
$321 / Annually
Amenities
Club House

Listing & Financials

Property Taxes
$6,257 / Annually
Days on Market
68
MLS #
24176978
MLS Status
Under Contract - Continue to Show

Similar Properties

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Listed By

Tracy Molloy

(860) 573-8525

Coldwell Banker Realty

(860) 633-3661

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 6:20 AM UTC.