514 Main Street
Old Saybrook, Connecticut 06475
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,766
- Acres
- 2.26
- Year Built
- 2006
- Neighborhood
- Saybrook Point
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 514 Main Street, a waterfront custom-crafted home built in 2006 with unobstructed, expansive views of North Cove. This coastal-inspired retreat blends sophisticated elegance with everyday functionality. Boasting 3,766 square feet, this home has 4-bedrooms, 3.1-baths with an open-air concept that centers around a spectacular great room, setting the stage for seamless entertaining and comfortable daily living. Steeped in high-end finishes, the main level features an expansive chef's kitchen equipped with granite countertops, a large island, a dedicated walk-in pantry, separate bar/prep sink and double wall ovens. It transitions effortlessly into the dining area, which opens onto a tranquil screened porch directly overlooking North Cove-your future favorite spot for morning coffee or relaxing summer evenings. The highly desirable first-floor layout includes a luxurious primary master suite complete with a spa-like bath. Ideal for modern remote work, the main level offers a dedicated home office plus a separate quiet study. Upstairs, the home continues to impress with a playroom/rec room outfitted with custom built-in bookshelves. Tucked away on yet another level is a unique "Crow's Nest"-a perfect reading nook or a great space for a spin cycle with an amazing view of both North and South Coves. Complete your day with your favorite beverage on the balcony, watching the sailboats as they return to their moorings in the protected cove.
Key Facts
- City/Town
- Old Saybrook
- Neighborhood
- Saybrook Point
- Property / Style
- Single Family · Contemporary
- Year Built
- 2006
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,766 sq ft
- Lot Size
- 2.26 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $16,800 / Annually
Market Snapshot
The Old Saybrook Market
Single Family · trailing 12 months
Active Listings
34
13 under contract
Median List Price
$930,000
34 active listings
Median Closed Price
$748,000
132 sales
Median Days on Market
76
34 active listings
Median $ / Sq Ft
$466
34 active listings
Sale-to-List Ratio
99.3%
132 sales
How this home compares
List Price
$2.50M
vs $930,000 median
2.7× the median
Price / Sq Ft
$663
vs $466 median
42.3% above median
Days on Market
0 days
vs 76 days median
76 days fresher than median
Based on 34 active and 132 closed sales (trailing 12 mo) of single family in Old Saybrook. Source: SmartMLS · As of October 24, 2026.
Location
514 Main Street, Old Saybrook, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$13,711
- Property Taxes$1,400
- Insurance$832
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Old Saybrook
- Neighborhood
- Saybrook Point
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 2006
- New Construction
- No/Resale
- Living Area
- 3,766 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Old Saybrook
Interior
- Heating
- Hot Air
- Heat Fuel
- Gas In StreetNatural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherElectric DryerWine Chiller
- Basement
- Crawl Space
- Interior Features
- Audio SystemOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 2.26 acres
- Zoning
- A
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- HarborRiver
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- ShakeCedar
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level LotWater View
Listing & Financials
- Property Taxes
- $16,800 / Annually
- Days on Market
- 0
- MLS #
- 24197382
- 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 10/24/2026. 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 10/24/2026 at 5:00 PM UTC.