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$1,075,000
4 Beds 2 Baths Siestas Bayside Waterside SubDv. 34242 Zip Code
Under the canopy of grand oaks and banyan trees, this move-in-ready FURNISHED Siesta Key POOL home offers the perfect blend of luxury and coastal charm. Located minutes from the world-famous beach and village, this retreat has been redesigned for island living with almost every inch of the home renovated to perfection! A freshly painted exterior, paver driveway, and xeriscape landscaping create a warm welcome. Inside, an open floor plan creates effortless indoor-outdoor living with tile flooring, bright living area, and pocket sliding glass doors seamlessly connecting to your private backyard oasis. The expansive paradise features a sparkling pool and hot tub with new pump/heater, surrounded by new privacy fencing, and an extended paver patio. The heart of the home is the renovated chef's kitchen, boasting duo-toned soft-close cabinetry, quartz countertops, and tile backsplash. The oversized kitchen island and adjacent dining area set the stage for lively gatherings, while the cozy den opens up to the patio for effortless pool-side alfresco dining. The primary suite features direct pool access and a newly updated bathroom with soaking tub, walk-in shower, and modern finishes. Thoughtfully designed for privacy, the split floor plan includes a poolside guest room along with two additional bedrooms tucked in a private wing with an updated bathroom. Additional updates include a NEW AC system/ductwork and NEW Hot Water Heater ensuring year-round comfort. The oversized two car garage offers plenty of parking and extra space for a golf cart and beach gear. Enjoy the tranquility of the tree lined streets while still having easy access on and off the island. This home is being enjoyed by seasonal renters, but now it’s your turn to enjoy island life! Whether you're looking for a lucrative FURNISHED short-term rental, a seasonal retreat, or a forever home, this renovated Siesta Key gem offers the best of island living!

567 Venice Lane, 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

$1,150,000
2 Beds 2 Baths Casarina SubDv. 34242 Zip Code
The least expensive unit in the sought-after Casarina on Siesta Key with another price reduction of $50,000! This Top-floor unit offers stunning views of Siesta Beach and all the comforts of home. The interior has been tastefully updated with modern finishes and stylish decor. The unit is being sold furnished (minus few staging items). The kitchen has newer cabinets and upgraded appliances. Enjoy the spaciousness of the living/dining combination area and be drawn to the expansiveness of the enclosed patio where you can enjoy evening sunsets. The 17-by-12-foot primary bedroom has luxury vinyl flooring and room for a small desk area. The primary bath has new vanities, mirrors and lighting. Casarina has seven acres of newly planted tropical landscaping and 200 feet of private beach. The main lobby has recently been updated. Spend your days swimming in the heated pool, soaking in the spa, playing tennis, pickleball, basketball or simply enjoying the quiet beauty of the #1 Siesta Key Beach. With covered parking, a secure lobby and an on-site manager, everything you need is right here. Enjoy being close to the shops and restaurants of Siesta Village and only minutes from downtown Sarasota’s arts, dining and world-class healthcare. This is your chance to own and live in beautiful Sarasota. Owner has paid all the present assessments for the new upgrades to the property and building.

5880 Midnight Pass Road Unit 906, Sarasota

$2,200,000
4 Beds 5 Baths Coronas Park SubDv. 34242 Zip Code
Welcome to La Linda Siesta Key Estates, an exclusive gated enclave that defines the pinnacle of coastal luxury living. Just one block from the sparkling waters of Siesta Key, this custom-built, three-story masterpiece spans 3,796 square feet and offers 4 bedrooms, 4.5 baths, a private elevator, and a spacious 4-car garage, a rare feature on the island. Designed with both elegance and endurance in mind, this home is constructed with solid concrete block, impact-rated windows and doors, and superior structural integrity to withstand even the wildest forces of Mother Nature. Despite recent storms in the area, this residence remained completely unaffected, a true testament to its exceptional build quality and engineering. Inside, every inch of the home showcases high-end custom craftsmanship, from exquisite flooring and designer lighting to handcrafted cabinetry and architectural detailing that exude sophistication. The gourmet kitchen is a show-stopping centerpiece, featuring premium appliances, quartz countertops, and a large island perfect for entertaining. The open-concept living spaces flow effortlessly onto multiple balconies and outdoor areas, blurring the line between interior comfort and the beauty of the Florida coast. Each bedroom offers its own private en-suite bath, while the primary suite boasts a spa-inspired bathroom, expansive walk-in closets, and a private terrace ideal for morning coffee or evening sunsets. Step outside to your personal resort-style paradise, complete with a heated pool and spa, custom tiki bar, and private putting green, all surrounded by lush tropical landscaping designed for both privacy and pleasure. Perfectly positioned near Ocean Boulevard and the Village of Siesta Key, you’ll enjoy easy access to boutique shopping, award-winning restaurants, and the world-famous Siesta Key Beach. Whether it’s a serene morning walk along the shoreline, a day spent boating on the Gulf, or an evening out in downtown Sarasota, this home embodies the ultimate coastal lifestyle-luxurious, resilient, and truly unforgettable.

