Waterfront Homes For Sale In Siesta Key

2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code

From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an impressive rental history—all within one of Siesta Key’s most recognizable beachfront communities. Beyond its appeal as a personal beachfront escape, #809 offers an established rental history. The residence averages more than $80,000 in annual gross rental income (2024 – 2026), with bookings extending through year-end, offering a compelling opportunity for buyers seeking to combine personal enjoyment with income potential. Inside, the 1,271-square-foot residence has been thoughtfully reimagined with a fresh coastal aesthetic, luxury vinyl wood-plank flooring throughout, custom architectural ceiling treatments, and an open floor plan that keeps the Gulf firmly in view. The designer kitchen is both polished and functional, featuring granite countertops, custom Shaker-style cabinetry, stainless steel appliances, and a refrigerator cleverly concealed behind coordinating custom cabinet panels. The kitchen opens naturally to the dining area, where a built-in banquette creates an inviting gathering space beneath a dramatic coffered ceiling accented by designer lighting and naturally stained solid-wood beams. Beyond, the Gulf-front living room is framed by walls of glass, drawing your eye directly toward the water and opening to the screened terrace. The terrace is where the Siesta Key lifestyle truly takes center stage. Stretching across the Gulf-facing side of the residence, this generous outdoor living space provides a front-row seat to turquoise water, passing boats, and spectacular Gulf sunsets. A desirable split-bedroom floor plan provides privacy for owners and guests, with both bedrooms positioned to enjoy Gulf views and direct access to the screened terrace. Each bedroom also features a walk-in closet with built-in organization. The primary suite is complemented by a beautifully renovated en-suite bath with dual sinks, granite countertops, extensive built-in linen storage, and an oversized walk-in shower with bench seating. The second bath is also well appointed with newer cabinetry, stone counters and a tub/shower combination. Crystal Sands is an iconic Siesta Key beachfront community distinguished by its classic architectural presence and exceptional location directly on the Gulf of Mexico. Residents and guests enjoy a heated community pool, gated entry, elevators, recreation facilities, covered and guest parking, and direct access to the beach and Gulf. The residence also includes one covered carport space. And when you are ready to venture beyond the beach, some of Siesta Key’s favorite destinations are close at hand. Head north to Siesta Key Village for its lively collection of restaurants, boutiques, cafés, and nightlife, or south toward Crescent Beach, Point of Rocks, and the restaurants and conveniences surrounding Stickney Point Road. The Siesta Key trolley makes exploring the island especially easy, with service along the Key connecting beaches, dining, shopping, and Siesta Key Village.

6300 Midnight Pass Road Unit 809, Sarasota

$625,000

2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

Turnkey and ready for its next chapter, this spacious residence in the curve of Harbor Towers Yacht & Racquet Club is one of the largest floor plans in the building, featuring a split layout with each bedroom offering its own private bathroom. Sold completely furnished, this unit makes it effortless to fly or drive down and start enjoying it immediately, or begin renting it out right away. A rare find: existing washer/dryer electric hookups are already in place beneath the kitchen counter, a feature the building no longer permits for new installations. There's also a washer and dryer room located on the second floor just a few doors down. Picture the perfect Florida day: morning coffee on your enclosed patio overlooking the peaceful pond, then a match on the on-site tennis courts before laying out by the beautiful pool, both with views over the dock and water. Hop the trolley or take a short drive to the rose quartz sand beaches of Siesta Key, then wind down with happy hour and live music in Siesta Key Village. This unit can be rented short-term with a two-week minimum, and owners have the flexibility to use the community's on-site property management or bring in their own. Just three minutes to Siesta Key's world-famous beaches and five minutes to the shops and restaurants of Siesta Key Village, this is the perfect Florida lifestyle. Schedule your private showing today. Buyer to verify HOA rules regarding laundry hookups, boat slip rental terms, property management options, and rental restrictions.

5855 Midnight Pass Road Unit 222, Sarasota

$12,500,000

5 Beds ⋅ 7 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining and entertaining. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.

