5244 Winding Way Sarasota, FL 34242
Estimated payment $7,417/month
Highlights
- In Ground Pool
- Open Floorplan
- Family Room Off Kitchen
- Phillippi Shores Elementary School Rated A
- Solid Surface Countertops
- Walk-In Closet
About This Home
Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here
Listing Agent
SHIRLEY INTERNATIONAL REALTY Brokerage Phone: 941-448-4872 License #3116512 Listed on: 10/23/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $9,776
Year Built
- Built in 1967
Lot Details
- 9,664 Sq Ft Lot
- North Facing Home
- Property is zoned RSF3
Parking
- 3 Car Garage
Home Design
- Bi-Level Home
- Shingle Roof
- Wood Siding
Interior Spaces
- 2,100 Sq Ft Home
- Open Floorplan
- French Doors
- Family Room Off Kitchen
- Living Room
- Crawl Space
Kitchen
- Range
- Microwave
- Dishwasher
- Solid Surface Countertops
Flooring
- Ceramic Tile
- Vinyl
Bedrooms and Bathrooms
- 4 Bedrooms
- Walk-In Closet
- 4 Full Bathrooms
Laundry
- Laundry in unit
- Dryer
- Washer
Pool
- In Ground Pool
- Gunite Pool
Utilities
- Central Heating and Cooling System
- Mini Split Air Conditioners
- High Speed Internet
- Cable TV Available
Community Details
- Property has a Home Owners Association
- Twin Oak Pond Community
- Twin Oak Pond Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 9
- Assessor Parcel Number 0082010022
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 |
|---|---|---|---|---|
| 2024 | $11,320 | $903,500 | $621,300 | $282,200 |
| 2023 | $11,320 | $926,700 | $584,900 | $341,800 |
| 2022 | $8,219 | $778,800 | $539,700 | $239,100 |
| 2021 | $6,609 | $537,400 | $362,100 | $175,300 |
| 2020 | $5,964 | $459,300 | $289,500 | $169,800 |
| 2019 | $5,555 | $438,600 | $241,300 | $197,300 |
| 2018 | $5,450 | $452,500 | $271,300 | $181,200 |
| 2017 | $4,976 | $318,593 | $0 | $0 |
| 2016 | $4,863 | $373,700 | $220,600 | $153,100 |
| 2015 | $3,991 | $263,300 | $126,300 | $137,000 |
| 2014 | $4,031 | $243,900 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/23/2025 10/23/25 | For Sale | $1,250,000 | -3.8% | $595 / Sq Ft | |
| 07/18/2022 07/18/22 | Sold | $1,300,000 | +4.4% | $619 / Sq Ft | View Prior Sale |
| 05/26/2022 05/26/22 | Pending | -- | -- | -- | |
| 05/24/2022 05/24/22 | For Sale | $1,245,000 | -- | $593 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Interfamily Deed Transfer | -- | -- |
Source: Stellar MLS
MLS Number: A4669581
APN: 0082-01-0022
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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