Homes For Sale in Sarasota 34242 - 380 homes

Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!

Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)

Listing Agent: Holly Parry (941-809-8050)

Remarks: Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house, and a separate waterfront cabana with bath. In total, the compound offers six bedrooms and six bathrooms, with gourmet kitchens in both the main house and guest house — each outfitted with high-end appliances throughout — ideal for multigenerational living, guest accommodations, or an exceptional private retreat. Throughout both residences, the finish detail is exceptional. Designer-selected materials create a cohesive and elevated aesthetic carried seamlessly across the entire compound. Custom wood flooring with intricate stone inlays, handcrafted stairwells featuring wood and stone risers, extensive crown molding, and refined architectural millwork highlight the level of craftsmanship invested in every space. Specialty stonework and thoughtfully curated finishes blend warmth with sophistication, creating interiors that feel timeless, substantial, and unmistakably high-end. Outdoor living is nothing short of spectacular. A dramatic infinity-edge pool with swim-assist system overlooks the water, enhanced by a striking waterfall feature that spills elegantly into the pool. New pool equipment (2025) supports the system. Natural rock waterfront frontage and a sculptural rock formation lead down to the shoreline, creating a one-of-a-kind coastal backdrop. Two docks serve the property — one with a double lift — offering outstanding boating access and rare protection on both sides of the point, with additional lift capacity for multiple watercraft. An outdoor shower provides added convenience after boating or swimming. Perched at the edge of the peninsula, the waterfront cabana and adjacent hot tub create a private, spa-like retreat suspended over the water — an unforgettable setting to take in sweeping sunset views. The residences were renovated separately: main house (2009) and guest house (2012). All A/C units have been renewed recently, along with the electric unit, and a new transformer (2024) services both properties. Sonos surround sound extends throughout all structures. Located on the highly desirable north end of Siesta Key, the estate offers convenient on-and-off island access while remaining just minutes from Southside Village and downtown Sarasota.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Nora Johnson (941-809-1700)

Remarks: An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Located within Siesta Beach House Condominiums, this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Rachel Tritschler (941-993-5892)

Remarks: BEST PRICED GULF-FRONT CONDO ON SIESTA KEY, in terms of VIEW, CONDITION, SIZE, AMENITIES and PROXIMITY to Siesta Key Village, the #1 BEACH IN America, and DOWNTOWN SARASOTA! Not ONE, but TWO heated GULF FRONT POOLS. Brand NEW fishing dock. This lovely unit can come partially furnished if you wish (a full list of items is available) and has a BRAND-NEW A/C. MOVE IN READY! Unobstructed GULF VIEWS, forever YOURS! And it’s PET FRIENDLY! HOA covers just about everything! Bring your suitcase, your toothbrush and your bathing suit! Wake up to breathtaking Gulf views, watch as dolphins swim, and enjoy legendary Siesta Key sunsets from this beautifully maintained 2-bed, 2-bath, perfectly positioned condo in a charming Gulf front community. Floor-to-ceiling glass sliders flood the open living area and primary bedroom with natural light, leading to your private screened lanai, where uninterrupted Gulf views are yours to behold. The primary bedroom features ample closet space and an ensuite bath with separate vanity. With 1,200 ft² of living space, this second-floor residence comes with an in-unit washer/dryer, as well as a free community laundry room and storage. The second bedroom is perfect for guests and family, and the well-appointed kitchen has upgraded appliances and a pass-through to the living area. This exceptional unit has had just one owner and has been in the family since the complex was built. Sea Village is a small community located exactly 1 mile north of Siesta Key Village and 1 mile to the #1 Beach in America. Amenities include two heated gulf front pools, a newly constructed fishing pier, and designated covered parking. ALL assessments have been PAID. Monthly HOA covers Community Pool, Escrow Reserves, Insurance, Exterior Maintenance (to include the roof), Maintenance of the Grounds, as well as Water, Sewer and Trash. Renowned for its vibrant coastal lifestyle, Siesta Key Village is bustling with restaurants, cafes, shops and miles of crystalline beaches. Downtown Sarasota’s Bayfront, with its world-class shopping, dining, & cultural events is 5 miles away. Nature lovers, sports enthusiasts, and patrons of the arts have the best of Sarasota at their fingertips with outdoor activities that include waterfront dining, boating, biking, golfing, hiking & fishing nearby. With easy access to state-of-the-art medical facilities, Sarasota International Airport, and the I-75, the location of this property offers the perfect blend of serenity & convenience and offers an extraordinary opportunity to LIVE YOUR BEST LIFE, whether it be used as a private retreat for your own personal enjoyment, or a seasonal or annual rental, with excellent income potential.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Robin Leonardi (941-685-6270)

