***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** 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.
Sold for $630,000
$630,000
5239 Winding Way, Sarasota, FL 34242
3beds
1,512sqft
Single Family Residence
Built in 1958
9,100 Square Feet Lot
$990,700 Zestimate®
$417/sqft
$5,602 Estimated rent
Home value
$990,700
$892,000 - $1.11M
$5,602/mo
Zestimate® history
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List your homeWhat's special
Rear waterPeninsula islandHeated poolLarge pantryLush treesPerimeter privacy fenceLarge backyard
Zillow last checked:
Listing updated:
Listing Provided by:
Brian Cirillo 321-231-1068,
BALDWIN PARK REALTY LLC 407-986-9800
Bought with:
Brian Cirillo, 577152
BALDWIN PARK REALTY LLC
Source: Stellar MLS,MLS#: O6278642
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Built-in Closet
- Level: First
- Area: 156 Square Feet
- Dimensions: 12x13
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 154 Square Feet
- Dimensions: 14x11
Primary bathroom
- Level: First
- Area: 35 Square Feet
- Dimensions: 5x7
Bathroom 2
- Level: First
- Area: 81 Square Feet
- Dimensions: 9x9
Dining room
- Level: First
- Area: 154 Square Feet
- Dimensions: 11x14
Foyer
- Level: First
- Area: 105 Square Feet
- Dimensions: 5x21
Kitchen
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Laundry
- Level: First
- Area: 42 Square Feet
- Dimensions: 7x6
Living room
- Level: First
- Area: 272 Square Feet
- Dimensions: 17x16
Heating
- Electric
Cooling
- Central Air
Appliances
- Included: Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, Living Room/Dining Room Combo, Open Floorplan
- Flooring: Luxury Vinyl
- Doors: French Doors
- Has fireplace: Yes
- Fireplace features: Electric, Family Room
Interior area
- Total structure area: 1,912
- Total interior livable area: 1,512 sqft
Property
Parking
- Total spaces: 2
- Parking features: Covered
- Carport spaces: 2
Features
- Levels: One
- Stories: 1
- Exterior features: Awning(s), Other
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground
- Fencing: Fenced
- Has view: Yes
- View description: Garden, Trees/Woods, Water, Pond
- Has water view: Yes
- Water view: Water,Pond
- Waterfront features: Lake Front, Pond
Lot
- Size: 9,100 sqft
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 0082010056
- Zoning: RSF3
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Frame (FSC Certified), Wood Siding
- Foundation: Other, Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1958
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Connected, Water Available, Water Connected
Community & neighborhood
Community
- Community features: Deed Restrictions
Location
- Region: Sarasota
- Subdivision: TWIN OAK POND
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $35 monthly
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 4/30/2025 | Sold | $630,000-21.2%$417/sqft |
Source:  Stellar MLS #O6278642 Report a problem | ||
| 4/17/2025 | Pending sale | $799,000$528/sqft |
Source: Stellar MLS #O6278642 Report a problem | ||
| 4/8/2025 | Price change | $799,000-8.2%$528/sqft |
Source: Stellar MLS #O6278642 Report a problem | ||
| 3/19/2025 | Price change | $870,000-7.3%$575/sqft |
Source: Stellar MLS #O6278642 Report a problem | ||
| 2/7/2025 | Listed for sale | $939,000-21.1%$621/sqft |
Source: Stellar MLS #O6278642 Report a problem | ||
| 8/14/2024 | Listing removed | -- |
Source: Stellar MLS #O6170281 Report a problem | ||
| 2/14/2024 | Pending sale | $1,189,900$787/sqft |
Source: Stellar MLS #O6170281 Report a problem | ||
| 1/19/2024 | Listed for sale | $1,189,900-6.7%$787/sqft |
Source: Stellar MLS #O6170281 Report a problem | ||
| 1/12/2024 | Listing removed | -- |
