Sarasota MLS Listings

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$3,500,000
New Listing

5058 WINDWARD AVENUE
SARASOTA, FL 34242

For Sale|Single Family Residence|Active
3
Beds
3
Total Baths
3
Full Baths
3,471
SqFt
$1,008
/SqFt
2019
Built
Subdivision:
SARA SANDS
County:
Sarasota
Call Now: 941-265-2455
Is this the listing for you? We can help make it yours.
941-265-2455
Upcoming Open Houses
Sat, Dec 13, 1:00 PM - 3:00 PM
Sun, Dec 14, 1:00 PM - 3:00 PM
5058 WINDWARD AVENUE5058 WINDWARD AVENUE5058 WINDWARD AVENUE5058 WINDWARD AVENUE
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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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Listing Snapshot
Price 
$3,500,000
Days On Site 
0 Days
Bedrooms 
3
Inside Area (SqFt) 
3,471 sqft
Total Baths 
3
Full Baths 
3
Partial Baths 
N/A
Lot Size 
0.33 Acres
Year Built 
2019
MLS® Number 
A4667422
Status 
Active
Property Tax 
$28,719.17
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Builder
Friends & Family
Recent Activity
10 minutes agoListing updated with changes from the MLS®
23 hours agoListing first seen on site
General Features
Acres 
0.33
Attached Garage 
Yes
Direction Faces 
East
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Green Energy Efficient 
Appliances
Levels 
One
Parking 
DrivewayGarage Door OpenerAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Security SystemSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
4800
Style 
Key West
Utilities 
Cable AvailableElectricity AvailableSewer AvailableWater Available
Water Source 
Public
Zoning 
RSF2
Interior Features
Appliances 
CooktopDisposalDryerMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWine Refrigerator
Cooling 
Central AirZoned
Flooring 
HardwoodTile
Furnished 
Unfurnished
Heating 
Heat Pump
Interior 
Built-in FeaturesCathedral Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsOpen FloorplanWalk-In Closet(s)
Laundry Features 
Laundry Room
Spa 
Yes
Bedroom 2 
Dimensions - 12x14Level - FirstFeatures - Ceiling Fan(s)
Bedroom 3 
Dimensions - 12x14Level - FirstFeatures - Ceiling Fan(s)
Dining Room 
Dimensions - 18x14Level - First
Game Room 
Dimensions - 14x17Level - First
Kitchen 
Dimensions - 19x14Level - FirstFeatures - Kitchen Island
Living Room 
Dimensions - 26x19Level - First
Master Bedroom 
Dimensions - 15x22Level - First
Office 
Dimensions - 12x15.5Level - First
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Exterior Features
Construction Details 
BlockConcreteStucco
Exterior 
Outdoor KitchenDock
Lot Features 
LevelPavedWaterfront
Other Structures 
Outdoor Kitchen
Patio And Porch 
Front Porch
Pool Features 
GuniteIn GroundTilePrivate
Private Pool 
Yes
Roof 
Metal
Spa 
Yes
Spa Features 
In Ground
View 
CanalWater
Waterfront 
Yes
Waterfront Features 
Canal Front
Waterview 
CanalWater
Community Features
Financing Terms Available 
CashConventionalFHAVA Loan
MLS Area 
34242 - Sarasota/Crescent Beach/Siesta Key
Roads 
Asphalt
Township 
37
Schools
School District
Unknown
Elementary School
Phillippi Shores Elementary
Middle School
Brookside Middle
High School
Sarasota High
Listing courtesy of KELLER WILLIAMS ON THE WATER S 9419293183



Listing information is provided by Participants of the Stellar MLS. 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. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-12-11 03:43 PM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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