6925 Bochi Circle, Sarasota

$1,150,000
3 Beds 3 Baths Sarasota Beach SubDv. 34242 Zip Code
Under contract-accepting backup offers. Exceptional opportunity on TWO buildable lots just 15 houses from Siesta Key Beach and a leisurely stroll from the village. The existing midcentury durable concrete block 3br/2ba home features pecky cypress siding and beamed ceilings. There is an additional free standing guest cottage. The home was impacted by last years storms, but has been stripped to the studs and is waiting for someone to put their finishing touches on it. Tremendous potential awaits. Restore and renew the existing structure or tear down and build your own tropical dream home. Investors may want to take advantage of the 2 lot configuration to develop TWO stunning residences. Plans and competitive pricing for new construction are available. Whether you delight in renovating this iconic midcentury gem, start fresh with a custom built masterpiece, or take advantage of the terrific investment opportunity of TWO buildable lots, this is a terrific opportunity to realize your dream in this desirable coastal paradise.

5453 Avenida Del Mare, Sarasota

$1,125,000
4 Beds 4 Baths Twin Oak Pond SubDv. 34242 Zip Code
Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here

5244 Winding Way, Sarasota

$1,266,700
3 Beds 2 Baths Paradise Island SubDv. 34242 Zip Code
It looks new, because it is new! Nearly every surface touched in this fresh remodel, you'll be the first to spend a night in it since completion. The roof, the AC, the plumbing lines, pool surface and pool equipment, all new. Owned by the same family for decades, and taken care of extremely well. Pocket sliders, a good-sized pool with covered area, and pavered patio. Windows newish as well, only couple years old. The home sits on a 1/3 acre lot, on Grand Canal, and walking distance to the Village and beach. It’s the perfect affordable blend of everything Siesta Key. The home next door is available as well, should you want to combine lots or create your own family compound. Dock quotes available upon request.

307 Avenida De Paradisio, Sarasota

$895,000
3 Beds 2 Baths Siestas Bayside SubDv. 34242 Zip Code
Discover luxurious coastal living on tropical Siesta Key, #1 beach in the US and #4 in the world! Set on an elevated lot that sustained NO storm damage, includes a NEW TAMKO hurricane proof ROOF with transferable workmanship warranty, new gutters, oversized side-entry 2-car garage, and circular driveway surrounded by lush tropical landscaping. Currently being used as an income producing home earning $58,800 annually! You are going to fall in love this beautifully updated 3-bedroom, 2-bath single-level residence offering nearly 2,300 sq. ft. of refined comfort. Perfectly situated just minutes from the world-famous powder-white sands and vibrant and eclectic Siesta Village, this home captures the essence of island elegance. The open-concept great room floor plan showcases soaring ceilings and a wall of sliding glass doors that seamlessly blend indoor and outdoor living, opening to a sparkling pool that consists of a brand new water heater, new pool water pump and fence as well as an expansive deck overlooking a serene lagoon—the ideal backdrop for entertaining or quiet relaxation. The gourmet kitchen features granite countertops, stainless steel appliances, and white soft-close cabinetry and oversized center island/bar, while the spacious primary suite offers a travertine-appointed bath, dual vanities, and a large walk-in closet. Experience the ultimate in coastal sophistication and island tranquility—all within moments of Sarasota’s finest beaches, dining, and culture.

