Location: Sarasota Beach, Sarasota
Do Not Show Listings
276 ISLAND CIR, SARASOTA, FL 34242
$3,100,000296 Days on yellowkey MLS ID: A4667090
0 Days Off yellowkey (back on 7/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 2026 Tax: $13,193 (2025)Community: Sarasota BeachSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,193
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Certificate of Occupancy received 5/27/2026 *Call today to schedule your private showing! Welcome to 276 Island Circle, an exceptional waterfront retreat nestled on an oversized lot in the highly sought-after Palm Island neighborhood of Siesta Key. Perfectly positioned along the Grand Canal and just a half-mile from the world-famous shores of Siesta Key Beach, this beautifully designed 4-bedroom, 3-bathroom residence captures the essence of luxury coastal living. Thoughtfully crafted with both elegance and functionality in mind, the home offers an open and inviting floor plan highlighted by soaring tray ceilings, abundant natural light, and impressive zero-corner sliding glass doors that seamlessly blend indoor and outdoor living. Impact-rated windows and sliders provide peace of mind while framing picturesque views of the waterfront setting. The heart of the home is a stunning chef's kitchen designed for entertaining and everyday enjoyment alike. Exquisite quartz countertops and backsplash, dramatic waterfall edges, custom solid wood cabinetry, a Wolf range with custom hood, paneled Sub-Zero refrigerator, paneled Bosch dishwasher, Sharp microwave drawer, hidden outlets, and a showstopping glass-front pantry complete with a wine cooler combine to create a space that is as beautiful as it is functional. The primary suite offers a private sanctuary with custom-designed his-and-her closets and a spa-inspired bathroom featuring dual vanities, a curbless walk-in shower, and a freestanding soaking tub. Outdoor living is equally impressive. Overlooking the Grand Canal, the resort-style backyard was designed to embrace Florida's year-round sunshine. Relax in the saltwater PebbleTec pool and spa, unwind on the sun shelf, or entertain guests on the expansive leathered marble paver deck. Boaters will appreciate the impressive, brand new 107 feet of seawall frontage, offering direct access to the waterways that make Siesta Key such a coveted waterfront destination. Beyond the property, the Siesta Key lifestyle awaits. Spend your mornings walking Siesta Key Beach, consistently ranked among the finest beaches in the world for its powder-soft quartz sand and crystal-clear Gulf waters. Enjoy afternoons exploring Siesta Key Village's collection of boutique shops, waterfront restaurants, lively cafés, and local entertainment. Whether boating, dining al fresco, watching spectacular sunsets, or simply enjoying the laid-back island atmosphere, every day feels like a vacation. Rarely does a home combine a premier Palm Island location, exceptional waterfront setting, luxurious finishes, and close proximity to Siesta Key Beach so effortlessly. 276 Island Circle offers a unique opportunity to experience the very best of Sarasota's island lifestyle.
Listing is courtesy of: CELLA'S REAL ESTATE INC (941-952-8649)
Listing Agent: Michael Cella (941-952-8649)
5453 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,150,000276 Days on yellowkey MLS ID: A4669037
0 Days Off yellowkey (back on 7/16/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1510 Built: 1950 Tax: $8,670 (2023)Community: Sarasota BeachSingle Family
Taxes:$8,670
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Exceptional opportunity on TWO buildable lots just 15 houses from Siesta Key Beach and a leisurely stroll from the village. The existing midcentury durable concrete block 3br/2ba home features pecky cypress siding and beamed ceilings. There is an additional free standing guest cottage. The home was impacted by last years storms, but has been stripped to the studs and is waiting for someone to put their finishing touches on it. Tremendous potential awaits. Restore and renew the existing structure or tear down and build your own tropical dream home. Investors may want to take advantage of the 2 lot configuration to develop TWO stunning residences. Plans and competitive pricing for new construction are available. Whether you delight in renovating this iconic midcentury gem, start fresh with a custom built masterpiece, or take advantage of the terrific investment opportunity of TWO buildable lots, this is a terrific opportunity to realize your dream in this desirable coastal paradise.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Sue Levin (941-650-9761)
617 CALLE DE PERU, SARASOTA, FL 34242
$902,00045 Days on yellowkey MLS ID: A4696360
