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$2,450,000
4 Beds ⋅ 4 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Repriced $250,000! A rare opportunity to reimagine a Gulf-front penthouse on Siesta Key. Set in a boutique condominium community near Siesta Village, this expansive four-bedroom, four-bath residence offers over 3,900 air-conditioned square feet, full Gulf views and the kind of scale, frontage and location that are seldom available. With nearly 80 feet of linear Gulf frontage, the penthouse captures sweeping vistas of the azure Gulf waters, Big Pass, Lido Key and downtown Sarasota from nearly every room. The floor plan is exceptionally spacious, with grand living areas, high ceilings, a fireplace, two balconies, an attached two-car garage and the rare flexibility that comes with a residence of this size and presence. The two-building, 22-unit complex features a pool overlooking the Gulf, offering a relaxed setting to enjoy the waterfront lifestyle. This residence presents a unique canvas for a complete custom renovation. A new owner can transform this property into a spectacular coastal showplace, tailored to today’s luxury lifestyle. The existing floor plan includes generous entertaining spaces, a large kitchen footprint, two primary-suite areas, one with a private sauna, all ready to be reinterpreted with a fresh vision and design. Just moments from Siesta Village, with its restaurants, boutiques, boating and waterfront activities, this residence also enjoys proximity to Siesta Key’s world-famous white quartz sand beach. It is an extraordinary chance to create a one-of-a-kind Gulf-front penthouse in one of the island’s desirable locations. Beyond the island, vibrant downtown Sarasota’s cultural, shopping, dining and entertainment areas are just minutes away.

4712 Ocean Boulevard Unit W10, Sarasota
$670,000
2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
Perfect Beach Life on Siesta Key! Tortuga Beach has so much to offer. Private 77 unit complex has the small intimate feel with a luxury with it's many offerings. Private Beachfront, Tennis & Pickleball across the street, Clubhouse with kitchen, library and entertainment area, indoor/outdoor community pool, sauna, sun deck with grills and seating, and boat slips across the street on the bay. There are 3 slips open for rental for $300 a year. Just fill out your application. With the friendly residents you can enjoy the relaxing atmosphere with the wonderful views of the Gulf of Mexico from daytime sunbathing to sunset pleasures. Upon arrival to the condo you will find an enclosed lanai to offer more living space in the 1650 Square feet. Kitchen has plenty of space with it's wood cabinets and granite countertops with pass through breakfast bar. New AC. Split Floor plan. Primary bedroom closet contains the washer dryer but Tortuga also offers a laundry facility if you are in need. Separate dining room just off the kitchen for entertainment. Covered Parking spot very close to the entrance and elevator for easy loading and unloading.

8710 Midnight Pass Road Unit 203B, Sarasota
$29,995,000
7 Beds ⋅ 11 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Under Construction. Under Construction. Welcome to 3990 Higel Avenue, set to be completed in August of 2026 and can be offered fully furnished. Where architectural brilliance meets unrivaled luxury on Sarasota’s exclusive Gulf-front shores. 3990 Higel is 1 of 1. Having direct ocean frontage, while having the ability to have your own private bock/lift. This 13,035 square-foot masterpiece is designed by the acclaimed DSDG Architects, built by Nutter Construction, and interior designed by Angela Rodriguez Interiors. This home sits gracefully on one acre of prime Gulf-front property, delivering an unparalleled coastal living experience. As you arrive, a grand private driveway lined with lush tropical landscaping and a stately entrance sets the tone for this extraordinary estate. The main residence features 5 spacious ensuite bedrooms, meticulously designed with ultra-luxurious finishes, custom millwork, and designer lighting throughout The interiors blend modern sophistication with timeless elegance, offering soaring ceilings, expansive walls of glass, and seamless transitions between indoor and outdoor spaces. The great room, bathed in natural light, showcases floor-to-ceiling windows that frame breathtaking views of the turquoise Gulf waters. A reflecting pool with fountain features mirrors the beauty of the estate’s serene surroundings, while retractable glass walls blur the lines between indoor comfort and outdoor splendor. The gourmet kitchen is a culinary dream, outfitted with custom cabinetry, designer hardware, and state-of-the-art appliances, including an oversized island ideal for both entertaining and everyday living. The primary suite is a sanctuary unto itself, complete with private sitting areas, a balcony with mesmerizing Gulf views, and a spa-inspired ensuite bath adorned with exquisite finishes, soaking tub, and oversized shower. Each additional bedroom offers equally luxurious accommodations, ensuring guests experience unrivaled comfort and style. Outdoor living rivals a world-class resort with multiple terraces, a sparkling infinity-edge pool, and expansive lounging areas surrounded by lush gardens. A firepit area and thoughtfully designed hardscaping invite al fresco dining and relaxation under the stars. For boating enthusiasts, a private deeded 20,000 lb boat lift provides direct access to the Gulf, seamlessly connecting the estate to Sarasota’s waters. Adding to the grandeur is a detached 2-bedroom guest house, complete with its own living space, ensuring the utmost privacy and convenience for family and friends. Designed for entertaining, the home also includes a dedicated party room and an elegant wine room to showcase your finest collection. Every detail has been carefully considered – from the structural integrity and elevation designed for storms to the cutting-edge smart home systems and incredible engineering. This estate represents the pinnacle of craftsmanship and design, set in one of Sarasota’s most coveted waterfront locations. 3990 Higel Avenue is more than just a home; it is a timeless retreat where luxury, tranquility, and Gulf-front beauty converge to create an extraordinary living experience.

