Video tour
$10,000 Closing Credit¹
#A4627841, Joanna Benante, Listing Office: MICHAEL SAUNDERS & COMPANY
$10,000
closing credit¹
5239 Winding Way Sarasota, FL 34242
$939,000 List price
$10,000
Closing credit¹
3 beds
2 full
1,512 sqft
0.2 acres
$621 / sqft
House
Property details
About 5239 Winding Way
Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining friends and family. The kitchen is fully equipped with a large pantry, ceiling-to-counter tiled backsplash, and a peninsula island. The living room is filled with natural lighting from the numerous windows, and features custom built-in shelves, a tongue and groove ceiling, ship lap paneling that makes the space feel inviting and cozy. The primary bedroom is filled with natural light and boasts two large windows. The primary bathroom is equally impressive with marble tile shower surround, penny tile shower floor and frameless glass shower frame. The secondary bedrooms are spacious and quaint. The large backyard and heated pool make outdoor events a breeze, and the perimeter privacy fence, lush trees, and rear water provide ultimate privacy. Siesta Key, is an 8-mile-long island located just a short bridge crossing west of Sarasota, offers stunning quartz-sand beaches and a plethora of outdoor recreational activities – from fishing to parasailing. <br></br> <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://tour.pinnaclerealestatemarketing.com/5239-Winding-Way-1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>
Highlights
Home typeSingle Family Residence
HeatingElectric
StatusActive
CoolingCentral Air
Size1,512 sqft
Lot size0.21 Acres
Year built1958
ParkingCovered
MLS #O6278642
WaterfrontLake Front, Pond
FireplaceElectric, Family Room
ViewGarden, Trees/Woods, Water
Private poolYes
Virtual tour
Summary
- MLS Number: O6278642
- MLS Name: MFRMLS
- Office Name: BALDWIN PARK REALTY LLC
- Office Phone: (407) 986-9800
- Listing Agent: Brian Cirillo
Listings courtesy of Stellar MLS as distributed by MLS GRID.
All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.
Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 2/8/2025, 2:20:37 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
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$939,000
5239 Winding Way
$10,000
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Jan 24, 2020 | Home Sold | $683,000 |
| Nov 30, 2018 | Home Sold | $655,900 |
| Dec 01, 2017 | Home Sold | $475,000 |
| May 10, 2013 | Home Sold | $475,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $861,698 | $10,096 |
| 2022 | $836,600 | $9,857 |
| 2021 | $592,900 | $9,857 |
| 2020 | $501,700 | $7,679 |
| 2019 | $410,000 | $5,498 |
| 2018 | $368,100 | $4,508 |
| 2017 | $351,200 | $4,823 |
History based on county public records data.
Nearby schools
8
Phillippi Shores Elementary School
Public Magnet PK-5
1.5 mi
•4747 S Tamiami Trl
10
Southside Elementary School
Public District PK-5
2.5 mi
•1901 Webber St
6
Gulf Gate Elementary School
Public District PK-5
2.6 mi
•6500 S Lockwood Ridge Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $109,115. Residents of Sarasota, FL typically earn between $100k-200k each year. Typical family type is married, no kids. Residents of this area typically have post secondary degree education.
How much money do the neighbors make?
14%
<35k
29%
35k-100k
38%
100k-200k
19%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
What types of families live nearby?
40%
Single, No Kids
4%
Single, with Kids
42%
Married, No Kids
14%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
8%
<11 yrs old
6%
12-17 yrs old
8%
18-34 yrs old
44%
35-64 yrs old
34%
65+ yrs old
What do the neighbors do for fun?
Men's Tennis
Hiking/backpacking
PGA/LPGA
Where do the neighbors shop?
Bloomingdales
Nordstrom Rack
Chico's
Where do the neighbors go to eat?
Bonefish Grill
Chipotle
California Pizza Kitchen
What do the neighbors drive?
Lexus
Mazda
Cadillac
What do the neighbors listen to?
News
Rock
Classical
All data provided by Home Junction and Claritas
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Frequently asked questions
About 5239 Winding Way
This home is located at 5239 Winding Way in Sarasota, FL and zip code 34242 in the Siesta Key neighborhood. This 1,512 square foot home, which was built in 1958, sits on a 0.21 acre lot. Features: 3 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since February 7, 2025 and is currently priced at $939,000.
Sarasota, FL housing market in January 2025 saw over 18 listings sold above listed price, more than 55 sold at listed price and over 283 sold below. The number of listings in Sarasota, FL increased by 16.8% between December and January 2025. In January 2025, listings were on the market for 66 days. During the same period, the median list price in this real estate market was $510,794.
From Rocket Homes Real Estate and based on county public records data.