5058 Windward Ave Siesta Key, FL 34242
Estimated payment $20,749/month
Highlights
- 93 Feet of Salt Water Canal Waterfront
- Dock made with concrete
- Open Floorplan
- Phillippi Shores Elementary School Rated A
- In Ground Pool
- Canal View
About This Home
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.
Listing Agent
KELLER WILLIAMS ON THE WATER S Brokerage Phone: 941-803-7522 License #3363878 Listed on: 12/10/2025
Open House Schedule
-
Saturday, December 13, 20251:00 to 3:00 pm12/13/2025 1:00:00 PM +00:0012/13/2025 3:00:00 PM +00:00Add to Calendar
-
Sunday, December 14, 20251:00 to 3:00 pm12/14/2025 1:00:00 PM +00:0012/14/2025 3:00:00 PM +00:00Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $28,719
Year Built
- Built in 2019
Lot Details
- 0.33 Acre Lot
- Lot Dimensions are 93x152x93x153
- 93 Feet of Salt Water Canal Waterfront
- Property fronts a saltwater canal
- Street terminates at a dead end
- East Facing Home
- Level Lot
- Irrigation Equipment
- Landscaped with Trees
- Property is zoned RSF2
Parking
- 3 Car Attached Garage
- Garage Door Opener
- Driveway
Home Design
- Key West Architecture
- Slab Foundation
- Stem Wall Foundation
- Metal Roof
- Concrete Siding
- Block Exterior
- Stucco
Interior Spaces
- 3,471 Sq Ft Home
- Open Floorplan
- Built-In Features
- Shelving
- Crown Molding
- Cathedral Ceiling
- Ceiling Fan
- Sliding Doors
- Great Room
- Family Room Off Kitchen
- Living Room
- Dining Room
- Home Office
- Bonus Room
- Game Room
- Inside Utility
- Canal Views
Kitchen
- Eat-In Kitchen
- Walk-In Pantry
- Built-In Oven
- Cooktop with Range Hood
- Microwave
- Wine Refrigerator
- Wolf Appliances
- Solid Surface Countertops
- Disposal
Flooring
- Engineered Wood
- Tile
Bedrooms and Bathrooms
- 3 Bedrooms
- Split Bedroom Floorplan
- Walk-In Closet
- 3 Full Bathrooms
- Soaking Tub
Laundry
- Laundry Room
- Dryer
- Washer
Home Security
- Home Security System
- Fire and Smoke Detector
- In Wall Pest System
Pool
- In Ground Pool
- In Ground Spa
- Gunite Pool
- Pool Tile
Outdoor Features
- Access to Saltwater Canal
- Seawall
- Dock made with concrete
- Outdoor Kitchen
- Front Porch
Schools
- Phillippi Shores Elementary School
- Brookside Middle School
- Sarasota High School
Utilities
- Zoned Heating and Cooling
- Heat Pump System
- Thermostat
- Tankless Water Heater
- High Speed Internet
- Cable TV Available
Additional Features
- Energy-Efficient Appliances
- Flood Zone Lot
Community Details
- No Home Owners Association
- Built by Nutter Custom Construction
- Sara Sands Subdivision, Anchorage Floorplan
- Sara Sands Community
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 17
- Assessor Parcel Number 0081120037
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $29,036 | $2,547,403 | -- | -- |
| 2024 | $28,304 | $2,475,610 | -- | -- |
| 2023 | $28,304 | $2,403,505 | $0 | $0 |
| 2022 | $27,696 | $2,333,500 | $897,600 | $1,435,900 |
| 2021 | $21,584 | $1,717,000 | $624,500 | $1,092,500 |
| 2020 | $6,558 | $522,200 | $510,600 | $11,600 |
| 2019 | $5,744 | $458,700 | $447,300 | $11,400 |
| 2018 | $6,303 | $510,500 | $504,300 | $6,200 |
| 2017 | $5,857 | $447,040 | $0 | $0 |
| 2016 | $5,300 | $406,400 | $401,700 | $4,700 |
| 2015 | $5,226 | $395,100 | $390,900 | $4,200 |
| 2014 | $4,836 | $316,500 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 12/10/2025 12/10/25 | For Sale | $3,500,000 | +62.4% | $1,008 / Sq Ft | |
| 11/20/2020 11/20/20 | Sold | $2,155,000 | -8.3% | $621 / Sq Ft | View Prior Sale |
| 10/30/2020 10/30/20 | Pending | -- | -- | -- | |
| 10/09/2020 10/09/20 | Price Changed | $2,349,500 | 0.0% | $677 / Sq Ft | |
| 10/09/2020 10/09/20 | For Sale | $2,349,500 | +2.2% | $677 / Sq Ft | |
| 09/09/2020 09/09/20 | Pending | -- | -- | -- | |
| 12/02/2019 12/02/19 | For Sale | $2,299,000 | +6.7% | $662 / Sq Ft | |
| 11/13/2019 11/13/19 | Off Market | $2,155,000 | -- | -- | |
| 10/11/2019 10/11/19 | For Sale | $2,299,000 | -- | $662 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $2,155,000 | Attorney | |
| Warranty Deed | $585,000 | Attorney | |
| Special Warranty Deed | $380,000 | Attorney | |
| Trustee Deed | $155,001 | Attorney | |
| Warranty Deed | $600,000 | Attorney | |
| Warranty Deed | -- | Attorney | |
| Warranty Deed | -- | Attorney | |
| Quit Claim Deed | -- | None Available | |
| Deed | -- | Attorney | |
| Quit Claim Deed | -- | -- | |
| Warranty Deed | -- | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $450,000 | Purchase Money Mortgage |
Source: Stellar MLS
MLS Number: A4667422
APN: 0081-12-0037
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
- 385 Avenida Madera
- 5012 Higel Ave
- 312 Avenida Leona
- 315 Avenida de Paradisio
- 0 Avenida Leona
- 310 Avenida Milano
- 307 Avenida de Paradisio
- 4920 Higel Ave
- 5174 Sandy Cove Ave
- 5219 Calle de Rio
- 4865 Featherbed Ln
- 5165 Sandy Cove Ave
- 4839 Primrose Path
- 117 Pass Key Rd Unit 117
- 308 Canal Rd
- 225 Hourglass Way Unit 103
- 143 Whispering Sands Cir Unit 30
- 238 Island Cir
- 262 Island Cir
- 643 Calle de Peru
- 345 Avenida Leona
- 339 Avenida de Paradisio
- 412 Treasure Boat Way
- 314 Avenida de Paradisio
- 327 Avenida Milano
- 301 Avenida Madera Unit B
- 301 Avenida Madera Unit A
- 5216 Calle de Costa Rica
- 4852 Featherbed Ln
- 357 Tierra Mar Ln Unit 5
- 143 Whispering Sands Dr
- 4900 Ocean Blvd Unit 501
- 137 Avenida Messina Unit 2
- 111 Pass Key Rd Unit 111
- 22 Sandy Cove Rd Unit 10-5
- 11 Sandy Cove Rd Unit 8F
- 211 Island Cir
- 4822 Ocean Blvd Unit 2D
- 95 Sandy Hook Rd S
- 4822 Ocean Blvd Unit 2F