3990 Higel Avenue, Sarasota
$745,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Location, location & views! Enjoy and experience luxury living at the Harbor Towers located just steps away from the world-famous Siesta Key beach. Highly desirable 4th floor unit, 2BR/2BTH with spectacular Gulf of America views from every room. Fully updated unit with new windows, new pipes, quartz countertops, new kitchen cabinets doors, new bathrooms and luxury vinyl flooring throughout. This turnkey furnished condo features an open floor plan, two suites split plan bedrooms and provides one parking space & additional storage room. New electrical panel and new water heater. Delight yourself at the HT amenities including heated resort style pools, 3 Har-Tru tennis courts, fitness center, sauna, clubhouse and a superb Marina & seating along the intercoastal waterway. HT has newly renovated building facade, common area including the lobby, spa area and hallways. A fantastic investment opportunity to own a rental income while enjoying the unit whenever you wish. Two-week minimum rentals are allowed 26 times/ year. Buyer can use the on-site property management company for rentals, or others.

5855 Midnight Pass Road Unit 420, Sarasota
$4,490,000
3 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living in this award-winning “Marlin Model” by Nutter Custom Construction, perfectly positioned on Siesta Key’s coveted Grand Canal. Completed in 2023 and showcased as the builder’s signature home, this completely custom Yacht-Modern residence blends refined elegance, contemporary design, and exceptional waterfront functionality. With 4,294 sq. ft. under air and 6,405 total sq. ft., this home offers 3 ensuite bedrooms (please note gym can be converted into 4th bedroom), 3 full baths, 2 half baths—including a dedicated pool bath—plus multiple flexible indoor and outdoor living spaces ideal for relaxed luxury and entertaining. Floor-to-ceiling glass doors reveal sweeping water views and seamless indoor-outdoor flow. Elevated construction and smart-home technology offer modern security and peace of mind. No water intrusion or damage during recent hurricanes. The chef’s kitchen is a standout, featuring a 10-ft waterfall island, European white dolomite counters, hidden walk-in pantry, Wolf appliances, built-in coffee system, under-cabinet toe lighting, and formal dining with wine cooler and ice maker. The primary suite is a private retreat with dual walk-in closets, hidden entry doors, freestanding soaking tub, oversized designer shower and steam room, and private outdoor shower garden. Outside, enjoy resort-style living with a multi-level pool and raised spa with infinity spillover, expansive lounging deck, covered living and dining with motorized screens, full outdoor kitchen, turf backyard with putting green, and multiple terraces. For boating enthusiasts, the property offers 104 ft of waterfront, a new concrete seawall, 104 ft of composite dock, two Golden Gear boat lifts with remotes (20,000lb & 5,000lb), water and shore power. Hop on your boat and be in the Gulf in less than 15 minutes. This property has received prestigious recognition, earning Best Custom Home, Best Kitchen, and Best Staircase in the Parade of Homes awards — reflecting exceptional craftsmanship and design distinction. The oversized 2.5-car garage provides excellent storage and functionality, offering space for a golf cart or the option to create a golf simulator setup. Located in Siesta Isles with a voluntary HOA, less than one mile to Siesta Key Beach and moments to Siesta Village by golf cart or bike. Click on the Virtual Tour Link to get a behind the scenes look! ** Furniture negotiable

