Location: Sarasota Beach, Sarasota
Do Not Show Listings
5201 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,560,00056 Days on yellowkey MLS ID: A4680975
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2802 Built: 2008 Tax: $6,145 (2025)Community: Sarasota BeachSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,145
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mary Kassen (941-900-9776)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,695,0007 Days on yellowkey MLS ID: A4687301
Bed: 8 Bath: 8.5 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSingle Family
Taxes:$25,684
Tax Year: 2024
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 is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
262 ISLAND CIR, SARASOTA, FL 34242
$3,995,000167 Days on yellowkey MLS ID: A4668568
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3455 Built: 2023 Tax: $24,321 (2024)Community: Sarasota BeachSingle Family
Taxes:$24,321
Remarks: Waterfront Sanctuary on Siesta Key - Outdoor Living Enthusiasts This is the One! Your party is in the back with your own Very Private Backyard and Pool Area ready for family gatherings, sunset hot tubs, sunrise fishing, & poolside cocktails. Being sold furnished. Move right in! Newer construction meeting all hurricane standards and building codes. All living space is above base flood elevation. Welcome to an unparalleled blend of sophistication and coastal charm. Located on the exclusive Palm Island neighborhood of Siesta Key, this exquisite residence offers an extraordinary island lifestyle—perfectly positioned along the Grand Canal with close proximity to the pristine, sand Beach of Siesta Key and the vibrant energy of Siesta Village. Spanning close to 3,500 square feet of meticulously designed living space, this newly built, custom home provides the ultimate in luxury and island living. The home includes 4 bedrooms, 4 full bathrooms, plus 2 additional half baths. Enjoy an additional, comfortable family room on the second floor. Every detail has been carefully curated to create a seamless balance of form and function. From the moment you enter, you'll be captivated by the open-concept layout, soaring ceilings, and walls of glass that flood the home with natural light, offering breathtaking panoramic views of the Grand Canal, playful manatees, water birds, and lush tropical landscapes. The chef-inspired kitchen is a culinary dream, featuring top-of-the-line Thermador appliances, custom cabinetry, and an expansive, Quartzite island perfect for both cooking and entertaining. The spacious living and dining areas flow effortlessly into the outdoor oasis, where a resort-style pool, hot tub, gas fire pit and outdoor kitchen await. Whether you're hosting guests or simply enjoying a quiet evening, this home offers the ideal setting for any occasion. The first floor primary suite is a true retreat, with ship lap ceiling and accent wall and a spa-like bathroom that includes a walk-in shower and dual vanities. Each additional bedroom/en-suite has been designed with comfort and luxury in mind, providing private, serene spaces for family and/or guests. In addition to the gorgeous interior, the property offers 80 feet of water frontage and unrivaled outdoor amenities including a private dock with 10,000 lb. boat lift ideal for boating enthusiasts to access Sarasota Bay and beyond. Situated just moments from the world-famous Siesta Key Beach, Iconic Siesta Village, and the vibrant downtown Sarasota scene, 262 Island Circle is the epitome of coastal, waterfront living. This is more than a home—it's an island lifestyle. This magnificent residence offers the perfect fusion of luxury, tranquility, and location. Discover your own slice of paradise on Siesta Key today. Call for a private showing.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Joe Kesslak (941-321-8585)
5263 AVENIDA DE CORTEZ, SARASOTA, FL 34242
$3,850,00061 Days on yellowkey MLS ID: A4678861
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3122 Built: 2018 Tax: $21,844 (2025)Community: Sarasota BeachSingle Family
Taxes:$21,844
Remarks: Welcome to a residence where inspired design meets the effortless elegance of Island living. Tucked away on the tranquil side of the Siesta Key Village, this extraordinary home places you at the heart of it all while having it all. With World-renowned beaches and the charming village just steps away… you truly can not beat the location. This 4 bedroom, 3100 sq.ft. home boasts a private boat dock, tropical backyard oasis and terraces with sunset views that never fail to inspire. The primary construction of this home was completed in 2018, with a full designer remodel in 2025. This home offers the confidence of modern construction throughout. Levels one through three are concrete block, with a two-by-six wood-frame fourth level and all exterior glass is hurricane impact rated. The home also boasts a standing-seam metal roof, a six-foot privacy wall with keypad-secured metal entry gates. A three-stop elevator services every floor, alongside a striking free-floating steel staircase framed by floor-to-ceiling glass, maintaining open sight-lines across the living spaces. Private bedrooms with en-suite bathrooms are thoughtfully positioned on levels two and four. Each floor opens to a generous covered balcony. Crowning the home is its most captivating feature: a spiral staircase leading from the fourth-floor balcony to a rooftop terrace with sweeping views of Siesta Village, Siesta Beach, Downtown Sarasota, and front-row vantage point to nightly stunning sunsets over the ocean. A comprehensive renovation brings a fresh, sophisticated vision to this home. The updates include new luxury hardwood