5244 WINDING WAY Sarasota, FL $ 1,250,000
5244 WINDING WAY
$ 1,250,000
Share Save

5244 WINDING WAY

Sarasota, FL, 34242
$ 1,250,000
Bedrooms4 Baths4.0 Sq 2,100

Monthly Estimate*

$ 7,798

5244 WINDING WAY, Sarasota, FL 34242 - Image 1
5244 WINDING WAY, Sarasota, FL 34242 - Image 2
5244 WINDING WAY, Sarasota, FL 34242 - Image 3
5244 WINDING WAY, Sarasota, FL 34242 - Image 4
5244 WINDING WAY, Sarasota, FL 34242 - Image 5
5244 WINDING WAY, Sarasota, FL 34242 - Image 6
5244 WINDING WAY, Sarasota, FL 34242 - Image 7
5244 WINDING WAY, Sarasota, FL 34242 - Image 8
5244 WINDING WAY, Sarasota, FL 34242 - Image 9
5244 WINDING WAY, Sarasota, FL 34242 - Image 10
5244 WINDING WAY, Sarasota, FL 34242 - Image 11
5244 WINDING WAY, Sarasota, FL 34242 - Image 12
5244 WINDING WAY, Sarasota, FL 34242 - Image 13
5244 WINDING WAY, Sarasota, FL 34242 - Image 14
5244 WINDING WAY, Sarasota, FL 34242 - Image 15
5244 WINDING WAY, Sarasota, FL 34242 - Image 16
5244 WINDING WAY, Sarasota, FL 34242 - Image 17
5244 WINDING WAY, Sarasota, FL 34242 - Image 18
5244 WINDING WAY, Sarasota, FL 34242 - Image 19
5244 WINDING WAY, Sarasota, FL 34242 - Image 20
5244 WINDING WAY, Sarasota, FL 34242 - Image 21
5244 WINDING WAY, Sarasota, FL 34242 - Image 22
5244 WINDING WAY, Sarasota, FL 34242 - Image 23
5244 WINDING WAY, Sarasota, FL 34242 - Image 24
5244 WINDING WAY, Sarasota, FL 34242 - Image 25
5244 WINDING WAY, Sarasota, FL 34242 - Image 26
5244 WINDING WAY, Sarasota, FL 34242 - Image 27
5244 WINDING WAY, Sarasota, FL 34242 - Image 28
5244 WINDING WAY, Sarasota, FL 34242 - Image 29
5244 WINDING WAY, Sarasota, FL 34242 - Image 30
5244 WINDING WAY, Sarasota, FL 34242 - Image 31
5244 WINDING WAY, Sarasota, FL 34242 - Image 32
5244 WINDING WAY, Sarasota, FL 34242 - Image 33
5244 WINDING WAY, Sarasota, FL 34242 - Image 34
5244 WINDING WAY, Sarasota, FL 34242 - Image 35
5244 WINDING WAY, Sarasota, FL 34242 - Image 36
5244 WINDING WAY, Sarasota, FL 34242 - Image 37
5244 WINDING WAY, Sarasota, FL 34242 - Image 38
5244 WINDING WAY, Sarasota, FL 34242 - Image 39
5244 WINDING WAY, Sarasota, FL 34242 - Image 40
5244 WINDING WAY, Sarasota, FL 34242 - Image 41
5244 WINDING WAY, Sarasota, FL 34242 - Image 42
5244 WINDING WAY, Sarasota, FL 34242 - Image 43
5244 WINDING WAY, Sarasota, FL 34242 - Image 44
5244 WINDING WAY, Sarasota, FL 34242 - Image 45
5244 WINDING WAY, Sarasota, FL 34242 - Image 46
5244 WINDING WAY, Sarasota, FL 34242 - Image 47
5244 WINDING WAY, Sarasota, FL 34242 - Image 48
5244 WINDING WAY, Sarasota, FL 34242 - Image 49
5244 WINDING WAY, Sarasota, FL 34242 - Image 50
5244 WINDING WAY, Sarasota, FL 34242 - Image 51
5244 WINDING WAY, Sarasota, FL 34242 - Image 52
5244 WINDING WAY, Sarasota, FL 34242 - Image 53
View a Virtual Tour

Single Family Home for sale in Sarasota, FL

for $1,250,000 with 4 bedrooms and 4 full baths. This 2,100 square foot home was built in 1967 on a lot size of 0.22.

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

See more

Single Family Active

Price

$ 1,250,000

Bedrooms

4

Full Bath

4

Property Type

Single Family

Taxes

$ 9,776

Style

Single Family Residence

Lot Size

0.22

Year Built

1967

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4669581

Features
Interior
Interior Amenities kitchen/family room combo open floorplan solid surface counters walk-in closet(s)
Flooring ceramic tile vinyl
Air Conditioning Y/N yes
Heating Y/N yes
Fireplace Y/N no
Half Baths 0
Laundry Features inside other
Total Bedrooms 4
Total Baths 4
See more
General
Sewer public sewer
Heating central
Cooling central air mini-split unit(s)
Utilities bb/hs internet available cable connected
Roof shingle
Appliances dishwasher dryer microwave range refrigerator washer
Zoning rsf3
Garage Spaces 3
Pool Features gunite in ground
Construction Materials wood siding
Pets Allowed yes
Year Built 1967
Levels two
Property Subtype single family residence
Tax Year 2025
Ownership fee simple
Assoc Fee Paid Per annually
County sarasota
New Construction no
Property Type residential
HOA N
Attached Garage no
Subdivision Name twin oak pond
Facing Direction north
Garage Y/N yes
Total Rooms 3
Full Baths 4
Status active
Directions higel to midnight pass * south on midnight pass to west on winding way * home is located at 5244 winding way
City sarasota
Senior Community Y/N no
MLS Area 34242 - sarasota/crescent beach/siesta key
Lot Size Units square feet
Lot Size Square Feet 9664
Carport Y/N no
Listing Terms cash conventional
Land Lease Y/N no
Tax Annual Amount 9776
Additional Parcels Y/N no
Lease Considered Y/N yes
Virtual Tour https://www.propertypanorama.com/instaview/stellar/a4669581
Building Area Units square feet
Living Area Units square feet
Standard Status active
Occupancy Type vacant
Tax Lot 9
Legal Description lot 9 twin oak pond
Minimum Lease 1 month
Water Access Y/N no
Water View Y/N no
Flood Zone Code ae
See more
Exterior
Exterior Amenities french doors
Water Source public
Lot Size Area 9664
Foundation Details crawlspace
Building Area Total 2100
Lot Size Acres 0.22
Road Surface Type asphalt
Private Pool yes
Waterfront Y/N no
Covered Spaces 3
See more
Internal Only
Street Number 1 5244
See more
* Excluded Features
List By
Shirley International Realty

Broker

jshir12@aol.com

Email

Affordability Calculator

$8,613
Per Month
91%
9%
0%
Monthly Principal & Interest
$7,798
Monthly Property Taxes
$815
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
266288 Elementary School
265661 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
10/24/2025$1,250,000 Listed Price

Map


See all

5244 WINDING WAY, Sarasota, FL, 34242 is a Single Family Home for sale at $1,250,000 with 2,100 sqft and a lot size of 0.22. 5244 WINDING WAY has 4 bedrooms, 4.0 baths, and was built in 1967. The property's zip code is 34242 which is in Sarasota, FL