1557 Winding Shore Dr

Off Market

1557 Winding Shore Dr

Midway FL 32563

2544 sq. ft.

15246 sq. ft.

Single-Family

Last sold for $975,000

Erika Wright, last sold this property on 26 August 2026 after 1099 days on market.

Overview

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.

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

2544 sq. ft. floor area

15246 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Midway over the last 12 months, the estimated median property value of 1557 Winding Shore Dr is $475.83k.

Median value

$475.83k

Estimated value range

$1 - $1.48m

Median days on market

Estimated value trend

-4%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Midway. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1557 Winding Shore Dr

2026

Sold

$975,000

26 Aug 2026 by Erika Wright, of Octavius Real Estate

2017

Sold

$60,000

29 Sep 2017 by Carol Brown, of Holley Properties

2017

Sold

$60,000

29 Sep 2017 by Carol Brown, of HOLLEY PROPERTIES

Happy sellers in Midway

90%

90% of sellers in Midway reported that their sale price either exceeded or met their price expectations.

Midway stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 14 reviews in Midway over the last 12 months.

Local market activity for 4 bedroom single-family properties in Midway

In the last 12 months, 285 four-bedroom single-family properties similar to 1557 Winding Shore Dr, have been sold.

This represents a 2% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Midway for a market analysis.

Peggy Braun

at Berkshire Hathaway HomeServices PenFed Realty

(53 reviews)

Get a market analysis

Vickie Wilson

at Levin Rinke Realty

(17 reviews)

Get a market analysis

Shonda Holifield

at Hurd Real Estate & Company LLC

(3 reviews)

Get a market analysis

Jennifer Keenan

at KELLER WILLIAMS REALTY GULF COAST

(3 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Midway

Peggy Braun

Sellers who recommend Peggy Braun have praised them for being clear communication, local expert, friendly, responsive, detail-oriented, well-prepared, and great negotiation