27 Gates Road
Old Saybrook, Connecticut 06475
- Beds
- 4
- Baths
- 1 | 1
- SqFt
- 1,088
- Acres
- 0.09
- Year Built
- 1926
- Neighborhood
- Cornfield Point
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Rare opportunity to own a classic Connecticut shoreline beach cottage in the highly sought-after Cornfield Point Beach Association. Located just three homes from the water, this seasonal cottage offers water views from the enclosed breezeway and captures the timeless charm of Old Saybrook coastal living. Original hardwood floors, knotty pine walls, authentic beadboard, oversized rooms, and a stunning beach stone fireplace showcase the character and craftsmanship rarely found today. Designed for generations of summer memories, this vintage beach home also features a detached garage, outdoor shower, and inviting indoor and outdoor living spaces perfect for entertaining after a day at the private sandy beach. Enjoy one of the Connecticut shoreline's most desirable golf cart-friendly beach communities with easy access to the beach, boating, kayaking, swimming, fishing, and breathtaking sunsets. Surrounded by beautiful custom coastal homes, this property offers exceptional flexibility to preserve its historic New England charm, renovate, expand, or build your dream waterfront-inspired beach house. Whether you're searching for a seasonal retreat, vacation home, weekend getaway, investment property, or future new construction opportunity, this rare Old Saybrook offering combines water views, private beach association access, an unbeatable location, and endless potential in one of Connecticut's premier shoreline communities.
Key Facts
- City/Town
- Old Saybrook
- Neighborhood
- Cornfield Point
- Property / Style
- Single Family · Colonial,Cottage
- Year Built
- 1926
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 1 full · 1 half
- Living Area
- 1,088 sq ft
- Lot Size
- 0.09 acres
- Garage / Parking
- 1 garage · 5 total
- Property Taxes
- $6,648 / Annually
- HOA Fee
- $300 / Quarterly
Market Snapshot
The Old Saybrook Market
Single Family · trailing 12 months
Active Listings
35
21 under contract
Median List Price
$1.10M
35 active listings
Median Closed Price
$750,000
126 sales
Median Days on Market
50
35 active listings
Median $ / Sq Ft
$573
35 active listings
Sale-to-List Ratio
99.0%
126 sales
How this home compares
List Price
$725,000
vs $1.10M median
34.0% below median
Price / Sq Ft
$666
vs $573 median
16.2% above median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 35 active and 126 closed sales (trailing 12 mo) of single family in Old Saybrook. Source: SmartMLS · As of August 8, 2026.
Location
27 Gates Road, Old Saybrook, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$3,739
- Property Taxes$554
- Insurance$242
- HOA$100
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Old Saybrook
- Neighborhood
- Cornfield Point
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Colonial,Cottage
- Year Built
- 1926
- New Construction
- No/Resale
- Living Area
- 1,088 sq ft
Schools
- Elementary
- Kathleen E. Goodwin
- High
- Old Saybrook
Interior
- Heating
- No Heat
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Off Kitchen
- Appliances
- Electric RangeRefrigerator
- Basement
- None
- Additional Rooms
- Breezeway
Exterior & Lot
- Lot Size
- 0.09 acres
- Zoning
- A
- Garage / Parking
- 1 garage space5 total parking spacesDetached GarageUnpaved
- Waterfront Details
- Walk to WaterBeach RightsWater CommunityView
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Shingle
- Color
- brown
- Roof
- Asphalt Shingle
- Foundation
- Piling
- Exterior Features
- BreezewayCovered Deck
- Lot Description
- Water View
HOA / Association
- Fee
- $300 / Quarterly
- Amenities
- Club House
Listing & Financials
- Property Taxes
- $6,648 / Annually
- Days on Market
- 0
- MLS #
- 24189749
- MLS Status
- Coming Soon
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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 8/8/2026. 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 8/8/2026 at 1:01 AM UTC.