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5058 WINDWARD AVENUE SARASOTA FL 34242

$3,500,000
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5058 WINDWARD AVENUE, SARASOTA, FL 34242 - MLS#MFRA4667422 5058 WINDWARD AVENUE, SARASOTA, FL 34242 - MLS#MFRA4667422 5058 WINDWARD AVENUE, SARASOTA, FL 34242 - MLS#MFRA4667422 5058 WINDWARD AVENUE, SARASOTA, FL 34242 - MLS#MFRA4667422

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 5058 Windward Ave

3 Bedrooms
3 Bathrooms
3 Car Garage
4,800 Square Feet
3,471SF Living Area
Pool:
Yes
Water
Year Built 2019
Listed For 4 Days

This custom-built home received the “best overall” award in the 2021 manatee and sarasota county parade of homes. Experience the pinnacle of siesta key waterfront living in this 2019-built masterpiece by nutter custom construction. Designed with precision and built to last, this solar-powered coastal retreat sits on high elevation and spans over 3,400 living square feet, offering 3 bedrooms, 3 baths, and two versatile flex rooms that redefine modern island living. Every element blends elegance, performance, and peace of mind. You walk into a wide-open floor plan that immediately draws you in. To the left, the primary suite offers total privacy with a spacious bedroom, spa-inspired bathroom featuring double vanities, a soaking tub, glass-enclosed shower with 4 shower heads, and a private outdoor shower with 2 shower heads, connected directly to the master bath a truly open-air sanctuary. To the right, your dedicated office provides focus and functionality, while the heart of the home opens to expansive living and dining spaces with a chef’s kitchen showcasing high-end cabinetry, premium flooring, designer lighting, and top-of-the-line sub-zero and wolf appliances. Each guest bedroom includes its own private en-suite bath, offering comfort and privacy for family and visitors alike. A large walk-in pantry and laundry room are conveniently positioned near the kitchen. A whole-home water softening system, an in-wall pest control system with access ports, 2 air conditioning systems to keep the home evenly comfortable during the warmest weather, and 2 tankless water heaters to provide plenty of hot water. An oversized three-car garage for everyday ease. An additional flex room opens to the pool through oversized sliders, perfect for a second office, game room, or guest suite. There are automated window shades in the living room and game room. The home runs entirely on solar power and includes a multi-room sound system that fills the home and outdoor living space with your favorite music. Massive hurricane-rated sliding glass doors wrap the back of the home, creating a seamless flow to your backyard oasis, including landscape lighting and an irrigation system. An integrated security system with perimeter cameras provides extra peace of mind. Step out onto the beautiful travertine pool deck, featuring a heated pool and champagne-edged spa, outdoor lounge, and covered dining area with a built-in outdoor chef’s kitchen powered by propane, perfect for entertaining in style, and all with a sunset view. Beyond the pool, enjoy a lush, manicured backyard with direct access to the wide siesta key grand canal. A dedicated 14,000-pound boat lift allows you to launch your boat with ease, making days on the water effortless. A separate private docking area is available for your friends to arrive by boat or for jet skis. Enjoy kayaking, paddleboarding, and scenic canal rides, or simply relax and take in the sunsets from your extended concrete pad with a built-in concrete firepit, ideal for gatherings by the water. Every detail of this home is custom-crafted, from its hurricane-rated construction and elevated-lot placement to its energy-efficient systems and timeless coastal design. 5058 windward ave isn’t just a home, it’s a statement in waterfront living: high elevation, solar-powered, elegant, and built for those who expect the very best on siesta key.

This luxury single family home was built in 2019 and features 3 bedrooms, and 3 full bathrooms. This home for sale is 4,800 square feet, with 3,471 sq ft being air conditioned living space. The home has a 3 car garage and has a private swimming pool.

Directions to this property are as follows: From S. Tamiami Trail - Turn Right Onto Siesta Dr. - Continue Onto Higel Ave; At The Traffic Circle Continue Straight; Higel Becomes Winward Place; The Destination Will Be On The Left #5058.

Please contact your ZFC agent for more information about MLS# MFRA4667422 or any other homes for sale in Sarasota or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Built-In Oven, Cooktop, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator

Other Equipment

Irrigation Equipment

Architecture

Key West

Cooling

Central Air, Zoned

Heating

Heat Pump

Flooring

Hardwood, Tile

Parking

Driveway, Garage Door Opener

Lot Dimensions

93x152x93x153

Lot Size

14184

View

Water view

Construction Materials

Block, Concrete, Stucco

Security Features

Security System, Smoke Detector(s)

Interior Features

Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, In Wall Pest System, Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Split Bedroom, Thermostat, Walk-In Closet(s)

Furnished

Unfurnished

Exterior Features

Outdoor Kitchen, Sliding Doors

Lot Features

Flood Zone, Level, Street Dead-End, Paved

Property Condition

Completed

Builder Name

Nutter Custom Construction

Builder Model

Anchorage

Patio And Porch Features

Front Porch

Pool Features

Gunite, In Ground, Tile

Roof

Metal

Utilities

B B/H S Internet Available, Cable Available, Electricity Available, Public, Sewer Available, Water Available

Waterfront Features

Canal-Saltwater

Laundry

Laundry Room

Spa Features

In Ground

Zoning

R S F2

Year Built

2019

Pets Allowed

Yes

Annual Real Estate Taxes

$28,719 (2025)

Legal Description

Lot 17, Sara Sands Unit 1

Property Type

Single Family Home

Other Structures

Outdoor Kitchen

Direction Faces

East

MLS Number

MFRA4667422

Universal Property Id

U S-12115-N-0081120037-R-N

Days On Market

4

Community Name

Sara Sands

5058 Windward Ave Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 5058 Windward Ave should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $28,719 but will likely change when this home sells. These estimations are calculated from a list price of $3,500,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 5058 Windward Ave

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRA4667422 Listing History

10/01/2025 Listed for sale by KELLER WILLIAMS ON THE WATER S with MLS# MFRA4667422 with a list price of $3,500,000.

Public Transportation

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

This listing of 5058 Windward Ave Sarasota FL 34242 was last updated on 2025-12-14 15:12:17. Listing courtesy of KELLER WILLIAMS ON THE WATER S.
MLS

Map of 5058 Windward Ave Sarasota FL 34242

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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