A private garden retreat in one of Sarasota’s most coveted West of Trail locations.** Nestled among lush tropical gardens and mature landscaping, 3424 Old Oak Drive is a captivating Sarasota bungalow where privacy, character, and effortless coastal living come together. From the moment you arrive, the home unfolds through a collection of intimate, inviting spaces. A charming front patio beneath a mature, vine-covered pergola offers a welcoming setting for morning coffee or an evening glass of wine. Winding garden paths and established tropical foliage create the feeling of a secluded sanctuary. The outdoor living experience continues around the heated pool, surrounded by greenery for exceptional privacy. A hot-and-cold outdoor shower adds resort-style convenience—ideal after a relaxing afternoon poolside or a day at nearby Siesta Key Beach. Multiple outdoor gathering areas invite you to follow the sun, unwind in a quiet garden corner, or entertain beneath the Florida sky. Inside, the three-bedroom, two-bath residence is filled with warmth and personality. Vaulted ceilings enhance the sense of openness, while a wood-burning fireplace creates an unexpected and inviting focal point. French doors connect the interior living spaces to the gardens and pool, creating a seamless flow between indoor and outdoor living. The home’s distinctive character is matched by its exceptional West of Trail location. Just over the North Bridge from Siesta Key, you are minutes from its renowned beaches while remaining conveniently close to Southside Village, Sarasota Memorial Hospital, downtown Sarasota, dining, shopping, arts, and entertainment. 3424 Old Oak Drive offers something increasingly difficult to find: an established tropical setting, mature gardens, exceptional privacy, and authentic Sarasota charm. In a location that keeps the best of the city and coast within easy reach.
- Built in 1953
- 1 garage space
- $759.50/sqft
- Lot size: 9,773 sqft
- 1 days on market
- Directions: From Bee Ridge Rd, Take Siesta Dr. Turn Right onto Old Oak Drive. Home is on Corner of Siesta Drive and Old Oak Drive.
- County: Sarasota
- Geo subdivision: SHORELAND WOODS
Nearby Schools
Southside Elementary
Brookside Middle
Sarasota High
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Steven Koleno
Consumer-First Real Estate Architect
- Source: Stellar MLS
- MLS #: A4702989
Listing updated: August 20, 2026 at 1:00PM
Listing provided by: Lise Wosick, EXP REALTY LLC
Last checked 1 day ago
Listing provided by: Lise Wosick, EXP REALTY LLC
Last checked 1 day ago
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