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$3,250,000
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Property Description
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 and can easily serve as a fourth bedroom, with the flex room ideal for a home office or bonus space. 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.
Full Property Details
Full Property Details for 5058 Windward Ave
General
- Sold For: $3,250,000
- Taxes: $28,719 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4667422
- Added to Site: 83 day(s) ago
Rental Information
- Min. Lease: 1 Month
Interior
- Number of Rooms: 8
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, In Wall Pest System, Kitchen and Family Room Combination, Open Floorplan, Solid Surface Counters, Split Bedroom, Thermostat, Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Engineered Hardwood, Porcelain Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Tile
- Spa: Yes
- Spa Description: In Ground
- Security/Safety: Security System, Smoke Detector(s)
Exterior
- Exterior Features: Irrigation System, Outdoor Kitchen, Sliding Doors
- Deck/Patio: Front Porch
- Porch/Patio/Deck: Front Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Door Opener
Location
- Area: 34242 - Sarasota/Crescent Beach/Siesta Key
- County: Sarasota
- Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Subdivision: SARA SANDS
- Driving 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.
- Direction Faces: East
School Information
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
Community
- Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Number of Pets: 2
- Pet Restrictions: Contact Sarasota County for Pet Restrictions
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Heat Pump
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Public, Sewer Available, Water Available
Structural Information
- Architectural Info: Key West
- Architectural Style: Key West
- Builder: Nutter Custom Construction
- Exterior Const.: Block, Concrete, Stucco
- Roof: Metal
- Stories/Levels: One
- Square Feet: 3,471
- Sq. Ft. Source: Builder
- Living Area: 3,471 Sq. Ft.
- Year Built: 2019
Additional Structures
- Other Structures: Outdoor Kitchen
Lot Features
- Property View: Water
- Lot Size (Acres): 0.33
- Lot Size (Sq. Ft.): 14,184
- Lot Size: 14184
- Lot Dimensions: 93 x 152 x 93 x 153
- Frontage: Street Dead-End, Street Paved
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Canal - Saltwater
- Water Extras: Yes
- Water Front Desc.: Saltwater Canal
Green Features
- Energy Efficient: Appliances
Financial Considerations
- Assoc Fee Desc.: None
- Tax Amount: $28,719.17
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 17, SARA SANDS UNIT 1
- Flood Zone Info: AE
- APN: 81120037
- Property ID: 81120037
Listed by Keller Williams On The Water S
Sold by Bright Realty
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Schools
Schools serving 5058 Windward Ave
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Phillippi Shores Elementary School 4747 South Tamiami Trail, Sarasota, FL 34231 | PK-5 | 2.1 mi |
Brookside Middle School 3636 South Shade Avenue, Sarasota, FL 34239 | 6-8 | 2.7 mi |
Sarasota High School 2155 Bahia Vista Street, Sarasota, FL 34239 | 9-12 | 3.8 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5058 Windward Ave
Date
Details
Price
Change
Source
2/09/2026
Sold
$3,250,000
-7.14%
MLS
12/10/2025
Listed
$3,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
5058 Windward Avenue, Sarasota, FL 34242 (MLS# A4667422) is a Single Family property that was sold at $3,250,000 on February 09, 2026. Want to learn more about 5058 Windward Avenue? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