5362 Shadow Lawn Drive, Sarasota
$2,210,000
4 Beds ⋅ 5 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code
You will absolutely fall in love with this carefully curated masterpiece on Siesta Key! Nestled in the coveted Siesta Cove neighborhood, this stunning, fully renovated home offers a rare blend of old Florida charm and modern luxury. Situated just half a mile from Siesta Beach, this exceptional residence rests on nearly half an acre, adorned with majestic live oak trees, creating a serene and private atmosphere. Gorgeous IPE decking surrounds the home, seamlessly uniting the indoors with the outdoors and infusing every space with a warm, tropical feel. Dine alfresco or lounge by the pool, shaded by retractable sunshades for ultimate comfort. An impressive array of windows gives the sensation of living among lush, mature foliage—your very own luxury treehouse. Plus, enjoy peace of mind with a brand-new roof installed in 2023! In addition to the 3,899 square feet of living space, stay active in your private 1,200 sq. ft. gym, located on the bottom, non-conforming level of the home. Take a refreshing swim in the extra-large pool, then unwind in your brand-new sauna for the ultimate relaxation experience. Retreat to the serene, spa-like marble master bathroom—a true sanctuary for rest and rejuvenation. Finally, gather in the spectacular chef’s kitchen to create memorable meals using top-of-the-line Wolf and Sub-Zero appliances. This multi-level, multidimensional home offers abundant space for grand-scale entertaining while still providing intimate, cozy retreats for quiet moments. Make sure to click on the video tour to get a better look at this fabulous home! Please see attached feature sheet for an extensive list of improvements.

5235 Siesta Cove Drive, Sarasota
$1,650,000
6 Beds ⋅ 6 Baths ⋅ Siesta Estates SubDv. ⋅ 34242 Zip Code
This luxurious John Cannon built home is in a small gated community that is just a short walk to the world famous Siesta Key beach. Enjoy privacy and security at the end of a Cul-de-sac in this well maintained 6 bedroom, 5 ½ bath home, and is being offered Turn-Key furnished. It's the perfect home for Vacationing with Family and Friends. Features include a beautiful Kitchen with granite counter tops and high end solid wood cabinets, 20’ tray Ceilings, state of the art security system, natural gas heated pool and hot-tub, gas fireplace, three A/C zones, Pool bath, and lots of beautiful artwork. The master Bedroom is on the first floor with large sliders leading to the pool deck and the stunning master bath includes double sinks, a soaking tub, and a separate shower with built-in sauna. There is a second Master bedroom suite on the first floor that is currently being used as an office, but has a it’s own bath and walk-in closet. On the second floor there are 5 large bedrooms and 3 full baths, one bedroom is being used as a billiards room. A new tile roof was just installed in 2024. Lawn maintenance is included in the HOA fee. Everything in the home (except a few personal items) can be included in the sales price. Call for a showing today, you will be impressed. The house and garage has never been flooded.

5598 Siesta Estates Court, Sarasota
$820,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Breathtaking Sunsets and Gorgeous Views: Fully Renovated Beach Condo on Siesta Key. Are you searching for a luxurious beach condo with stunning Gulf views and deeded beach access? Look no further than this newly available 2 bedroom/2 bathroom unit that has been completely updated with lavish finishes throughout. Step inside and get ready to be captivated by the mesmerizing views that await you. Enjoy your coffee, wine or simply relax on the spacious lanai which offers a comfortable space to soak in the gulf breezes while admiring the gorgeous landscape. This light-filled unit features a remodeled kitchen, including soft-close cabinets/drawers, stainless steel appliances, porcelain plank tile throughout, crown molding, and beautiful bathrooms. With ample storage space, in-unit laundry, new impact windows/sliding doors (2013) and A/C (2014), you can enjoy the gulf breezes or stay cool in the heat of summer. Peppertree Bay is a true Beach to Bay complex that spans 16 acres with private deeded beach access, a fishing pier, 2 heated pools, 2 clubhouses, fitness center, saunas, tennis/pickleball courts, and BBQ areas. Conveniently located near Siesta Key Village, you can easily access trolleys or frog hopper transportation, shopping, dining, and entertainment. Downtown Sarasota and the arts are just a short drive away. Contact us today to schedule a showing and experience the luxury of beachside living on Siesta Key.

