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4508 WOODSIDE RD Sarasota, FL 34242 Open Sun 1PM-4PM

UPDATED: 03/01/2026 01:05 AM ON MARKET: 81 days on market

$2,495,000

3 Beds2 Baths2,276 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 2,276 sqft

Price per Sqft $1,096

Subdivision Siestas Bayside Waterside Wood

MLS Listing ID A4674684

Bedrooms 3

Full Baths 2

Construction Status Completed

HOA Y/N No

Year Built 1969

Annual Tax Amount $7,045

Lot Size 0.260 Acres

Acres 0.26

Property Sub-Type Single Family Residence

Source Stellar MLS

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....

The neighboring lot just sold for $1.94M.
This home is effectively being offered at or near dirt value.