546 Freeling Drive, Sarasota

$874,900

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

ENDLESS POSSIBILITIES ON SIESTA KEY. Welcome to 19 Whispering Sands Drive, Unit 201, an exceptional opportunity to create your own Gulf Coast retreat in one of Siesta Key’s most established beachfront communities. Whether you choose to enjoy the residence as it is, renovate it over time, or completely reimagine the interior to reflect your own style, the possibilities are nearly endless. For buyers who want a more turnkey path, a renovation package can also be made available to help transform the residence into a beautifully updated coastal home. What cannot be recreated is the setting. Whispering Sands offers approximately 800 feet of private quartz-sand beach directly on the Gulf, two heated swimming pools, a beachside Tiki Hut and grills, fitness facilities, kayak and canoe storage, shuffleboard and beautifully maintained grounds. The community continues to invest in its future, with the Clubhouse and exclusive Tower Lounge undergoing renovation and improvements throughout the property. Here, the lifestyle begins outside your door. Spend mornings along the Gulf shoreline, afternoons by the pool and evenings watching Siesta Key’s celebrated sunsets. Siesta Key Village is just moments away, putting restaurants, boutiques, entertainment and island life within easy reach. Make it your own, renovate it with our available design and renovation package, or explore its rental possibilities subject to association requirements. The location is already extraordinary. The next chapter is yours to create.

19 Whispering Sands Drive Unit 201, Sarasota

$10,500,000

6 Beds ⋅ 7 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. This luxurious grand canal-front estate offers direct deep-water boating to the Gulf, out of one of the most exclusive neighborhoods on north Siesta Key. This in progress New Construction property by Pham Development is on an expansive 17,842 SF and 0.41 acre lot, with a 4,769 SF traditional-style home to be built. Enjoy two separate guests suites on top of the two 2-car garages, for a total of 4 garage spaces, both with elevator access to the above suites. The master bedroom will have water views, and the grand entry home hosts a total of 6 bedrooms, 6 baths, and 1 powder bath. This property's deep-water grand canal with no bridges is ideal for yachts and boats, with up to a 13-foot draft. A new dock and boat lift is set to be installed. Inside, expansive living spaces boast high-end finishes and top-of-the-line appliances, blending timeless elegance with modern comfort. Enjoy the water, and a large backyard perfect for entertaining, a private pool, and new lush landscaping—making this the ultimate waterfront estate for family.

3441 Gulfmead Drive, Sarasota

$2,995,000

3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

For the buyer who believes the best of Siesta Key is experienced by boat, 5178 Oakmont Place delivers an exceptional combination of deep-water canal frontage, estate-sized privacy, refined island living, and effortless access to Sarasota Bay. Set on more than half an acre along Siesta Key’s coveted Grand Canal, this tastefully updated custom residence pairs Caribbean-inspired architecture with 93 feet of waterfront, a private dock, and impressive 30,000-lb boat lift—creating a true luxury retreat for boating enthusiasts just minutes from the bay. A winding paver driveway introduces the private tropical setting, leading to a gracious residence by award-winning builder Lee Wetherington. Inside, high ceilings, substantial crown molding, elegant archways, tray ceilings, recessed lighting, and expansive windows create an airy sense of scale, while warm bamboo flooring brings natural sophistication throughout the primary living spaces. Designed for relaxed island living and entertaining, the open great room is anchored by a striking coral stone gas fireplace and framed by French doors connecting the interior to the expansive covered veranda. The updated kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, breakfast-bar seating, generous storage, and an adjacent service bar, complemented by a separate dining area for effortless entertaining. The spacious primary suite overlooks the tropical grounds, pool, and waterway and features a tray ceiling, two walk-in closets, dual vanities, large shower, and jetted soaking tub. A desirable split-bedroom floor plan provides two additional bedroom suites, while a large private office offers flexibility for working from home, a media room, or additional lounge space. Outdoor living is a defining feature of this Siesta Key waterfront home. The wide covered veranda provides generous spaces for dining and lounging while overlooking the private swimming pool and lush tropical landscape. Beyond the pool, a pathway leads directly to the Grand Canal and an outstanding boating setup featuring approximately 93 feet of deep-water frontage, a large dock, and 30,000-lb boat lift. Cruise to Sarasota Bay, waterfront dining, or Gulf waters before returning home to enjoy sunset along the canal. Built with quality and longevity in mind, the residence was constructed above base flood elevation and includes hurricane shutters, UV window film, foil roof insulation, floored attic storage, central vacuum, and construction to Miami-Dade standards. An oversized three-car garage offers excellent space for vehicles, bikes, kayaks, paddleboards, fishing equipment, and additional storage. Despite its private, estate-like setting, the home is ideally positioned near Siesta Village, world-famous Siesta Key beaches, boating, dining, and island attractions, with downtown Sarasota approximately 15 minutes away by car. For the luxury buyer seeking a Siesta Key waterfront pool home with deep-water boating access, substantial boat lift, oversized private lot, and proximity to Sarasota Bay, 5178 Oakmont Place offers an extraordinary opportunity to embrace the coastal Florida lifestyle