flooring throughout, designer kitchen complete with dry-bar and a luxurious primary bathroom update. The second level serves as the home’s central gathering space, featuring an open-concept living room, dining area, and kitchen designed for both entertaining and everyday luxury. The kitchen has been elevated with brand-new custom floor to ceiling cabinetry complete with specialty lighting, premium Cambria countertops, as well as new appliances. The space is complimented by a beautifully designed dry bar and pantry for a refined, luxury finish.The high end finishes are complimented by designer furnishings and decor that convey with the sale of the home. At ground level, a two-car garage is complemented by a substantial 440-square-foot covered lanai overlooking a refreshing heated outdoor pool. The addition of an outdoor kitchen and upgraded, easily maintained, turf and stone landscape create seamless indoor-outdoor living and entertainment. Privacy is not an issue as this home boasts lush landscape and an impressive block wall enclosed yard. With Siesta’s gorgeous white sand beaches just a short walk from the home and a private boat dock just across the street enjoying the Ocean is a breeze from this property. The boat dock includes a 10,000-pound lift and space for a second lift, allowing for effortless access to the ocean via a canal. Siesta Key Village is a cherished walkable community rich with dining, boutiques, and local small businesses, including a Market, that evoke feelings of nostalgia. Yet the greatest luxury remains the timeless evening sunset strolls on the soft white sandy beaches. The Island’s effortless serenity reaffirms why Siesta Key is not merely a destination, but an exceptional place to call home.
Listing Agent: Jessica Hoffman (941-400-5778)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,695,0008 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSingle 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)
605 AVENIDA DE MAYO, SARASOTA, FL 34242
$2,195,00053 Days on yellowkey MLS ID: A4681389
0 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 4210 Built: 2003Community: Sarasota BeachSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Under contract-accepting backup offers. Live the Siesta Key lifestyle at its best in this exceptional, elevated waterfront residence, positioned just one block from Siesta Village and only three blocks to Sunset Pier and world-famous white quartz sands and aqua waters of Siesta Beach. Whether you’re seeking a primary residence, vacation retreat or potential income-producing investment, this home offers the location, boating access and peace of mind today’s buyers value most. Custom-designed and built by the engineer-owner, this striking Key West–inspired, three-story home offers approximately 4,210 square feet of air-conditioned living space, thoughtfully engineered for energy efficiency, durability and low maintenance. The main living level begins at approximately 19 feet above base flood elevation, a significant advantage that helps reduce flood risk and insurance costs. Built in compliance with FEMA and Florida building codes, the home earned Florida Power & Light’s Build Smart designation, verified to be 40% more energy-efficient than required by Florida energy standards. Designed for everyday living and entertaining, the expansive open-concept main level features soaring tray ceilings, glass block accents, porcelain tile with marble inlays and abundant natural light. The chef’s kitchen offers extensive custom cabinetry, abundant quartz countertop workspace, an oversized island and stainless-steel appliances, seamlessly flowing into an expansive formal dining room ideal for hosting family and friends. The home offers five bedrooms and five baths, including a spacious owner’s suite with vaulted ceilings, spa-style bath and an oversized bonus room opening to multiple balconies with tranquil water views. A large recreation room, workshop, and generous storage add flexibility for full-time living or guest accommodations. Additional features include impact windows, wind-rated low-maintenance exterior siding, zoned HVAC with UV filtration, central vacuum, oversized four-car garage, additional driveway parking and landscaped, maintenance-free grounds. Outdoor living is a highlight, featuring a saltwater pool with titanium heat pump and hydraulic cover, expansive paver deck, outdoor kitchen with a seven-foot stainless steel grill, wet bar, pergola, gazebo and ambient LED lighting, ideal for relaxed island entertaining. Boaters will appreciate the canal-front setting with a 7,000-pound boat lift, providing easy access to Sarasota Bay and downtown by water. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Offering exceptional value as one of the lowest price-per-square-foot elevated waterfront homes on Siesta Key, this residence combines location, construction quality, efficiency and lifestyle, an outstanding opportunity to own in the heart of Siesta Key.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
105 ISLAND CIR, SARASOTA, FL 34242
$2,680,950349 Days on yellowkey MLS ID: A4647817
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2750 Built: 1953Community: Sarasota BeachSingle Family
Remarks: 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)
421 ISLAND CIR, SARASOTA, FL 34242
$1,275,00056 Days on yellowkey MLS ID: A4681301
3 Days Off yellowkey (back on 3/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1444 Built: 1999Community: Sarasota BeachSingle Family