Remarks: Under contract-accepting backup offers. Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)

Listing Agent: Rachelle Golden (941-538-8998)

Remarks: Under contract-accepting backup offers. PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought-after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide additional protection and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Halie Monde (941-735-4707)

Remarks: Under Construction. Incredible opportunity in highly desirable Bay Island, easy access to downtown Sarasota and Siesta beaches. Currently under construction with acclaimed Voigt Brothers construction, early 2027 completion date. Please request floor plans and finishes, you will be ecstatic with the choices

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Fred Sassen (404-408-5956)

Remarks: Welcome to an exceptional new offering in the highly sought-after Sarasota Surf & Racquet Club. Perfectly positioned on the 7th floor of the coveted tower building, this beautifully upgraded two-bedroom, two-bath residence captures expansive views and cooling Gulf breezes while delivering a refined, move-in-ready coastal experience. The thoughtfully renovated kitchen has been redesigned to enhance both form and function, opening sight lines to the living space and creating a true gathering hub. White cabinetry, quartz countertops, and a newly added kitchen island replace the former peninsula, while the removal of the original owner’s closet provides additional counter and storage space—ideal for your coffee bar, display of fine spirits or to lay out your coastal cuisine buffet style. Both bathrooms have been upgraded with matching quartz countertops, creating a cohesive and modern aesthetic throughout. The primary suite offers a spa-inspired bath with an expanded layout, a sleek stand-up shower with frameless glass doors, and a newly added water closet for enhanced comfort and privacy. A locked owner’s closet allows for easy “lock-and-leave” ownership, perfect for seasonal use or rental flexibility. The guest bedroom comfortably accommodates two queen beds and features a generous walk-in closet with existing washer/dryer vent access, ready for a future installation if desired. Ownership at Sarasota Surf & Racquet Club feels effortless and exclusive as it includes access to two heated swimming pools, a fitness center, BBQ pavilion and recreation hall. An active tennis community brings residents together for fitness, fellowship, and a little competitive fun. The onsite rental management team cares for your investment, with a rare and advantageous 3-night rental minimum policy, and organizes all of the reservations and turnovers while you enjoy your return on investment. Ideally poised on Siesta Key’s pristine shoreline, this residence offers a rare blend of elevated design, resort-style amenities, and effortless island living.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Rudy Dudon (941-234-3991)

Remarks: Beautifully renovated 4-bedroom, 4-bath pool home tucked behind the gates of the exclusive Sanderling Club. Surrounded by a grandfathered privacy wall and lush tropical foliage, the property is just steps from your own private beach. 2023 updates include - new roof, hurricane-impact windows/sliders and plumbing. Meticulously renovated in 2025–2026 with top-of-the-line finishes throughout the entire home. Luxury vinyl plank flooring flows through the open floor plan, complemented by granite countertops and a oversized granite island with lots of storage, Samsung appliances and an open-concept layout ideal for entertaining, with abundant indoor/outdoor living space with views of the oversized sparkling pool. The primary suite is a tranquil retreat with two walk-in closets and an en-suite bath featuring a double vanity and soaking tub. A thoughtful split plan offers two additional spacious bedrooms each with en-suite baths. A fully renovated pool house/mother-in-law suite with its own full bath adds flexible living options. Located in a waterfront community, residents of the Sanderling Club have exclusive beachfront access, tennis and pickleball courts, clubhouse and 24-hour security This home blends refined luxury with coastal lifestyle and privacy.

Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)

Listing Agent: Amy Nadell (941-539-5424)