Source: Stellar MLS #A4590359 Report a problem | ||
| 12/19/2023 | Price change | $1,274,900-3.8%$843/sqft |
Source: Stellar MLS #A4590359 Report a problem | ||
| 11/22/2023 | Listed for sale | $1,324,900+94%$876/sqft |
Source: Stellar MLS #A4590359 Report a problem | ||
| 12/3/2020 | Listing removed | $6,000$4/sqft |
Source: ASCENDIA REAL ESTATE #A4465647 Report a problem | ||
| 4/22/2020 | Listed for rent | $6,000$4/sqft |
Source: ASCENDIA REAL ESTATE #A4465647 Report a problem | ||
| 2/7/2020 | Listing removed | $6,000$4/sqft |
Source: ASCENDIA REAL ESTATE #A4426534 Report a problem | ||
| 1/24/2020 | Sold | $683,000-2.3%$452/sqft |
Source: Stellar MLS #A4455170 Report a problem | ||
| 1/24/2020 | Listed for sale | $699,000$462/sqft |
Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem | ||
| 1/8/2020 | Pending sale | $699,000$462/sqft |
Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem | ||
| 1/6/2020 | Listed for sale | $699,000+6.6%$462/sqft |
Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem | ||
| 2/5/2019 | Listed for rent | $6,000$4/sqft |
Source: ASCENDIA REAL ESTATE #A4426534 Report a problem | ||
| 11/30/2018 | Sold | $655,900-0.6%$434/sqft |
Source: Public Record Report a problem | ||
| 10/21/2018 | Pending sale | $659,900$436/sqft |
Source: Coldwell Banker Residential Real Estate - Sarasota Downtown #A4415304 Report a problem | ||
| 10/10/2018 | Price change | $659,900-10.7%$436/sqft |
Source: Coldwell Banker Residential Real Estate - Sarasota Downtown #A4415304 Report a problem | ||
| 10/5/2018 | Listed for sale | $739,000+55.6%$489/sqft |
Source: COLDWELL BANKER RES R E #A4415304 Report a problem | ||
| 12/1/2017 | Sold | $475,000-4.6%$314/sqft |
Source: Public Record Report a problem | ||
| 10/28/2017 | Listed for sale | $498,000+4.8%$329/sqft |
Source: ROSEBAY INTERNATIONAL, INC #A4200024 Report a problem | ||
| 5/10/2013 | Sold | $475,000$314/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,252 -20.6% | $662,100 -25.4% |
| 2024 | $10,388 +2.9% | $887,549 +3% |
| 2023 | $10,096 +2.4% | $861,698 +3% |
| 2022 | $9,858 +28.4% | $836,600 +41.1% |
| 2021 | $7,680 +19.7% | $592,900 +31.5% |
| 2020 | $6,415 +16.7% | $451,000 +10% |
| 2019 | $5,498 | $410,000 +11.4% |
| 2018 | $5,498 +21.9% | $368,100 +4.8% |
| 2017 | $4,509 -8.9% | $351,200 -2.4% |
| 2016 | $4,951 | $359,700 +4.2% |
| 2015 | $4,951 | $345,300 +86.2% |
| 2014 | $4,951 +106.5% | $185,434 -29.7% |
| 2013 | $2,397 +2.5% | $263,700 +44.6% |
| 2012 | $2,339 +4.7% | $182,334 +3% |
| 2011 | $2,234 -1% | $177,023 +1.5% |
| 2010 | $2,256 +10% | $174,407 +2.7% |
| 2009 | $2,051 | $169,822 +0.1% |
| 2008 | $2,051 -4.1% | $169,652 +3% |
| 2007 | $2,138 | $164,711 +2.5% |
| 2006 | -- | $160,694 +3% |
| 2005 | -- | $156,014 +3% |
| 2004 | $2,206 -0.8% | $151,470 +1.9% |
| 2003 | $2,224 +1.6% | $148,646 +2.4% |
| 2002 | $2,189 +6.9% | $145,162 +1.6% |
| 2001 | $2,047 +2.1% | $142,876 +3% |
| 2000 | $2,004 | $138,715 |
Find assessor info on the county website
Neighborhood: 34242
Nearby schools
GreatSchools rating
- 9/10Phillippi Shores Elementary SchoolGrades: PK-5Distance: 1.4 mi
- 6/10Brookside Middle SchoolGrades: 6-8Distance: 2.3 mi
- 5/10Sarasota High SchoolGrades: 9-12Distance: 3.6 mi
Schools provided by the listing agent
- Elementary: Phillippi Shores Elementary
- Middle: Brookside Middle
- High: Sarasota High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$990,700
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Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$990,700
- Florida
- Sarasota County
- Siesta Key
- 34242
- 5239 Winding Way
Nearby cities
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