5178 Oakmont Place, Sarasota

$798,000

1 Beds ⋅ 1 Baths ⋅ Siesta Sands Resort (Timeshare) SubDv. ⋅ 34242 Zip Code

Located directly on Siesta Key Beach, Unit 310 at Siesta Sands is situated on the third floor and features a private balcony with sweeping Gulf views, tropical breezes, and unforgettable sunsets year-round. Offered furnished, this residence provides a turnkey opportunity to enjoy your own Siesta Key retreat. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service with lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room, and the serene Bamboo Lounge. With just 31 units, this gated beachfront community offers a private and secluded setting with exclusive access to beautiful Crescent Beach, all just steps from the shops, restaurants, and conveniences of Siesta Key's South Village. For those looking to offset ownership costs, Siesta Sands allows weekly rentals and offers the convenience of an established on-site rental office to manage the condominium when not being enjoyed for personal use. Unit 310 has a strong rental history with future bookings already in place, providing the opportunity to benefit from rental income while away.

1001 Point Of Rocks Road Unit 310, Sarasota

$669,000

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on the Gulf side and just steps from the tennis and pickleball courts, heated pool, and private beach access, this second-floor residence offers a peaceful setting with scenic pond views. The interior has been thoughtfully updated with a renovated kitchen and bathrooms, crown molding, fresh paint, new impact windows on lanai and new flooring throughout. The spacious primary suite easily accommodates a king-size bed and features a generous walk-in closet. Additional conveniences include a full-size washer and dryer, tankless water heater, dedicated parking space, and a private storage unit located just outside the front door. Offered fully furnished and truly move-in ready, this condo makes it easy to begin enjoying the Siesta Key lifestyle from day one. Peppertree Bay offers an exceptional Gulf-to-Bay lifestyle with private beach access, a fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ areas, beach chairs, car wash stations, on-site management, and a rental program. The fitness center and clubhouses are currently being renovated, adding even more to this amenity-rich community. This beautifully maintained residence is an excellent opportunity for a full-time home, seasonal retreat, or Siesta Key getaway. Just bring your suitcase and start enjoying island life!

1141 W Peppertree Drive Unit 1141, Sarasota

$729,500

2 Beds ⋅ 2 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code

Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gulf of America, with a 5-minute walk down community path. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. One bedroom has a 1 king bed and one with a 1 queen bed, queen sofa bed in living room. Cozy Electric Fireplace, Heated Pool, Area for lounging in the sun, dock area for fishing, Tiki Hut with chairs & charcoal grills. This fabulous property offers a comfortable and inviting space for guests- enclosed lanai and a large private deck overlooking the Bay with a gas grill and outdoor furniture. You'll find all the essentials you need, including 2 yr. old AC, hair dryer, Wi-Fi, an iron, coin laundry, beach chairs, wagon and umbrella, beach towels included in this turn-key sale! Move in and enjoy your new purchase. Laundry hook-ups but there are coin laundry machines on the 1st floor. Pets are not allowed. Minutes from Restaurants, Shopping, Entertainment, Grocery Store and Downtown Siesta Key Village. Public Stop for the Trolly is steps from the Condo Entrance! The views are exceptional of the ICW and bay as this the bayfront unit on the second floor, the only one with the large patio. This unit comes with a one car garage that only a few units are lucky enough to have. This two-bedroom unit has a deluxe bathroom and a half bathroom as well. Nice kitchen with granite tops and island L bar seating. Dinig table next to kitchen for those family dinners to make memories at. There is a community marina to bring your boat and enjoy this true Florida Beach and Bay lifestyle!!