Remarks: The Fastest Open-Water Access Available on Siesta Key Under $2.5 Million Less than 3 minutes to Sarasota Bay, 95 feet of waterfront, and a 75-foot dock designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key. Why spend 30–45 minutes idling through canals when you can be in Sarasota Bay in under 3 minutes? Positioned on one of Siesta Key’s premier deep-water canals, this exceptional waterfront residence offers the rare combination of protected dockage and near-immediate access to open water. For boaters who value time on the water, this location is difficult to replicate at any price point. Designed with larger vessels in mind, the property features approximately 95 feet of waterfront, a 75-foot dock, 200-amp dock service, and four 50-amp shore power connections. Whether you’re heading offshore, cruising the Intracoastal, or enjoying a sunset cruise across Sarasota Bay, this home delivers a level of boating convenience that few waterfront properties can match. Boater Highlights?• Less than 3 minutes to Sarasota Bay?• Approximately 95 feet of waterfront?• 75-foot dock?• Four 50-amp shore power connections?• 200-amp dock service?• Deep-water canal location?• Protected dockage with quick open-water access Inside, the home has been thoughtfully renovated with a clean coastal-modern design featuring designer tile flooring, an open-concept floor plan, Viking gas appliances, custom cabinetry, and expansive waterfront views. The spacious living areas flow seamlessly into the kitchen and entertaining spaces, creating an ideal environment for both everyday living and hosting guests. The private primary suite serves as a luxurious retreat, complete with an oversized walk-in closet, spa-inspired bathroom, glass-enclosed shower, and direct outdoor access. An additional flexible space offers the opportunity to create a fourth bedroom, private guest suite, office, or media room. Outdoor living is centered around the waterfront lifestyle. Enjoy a saltwater pool and spa, tropical landscaping, integrated lighting, retractable awning, propane fire pit, outdoor shower, and multiple seating and entertaining areas overlooking the canal. Additional features include a 13.5 kW generator, hurricane protection, epoxy-finished garage, updated HVAC system, newer water heater with circulation system, 250-gallon propane tank, and valuable dry storage space. Originally introduced at $2,690,000 and now offered at $2,450,000, this property represents one of the strongest values currently available for buyers seeking deep-water dockage, exceptional boating access, and luxury waterfront living on Siesta Key. Luxury yacht available separately.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Derek Edwards (941-929-3183)

Remarks: Ideally on the south end of Siesta Key, directly across from the free Siesta Key trolley and less than a quarter mile to Turtle Beach, this two-bedroom, two-bath residence offers 1,093 square feet of living space with panoramic Sarasota Bay views and glimpses of the Gulf. The open-concept great room is designed to maximize the water views and features luxury vinyl tile flooring, built-in surround sound and direct access to the screened lanai. Motorized blinds enhance the lanai, creating a comfortable space to enjoy the serene bayfront scenery. The kitchen is open to the living area and offers granite countertops, stainless steel appliances, creamy white cabinetry, a spacious pantry, and views of the Gulf and Sarasota Bay. Water views continue into the primary suite, where owners can wake to spectacular sunrises from the comfort of their bedroom. The primary suite also features a custom walk-in closet system and en-suite bath. The guest bedroom offers Gulf views and a large walk-in closet. Additional conveniences include a dedicated storage space, communal laundry facilities on the same floor adjacent to the elevator, an assigned covered carport space near the elevator and abundant guest parking. Recent improvements include a new electrical panel in 2021 and a new water heater in 2026. Sunrise Cove offers an array of amenities, including a renovated clubhouse with social spaces and kitchen, fitness center, library, billiards and table tennis, two heated swimming pools, tennis courts, pickleball courts, grilling areas and boat slips available for lease. Residents can also take advantage of the kayak, canoe and paddleboard storage available for lease, along with convenient marina access nearby. Enjoy easy access to Turtle Beach, boating, waterfront recreation and all the shopping, dining and entertainment of Siesta Village. Experience the best of Siesta Key living with bayfront views, beach access and resort-style amenities in one exceptional location.

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)

Listing Agent: Beth Sargent (941-716-1277)

Remarks: Gulf-Front Luxury with Investment Appeal Experience elevated beachfront living at Ten35 Seaside, a boutique Gulf-front community on the quiet southern end of Siesta Key. This beautifully designed 2-bedroom, 2.5-bath residence offers private beach access, resort-style amenities, and strong luxury rental potential. The open-concept layout features Wolf and Sub-Zero appliances, custom cabinetry, sleek coastal finishes, and spacious living areas filled with natural light. Sliding glass doors open to a private terrace perfect for enjoying Gulf breezes and sunset skies. The primary suite offers a spa-style bath and walk-in closet, while the guest suite includes built-in bunk beds for added flexibility and rental appeal. Residents enjoy a beachfront pool and spa, private cabanas, fitness center, and direct access to Siesta Key’s world-famous beaches — all just minutes from Siesta Key Village and downtown Sarasota. Ideal as a luxury beachfront retreat, full-time residence, or income-producing coastal investment property. Buyer to verify rental policies, restrictions, and all room dimensions.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Rex Glasson (941-587-6135)

