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$2,690,000
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Property Description
Luxury Exclusive Living - Boaters' Paradise Welcome to 4508 Woodside Rd., a true waterfront retreat on Siesta Key offering privacy, boating convenience, and refined coastal living. Positioned on one of the deepest canals on the island, this home delivers three-minute access to the Intracoastal and Sarasota Bay. With 97 feet of water frontage and a 75-foot new dock, this is a legitimate boater's setup designed for ease, speed, and functionality. Step inside to a fully renovated interior featuring designer tile flooring throughout and an open-concept living space framed by massive sliding glass doors with uninterrupted views to the tropical outdoor living area. The chef-inspired kitchen showcases custom kitchen cabinetry and counters, a premium viking hood system and gas cooktop, updated appliances, and a temperature-controlled enclosed walk-in wine cellar that makes an immediate statement. The primary bedroom suite is its own private retreat, offering a spacious layout with large windows overlooking lush tropical landscaping and tranquil water views. Sliding doors provide direct access to the backyard for seamless indoor-outdoor living. The suite includes an oversized walk-in closet and a beautifully updated spa-style bathroom featuring a glass-wrapped indoor shower plus a private outdoor shower. The home is also equipped with a 250-gallon propane tank, supporting the property's enhanced functionality and systems. Outdoors, the backyard lives like a private luxury resort. A stunning saltwater pool and spa are surrounded by lush, mature landscaping, integrated LED landscape lighting, and thoughtfully designed pavered hardscape. In addition to the pool and spa, a private therapeutic Jacuzzi is tucked into its own secluded setting, offering a quiet escape at the end of the day. A massive covered 18' x 36' pergola oasis anchors the outdoor living area, featuring large cooling fans, comfortable lounge seating, a propane fire pit, and space to watch TV while enjoying expansive water views. A 32-foot retractable awning adds flexibility and shade, making this outdoor environment functional year-round. Directly beneath the pergola, the outdoor wet bar with ability to add more and entertainment area make hosting effortless. As you walk toward the dock, you'll pass the dedicated tiki bar area perfect for parties and entertaining, whether you're heading out for a day on the boat or coming back in to grab a drink and unwind. The layout is intentionally designed for effortless waterfront living. Additional Property Features Include: Metal roof replaced in 2020 HVAC replaced four years ago Updated hot water heater with circulating system Backup generator 14.5 KW Flood shield barriers for perimeter openings Epoxy-finished garage flooring Updated interior and exterior paint Updated doors, trim, and baseboards Custom kitchen cabinetry and counters Updated appliances Front and rear privacy hedging and landscaping 550 double wall diesel tank for your boat with pump This property is priced to sell. Builders on Siesta Key are constructing similar-sized homes on comparable deep-water lots for $4M+ before adding docks, pools, generators, outdoor living features, and landscaping. The replacement cost of this lifestyle is unmatched. PLUS ALSO AVAILABLE FOR PURCHASE A LUXURY YACHT INQURE FOR MORE INFO....
Full Property Details
Full Property Details for 4508 Woodside Rd
General
- Price: $2,690,000
- Taxes: $7,045 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4674684
- Updated: 12/26/2025
- Added to Site: 38 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Open Floorplan, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s)
- Appliances: Dishwasher, Electric Water Heater, Range, Range Hood, Refrigerator
- Furnishings: Unfurnished
- Flooring: Porcelain Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground, Salt Water, Solar Cover
- Spa: Yes
- Spa Description: Above Ground, Heated, In Ground
- Security/Safety: Security System, Smoke Detector(s)
Exterior
- Exterior Features: Awning(s), Irrigation System, Lighting, Other, Outdoor Shower, Sidewalk, Sliding Doors
- Deck/Patio: Patio
- Porch/Patio/Deck: Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Circular Driveway, Driveway, Ground Level, Off Street
Location
- Area: 34242 - Sarasota/Crescent Beach/Siesta Key
- County: Sarasota
- Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Subdivision: SIESTAS BAYSIDE WATERSIDE WOOD
- Driving Directions: Head south on S Tamiami Trl toward Bougainvillea St, Turn right onto Siesta Dr, Continue onto Higel Ave, Continue straight to stay on Higel Ave, At the traffic circle, continue straight to stay on Higel Ave, Turn left onto Mangrove Point Rd, Turn right onto Woodside Rd, home will be on the right
- Direction Faces: Northwest
School Information
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
Community
- Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Pet Restrictions: Verify all pet restrictions with the county
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water District: INTRACOASTAL AND SARASOTA BAY
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Propane, Public, Sewer Connected, Water Connected
Structural Information
- Exterior Const.: Stucco
- Roof: Metal
- Stories/Levels: One
- Square Feet: 2,238
- Sq. Ft. Source: Owner
- Year Built: 1969
Additional Structures
- Other Structures: Other
Lot Features
- Property View: Trees/Woods, Water
- Lot Size (Acres): 0.26
- Lot Size (Sq. Ft.): 11,400
- Lot Size: 11400
- Frontage: Street Paved
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Canal - Saltwater
- Water Front Name: INTRACOASTAL AND SARASOTA BAY
- Water Front Desc.: Saltwater Canal
Financial Considerations
- Tax Amount: $7,045.29
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 20 SIESTAS BAYSIDE WATERSIDE-WOOD UNIT B
- Flood Zone Info: AE
- APN: 79100024
- Property ID: 79100024
Listed by Keller Williams On The Water S
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Schools
Schools serving 4508 Woodside Rd
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Phillippi Shores Elementary School 4747 South Tamiami Trail, Sarasota, FL 34231 | PK-5 | 1.9 mi |
Brookside Middle School 3636 South Shade Avenue, Sarasota, FL 34239 | 6-8 | 2.2 mi |
Sarasota High School 2155 Bahia Vista Street, Sarasota, FL 34239 | 9-12 | 3.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 4508 Woodside Rd
Date
Details
Price
Change
Source
12/10/2025
Listed
$2,690,000
529.98%
MLS
10/18/1999
Sold
$427,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 4508 Woodside Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,558
-18%
$606,886
-9%
2024
$7,987
3%
$666,782
3%
2023
$7,731
4%
$647,361
4%
2022
$7,454
—
$621,918
3%
2021
$7,450
—
$603,804
3%
2021
$7,450
4%
$586,789
2%
2019
$7,155
2%
$573,596
2%
2018
$7,012
1%
$562,901
3%
2017
$6,951
—
$548,769
2%
2016
$6,926
-2%
$537,482
1%
2015
$7,057
—
$533,746
1%
2014
$7,032
—
$529,510
1%
2013
$7,032
—
$521,685
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 4508 Woodside Rd
4508 Woodside Road, Sarasota, FL 34242 (MLS# A4674684) is a Single Family property with 3 bedrooms and 2 full bathrooms. 4508 Woodside Road is currently listed for $2,690,000 and was received on December 10, 2025. Want to learn more about 4508 Woodside Road? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