1200 E Peppertree Lane Unit 407, Sarasota
$1,769,000
4 Beds ⋅ 4 Baths ⋅ Paradise Island SubDv. ⋅ 34242 Zip Code
Step into your very own haven, nestled at the peaceful end of a Siesta Key street. This exceptional property embodies the coastal lifestyle, complete with a pool, dock, and boat lift. Just moments away, Siesta Key Village unfolds with its charming boutiques and great dining spots, inviting you to explore and indulge. This three-story residence is wonderful for entertainment, boasting an expansive great room that seamlessly merges with sliding doors onto a sprawling deck, providing captivating views of the serene canal. Upstairs, three bedrooms and three baths offer a sanctuary of comfort. On the lower level, discover a separate bonus living area with its own full bath, perfect for an in-law suite or a delightful poolside bar retreat, accompanied by a full sauna for ultimate relaxation. For boating enthusiasts, the convenience of just one bridge to the open bay is a cherished feature. Your own private paradise is here, inviting you to make it your own.

365 Avenida De Paradisio, Sarasota
$14,500,000
6 Beds ⋅ 8 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
Imagine your very own resort-like estate in the heart of the most sought after community in all of Sarasota!  Sanderling Club is nestled on the south end of the world renown barrier island of Siesta Key.  This ultimate beachfront experience is the true definition of living in paradise.  This property offers the most exquisite home on almost 4.5 acres with over 300 feet of beachfront.  The primary residence with over 8,600 square feet of living space is ideally positioned, capturing the amber skyline and emerald green waterways of the Gulf of Mexico from every angle.  The interior design of this magnificent home is perfect for entertaining with the main living areas and spacious dining room facing the west to enjoy Southwest Florida sunsets every evening.   The custom kitchen features Rutt cabinetry, a large island with plenty of seating, Wolf and Sub-Zero appliances, gorgeous marble countertops accented by brushed gold hardware creating an elegant experience in the heart of the home. The family room creates a warm inviting feeling as soon as you enter the space.  The attention to detail throughout including custom moulding, built in shelving, views of mature tropical foliage, and the sparkling pool create such an incredible ambiance and place to create many fond experiences with family and friends.  The home office, only accessed through a secret hidden door, makes working from home a pleasure.  This property is meticulously well maintained with many recent updates to the main house including: brand new roof installed in 2023, new custom kitchen, beautifully renovated bathrooms, new engineered walnut flooring throughout, elegant marble flooring, custom wood millwork, a butler’s kitchen, LED lighting throughout, newer HVAC systems and ductwork, elevator, exterior patio railings, gated entry, Smart Home Wi-Fi enabled automation, and brand new hurricane impact window and doors installed in 2023.  The private owner's suite is on one level featuring a spa-like bathroom with tranquil water views.  The suite offers a private waterfront terrace and dual custom closets. The two guest suites also offer breathtaking views.  The lower level features another full service kitchen, an additional guest space or gym, two full bathrooms, a steam room, a sauna, an expansive garage, and additional storage room.  The second kitchen is easily accessible to the salt water pool and spa, a lighted tiki hut, outdoor fire pit, tennis courts, and a new paved drive space.  The guest house with over 2,300 square feet of living space was built in 2007 and is a kayaker's dream located on Heron Lagoon with 316 ft of waterfront .  With an open great room plan and high ceilings your guests will feel like they are in a tropical oasis. The guest house has a full kitchen, 2 en-suite, bedrooms, a large screened in terrace, and a large deck leading out to the boat dock.  The dock is ideal for launching your kayak or canoe.  Relax and simply sit on the dock and enjoy the sounds of birds chirping and the sound of palm trees swaying in the wind.  This estate is within the guarded & gated community of Sanderling Club. The community offers amenities such as:  a beach club, tennis and pickleball courts, Paul Rudolph-designed beach cabanas, playground, and dockage on the bay.

8218 Sanderling Road, Sarasota