Remarks: Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming arms" staircases . Very close to the Village and Beach , yet equally convenient to Downtown . This sophisticated townhome has been completly renovated with fine finishes , wood and stone prevail with architectural beauty . Soaring ceilings bring in the most elegant lighting . The kitchen with its sweeping bar of magnificent granite can accomodate a large party-open to the Great Room , it is both sleek and inviting .Premium appliances include Miele, Bosch , GE and KitchenAid .Expansive counter space , built in shelving and a variety of pantries and drawers add to the incredible functionality. The Great Room with 20 foot ceilings opens to the screened balcony with a charming view of the lagoon and pool area . The primary bedroom is enhanced by the stunning view of treetops and is all the more cozy for having its own fireplace . Impact rated windows and a metal roof combine to make this solid structure weather worthy . On the ground floor , in addition to the oversized two car gargage is a climate controlled bonus room which opens to the ground floor lanai . Boating , swimming , tennis and walking paths , within a private and peaceful environment close to everything -that is the Hamilton Club .

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Barbara Dumbaugh (941-349-3444)

Remarks: BAY OAKS - JUST MINUTES FROM WORLD FAMOUS SIESTA KEY BEACH. Now is the time to make this 2-bedroom, 2-bath condo your island paradise. With weekly rentals allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and move-in ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Greg Hudson (941-302-1485)

Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Drew Jacobsen (941-253-6309)

Remarks: Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted. Photos 1 and 2 reflect the new colors that the home is being painted.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Jennifer Linehan (941-266-7555)

Remarks: Own a piece of paradise at the Palm Bay Club tower, where Siesta Key sunsets and Gulf views become a part of daily life. Positioned in the waterfront tower, this airy corner residence captures a rare perspective down Siesta Key’s shoreline, where wide Gulf views, turquoise water, and the movement of the surf are visible from every room. Its unique southern orientation is one of the reasons the current owner fell in love with the property. It offers the beauty of a true Gulf-front setting without the harsh afternoon sun that many beachfront residences contend with. It is low enough to remain connected to the beach and water below, yet elevated enough to frame a panorama of the coastline. The experience from within the residence is both soothing and unforgettable. Floor-to-ceiling windows fill the unit with natural light throughout the day. Morning sunrises arrive softly through the eastern-facing windows, while the southern exposure continuously reflects the changing colors of the Gulf, beach, and sky across the living spaces. Lovingly maintained as a private coastal retreat for the owner, the residence has been thoughtfully and continually improved with an emphasis on luxurious comfort, quality, and ease of ownership. Features include custom cabinetry and generous storage, KitchenAid and Kohler appliances, Brizo fixtures, designer lighting and furnishings, top-of-the-line custom Hunter Douglas blackout blinds, hurricane-rated window protection, a private in-unit washer and dryer — a rare convenience within the building, and much more. The interiors feel refined yet relaxed, designed for extended stays, entertaining guests, or simply enjoying quiet mornings overlooking the water. While this residence has primarily been enjoyed privately, Palm Bay Club’s highly regarded in-house rental program and flexible three-day minimum rental policy provides an exceptional option for owners seeking to generate income alongside personal enjoyment. The property includes 24-hour onsite security as well as full-time management, front desk and maintenance personel 7 days/week. Many long-term staff members contribute to the welcoming and established feel that owners value so highly. The Palm Bay Club's beach resort lifestyle comes with a level of service and atmosphere that sets it apart on Siesta Key. Available beach staff will take the complimentary loungers anywhere on the private beach by ATV. Owners and guests enjoy one of the largest expanses of direct access private beach frontages on the Key, with an outdoor grill, covered pavilions, a rinse station, and additional premium beach cabana services. The Gulf side amenities also include poolside bathrooms and showers, and a fitness center that looks out to the big heated pool and tennis/pickleball courts. A brand new shuffeboard court has been added in 2026. For a different laidback vibe, residents and guests simply walk to the Bay side to lounge by the heated pool and hot tub, where they can watch the boats go by amidst the boat docks, fishing pier, and palm trees. Must see to appreciate this rare tower unit with one of the most desirable and requested orientations at this exceptionally well maintained gulf-to-bay resort condo complex. This fully furnished turnkey property is move-in ready for immediate enjoyment or future rental use.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Skrzypkowski (941-328-8307)