635 Tropical Circle, Sarasota

$5,600,000
4 Beds 4 Baths Cocoanut Bayou SubDv. 34242 Zip Code
This award-winning Modernist home was designed to provide privacy while maintaining direct tranquil water views framed by mature tropical landscaping. In the desired and private lot enclave of Cedar Park, one approaches the residence via a canopied private lane before entering the ideal spot for boaters, car enthusiasts, or those who just enjoy the serenity of the .6-acre grounds with plus/minus 350 feet of frontage on Cocoanut Bayou. The car enthusiast will appreciate the twin garages accommodating five cars, while boaters will be impressed by the water depth of plus/minus 4 feet, substantial IPE wood dock with 10,000-pound and 7,000-pound lifts, and immediate access to the Bay and Gulf. Designed with practicality and easy living in mind, the light-filled rooms feature high ceilings, wall-to-wall stacking glass doors, a chef’s kitchen with Miele appliances and Italian cabinetry, elevator, a generator, and an open concept plan that incorporates nearly 900 sq ft of non-conforming space in the most ingenious fashion, and transitions seamlessly between indoor and outdoor living spaces. Enjoy outdoor dining and relaxing on the expansive covered terrace, lounge by the private 40-foot saltwater pool with spa or just drink in the tranquility offered by this special property. The split plan with four bedrooms (one makes an ideal office) and 3½ baths allows for flexibility of use and manageable size. Private, gated beach access is available. This is the ideal home base to enjoy island lifestyle and for you and yours to take advantage of all Sarasota and Siesta offer. Set out by land or sea to enjoy the world-renowned sugar sand beaches, downtown cultural venues, museums, multiple restaurants and shopping. An exceptional opportunity for the discerning.

251 Cedar Park Circle, Sarasota

$3,542,717
4 Beds 6 Baths Siesta Rev SubDv. 34242 Zip Code
Motivated sellers! In fact, they are moving right next door! The sellers are nearing completion of their new home, which was deliberately designed and positioned to preserve the breathtaking Gulf views of this beachfront retreat. Feel the captivating energy of this home from the moment you enter the private gate to the meticulously landscaped grounds, including an award-winning heated saltwater pool with spa jets, a sun shelf, and custom-designed waterfall. Mornings begin with a soft breeze from the Gulf as you take in the magical sunrise from your 4th-floor deck. Retreat at the day’s end to your 3rd-floor lanai to relieve all the day's stresses. You have a front row seat nightly for nature’s most spectacular show. North Shell Road is the ultimate destination to witness Siesta Key’s most enchanting sunsets, where the sky ignites in hues of gold and crimson over Lido Key. The Gulf’s shimmering waters stretch endlessly before you, bathed in the warm glow of dusk, transforming your private retreat into a masterpiece of light and color. The panoramic views from this prestigious North Siesta Key home are simply magnificent. This home charms with its bold contemporary lines and warm, seamless connection to its pristine surroundings. The sophisticated design blends easily with the warmth and energy of the natural light that flows throughout. Quartz, concrete, soapstone, and live-edge designs blend with soft bamboo floors. This one-of-a-kind sanctuary boasts every upgrade you can imagine. 3916 North Shell Road is where ultimate luxury intersects with coastal splendor. ***Private showings for discerning buyers are available by appointment. Sellers respectfully request that potential buyers wear the shoe booties provided for showings.

3916 N Shell Road, Sarasota

$1,000,000
2 Beds 2 Baths Siesta Rev SubDv. 34242 Zip Code
Tucked away on the quiet, residential north side of Siesta Key, this once-charming 2-bedroom pool home is ready for its next chapter. The property was impacted by last summer’s hurricanes, but the good news is: the metal roof held strong and didn’t leak. With solid bones, a private pool, and a cute backyard that still hints at the home’s former charm, this is a golden opportunity for someone with vision to bring it back to life. The location alone makes this one special, just minutes to the beach, village shops, and dining, yet surrounded by peaceful island neighborhoods. Whether you’re looking to restore it as your island getaway, rebuild for modern coastal living, or invest in a premium piece of Siesta Key real estate, this property is full of potential and promise. Come see what’s possible in one of the most desirable corners of Sarasota’s barrier islands.

