Browse All Bay Island Park Properties for Sale

4 Beds ⋅ 3 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code

A Rare Weekly Rental Opportunity on Siesta Key! Attention second homeowners and investors: opportunities like this are exceptionally rare on Siesta Key. Located in coveted Bay Isle, this private pool home is legally zoned for seven-day minimum rentals - a major advantage on an island where most properties require 30-day stays. The result? Strong income potential in one of America’s most in-demand vacation destinations, with average daily rental rates of $613 since 2022. Offered turnkey furnished, this three-story coastal retreat is ideal as a personal escape, income-producing vacation home, or a blend of both. Just a short golf cart ride to Siesta Key Village and the world-famous Siesta Key Beach—voted #1 in the U.S., the home is tucked behind lush, professionally landscaped tropical foliage, creating a true sense of privacy and serenity. A brick-paver driveway winds through the greenery to an oversized two-car garage, providing plenty of room for beach gear, bikes, and toys. Inside, the home is thoughtfully designed with bedrooms and bathrooms spread across three levels, offering exceptional privacy for guests and groups. The first floor addition (2011) includes a fourth bedroom, third bathroom, and sitting area—expanding the home’s capacity to comfortably accommodate up to 10 guests. The dining area flows seamlessly to a screened porch, perfect for alfresco meals surrounded by palms and tropical breezes. The entire third floor is dedicated to the owner’s suite, a private sanctuary featuring an en-suite bath and direct access to a secluded sun deck—ideal for morning coffee, sunbathing, or unwinding as the sun sets over Siesta Key. Outdoor living shines with recent upgrades, including a new putting green, expansive two-story deck with screened enclosure and paneled ceiling (2024), and a 2024 six-passenger street-legal golf cart—included. Additional improvements include a metal roof (2021), new 50-gallon water heater, and updated AC and heat pump. Whether you’re looking to generate immediate rental income, enjoy a personal island retreat, or both, this property delivers on every level. With its rare weekly rental eligibility, upscale amenities, private tropical setting, and prime Siesta Key location, this is a truly exceptional Gulf Coast opportunity.

3446 Anglin Drive, Sarasota

$1,100,000

3 Beds ⋅ 2 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code

Welcome to Flamingo Avenue, one of Sarasota's most coveted streets. Set on Bay Island, this classic Sarasota home presents an excellent opportunity to own on a street accompanied by iconic estates. You'll feel the ocean breeze at this location, and even enjoy partial water views from balconies! This Key West style home offers an elevated living area with features such as wood floors, fireplace, plantation shutters and much more! From the moment you arrive at this property, you'll notice the walled-in pool and patio area which creates a private island oasis with covered seating area. The first level of the home features a two-car garage and abundant storage. The main living level is on the second story and features a generously-sized living area, dining room, kitchen and two bedrooms with access to the hall bath. The primary bedroom is on the third level and features its own west facing balcony for incredible sunset viewing. This spacious suite offers plenty of room, an oversized walk-in closet, and spacious bathroom. This home has a metal roof and two brand new HVAC units for low maintenance peace of mind. This small and private dead-end street is unique to Bay Island and presents a fine opportunity to own in one of Sarasota's best neighborhoods. Easy access off the north bridge to downtown Sarasota is yours, and as well as just a short distance to amazing Gulf beaches. Schedule your private showing today!

3455 Flamingo Avenue, Sarasota

$700,000

3 Beds ⋅ 4 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code

INVESTOR'S DREAM!!!! On Siesta Key's coveted Bay Island awaits this former beauty. It needs almost a full rehab to be restored to its former glory after recent hurricane damage, but the major components, such as the HVAC (4 years) and water heater (1 year old) are still intact and functional. From the circular driveway, you are welcomed by a garden courtyard. You'll enter the double French front doors into a foyer and an open floor plan creating a natural flow throughout the one-level living space. Open the sliding glass doors to the south facing screened lanai that showcases the heated saltwater pool with a waterfall, paver deck, and poolside patio with a retractable awning. In addition, there is an east-facing screened lanai with enough space for a seating area and grill. Two primary bedroom suites on opposite sides of the home offer lots of privacy. One of the primary suites has a large walk-in closet, dressing area and a beautiful Japanese soaking tub and zero-entry rain shower. The adjoining office has a view of the charming courtyard with separate access, if desired, through sliding doors. Located minutes from Siesta Key North Bridge offers quick access to downtown Sarasota's entertainment, dining, and shopping. Take a quick visit to Shell Road Beach, less than one mile away to enjoy Florida's sunset.

3455 Anglin Drive, Sarasota

$2,275,000

4 Beds ⋅ 3 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code

Welcome to Bay Island, the Gateway to Siesta Key! This beautiful home is the beginning of enjoying the Siesta Key lifestyle. With 3500 sf under roof you can enjoy all the amenities Siesta has to offer. The tropical landscaping of the property alone will make you feel like you are on vacation. The home sits on 2 lots -located on both Anglin Drive and Flamingo Drive - offers you complete and total privacy. The open air pool is surrounded by beautiful travertine, a large area for entertaining, and covered decks on the front and back of the second level. The back deck is completely tiled and has ceiling fans as well as wired for outdoor speakers. It truly feels like you are at a fine resort! Everything from the inside out is just 4 years old. Arrive through a beautiful entryway with new staircase and new LVP flooring throughout. When you turn the corner you are welcomed into an open floor plan that is filled with lots of natural light. The living room has a new natural gas fireplace that adds a beautiful ambiance and a touch of elegance. The kitchen boasts an expansive quartzite island and features all Thermador appliances - including a gas stove, fridge and freezer columns and a dishwasher. The island is filled with storage drawers and undercounter pull out shelving. All cabinet drawers and doors are soft close. Walk out the new French doors onto an oversized, covered deck and take in the beautiful tropical landscaping. The owner's suite is located on the main living level and comes equipped with a spacious walk-in closet, a beautiful bath with a 10' double vanity and large walk-in shower. The main living area also features a nice cozy den that can easily be turned into a 4th bedroom. Located on the third level are two very large guest rooms as well as a fully remodeled bathroom. At the end of the day step out onto the third-floor deck and enjoy spectacular sunsets in your own home! The home as of late 2019 has all new siding, new roof, electrical and plumbing and irrigation. All the French doors and windows are hurricane rated. There are two new HVAC units as well. This home is perfect for weekly short term rentals within Sarasota City limits. Living on the North end of the island is perfect for a quick getaway to the beautiful chrystal sands of Siesta beach or a night in the village. Take a short trip over the bridge and enjoy all the amenities that Sarasota has to offer. You are close to downtown, Selby Gardens or shopping at the beautiful St. Armands.

3458 Anglin Drive, Sarasota

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