18 Shepard Street
Old Saybrook, Connecticut 06475
- Beds
- 3
- Baths
- 2
- SqFt
- 2,114
- Acres
- 0.21
- Year Built
- 1958
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Enjoy the best of Old Saybrook from this spacious 3-bedroom, 2-bath Cape offering over 2,100 square feet of living space in a residential setting close to downtown and the shoreline. Just beyond Main Street and The Kate, with convenient access to Saybrook Point, restaurants, shopping, the train station and area amenities. Inside, an expansive living and family room offers hardwood floors, a brick fireplace and an abundance of natural light. The generously sized kitchen and dining area features ample cabinetry, granite countertops, stainless steel appliances and a large center island with seating. The flexible floor plan includes a first-floor bedroom and full bath, with two additional bedrooms and a second full bath upstairs. Two ductless mini-splits provide added comfort. Outside, enjoy a fenced backyard with a paver patio and mature trees, offering a great space for relaxing, gardening or entertaining. Additional highlights include a roof less than one year old, a detached one-car garage with electricity, paved driveway and full basement. A wonderful opportunity to enjoy generous living space and a convenient location near the heart of Old Saybrook and the Connecticut shoreline.
Key Facts
- City/Town
- Old Saybrook
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1958
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,114 sq ft
- Lot Size
- 0.21 acres
- Property Taxes
- $5,165 / Annually
Market Snapshot
The Old Saybrook Market
Single Family · trailing 12 months
Active Listings
34
23 under contract
Median List Price
$1.07M
34 active listings
Median Closed Price
$750,000
127 sales
Median Days on Market
59
34 active listings
Median $ / Sq Ft
$551
34 active listings
Sale-to-List Ratio
99.2%
127 sales
How this home compares
List Price
$699,900
vs $1.07M median
34.7% below median
Price / Sq Ft
$331
vs $551 median
39.9% below median
Days on Market
0 days
vs 59 days median
59 days fresher than median
Based on 34 active and 127 closed sales (trailing 12 mo) of single family in Old Saybrook. Source: SmartMLS · As of August 25, 2026.
Location
18 Shepard Street, Old Saybrook, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$3,594
- Property Taxes$430
- Insurance$233
- 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
- Cape Cod
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 2,114 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Old Saybrook
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- DuctlessWall Unit
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Off Kitchen back Hallway
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullFull With Hatchway
Exterior & Lot
- Lot Size
- 0.21 acres
- Zoning
- A
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- Shake
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Fence - WoodFence - FullLevel Lot
Listing & Financials
- Property Taxes
- $5,165 / Annually
- Days on Market
- 0
- MLS #
- 24201611
- MLS Status
- Coming Soon
Similar Properties
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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 8/25/2026. 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 8/25/2026 at 3:55 PM UTC.