Remarks: Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand beaches and charming Siesta Village easy and convenient. The free-flowing plan, offering 3,034 sq. ft. of open living, will seduce you with its inviting atmosphere wrapped in casual elegance and modern sophistication. With plenty of natural light, the great room boasts double-height ceilings adorned with rich architectural detail, an elaborate floor-to-ceiling fireplace wall, and see-through views to the expansive outdoor space and coveted canal setting. Beyond the great room’s glass doors, an entertaining lounge with wood ceiling accents, a professional grill station, and a heated pool/spa await your plans for spending cherished time with family and friends. As evening approaches, night lighting transforms the beautiful backyard and creates a timeless ambiance that encourages relaxation and reflection. A gorgeous kitchen is enhanced with an abundance of amenities including a premium Sub-Zero and Wolf appliance package, stone counters, stylized fixtures and finishes, a walk-in pantry, and adjoining laundry. The formal dining room features a built-in buffet and French doors leading to a brick paver patio, making it a wonderful spot for dining alfresco under the stars. The bonus room, with wet bar and pool bath, features two walls of glass sliders showcasing the extensive outdoors and picturesque water views. The primary suite is an oasis of serenity with an office outfitted with built-ins, a generous wardrobe for two, and an exquisite bath intended to pamper and spoil with a free-standing tub, a frameless glass shower with rain head, separate vanities with stone tops, and a water closet. Two additional en-suites offer plenty of room to unwind and rejuvenate in comfortable privacy. A brick paver drive, a 3-car garage, professional landscaping with timed irrigation, eye-catching curb appeal, and other notable customizations inside and out, complete this magnificent waterfront home. This fresh new residence, designed by the award-winning team at Allegra Homes, has been artfully designed and crafted to offer the highest quality to those who live here. An exciting opportunity to make this island paradise yours!

Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)

Listing Agent: Karen Greco (941-504-6927)

Remarks: Experience full gulf-front views and the lifestyle of island living on the world-renowned Siesta Key beach. This beautiful fifth-floor end-unit residence is in the south tower of Whispering Sands, a community in the heart of Siesta Key Village. This property offers the ideal blend of serenity and convenience. Residents enjoy private beach access and 800 feet of quartz sand beach, yet you are just a short distance from all the shops, boutiques and restaurants of the village. With open-air hallway corridors, you will feel the island breeze as you enter the front door of the residence. An abundance of natural light immediately welcomes you from the windows and large wall of glass sliders in the living and dining area, designed to showcase the dreamy turquoise water views of the Gulf. This two-bedroom, two-bath unit features light and bright neutral tones providing a warm yet coastal feel. The highlight of this unit is the 25-foot terrace accessible through two sets of hurricane/impact rated floor-to-ceiling glass sliders with remote-controlled shades. Here is where you will want to sit, relax and take in the expansive and postcard-worthy beach views. The kitchen has been upgraded with granite countertops, breakfast bar, new cabinets, stainless steel appliances, a built-in desk area and a closet pantry. From your primary suite, you will enjoy views of the turquoise water by day and golden sunsets by night through the floor-to-ceiling glass sliders. This cozy retreat also offers an updated en-suite bath, generous walk-in closet and a wall of custom built-in drawers. The guest bedroom is versatile and large enough for two queen beds or could be used as a den or home office. Whispering Sands is a 55-plus community and is resort-inspired, featuring two heated pools with new travertine decks, canoe/kayak storage, shuffleboard, a beachside tiki hut with barbecue grills and lush landscaped grounds. The main clubhouse, featuring a fitness center, community room and lounge area, is undergoing a complete remodel with an expected completion date of late 2026. When you are ready to venture out beyond the sandy beaches, you’ll be just a short drive to downtown Sarasota and its world-class arts, dining and culture scene. This property is more than just a condominium, it’s a lifestyle. Come live it today!

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Christopher Bush (941-404-9504)

Remarks: Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, two baths and two private balconies, has been completely renovated, tastefully decorated and furnished, with in-unit laundry, a reserved parking space and a nice view of the blue waters of the Gulf, as well as a good view of one of the resort’s pools. The resort-style condominium is on a beautiful private beach featuring what has been rated as the whitest sand, consisting of 99 percent pure quartz, which stays cool under your feet. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room and serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you near Siesta Key's South Village. Siesta Sands allows weekly rentals and has an excellent on-site rental office to keep the condominium rented when not being utilized for personal use. The Point of Rocks is an area known for its coral formations and marine life, ideal for fishing or snorkeling. This resort condominium is offered turnkey furnished with solid rental history and further bookings in place. This is must-see. Don’t miss out.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Ziad Sleit (941-928-5493)