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1959 Tax: $9,721 (2025)Community: Sarasota BeachSingle Family
Taxes:$9,721
Remarks: Exceptional opportunity just a short steps away from Siesta Village and the world-famous Siesta Key Beach, consistently ranked among the best beaches in the United States. Situated on a rare double lot, this property offers endless possibilities—remodel the existing home, create a luxury beach retreat, develop a high-performing vacation rental, or build your custom dream home. The existing residence features solid block construction, a private pool, and a detached guest house, providing a strong foundation for renovation or redevelopment. The flexible layout and prime location make this an ideal opportunity for those seeking a primary residence, second home, or income-producing property. Enjoy the ultimate Siesta Key lifestyle with the beach, Siesta Village's restaurants, boutiques, nightlife, and entertainment all within walking distance. The combination of a double lot, guest house, pool, and proximity to the beach creates exceptional potential for a vacation rental property in one of Florida's most desirable destinations. Rarely does a property with this much potential become available so close to Siesta Key Beach and Siesta Village. Don't miss this chance to create your vision and maximize the possibilities in one of Sarasota's most sought-after coastal communities.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Beverly Perez (941-323-4600)
471 ISLAND CIR, SARASOTA, FL 34242
$2,100,00022 Days on yellowkey MLS ID: A4698115
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2922 Built: 2014 Tax: $13,929 (2025)Community: Sarasota BeachSingle Family
Taxes:$13,929
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Offered for the first time, 471 Island Circle is a private contemporary coastal retreat designed for modern luxury, effortless living and the ease of a low-maintenance Siesta Key lifestyle. Ideally positioned in the community of Palm Island, close to Siesta Beach and the charm of Siesta Village, this three-level residence offers a rare blend of privacy, quality construction and everyday comfort in one of the island’s most desirable settings. From the gated entry and walled-courtyard approach to the private pool area, the home feels wonderfully tucked away while remaining moments from the beach, boutiques, dining and the relaxed energy that makes Siesta Key so loved. Built by MGB (My Green Building) with a focus on strength, efficiency and peace of mind, the residence features solid concrete block construction, reinforced with rebar and poured concrete tied to the roof structure, impact-rated materials and a low-maintenance exterior. It is an ideal lock-and-leave island home for those who want to enjoy the beauty of coastal living without the demands of a more traditional high-maintenance property. Inside, a striking floating steel staircase with stainless steel cable detailing creates a memorable first impression, while the elevator provides easy access to all levels. The upper main living level is filled with natural light, with open dining and family spaces designed for comfortable everyday living and easy entertaining. The sleek Cucina Ricci kitchen features abundant contemporary cabinetry, quartz countertops and premium Thermador appliances, including dual ovens, an icemaker, a five-burner induction cooktop, a concealed refrigerator and wine refrigeration. A cleverly designed hidden television rotates to be viewed from both the kitchen and living areas. Just beyond, a large west-facing balcony extends the living space outdoors and offers a beautiful setting for open-air dining, sunset cocktails and evening breezes. A stylish half bath completes the main living level. The second floor offers three en suite bedrooms, each thoughtfully designed with privacy and comfort in mind. Contemporary baths feature striking tile selections, floating vanities and clean modern finishes. An additional balcony overlooks the private courtyard pool below, creating a quiet connection between the interiors and outdoor living spaces. A convenient laundry room is located nearby. Outdoors, the walled pool courtyard is designed for privacy, sunning, swimming and relaxed coastal enjoyment, offering the feel of a private resort with minimal upkeep. Additional features include two-zone air conditioning for enhanced efficiency, generous storage and a two-car tandem garage. From morning at the beach to evenings near the Village or sunset views from your own balcony, every day here feels like a vacation. When you are ready to explore beyond the island, vibrant downtown Sarasota is just a short drive away, offering world-class dining, arts and culture and entertainment.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5610 AVENIDA DEL MARE, SARASOTA, FL 34242
