5103 Windward Avenue

Off Market

5103 Windward Avenue

Siesta Key FL 34242

4410 sq. ft.

14490 sq. ft.

Single-Family

Last sold for $3,200,000

Karen Greco, last sold this property on 02 November 2026 after 594 days on market.

Overview

Freshly completed and built safely 10 feet above the island’s flood plain, 5103 Windward is a spectacular new waterfront residence where elevated design meets effortless island living. Set on nearly one-third of an acre along the Grand Canal, with 90 feet of new seawall and saltwater boating access to the Intracoastal Waterway and Gulf beyond, this is the kind of home that turns everyday life into a vacation. And the location? Hard to beat. From this central Siesta Key setting, the island’s legendary white-sand beaches and the laid-back charm of Siesta Village are just minutes away. Beach morning, boat afternoon, cocktails by the pool — it’s all within easy reach. Inside, 3,034 square feet of beautifully designed living space unfolds with an easy, open flow made for both relaxing and entertaining. The great room immediately draws you in with soaring double-height ceilings, rich architectural details, and a dramatic floor-to-ceiling fireplace wall. Walls of glass bring the outdoors in, framing expansive views of the pool, backyard, and sparkling canal beyond. Step outside and the fun really begins. A stylish outdoor lounge with wood ceiling accents, a professional grill station, and a heated pool and spa create the perfect backdrop for everything from lazy afternoons to unforgettable evenings with family and friends. As the sun goes down, thoughtfully designed landscape lighting takes over, casting the backyard in a warm, magical glow. The kitchen is every bit as impressive — and ready for everything from morning coffee to dinner parties. A premium Sub-Zero and Wolf appliance package, beautiful stone countertops, designer fixtures and finishes, a walk-in pantry, and adjoining laundry combine style with serious functionality. When it’s time to dine, the formal dining room delivers with a custom built-in buffet and French doors opening to a brick-paver patio. Picture dinner under the stars, a cool island breeze, and nowhere else you need to be. Need a little more room to play? The bonus room checks all the wit a pool bath, and two walls of glass sliders opening to the expansive outdoor living areas and picturesque water views. It’s the perfect spot for game day, movie night, guests, or simply kicking back after a day on the water. The primary suite is your private retreat. An adjoining office with custom built-ins, an oversized wardrobe designed for two, and a spa-inspired bath create a serene escape of your own. Soak in the freestanding tub, refresh in the frameless glass shower with rain head, or start the day at separate stone-topped vanities designed for effortless mornings. Two additional en-suite bedrooms give family and guests their own comfortable spaces to relax and recharge. Outside, the details continue with a brick-paver driveway, three-car garage, professional landscaping with timed irrigation, and exceptional curb appeal. Inside and out, thoughtful custom touches reflect the quality and craftsmanship you’d expect from Allegra Homes’ award-winning team. This is more than brand-new construction. It’s an invitation to embrace the Siesta Key way of life — mornings on the water, afternoons by the pool, evenings under the stars, and the beach always just a short drive away.Fresh. Waterfront. Effortlessly luxurious. Completely island. Your Siesta Key paradise is ready.

Features

3 bedrooms

5 bathrooms

3 carspaces

3 garage spaces

4410 sq. ft. floor area

14490 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Siesta Key over the last 12 months, the estimated median property value of 5103 Windward Avenue is $1.4m.

Median value

$1.4m

Estimated value range

$500k - $12m

Median days on market

Estimated value trend

17%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Siesta Key. 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 5103 Windward Avenue

2026

Sold

$3,200,000

02 Nov 2026 by Karen Greco, of GRECO REAL ESTATE

Happy sellers in Siesta Key

90%

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

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

This is based on voluntary sentiment collected from 13 reviews in Siesta Key over the last 12 months.

Local market activity for 3 bedroom single-family properties in Siesta Key

In the last 12 months, 71 three-bedroom single-family properties similar to 5103 Windward Avenue, have been sold.

This represents a 11% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

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