226 Ogden Street, Sarasota

$762,000
3 Beds 3 Baths Siesta Bayside SubDv. 34242 Zip Code
POOL HOME!! Priced To Sell!! Nestled on the peaceful tranquil island of Siesta Key, renowned for its world-class beach and romantic sunsets. JUST MINUTES FROM Siesta Beach & Village. This is the most wonderful place to embrace island-style living. This north island location on a quiet canopy street is walkable to the village, beach, and renowned Out-of-Door Academy. This 3 Bedroom and 2 & 1/2 Bathroom home is ready for your personal touches. Enjoy relaxing in your Caged Pool & Patio area. This Single family home has approximately 1834 sq.ft. +/- living area and a 2 car garage. The existing home—professionally remediated after flood damage—presents a unique opportunity for those looking to reimagine or completely rebuild. Almost 13,000 sq.ft lot with luscious natural landscaping and mature oaks. Updated roof in late 2019.

4894 Oxford Drive, Sarasota

$59,000
3 Beds 3 Baths Siesta Key Beach Residences SubDv. 34242 Zip Code
Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the full-time cost or commitment. This expansive and elegantly appointed residence features a primary suite, junior suite, and a guest bedroom, providing plenty of space for family and guests. The entire property has recently undergone a full furniture and furnishings update, giving every residence a fresh, modern coastal look—with no special assessment passed along to owners. Each residence features custom furnishings valued at over $150,000, a chef’s kitchen with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, and imported linens throughout. As an owner, you’ll enjoy the legendary Hyatt Vacation Club experience, including full-service concierge and recreation staff, valet parking, 24-hour security, housekeeping services, and assistance with local activities. Ownership also includes access to the exclusive Cabana Club, which provides beach access 365 days a year, subject to availability. All the resort-style services, amenities, and comforts of a world-class beachfront property—at just a fraction of the cost.

915 Seaside Drive Unit 607, Weeks 14-15, Sarasota

$59,000
3 Beds 3 Baths Siesta Key Beach Residences SubDv. 34242 Zip Code
Fractional Ownership. Winter Fractional Package – 1/16th Share of Ownership-Your dream of owning a luxury home on Siesta Key Beach can now be a reality! Experience an enviable lifestyle on America’s #1 rated beach through this exclusive Winter Fractional Ownership Package at The Residences on Siesta Key Beach, Hyatt Vacation Club. Enjoy all the benefits of luxury beachfront living without the full-time cost or commitment. This expansive and elegantly appointed residence features a primary suite, junior suite, and a guest bedroom, providing plenty of space for family and guests. The entire property has recently undergone a full furniture and furnishings update, giving every residence a fresh, modern coastal look—with no special assessment passed along to owners. Each residence features custom furnishings valued at over $150,000, a chef’s kitchen with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, and imported linens throughout. As an owner, you’ll enjoy the legendary Hyatt Vacation Club experience, including full-service concierge and recreation staff, valet parking, 24-hour security, housekeeping services, and assistance with local activities. Ownership also includes access to the exclusive Cabana Club, which provides beach access 365 days a year, subject to availability. All the resort-style services, amenities, and comforts of a world-class beachfront property—at just a fraction of the cost.

915 Seaside Drive Unit 606, Weeks 12-13, Sarasota

$1,230,000
4 Beds 4 Baths Sarasota Beach SubDv. 34242 Zip Code
Tucked away on Palm Island, one of Siesta Key’s most exclusive neighborhoods, this stunning Spanish-inspired home is more than a place to live, it’s a way of life. Just a short stroll from the sugar-white sands of Siesta Key Beach and the boutiques and cafés of the Village, every day feels like a vacation. Step inside and you’re instantly transported. Arched windows frame the open courtyard, hand-painted tiles tell a story, and sunlight dances across terracotta and hardwood floors. The airy living spaces flow effortlessly, with exposed beams, a handcrafted fireplace mantle, and a warmth that only a true Mediterranean home can offer. Recent updates including a new roof, new appliances, new water heater, newer AC, and impact-rated windows and doors bring modern peace of mind while maintaining timeless style. Whether you’re hosting friends under the glow of the courtyard lights, retreating to the private mother-in-law suite, or walking to the beach for sunset, this home embodies Siesta Key living at its finest!