5955 Midnight Pass Road Unit 21E, Sarasota

$1,099,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code

Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi, thermostat keyless entry! Your new condominium will be sold turnkey furnished, nothing to do except move in. Open floor plan great for entertaining. A super beverage cooler has been installed in the kitchen. You will find pull-outs and soft close doors & drawers. Two full sized beds in the guest room, and the main suite has gulf views, double vanities for convenience. Both bathrooms have walk-in showers. This is a split plan as well. What I really want you to see are the community grounds… the condo is fabulous, and this community is spectacular!!! You can search the state of Florida... no other community can compare itself to Gulf & Bay. Plus, END UNIT condos are the best - nothing compares to having an END UNIT. Gulf & Bay has 2 pools, new fitness center just steps away from the elevator plus saunas, tennis & PICKLEBALL courts, basketball, electric car charging stations, clubhouse, indoor hot tub. Another cool item is the complex is mapped out with its own app. Owners can easily navigate in and out of the grounds with your phone. No more fobs. Gulf & Bay is great for rental income. If you want rental income, this condo has it for 2027. Rentals must be a 30-day minimum 12 times a year. I know it just got better, right? Want to head to the village? Just hop on the free trolley out of the gates and head to the village for dinner and shopping. The condo is easy to show. Don’t miss seeing this community and condominium… the search is over... get here before this opportunity is gone! here are the dates booked for this coming season! Feb 1, 2027-Feb 28, 2027 27 nights $8,913.00 Mar 1, 2027-Mar 29, 2027 28 nights $10,052.00 Jan 1, 2027-Jan 31, 2027 30 nights $6,760.10 _____________ $25,725.10 As of 8-10-2026

5770 Midnight Pass Road Unit 301, Sarasota

$8,190,000

5 Beds ⋅ 5 Baths ⋅ Elliot M A Property Siesta Key SubDv. ⋅ 34242 Zip Code

A double waterfront, rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.

4034 Roberts Point Road, Sarasota

$2,799,000

3 Beds ⋅ 3 Baths ⋅ Sub Of Us Lt 7 Of 20-37-18 SubDv. ⋅ 34242 Zip Code

It's All About the View. Some homes are defined by their architecture. Others by their location. This one is defined by what you see the moment you walk through the front door. Tucked away at the end of one of Siesta Key's most private, tree-lined streets, this exceptional bayfront retreat enjoys nearly 180-degree panoramic views across Sarasota Bay, where endless open water, spectacular sunrises, and distant estate homes create a setting that is nothing short of mesmerizing. It is a view that changes by the hour and never gets old. Originally designed by Tollyn Twitchell, son of Sarasota architectural pioneer Ralph Twitchell, this distinctive mid-century residence embraces its architectural heritage with soaring ceilings, expansive walls of glass, and light-filled living spaces designed to celebrate the waterfront. The main residence offers two bedrooms, two baths, plus a spacious office or den, while the detached one-bedroom guest house provides the perfect private retreat for family, friends, or extended stays. With 75 feet of Sarasota Bay frontage, a newly updated dock featuring composite decking and a 13,500-pound boat lift, mornings can begin with coffee overlooking the bay before heading out for a day of boating, fishing, paddleboarding, or simply enjoying the peaceful waterfront surroundings. Tucked behind a natural mangrove shoreline, the property offers both beauty and protection while remaining just minutes from Siesta Beach, Siesta Village, and convenient access on and off the island. Whether you're searching for a peaceful island escape, an architecturally significant waterfront residence, or the perfect site to create a future dream home, opportunities like this rarely become available. Professional photography is coming soon, but the sellers couldn't wait to introduce one of Siesta Key's most captivating bayfront settings.

1275 Port Lane, Sarasota

$1,300,000

2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code

Virtually Staged. Rarely available 5th-floor residence in Siesta Gulf View’s coveted 08 stack. This exceptional beach retreat showcases an extended wrap balcony with unobstructed west and south panoramic views of Siesta Key’s white-sand beaches and glowing Gulf sunsets. Bathed in natural light, the spacious split-bedroom layout offers walk-in closets in both bedrooms, motorized storm shutters, an interior laundry room, and abundant flexibility to create a tailored coastal home—reimagine the breakfast nook as a den or keep the expansive office area. Offered for the first time in nearly 30 years, this is a rare opportunity to personalize a premier view property. Enjoy deeded beach access via the private community boardwalk, along with a pool, tennis, pickleball, fitness room, clubhouse with meeting room and kitchen, and beachside grilling and seating area—all within Siesta Gulf View’s intimate 59-residence setting, just two blocks to famous Siesta Key Village.

