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Property Description
Experience coastal living at its finest in this stunning 2021 custom-built home, positioned directly across from the water in beautiful Gulf Breeze. Situated on a 0.35-acre lot, this three-story residence offers breathtaking panoramic water views, including unforgettable sunrises and sunsets. Dolphins are often spotted playing in the mornings, and the iconic Blue Angels can occasionally be seen soaring overhead as they return home. The home features two expansive wrap-around balconies spanning the upper levels, creating the perfect setting for morning coffee, evening cocktails, or simply taking in the waterfront views. Inside, soaring 12-foot ceilings and an abundance of windows fill the home with natural light while showcasing the spectacular surroundings from nearly every room. The open-concept living area on the third floor is warm and inviting, complete with a gas fireplace and seamless access to the balcony. The chef's kitchen is equally impressive, featuring a large granite island, gas range, and ample space for entertaining family and friends. A second gas fireplace creates a cozy workspace in the dedicated office on the second level. The spacious primary suite offers a relaxing retreat with a large walk-in closet, while thoughtful design and quality finishes are found throughout the home. A durable metal roof provides lasting peace of mind, and the oversized two-car garage offers plenty of storage. Step outside to enjoy the backyard area, where a covered patio with a hot tub creates the perfect outdoor oasis. Also in the backyard, you will find dedicated RV parking complete with full RV hookups, a valuable feature for outdoor enthusiasts. Adding to the lifestyle, residents enjoy access to the community dock and picnic area, located just steps from the property-ideal for fishing, kayaking, or paddleboarding. Whether you're searching for a primary residence or a coastal retreat, this exceptional Gulf Breeze home checks all the boxes.
Full Property Details
Full Property Details for 1557 Winding Shore Dr
General
- Price: $975,000
- HOA FEE: $300
- Status: Active
- Type: Single Family
- Source: Pensacola
- MLS ID: 686241
- Updated: Today (7/21/2026)
- Added to Site: Today
Interior
- Interior Features: Baseboards, Bookcases, Ceiling Fan(s), Elevator, High Speed Internet, Recessed Lighting, Office/Study
- Fireplace: Yes
- Fireplace(s): Two or More
- Appliances: Gas Water Heater, Built In Microwave, Dishwasher, Disposal, Refrigerator
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: 12 x 16, Second Level, 192 Sq. Ft.
Other Rooms
- Living Room: 14 x 16, Third Level, 224 Sq. Ft.
- Kitchen: Not Updated, Granite Counters, Kitchen Island, Pantry, 14 x 10, Third Level, 140 Sq. Ft.
- Dining Room: Kitchen/Dining Combo
- Laundry: Inside, W/D Hookups
Additional Information
- Shared Amenities: Dock, Picnic Area
- Spa: Yes
- Security/Safety: Security System, Smoke Detector(s)
Exterior
- Exterior Features: Balcony
- Deck/Patio: Covered, Porch
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: 2 Car Garage, RV Access/Parking, Garage Door Opener
Location
- County: Santa Rosa
- Subdivision: Lighthouse Pointe
- Driving Directions: Head west on Gulf Breeze Pkwy, turn left on Nantahala Beach Rd, then right on Winding Shore Dr.
School Information
- Elementary School: West Navarre
- Middle School: WOODLAWN BEACH
- High School: Navarre
Community
- Association: Yes
Heating & Cooling
- Cooling Type: Central Air, Ceiling Fan(s)
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Architectural Style: Contemporary
- Construction: Frame
- Roof: Metal
- Stories/Levels: 3
- Square Feet: 2,544
- Year Built: 2021
- Property Condition: Resale
Lot Features
- Property View: Water
- Lot Size (Acres): 0.35
- Lot Dimensions: 90 x 159
- Road Maintenance: Private Maintained Road
- Zoning: Res Single
- Fencing (Description): Back Yard, Privacy
Water Features
- Water View: Yes
Financial Considerations
- Price Per Sq. Ft.: $383.25
- Association Fee: $300
Disclosures and Reports
- Property ID: 282S27231300A000330
Listed by Octavius Real Estate
Get Pre-Approved Today
Schools
Schools serving 1557 Winding Shore Dr
School District:Santa Rosa County School District
| Name | Grades | Distance |
|---|---|---|
West Navarre Intermediate School 1970 Cotton Bay Lane, Navarre, FL 32566 | 3-5 | 1.7 mi |
West Navarre Primary School 1955 Lowe Road, Navarre, FL 32566 | PK-2 | 2.4 mi |
Woodlawn Beach Middle School 1500 Woodlawn Way, Gulf Breeze, FL 32563 | 6-8 | 3.1 mi |
Navarre High School 8600 High School Boulevard, Navarre, FL 32566 | 9-12 | 6.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1557 Winding Shore Dr
Date
Details
Price
Change
Source
7/21/2026
Listed
$975,000
1447.62%
MLS
9/19/2002
Sold
$63,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1557 Winding Shore Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,066
-5%
$586,300
3%
2023
$7,429
777%
$569,223
776%
2021
$847
-88%
$65,000
-88%
2022
$7,258
757%
$552,644
1005%
2021
$847
31%
$50,000
11%
2019
$649
-1%
$45,000
—
2018
$658
10%
$45,000
11%
2017
$596
-1%
$40,500
—
2016
$600
-2%
$40,500
—
2015
$611
-11%
$40,500
-10%
2014
$690
-2%
$45,000
—
2013
$702
—
$44,887
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1557 Winding Shore Dr
1557 Winding Shore Dr, Gulf Breeze, FL 32563 (MLS# 686241) is a Single Family property with 4 bedrooms and 3 full bathrooms. 1557 Winding Shore Dr is currently listed for $975,000 and was received on July 21, 2026. Want to learn more about 1557 Winding Shore Dr? Do you have questions about finding other Single Family real estate for sale in Gulf Breeze? You can browse all Gulf Breeze real estate or contact a Coldwell Banker agent to request more information.