5354 Calle Florida, Sarasota

$3,845,000
3 Beds 4 Baths Bay Island SubDv. 34242 Zip Code
Look no further. Welcome home to your coastal Siesta Key waterfront retreat, a boater’s dream come true. On the desired north end of Siesta Key, this four-bedroom, four-bath residence spans 4,622 square feet of meticulously designed living space. Elevated above flood plain, the residence blends architectural craftsmanship with a premier waterfront lifestyle. Directly on the Intracoastal Waterway with no fixed bridges, the property offers swift access to Big Pass and open Gulf waters. The dock presents panoramic bay views and a new 95-foot seawall with a 40-foot slip equipped with power, water and solar lit pilings, ideal for boating or serene sunrise and sunset viewing. The outdoor experience is elevated by a heated saltwater pool and spa, complete with smart controls, waterfall features and porcelain shellstone decking. Inside, a gourmet kitchen centers the home, featuring a Sub-Zero refrigerator, six-burner Dacor gas range with stainless vent hood, Advantium microwave-convection oven, wine refrigerator, wet bar, soft-close cabinetry with glass uppers, decorator granite surfaces, expansive island and illuminated custom cabinetry. The open-concept family room showcases a cathedral ceiling with sweeping bay vistas, creating a striking indoor-outdoor connection. The expansive primary suite features a private waterfront balcony, new carpet, custom walk-in closet and a spa-style en-suite with a deep soaking tub, frameless rain shower, and dual vanities. Two guest bedrooms are on the first floor, including a rear en-suite with a private entrance that also serves as a dedicated pool bath. A bonus room used as a game and fitness space offers flexible potential and can easily be converted into a fourth bedroom. This residence is within the city limits, allowing for potential short-term rental income, making it an attractive opportunity for personal enjoyment and investment. Additional highlights include hurricane-impact windows and doors, Hunter Douglas custom treatments, crown molding, Brazilian cherry wood flooring and refined interior finishes throughout. Professionally landscaped grounds with new sod, an irrigation system and hardscape pathways complete the setting. Minutes from Siesta Key Beach and Village and a short drive to Southside Village and downtown Sarasota, this residence merges waterfront access with design, privacy and location, offering a rare opportunity to own a premier property on Florida’s Gulf Coast. Click on the fly-through video and Matterport walk-through for more images. Live where every day feels like a resort vacation, make it come true!

810 Siesta Drive, Sarasota

$3,295,000
4 Beds 4 Baths Sanderling Club SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water’s edge. At the heart of the home lies a state-of-the-art culinary haven. The chef’s kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you’ll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.

1253 N Basin Lane, Sarasota

$2,600,000
5 Beds 6 Baths Sarasota Beach SubDv. 34242 Zip Code
Welcome to your dream coastal retreat—where luxury meets relaxation—just 3 blocks from the award-winning Siesta Key Beach. This custom-built all block elevated home is crafted for those who crave the ultimate Florida lifestyle. Perfect for a full-time resident or a part-time snowbird. A stunning 5-bedroom, 4 full baths, with 2 powder rooms affords unmatched elegance. Step into your backyard oasis featuring a saltwater pool, hot tub, screened lanai, and an open patio, perfect for entertaining or unwinding after a day at the beach. With wide water views, a private kayak launch, and a 10,000-lb boat lift, you’ll have seamless access to the intracoastal, Sarasota Bay and Gulf of Mexico, right from your backyard. The heart of the home is a chef’s dream, featuring solid wood cabinets, Wolf and Sub-Zero appliances, and quartz countertops. The reverse-osmosis water system and whole-house soft-water conditioner elevate the whole home water experience. With two laundry rooms, two new tankless water heaters, two A/C units, and an oversized 2-car garage, this home is designed for comfort and efficiency. From quartz countertops in the bathrooms to premium finishes throughout, no detail is overlooked. Located in a quiet tree lined neighborhood, with new homes being sold at $4 to $5 million, and a beach access at the end of the street, and less than a mile to the vibrant Siesta Key Village for dining, shopping, and entertainment. Practicality matches the luxury: this newer home’s base elevation is above 10 ft which allow for low insurance premiums. This home is equipped with hurricane rated impact glass windows and sliders throughout the home. This Siesta Key gem blends coastal charm with modern amenities—whether you’re kayaking or boating from your backyard, hosting friends’ poolside, or strolling to the village for a night out, this home delivers the Florida lifestyle you’ve been dreaming of. Schedule your private tour today and make this piece of paradise your own!