420 Beach Road Unit 508, Sarasota

$17,650,000

4 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

3799 Flamingo Avenue, Sarasota

$2,800,000

4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Privately set on Palm Island in the heart of Siesta Key, this residence offers an exceptional combination of generous living space, thoughtful design and effortless access to the island’s most celebrated destinations. Just a short distance from the powdery, white quartz sands of Siesta Beach and the boutiques, dining and lively atmosphere of Siesta Village, this beautifully reimagined waterfront residence presents a rare opportunity to enjoy a relaxed coastal lifestyle without compromising comfort, privacy or quality. Nearly every aspect of the home was transformed, creating a fresh, modern interior, designed for both everyday living and gracious entertaining. Soaring ceilings, abundant natural light, a contemporary custom staircase and impact-rated windows and doors establish an open, airy atmosphere, while luxury vinyl and engineered hardwood flooring, recessed lighting and thoughtfully integrated storage add warmth and architectural interest. The expansive kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, upgraded stainless steel appliances, wine storage and an oversized quartz island with generous seating. Designed to accommodate everything from casual mornings to larger gatherings, the kitchen flows naturally into the surrounding living and dining spaces and continues outdoors to the pool, lawn and waterfront beyond. The main-level primary suite provides a serene private retreat with direct access to the pool area, a spacious custom-fitted closet and a beautifully appointed spa-inspired bathroom. Three additional bedrooms offer comfortable accommodations for family and guests, while an upstairs, separate flex space is ideally suited for a private office, exercise room or personalized retreat. A sunroom and conveniently positioned pool bath further enhance the home’s easy indoor-outdoor connection. Outside, the property reveals one of its most distinctive features: an unusually spacious backyard for Siesta Key. A broad lawn surrounds the heated pool, creating room for outdoor dining, recreation, pets and relaxed afternoons beneath the Florida sun. Beyond the pool, peaceful canal views and a private dock provide a tranquil waterfront setting with boating access. A well supplies the irrigation system, helping maintain the lush tropical landscape. A detached two-car garage offers valuable parking and additional storage for beach equipment, bicycles, paddleboards and other island essentials to enjoy the Siesta Key lifestyle. Morning walks along Siesta Beach, afternoons beside the pool and evenings dining in Siesta Village can all become part of everyday life. Spacious, extensively remodeled, and ideally positioned near the beach, Village and boating water, 430 Island Circle is a sophisticated yet wonderfully comfortable island retreat designed for those who want to experience the very best of Siesta Key.

430 Island Circle, Sarasota

$1,150,000

Roberts Point SubDv. ⋅ 34242 Zip Code

An exceptional opportunity to create a custom waterfront residence in one of North Siesta Key’s most desirable neighborhoods. Surrounded by substantial luxury homes, this property offers a peaceful bayou setting with direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards. The site is enhanced by mature tropical landscaping and tranquil water views, providing an inviting natural backdrop for a thoughtfully designed new home. Multiple outdoor living areas, terraces and elevated gathering spaces could be incorporated to take full advantage of the waterfront setting and relaxed Siesta Key lifestyle. An existing residence currently occupies the property, offering flexibility for use, rental or renovation while future building plans are developed. The home includes a roof completed in August 2023, hurricane shutters and completed storm remediation; however, the property’s compelling value lies in its land, location and potential to build new within a neighborhood known for impressive coastal residences. Conveniently positioned on North Siesta Key, the property provides easy access to Siesta Beach, Siesta Village, downtown Sarasota, shopping, dining and entertainment. Whether envisioned as a full-time residence or private island retreat, this is a rare opportunity to design a home tailored to your lifestyle in an established waterfront community.

4114 Roberts Point Circle, Sarasota

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code

Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive luxury residences. The primary living spaces are positioned on the upper level, where vaulted ceilings and an open layout create a bright, comfortable setting for everyday living and entertaining. Multiple decks extend the living areas outdoors, offering peaceful views of the water and surrounding tropical landscape. A hot tub overlooking the bayou provides a relaxing place to unwind at the end of the day. The legal ground level (non-conforming) adds valuable versatility with a private bedroom and bath, bonus room, screened lanai and two-car garage, well suited for guests, extended family, a home office or a recreational space. A new roof completed in August 2023, hurricane shutters and completed storm remediation provide added peace of mind. The property offers direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards, making it easy to enjoy Siesta Key’s natural surroundings from your own backyard. Ideally located near Siesta Beach, Siesta Village, shopping, dining, and entertainment, and easy access to mainland Sarasota, this is a distinctive opportunity to live, renovate or rebuild in a coveted North Siesta Key setting.