Remarks: Under contract-accepting backup offers. Ideally located on Palm Island in the heart of Siesta Key, this elevated block-construction home offers the ultimate blend of style and resilience. Situated on nearly a quarter-acre, this 2-bedroom, 2-bathroom residence includes a generously-sized office currently utilized as a 3rd bedroom. Elevated over 10 feet, the home features a metal roof (2019), hurricane impact windows (2019), newer HVAC (2022) and new exterior paint (2026). The interior shines with fresh paint, designer lighting, and a custom statement banquette. An updated kitchen with marble countertops is open to the ample living and dining space, perfect for entertaining. The oversized owner’s suite boasts a walk-in closet and an ensuite bath with dual sinks, and double doors opening to the deck and pool area. Outside, enjoy the newly installed heated pool and paver deck overlooking a tranquil saltwater pond, which provides additional privacy. Just blocks from the world-famous Siesta Key Beach and less than a mile from the Village, this is island living at its finest.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Jaya Brossard (941-914-8414)
5334 CALLE FLORIDA, SARASOTA, FL 34242
$1,870,00095 Days on yellowkey MLS ID: A4676260
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2838 Built: 1998Community: Sarasota BeachSingle Family
Remarks: Fantastic opportunity to own a unique home on Palm Island, in this exceptional Siesta Key residence, ideally located at 5334 Calle Florida. Situated on a large lot and elevated approximately 10 feet above sea level, the main home has never flooded during any storms, offering peace of mind along with island luxury. This 4-bedroom, 3-bathroom home features 2,838 square feet of thoughtfully designed living space highlighted by a dramatic great room with soaring 20-foot ceilings, creating an open and airy coastal feel. The large primary suite has a custom built window seat, 2 walk in closets and an oversized primary bathroom. The entire home features built in speakers, including the back porch. Designed for comfort and efficiency, the home is equipped with a three-zone air conditioning system and hurricane-rated Kevlar screens, hurricane rated garage and front door for added protection. The spacious two-car garage provides ample storage, perfect for island living. The exterior is landscaped with outdoor lights and power in soffits for seasonal or all year round lighting. Outdoor living is elevated—literally—with an elevated, heated pool and hot tub, an outdoor shower, and plenty of space to relax or entertain in true Florida style. Located on Palm Island, just moments from the world-renowned Siesta Key Beach, this property offers the perfect blend of privacy, elevation, and coastal charm. Whether as a primary residence or luxury retreat, this home is a rare opportunity to own a high-and-dry island property in one of Sarasota’s most sought-after neighborhoods. Roof replaced 2021, Pool resurfaced 2024, Pool cage repainted and rescreened 2025, Water heater 2025. Unique Architectural Details *** Custom Built *** Oversized Primary Suite *** Soaring Ceilings *** Open Concept *** Elevated Key West Style *** Screened Lanai
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Niall Phelan (941-914-8589)
5453 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,150,000 MLS ID: A4669037
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1510 Built: 1950Community: Sarasota BeachSingle Family
Remarks: 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)
2 ISLAND CIR, SARASOTA, FL 34242
$1,600,000 MLS ID: A4662842
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3855 Built: 1948Community: Sarasota BeachSingle Family
Remarks: Under contract-accepting backup offers. *2 BUILDABLE WATERFRONT LOTS* Palm Island IS the "Heart of Siesta Key". Don't miss this rare opportunity to live in Siesta Key's most sought-after neighborhood and experience the quiet, friendly, yet close to everything community of Palm Island. Build your tropical dream home on one lot and sell the other, or go "all in" and create your ideal island estate on the 17,883 sq ft lot. If restoration is more your style, this home was built using the Lamolithic poured in place construction method developed by John Lambie Jr and was a key design element in the Sarasota School of Architecture. As a result, most of the primary structure and walls are made of 12 inch poured concrete, providing unsurpassed strength and durability. This spacious property located in one of the finest and friendliest communities on Siesta Key is situated a mere 600 feet from arguably the best beach on the planet. Situated on the Grand Canal, it is minutes by boat to the Intercoastal Waterway and a short walk or bike ride to Siesta Key Village. This sought after Palm Island address sits on two county approved building lots and is a rare opportunity for all interests. Maximize your Island experience and treat yourself to this rare, peaceful island escape limited only by your imagination. *House Plans and Budget available for both lots
Listing Agent: George Miller (941-374-1000)
515 AVENIDA DE MAYO, SARASOTA, FL 34242
$812,000 MLS ID: A4684098
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1346 Built: 1952Community: Sarasota BeachSingle Family
Remarks: LOWEST PRICED WATERFRONT ON SIESTA AT TIME OF LISTING In Siesta Village just several blocks to famous Siesta Village, shops dining and beach. Build your waterfront dream home here or possibly rehab existing home. Boatable canal to ICW with seawall and view of mangroves. Live the Florida lifestyle in this lovely bird sanctuary just a few miles from downtown Sarasota. Structures flooded, sold As-Is at land value, no warranties or disclosures.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Bob Stahlschmidt Ii (941-266-2684)
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