5246 Avenida Del Mare, Sarasota

$2,200,000
4 Beds 4 Baths Ocean View SubDv. 34242 Zip Code
Exceptional waterfront living can be yours at this durable, block construction three-story single-family home set alongside the picturesque Heron Lagoon on Siesta Key. This home is completely move in ready after an extensive, luxury renovation. An attractive, paver drive flanked with lush landscaping offers ample parking while the four-car tandem garage is outfitted for the car enthusiast with a small non-conforming space and access to the backyard pool and spa. The first floor over parking features two en-suite bedrooms with large closets and the smart placement of the laundry closet. Stretching across the entire width of the home with a private office and relaxing, private terrace is the primary en-suite. The perfect place to rest, recharge and pamper with stunning views and a unique primary bath featuring dual vanities, soaking tub, walk-in shower and state of the art design. Ascend to the top floor by stairs or elevator to find an additional bedroom and full bath as well as the open concept living space offering three sets of hurricane rated French doors, allowing loads of natural light and panoramic views of the lagoon. The chef-inspired kitchen is equipped with a Viking stove & Frigidaire refrigerator (2021), custom cabinetry, glimmering quartz counters with an ocean inspired backsplash, and an additional built-in area for your private collection of spirits or prized glass ware. The gas fireplace in the dining area provides warmth and intimacy as you host your family and friends to enjoy your creative cuisine and offer a nightcap on the third-floor terrace overlooking the backyard designed for entertainment. A spiral staircase is your invitation to soak up the warm Florida sunshine in the refreshing pool (new mechanics 2024), challenge your guests to a putting contest on the integrated putting green, float peacefully alongside the mangroves from the kayak or paddleboard launch (new 2022) or drop a fishing line in the lagoon for the fresh catch of the day. On mild evenings, star gaze from the cozy hot tub (new 2024) or share stories of your Siesta Key adventures around the gas fire pit. Take a short stroll and find yourself at Turtle Beach Park, where beach access, grills, pavilions, a playground and much more can be your destination for hosting a gathering or a quiet day on the beach to yourself. With western views and exquisite attention to detail, this exceptional Siesta Key family retreat offers a rare opportunity to own a piece of paradise. A list of additional upgrades and details of renovation dates available upon request

8258 Midnight Pass Road, Sarasota

$2,700,000
3 Beds 4 Baths Beach Residences SubDv. 34242 Zip Code
Experience luxury living at the highly-regarded Hyatt Beach Residence Club of Siesta Key! This stunning 4th-floor condominium boasts 3 bedrooms and 3.5 baths, offering incredible Gulf Views for breathtaking sunsets from your private balcony. From the moment you enter through the elegant foyer, you’ll be transported to a tropical paradise. Every detail in this home has been meticulously designed to create a sense of comfort and sophistication. The master suite is a true sanctuary, featuring a spa-like bath and private access to an outdoor terrace that overlooks the powdery quartz sand beaches of Siesta Key. The deluxe chef’s kitchen is a culinary enthusiast's dream, equipped with top-of-the-line appliances, including a wine refrigerator, making it perfect for entertaining guests. Unwind at the beachfront pool, complete with private cabanas, a hot tub, and a cozy fire pit. Indulge in food and drinks at the Tiki Bar, or head straight to the beach and take advantage of the resort’s paddleboard and beach chair services. The waterfront terrace features a Ping Pong and billiards table, ensuring fun-filled days. Hyatt hospitality is renowned for its legendary concierge services, offering a front desk staff, valet parking, and 24-hour security. Electric charging stations are conveniently located on-site. NIGHTLY RENTALS are permitted, providing an excellent investment opportunity. An onsite program director is available to offer recommendations for recreational activities, and residents have access to an indulgent spa facility and fitness center featuring a steam room. The condo fee covers ALL YOUR MONTHLY EXPENSES, including cable, electric, gas, and water. Plus, enjoy complimentary breakfast each morning! Located just a short distance from Siesta Key Village, you'll find a vibrant array of shopping and dining options, making it the entertainment hub of the island. Proximity to the cultural arts of downtown Sarasota and St. Armand's Circle means even more fantastic dining and shopping experiences right at your fingertips. Don’t miss out on this extraordinary opportunity to own a piece of paradise!

