CONTACT
FAVORITE
SHARE
CLAIM

5244 WINDING WAY SARASOTA FL 34242

$1,250,000
USD CAD EUR GBP BTC
5244 WINDING WAY, SARASOTA, FL 34242 - MLS#MFRA4669581 5244 WINDING WAY, SARASOTA, FL 34242 - MLS#MFRA4669581 5244 WINDING WAY, SARASOTA, FL 34242 - MLS#MFRA4669581 5244 WINDING WAY, SARASOTA, FL 34242 - MLS#MFRA4669581

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Request Info, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

Overview of 5244 Winding Way

4 Bedrooms
4 Bathrooms
3 Car Garage
2,100 Square Feet
2,100SF Living Area
Pool:
Yes
Water: None
Year Built 1967
Listed For 1 Days

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

This luxury single family home was built in 1967 and features 4 bedrooms, and 4 full bathrooms. This home for sale is 2,100 square feet, with 2,100 sq ft being air conditioned living space. The home has a 3 car garage and has a private swimming pool.

Directions to this property are as follows: Higel To Midnight Pass * South On Midnight Pass To West On Winding Way * Home Is Located At 5244 Winding Way.

Please contact your ZFC agent for more information about MLS# MFRA4669581 or any other homes for sale in Sarasota or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer

Cooling

Central Air, Mini-Split Unit(s)

Heating

Central

Flooring

Ceramic Tile, Vinyl

Lot Size

9664

View

view

Construction Materials

Wood Siding

Interior Features

Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-In Closet(s)

Exterior Features

French Doors

Pool Features

Gunite, In Ground

Roof

Shingle

Utilities

B B/H S Internet Available, Cable Connected

Laundry

Inside, Other

Zoning

R S F3

Year Built

1967

Pets Allowed

Yes

Annual Real Estate Taxes

$9,776 (2025)

Legal Description

Lot 9 Twin Oak Pond

Property Type

Single Family Home

Direction Faces

North

MLS Number

MFRA4669581

Universal Property Id

U S-12115-N-0082010022-R-N

Days On Market

1

Community Name

Twin Oak Pond

5244 Winding Way Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 5244 Winding Way should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $9,776 but will likely change when this home sells. These estimations are calculated from a list price of $1,250,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 5244 Winding Way

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRA4669581 Listing History

10/23/2025 Listed for sale by SHIRLEY INTERNATIONAL REALTY with MLS# MFRA4669581 with a list price of $1,250,000.

Public Transportation

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

This listing of 5244 Winding Way Sarasota FL 34242 was last updated on 2025-10-24 07:13:02. Listing courtesy of SHIRLEY INTERNATIONAL REALTY.
MLS

Map of 5244 Winding Way Sarasota FL 34242

Similar Homes For Sale

5222 Winding Way, SARASOTA
Under Contract
$569,900

MLS#MFRA4659769

5222 Winding Way
Sarasota, FL 34242

2

2

1,900 SqFt

0.14 Acres

5218 Winding Way, SARASOTA
Under Contract
$469,900
$579,900

MLS#MFRTB8354445

5218 Winding Way
Sarasota, FL 34242

2

2

1,200 SqFt

0.14 Acres

3339 Sheffield Cir, SARASOTA
Reduced
$619,000
$649,000

Village Green

3339 Sheffield Cir
Sarasota, FL 34239

4

4

2

2,612 SqFt

0.24 Acres

2400 Appaloosa Cir, SARASOTA
Under Contract
$459,000

The Paddocks

2400 Appaloosa Cir
Sarasota, FL 34240

4

3

2

2,624 SqFt

Water Front

0.2 Acres

5499 Oak Crest Blvd, SARASOTA
Under Contract
$575,000
$585,000

Three Oaks

5499 Oak Crest Blvd
Sarasota, FL 34233

4

2

2

2,622 SqFt

0.24 Acres

763 Siesta Dr, SARASOTA
Reduced
$1,699,000
$1,799,000

Bay Island

763 Siesta Dr
Sarasota, FL 34242

4

3

2

2,622 SqFt

0.3 Acres

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. 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.

Currency