$6,400,000153 Days on yellowkey MLS ID: A4683170
Bed: 8 Bath: 8.5 Gar: 3 Liv Area Sq Ft: 5313 Built: 1955 Tax: $21,150 (2025)Community: Sarasota BeachSingle Family
Taxes:$21,150
Remarks: Prime Siesta Key investment opportunity or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence. Enjoy breathtaking Gulf sunrises and sunsets, a heated exotic lagoon-style pool with waterfall, Rocky Mountain quartz deck, professional tropical landscaping (updated 2024/2025), Miami-Dade impact windows/doors, newer roofs/insulation, and meticulous maintenance throughout. One building designed by renowned Lee Wetherington. Wake up to morning coffee overlooking the sugar-white sands, with Siesta Key Village shops and dining 0.5 miles away. Turnkey, versatile, and perfectly positioned for endless possibilities—your beachfront lifestyle awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Tonna Gruber (941-232-8950)
105 ISLAND CIR, SARASOTA, FL 34242
$2,680,950466 Days on yellowkey MLS ID: A4647817
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2750 Built: 1953 Tax: $7,593 (2024)Community: Palm IslandSpa: YesSingle Family
Taxes:$7,593
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be tailored to your lifestyle. This stunning 4-bedroom, 3.5-bath home includes an open Concept Floor Plan, Gourmet Kitchen with custom cabinetry, luxury appliances, and a walk-in pantry—ideal for entertaining. Enjoy a First-Floor Master Suite with a spa-inspired en suite bath and a large walk-in closet. The Second Floor boasts 3 bedrooms, a second gathering room, an office, a laundry room, and a Balcony to relax and enjoy island breezes and views. Be inspired to grill in your Outdoor Kitchen on the expansive covered lanai, perfect for alfresco dining. Lounge in your Custom Designed Private Pool, appreciating outdoor living. You also have an Oversized 2-Car Garage with easy access to the downstairs Laundry/Mudroom entry. Set on 2 lots, totaling 0.45 acres (19,456 sf), this property offers a rare combination of space and luxury. Just a 2 block stroll to sink your toes into the luxurious quartz sand and sparkling water of our award-winning Siesta Key Beach. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Your dream coastal lifestyle awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Linda Scheller, Llc (941-806-7981)
238 ISLAND CIR, SARASOTA, FL 34242
$2,900,000459 Days on yellowkey MLS ID: A4650032
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2854 Built: 1965Monthly Fee: $4 Tax: $22,636 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$22,636
Remarks: Welcome to your dream island retreat, perfectly nestled in the heart of Siesta Key’s Palm Island, just minutes away from the world-famous Siesta Beach and vibrant Siesta Village. This beautifully renovated 4-bedroom, 4-bathroom home is the epitome of coastal luxury, offering the ultimate island lifestyle where you can enjoy sun, sand, and all the amenities of this exclusive locale. Meticulously transformed by the renowned Nautilus Homes, this home boasts an open floor plan with soaring high ceilings, making it the perfect space for both relaxation and entertaining. Every inch of the property has been updated with the finest finishes and state-of-the-art features, including: Gourmet Kitchen with new appliances, Impact-Resistant Windows for peace of mind, New 17KW Solar System with backup generator, keeping your electric bill at an incredibly low $20-$30 month, New Boat Lift Motors and a private dock, perfect for boating enthusiasts, Saltwater Pool System and spa, enclosed in a serene, waterside cage for privacy, Custom Treehouse for a fun and unique retreat, Whole House Water Conditioner and new water heater, Two New A/C Units ensuring year-round comfort and a Xeroflood water barrier system has been installed. Natural light pours into every room, highlighting the spacious living areas and creating an inviting atmosphere throughout. The sumptuous Primary Suite offers a private sanctuary, featuring views of the lush tropical surroundings. Step outside to your own private oasis where you can unwind by the pool, entertain in style, or take your boat out for a sunset cruise – all right in your backyard. With Siesta Key's famous restaurants, shops, and nightlife just moments away, you’ll have everything you need to experience the best of island living. This is a rare opportunity to own a piece of paradise on Palm Island, where the ultimate lifestyle meets extraordinary design and function.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tom Cail, Pa (941-780-2245)
618 AVENIDA DE MAYO, SARASOTA, FL 34242
$1,200,00087 Days on yellowkey MLS ID: A4692001
