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3424 OLD OAK DRIVE
About This Property
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.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Aug 11, 2026 | Listed by EXP REALTY LLC | $1,039,000 | |
| Listed by EXP REALTY LLC | |||
| Apr 29, 2026 | Price Decreased |
$1,095,000
↓ $100K
(8.4%) | |
| Price Decreased | |||
| Mar 31, 2026 | Listed by COMPASS FLORIDA LLC | $1,195,000 | |
| Listed by COMPASS FLORIDA LLC | |||
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Craving a low-maintenance, island-inspired lifestyle just moments from sparkling open water, world-famous beaches, and Sarasota’s most coveted destinations? This quaint Florida bungalow located in west of trail delivers the perfect blend of charm, location, and effortless living—just minutes to Siesta Key and steps from the coastal lifestyle you’ve been dreaming of.
Tucked away in one of Sarasota’s most desirable “West of the Trail” neighborhoods, 3424 Old Oak Dr has been thoughtfully redesigned to preserve its original character while introducing timeless, modern updates. From the moment you arrive, the lush tropical landscaping, winding garden paths, and private courtyard-style entry create a warm, inviting ambiance that feels like your own hidden oasis.
Inside, the home showcases a light-filled, airy design highlighted by vaulted wood-beam ceilings, soft coastal tones, and an open-concept layout that seamlessly blends comfort and style. The beautifully updated kitchen features granite countertops, open shelving, stainless steel appliances, and designer finishes, creating a space that is both functional and visually stunning. The living area centers around a charming wood-burning fireplace, adding warmth and character, while French doors invite natural light and connect indoor and outdoor living spaces effortlessly.
The home offers flexible living spaces ideal for a primary residence, seasonal retreat, or income-producing property. Each room reflects a curated, coastal aesthetic with tasteful updates while maintaining the home’s unique bungalow charm.
Step outside to your private backyard sanctuary, where a screened-in heated pool is surrounded by mature tropical landscaping, creating a serene and secluded environment perfect for relaxing or entertaining. An outdoor shower adds to the coastal lifestyle experience, while multiple seating areas and garden spaces enhance the home’s tranquil, resort-like feel.
Located just minutes from Siesta Key Beach, Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and top-rated dining and shopping, this home offers unmatched convenience paired with a laid-back coastal lifestyle.
Rarely does a property combine location, charm, income potential, and lifestyle so seamlessly. This is your opportunity to own a truly special Sarasota bungalow where every day feels like a vacation.
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| Apr 5, 2021 | Sold | ||
| Sold | |||
| Nov 27, 2020 | No longer available | - | |
| No longer available | |||
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017