4114 Roberts Point Circle, Sarasota

$2,600,000

4 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code

Stroll to the Village. Walk to the Beach. Cruise to the Gulf of Mexico. Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience, and the quintessential Siesta Key lifestyle are prepared for you to move in ready. A brief stroll from the vibrant energy of Siesta Key Village and the quartz sands of Siesta Beach. With an astounding approximately 240 feet of private seawall and offering long-range canal views creating a lagoon-like setting, this opportunity simply cannot be replicated. While offering crisp, clean lines of modern contemporary style, the infrastructure is strictly 2026-ready. This unique residence provides both luxurious aesthetic appeals, featuring a fully updated chef’s kitchen and designer baths, and "invisible luxury". The peace of mind that comes from the resilience of a durable metal roof, new seawall, and all-new high-velocity hurricane windows and doors, new flooring, wood burning fireplace, and new electrical, plumbing, as well as new three-zone HVAC and mechanical systems, has been thoughtfully provided. And, for your peace of mind, professional night vision high-tech security cameras and systems were installed in 2026. The preferred split plan offers three additional bedrooms, including a private guest suite with its own separate entrance and ensuite bath. Life at 339 Treasure Boat Way centers around the water. Venture out onto the paved, open-air pool deck to find a 2026 freshly re-finished Aqualink-controlled, saltwater, heated pool and spa with LED lighting. Enjoy gentle, golden morning sun and cool, shaded afternoons—perfect for entertaining and alfresco dining. An oversized detached two-car air-conditioned garage, fenced yard for pets, and ample guest parking.

339 Treasure Boat Way, Sarasota

$549,000

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Experience the best of Siesta Key living in this beautifully updated 2 bedroom, 2 bath 3rd floor condo in Sunrise Cove, offered turnkey furnished and ready for you to move in and start enjoying island life immediately. Enjoy next level comfort with a brand-new 2026 A/C system and an LED whole home in duct air purifier cool, refreshing comfort and cleaner, fresher indoor air all year long. Take in stunning back bay views from your home and enjoy an unbeatable location directly across from Turtle Beach and Park, with boat, kayak, and canoe launches, a playground, and a convenient trolley stop. Sunrise Cove delivers an exceptional amenity lineup, including two community pools, a fitness center, tennis and pickleball courts, kayak and bike storage, bayside BBQ grills, and picnic areas overlooking the water. Boat slips are available for rent with water and electric hookups, and the community includes full-time onsite facility and maintenance managers for added peace of mind. Step outside to Turtles Pub & Café, Turtles Restaurant, and a nearby marina right next door. Plus, you’re moments away from world famous Siesta Key Beach, known for its powdery quartz sand, sparkling water, and unforgettable sunsets.

9011 Midnight Pass Road Unit 329, Sarasota

$4,000,000

2 Beds ⋅ 3 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code

Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create an extraordinary 2,365-SF home. Completely reimagined by award-winning architect Michael Halflants of Halflants + Pichette Studio for Modern Architecture, the residence received the prestigious AIA Florida/Caribbean Honor Award of Excellence in Interior Design and was featured in Sarasota Magazine's Dream Homes issue. Original interior walls were removed to reveal uninterrupted vistas that extend along the shoreline of Siesta Key, across Sarasota Bay, and to the downtown Sarasota skyline. The result is a flowing two-bedroom, two-and-a-half-bath residence where panoramic views, exceptional materials, and thoughtful design exist in perfect balance. At the center of the home, a sculptural Etimoe hardwood core houses the kitchen, storage, primary bath, and an expansive walk-in closet, bringing warmth and architectural definition to the open floor plan. Floor-to-ceiling, seven-panel bi-fold glass doors disappear completely at the corners, creating a seamless connection to the Gulf and inviting coastal breezes into the living spaces. Custom folding partitions provide privacy between the primary suite and main living areas without compromising the home's openness or visual continuity. Thoughtful custom details continue throughout the residence, including a custom steel desk overlooking the Gulf of Mexico, creating a work-from-home setting few could rival. The raw concrete ceiling from Smith's original 1969 design was scraped and clear-coated to a soft sheen, transforming a defining element of the building into a striking contemporary feature. Large-format porcelain tile, custom steel detailing, and carefully selected wood finishes complete a sophisticated material palette that feels both timeless and contemporary. Residents of The Terrace enjoy private access to Siesta Key's renowned beach and are just moments from the shops, restaurants, and energy of Siesta Village. More than a luxury beachfront residence, this is a rare opportunity to own an award-winning home within one of Sarasota's most recognizable waterfront landmarks, where exceptional architecture and Gulf-front living are seamlessly intertwined.

5400 Ocean Boulevard Unit 15 1-4, Sarasota

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