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2961 Built: 1948 Tax: $8,283 (2025)Community: Sarasota BeachSingle Family
Taxes:$8,283
Remarks: This Charming Old 1948 Bungalow located just 3 Blocks behind Siesta Key Village and 4 Blocks to Siesta Key Beach!! It is quite the Interesting Property! It was converted into a Triplex many moons ago. It can easily be converted back to a single family residence. Currently, there are 2 Beds and 2 Baths downstairs and 2 Beds 1 Bath upstairs. There are 3 Kitchens, 3 Liv Areas 2 down, 1 up and there is a Bonus Rm down as well as a Screened in Patio on the front West side of the Home, an Open Patio on the East Side and a Closed in Upstairs. And, there's more... At the Rear of the Property is a Cottage, perfect for a Mother In Law Suite or Rental. It is a 1/1 with a full Kitchen and Liv Area. The grounds are Etherical, as there are private little Sitting Areas for each sector and in the center of the Backyard there is a Wash House for Laundry as well as an attached Storage Shed for Gardening. There are additional Outside Storage Units for each of the apartments, again, really a cool old school house with so much to offer. Make it back into a single family or keep it the way it is and rent the house and utilize the cottage for a personal vacay spot! Questions, call me!!
Listing is courtesy of: BLAKELEY & ASSOCIATES REALTY (941-567-3100)
Listing Agent: Lisa Blakeley (941-809-1647)
316 BEACH RD, SARASOTA, FL 34242
$5,249,000152 Days on yellowkey MLS ID: A4683801
REDUCED by $250,000 (4.5%) on 06/16/2026
Bed: 8 Bath: 9.0 Gar: 2 Liv Area Sq Ft: 4681 Built: 1996 Tax: $37,822 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$37,822
Remarks: Just steps from the shoreline, this coastal home offers deeded beach access and sweeping panoramic views of the Gulf. Completely remodeled in 2021, the property lives and performs like new construction, blending modern coastal design with durable, rental-ready finishes throughout. Thoughtfully designed across three living levels and serviced by a private elevator, the home features 8 bedrooms, 8 full baths, and 2 half baths, with expansive gathering spaces suited for both everyday living and hosting. With a proven track record as a high-performing short-term rental, the property generates approximately $400,000 to $500,000 annually, offering strong income potential alongside its lifestyle appeal. The top floor serves as the heart of the home, where the main kitchen and primary living area open directly to a Gulf-facing balcony showcasing breathtaking, unobstructed water views. This elevated vantage point creates a stunning backdrop for daily living, with the kitchen, dining space, and great room all positioned to take in the scenery. A secondary club room with wet bar provides an additional space to gather, while multiple balconies throughout the home frame the coastal setting from different vantage points, including select bedroom suites. Below, the outdoor living space features a private pool and integrated spa surrounded by lush landscaping, along with a fully equipped outdoor kitchen with built-in grill, refrigeration, and dining area. All eight bedroom suites offer ensuite baths and generous accommodations, with several enjoying Gulf views and private balcony access. Located near beach access and Siesta Key Village, this is a rare opportunity to own a fully renovated coastal home that delivers both luxury living and compelling investment performance.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000124 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.7%) on 06/11/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing Agent: Samantha Callaway (630-865-3189)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000125 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
643 CALLE DE PERU, SARASOTA, FL 34242
$1,996,000360 Days on yellowkey MLS ID: A4658846
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1982 Built: 1980 Tax: $8,733 (2024)Community: Sarasota BeachSingle Family
Taxes:$8,733
Remarks: Pre-construction. To be built. Custom beach home opportunity! Less than a mile to the #1 Rated Beach in the Nation- Siesta Beach! Almost 1/4 acre lot in a charming neighborhood with close proximity to public beach and Village. The existing structure is a tear down, leaving a beautiful canvas to create your dream home or investment property! Optional Island Series plans by Yoder Custom Homes are available, or choose the builder of your choice, or land only. Just 6.4 mi to downtown Sarasota- known for it's Arts & Culture. Call today for more information! Land only listed in vacant land.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rachelle Tirey (941-301-9187)
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