5239 Winding Way, SARASOTA, FL 34242
Property Photos

Would you like to sell your home before you purchase this one?
Priced at Only: $870,000
For more Information Call:
Address: 5239 Winding Way, SARASOTA, FL 34242
Property Location and Similar Properties
- MLS#: O6278642 ( Residential )
- Street Address: 5239 Winding Way
- Viewed: 41
- Price: $870,000
- Price sqft: $455
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake,Pond
- Year Built: 1958
- Bldg sqft: 1912
- Bedrooms: 3
- Total Baths: 2
- Full Baths: 2
- Garage / Parking Spaces: 2
- Days On Market: 54
- Additional Information
- Geolocation: 27.2755 / -82.549
- County: SARASOTA
- City: SARASOTA
- Zipcode: 34242
- Subdivision: Twin Oak Pond
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
- Provided by: BALDWIN PARK REALTY LLC
- Contact: Brian Cirillo
- 407-986-9800
- DMCA Notice
-
Description**SELLER MOVTIVATED** 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.
Payment Calculator
- Principal & Interest -
- Property Tax $
- Home Insurance $
- HOA Fees $
- Monthly -
For a Fast & FREE Mortgage Pre-Approval
Apply Now

Features
Building and Construction
- Covered Spaces: 0.00
- Exterior Features: Awning(s), French Doors, Other
- Fencing: Fenced
- Flooring: Luxury Vinyl
- Living Area: 1512.00
- Roof: Shingle
School Information
- High School: Sarasota High
- Middle School: Brookside Middle
- School Elementary: Phillippi Shores Elementary
Garage and Parking
- Garage Spaces: 0.00
- Open Parking Spaces: 0.00
- Parking Features: Covered
Eco-Communities
- Pool Features: Gunite, Heated, In Ground
- Water Source: Public
Utilities
- Carport Spaces: 2.00
- Cooling: Central Air
- Heating: Electric
- Pets Allowed: Yes
- Sewer: Public Sewer
- Utilities: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Connected, Water Available, Water Connected
Finance and Tax Information
- Home Owners Association Fee: 414.00
- Insurance Expense: 0.00
- Net Operating Income: 0.00
- Other Expense: 0.00
- Tax Year: 2024
Other Features
- Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
- Country: US
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, High Ceilings, Living Room/Dining Room Combo, Open Floorplan
- Legal Description: LOT 41 TWIN OAK POND
- Levels: One
- Area Major: 34242 - Sarasota/Crescent Beach/Siesta Key
- Occupant Type: Owner
- Parcel Number: 0082010056
- View: Garden, Trees/Woods, Water
- Views: 41
- Zoning Code: RSF3
Similar Properties
Nearby Subdivisions
0073 Siesta Rev Plat Of
Bay Island
Bay Island Park
Bay Island Shores
Bayou Louise 28
Cedars Of Siesta Key The
Cocoanut Bayou
Fidder Bayou
Harbor Towers Y R
Harmony
Harmony Sub
Hidden Harbor
Horizons West
La Siesta
Lake Rittwood
Lot 5 Sara Sands
Mangroves Sub The
Midnight Harbor Sub
Midnight Pass Road
Mira Mar Beach
Mira Mar Sub
No Subdivision Sarasota County
Npne
Ocean Beach Rep
Ocean View
Palm Bay Club Ii
Paradise Island
Point Crisp Add
Point O Rocks Terrace Add
Point Of Rocks
Polynesian Gardens
Riegels Landing
Roberts Point
Roberts Point 2
Royal Palm Harbor
Sanderling Club
Sanderling Club Siesta Key
Sanderling Club Siesta Propert
Sanderling Clubsiesta Properti
Sandy Hook
Sara Sands
Sarasota Beach
Secluded Harbour 02
Siesta Beach
Siesta Cove Sub
Siesta Isles
Siesta Key
Siesta Manor Sec 3
Siesta Pines
Siesta Rev Of
Siesta Rev Plat Of
Siesta Rev Resub
Siestas Bayside
Siestas Bayside Bayside Club 0
Siestas Bayside Waterside East
Siestas Bayside Waterside Sout
Siestas Bayside Waterside Wood
Siestas Bayside Watersidewood
Stickney Point Sub
Tortoise Estates
Twin Oak Pond
Twitchell Ralph S Siesta Key P
Village Sands 1
Vista Hermosa
Whispering Sands
White Beach Fruit Co Prop

- Nicole Haltaufderhyde, REALTOR ®
- Tropic Shores Realty
- Mobile: 352.425.0845
- 352.425.0845
- nicoleverna@gmail.com