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18 Shepard Street

Old Saybrook, Connecticut 06475

COMING SOON - NEW$699,900
Beds
3
Baths
2
SqFt
2,114
Acres
0.21
Year Built
1958
Matt Caiola

Matt Caiola

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1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,257

per 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

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

Listed By

Tony Walstra

(860) 460-8825

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 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.