5058 WINDWARD AVENUE Sarasota, FL $ 3,500,000
5058 WINDWARD AVENUE
$ 3,500,000
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Open House 12/17 1pm - 3pm
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5058 WINDWARD AVENUE

Sarasota, FL, 34242
$ 3,500,000
Bedrooms3 Baths3.0 Sq 3,471

Monthly Estimate*

$ 21,835

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Single Family Home for sale in Sarasota, FL

for $3,500,000 with 3 bedrooms and 3 full baths. This 3,471 square foot home was built in 2019 on a lot size of 0.33.

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.

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Open House

12/17/2025 1:00 PM - 3:00 PM
5058 WINDWARD AVENUE Sarasota, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 3,500,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 28,719

Style

Key West

Lot Size

0.33

Year Built

2019

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4667422

Features
Interior
Interior Amenities built-in features cathedral ceiling(s) ceiling fan(s) crown molding eating space in kitchen high ceilings in wall pest system kitchen/family room combo open floorplan solid surface counters split bed
Flooring engineered hardwood porcelain tile
Furnished Y/N unfurnished
Air Conditioning Y/N yes
Heating Y/N yes
Fireplace Y/N no
Half Baths 0
Laundry Features laundry room
Total Bedrooms 3
Total Baths 3
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General
Sewer public sewer
Heating heat pump
Cooling central air zoned
Utilities bb/hs internet available cable available electricity available public sewer available water available
Possession close of escrow
Roof metal
Appliances built-in oven cooktop disposal dryer microwave range range hood refrigerator tankless water heater washer wine refrigerator
Zoning rsf2
Garage Spaces 3
Patio/Porch Features front porch
Architectural Style key west
Pool Features gunite in ground tile
Security Features security system smoke detector(s)
Construction Materials block concrete stucco
Pets Allowed yes
Year Built 2019
View water
Levels one
Property Subtype single family residence
Tax Year 2025
Ownership fee simple
Waterfront Features canal - saltwater
County sarasota
New Construction no
Property Type residential
HOA N
Attached Garage yes
Energy Efficient appliances
Subdivision Name sara sands
Facing Direction east
Garage Y/N yes
Other Structures outdoor kitchen
Total Rooms 8
Full Baths 3
Status active
Directions 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.
High School sarasota high
City sarasota
Senior Community Y/N no
MLS Area 34242 - sarasota/crescent beach/siesta key
Lot Size Units square feet
Lot Size Square Feet 14184
Carport Y/N no
Listing Terms cash conventional fha va loan
Spa Features in ground
Elementary School phillippi shores elementary
Land Lease Y/N no
Tax Annual Amount 28719.17
Middle/Junior High School brookside middle
Property Condition completed
Additional Parcels Y/N no
Lease Considered Y/N yes
Virtual Tour https://my.matterport.com/show/?m=xattbun7g94 https://my.matterport.com/show/?m=xattbun7g94
Building Area Units square feet
Living Area Units square feet
Builder Name nutter custom construction
Standard Status active
Occupancy Type vacant
Tax Lot 17
Legal Description lot 17 sara sands unit 1
Water View canal
Water Access Type canal - saltwater
Pet Size Limit extra large (101+ lbs.)
Minimum Lease 1 month
Water Access Y/N yes
Additional Rooms bonus room den/library/office great room inside utility
Water View Y/N yes
Flood Zone Code ae
DockY/N yes
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Exterior
Exterior Amenities irrigation system outdoor kitchen sliding doors
Vegetation trees/landscaped
Parking Features driveway garage door opener
Lot Features floodzone level street dead-end
Water Source public
Lot Size Area 14184
Foundation Details slab stem wall
Spa yes
Building Area Total 4800
Lot Dimensions 93 x 152 x 93 x 153
Lot Size Acres 0.33
Road Surface Type paved asphalt
Private Pool yes
Waterfront Y/N yes
Covered Spaces 3
Road Frontage Type street dead-end street paved
Number of Lots 1
Builder Model anchorage
Road Responsibility public maintained road
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Internal Only
Street Number 1 5058
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* Excluded Features
List By
Keller Williams On The Water S

Broker

derek.edwards1123@gmail.com

Email

Affordability Calculator

$24,229
Per Month
90%
10%
0%
Monthly Principal & Interest
$21,835
Monthly Property Taxes
$2,393
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3325910 Elementary School
3326155 Middle School
Sarasota High High School
Pricing History
DatePricePrice ChangeDescription
12/11/2025$3,500,000 Listed Price

Map


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5058 WINDWARD AVENUE, Sarasota, FL, 34242 is a Single Family Home for sale at $3,500,000 with 3,471 sqft and a lot size of 0.33. 5058 WINDWARD AVENUE has 3 bedrooms, 3.0 baths, and was built in 2019. The property's zip code is 34242 which is in Sarasota, FL