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Discover the best of island living at Bay Oaks on world-famous Siesta Key, where bayside tranquility meets unbeatable convenience. Just moments from the powdery white sands of America's #1 Beach, this beautifully maintained first-floor 2-bedroom, 1-bath condo offers the ultimate blend of relaxation, location, and rare WEEKLY rental income potential. Perfect as a serene personal retreat, vacation escape, or high-demand investment, this residence embodies the laid-back luxury and everyday joy of the Siesta Key lifestyle. BRAND NEW A/C (Aug 2025) | WEEKLY rentals allowed | In-unit laundry | TURNKEY furnished | WALK to beach | HEATED pool | FREE island trolley pickup | Keep reading... UPCOMING COMMUNITY IMPROVEMENTS THAT HAVE BEEN PAID FOR INCLUDE: the parking lot will be paved and the carports will also be redone after 2026 season and are already scheduled! NEW Pool furniture has already been ordered. Concrete stamped floors in G building are also slated to be repaired in 2026. All that "revamping" is scheduled soon. ALL WORK HAS BEEN PREPAID! Nestled on the bayside of Siesta Key, Bay Oaks is just a short stroll to the beach and ideally positioned between Siesta Key Village and Crescent Beach Village"”offering easy access to restaurants, boutique shops, and entertainment. Surrounded by lush tropical landscaping, majestic live oaks, and swaying palms, the community provides direct access to Sarasota Bay for fishing, kayaking, or simply soaking in breathtaking sunrise views. The free Siesta Key trolley stops right outside, making car-free island living effortless. Resort-style amenities include a private fishing pier, heated pool with sundeck, waterfront picnic and BBQ areas, tennis and pickleball court, clubhouse with kitchen, pool table, and library, assigned covered parking, guest parking, covered bike storage, laundry facilities, onsite management, and 24-hour video surveillance. Low monthly fees make Bay Oaks an exceptional value"”especially for those seeking a short-term rental investment. Inside, the light-filled interior features a split bedroom layout for privacy, all-tile flooring for easy maintenance, and an open living area that flows onto a private covered balcony"”ideal for morning coffee or evening cocktails. The open galley kitchen offers a cozy eat-in nook, while the primary suite features a shared vanity, private glass walk-in shower, and convenient in-unit washer/dryer combo. The guest bedroom enjoys natural light and separation from the primary suite for added privacy. Additional perks include an assigned covered carport (#59) conveniently located outside your door, a 2' x 5' storage closet for beach gear, and ceiling fans in every room. Sold TURNKEY furnished with linens, towels, kitchenware, and décor"”ready for Airbnb, VRBO, or seasonal rental use. With flexible weekly rentals, this property offers impressive cash flow potential and excellent ROI, particularly during Siesta Key's peak winter and spring seasons. Constructed of masonry stucco and concrete on an elevated gradient, this building has never experienced flooding or storm damage. Discover the best of Siesta Key living"”close to world-class beaches, vibrant island life, and the cultural attractions of downtown Sarasota. More than a home, this bayside condo is a lifestyle, an investment, and an invitation to live your best island life.
| DAYS ON MARKET | 129 | LAST UPDATED | 11/13/2025 |
|---|---|---|---|
| TRACT | BAY OAKS | YEAR BUILT | 1974 |
| COMMUNITY | 34242 - Sarasota/Crescent Beach/Siesta Key | COUNTY | Sarasota |
| STATUS | Active | PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Phillippi Shores Elementary |
|---|---|
| Jr. High School | Brookside Middle |
| High School | Sarasota High |
| PRICE HISTORY | |
| Prior to Sep 15, '25 | $399,000 |
|---|---|
| Sep 15, '25 - Nov 13, '25 | $370,000 |
| Nov 13, '25 - Today | $369,999 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Insurance, Internet, Maintenance Grounds, Maintenance Structure, Pest Control, Security, Sewer, Trash, Water |
| APPLIANCES | Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer |
| AREA | 34242 - Sarasota/Crescent Beach/Siesta Key |
| CONSTRUCTION | Block, Cement Siding, Stucco |
| EXTERIOR | Balcony, Dock, Lighting, Storage, Tennis Court(s) |
| HEAT | Central |
| INTERIOR | Eat-in Kitchen, Elevator |
| LOT | 4.26 acre(s) |
| LOT DESCRIPTION | Greenbelt, Landscaped, Near Public Transit, Paved, Private, Waterfront, Wooded |
| PARKING | Assigned, Covered, Deeded, Guest |
| POOL | Yes |
| POOL DESCRIPTION | Gunite, Heated, In Ground |
| SEWER | Public Sewer |
| STORIES | 1 |
| STYLE | Florida |
| SUBDIVISION | BAY OAKS |
| TAXES | 3634 |
| UTILITIES | Cable Available, Electricity Connected, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Park/Greenbelt, Trees/Woods |
| WATER | Public |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Beach Access |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Shayla Twit, CORCORAN DWELLINGS REALTY, 941-200-4663
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/19/25 3:58 AM PST.
This IDX solution is (c) Diverse Solutions 2025.