95 Middletown Avenue
Old Saybrook, Connecticut 06475
Reduced from $1,099,900
- Beds
- 4
- Baths
- 2
- SqFt
- 1,566
- Acres
- 0.15
- Year Built
- 1926
- Neighborhood
- Saybrook Manor
- Property Type
- Single Family

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
Active Listings
33
25 under contract
Median List Price
$1.07M
33 active listings
Median Closed Price
$750,000
127 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 6:20 AM UTC.