915 Seaside Drive Unit 407, Sarasota

$4,700,000
4 Beds 5 Baths Bay Island Shores SubDv. 34242 Zip Code
Welcome to Casa Della Fontana — The Fountain House. Nestled on the tranquil north end of Siesta Key, this gated waterfront estate is a blend of seaside serenity, architectural distinction, and lifestyle luxury. Perched on a deep, sailboat-accessible bayou that connects to the Intracoastal Waterway, the almost half acre lot provides generous room for outdoor living, boat docking, and privacy. Built by Magnum Builders, this residence was recently transformed through a multi-year, high-end renovation to blend modern amenities with timeless character. The home is engineered with concrete footings, steel pilings, and reinforced concrete/rebar, designed for storm resilience. A Spanish barrel tile roof (2024), hurricane-rated garage doors and a whole-house generator round out the safety and durability features. This residence spans 6,827? square feet of air-conditioned living space offering 4 bedrooms, 4 full baths, and 1 half bath. At the heart of the home is the great room, soaring to 20-foot ceilings, commanding sweeping water views, and anchored by a two-story library wall. A gallery and loft overlook the formal dining space, and elegant iron railings and hand-hewn wood trestles bring an artisanal, Old World feel. A hidden wood-paneled staircase adds a dramatic, secretive touch. The gourmet kitchen is outfitted with Wolf, Sub-Zero, and Miele appliances, quartzite countertops, a coffered ceiling, a waterfront breakfast nook, and a walk-in pantry. Hand-hewn beams extend throughout the kitchen and lanai, harmonizing the interior and exterior aesthetic. The primary suite is a sanctuary: two private balconies, dual bathrooms, a central walk-in shower with dual entry, and twin walk-in closets. The guest wing, with three bedrooms and three baths, provides privacy and independent access to the driveway. Additional interior amenities include a media/game room, office/library, elevator, high ceilings, built-in features, central vacuum, and smart home automation. Designed for entertaining and coastal living, the property features a heated/in-ground gunite pool with spa, a sizable lanai with kitchen and multiple alfresco seating areas. For boating enthusiasts, the dock features three lifts and docking for large vessels. Living here means effortless access to both island leisure and Sarasota urban life. You’re just minutes from Siesta Beach’s famed white sand, Siesta Key Village’s shops and restaurants, and the art, culture, dining, and amenities of downtown Sarasota. The home’s deep-water location makes boat outings to the Gulf a delight. Casa Della Fontana is more than a house — it’s a waterfront masterpiece built for those who demand beauty, durability, and lifestyle in equal measure. With its structural reinforcements, state-of-the-art systems, and sophisticated design, it offers both peace of mind and the romance of island water front living.

749 Freeling Drive, Sarasota

$1,175,000
3 Beds 3 Baths Bay Island SubDv. 34242 Zip Code
Restore a piece of architectural history or build your dream home on this prime waterfront lot on Bay Island, the gateway to Siesta Key and one of the island’s exclusive communities. Designed by renowned architect Ben Baldwin, a leading figure in the Mid-Century Modern movement, this residence offers timeless design and exceptional potential. The existing 3,321-square-foot concrete block home features 14 glass sliders, skylights and serene views of bamboo, palms and the lagoon. Baldwin’s vision of light, scale and nature is intact—awaiting restoration after flood remediation. The property includes an 11,458=-square-foot corner lot with lush landscaping, a tranquil lagoon/canal with easy bay access, and a detached space once used as a professional darkroom—ideal for conversion to a guest suite. Featured in the February 2024 issue of Key Life Magazine. In the City of Sarasota limits, an excellent investment with seven-day minimum rental period. Minutes to Siesta Key Beach, Siesta Village and Sarasota’s mainland. This is the lowest-priced waterfront home in Bay Island, offering a rare opportunity to own and restore a Sarasota architectural treasure.

3721 Flamingo Avenue, Sarasota

$1,761,000
3 Beds 2 Baths Siesta Beach SubDv. 34242 Zip Code
Welcome to your Siesta Key waterfront retreat—radiant with natural light and perfectly positioned on the Grand Canal. Elevated for peace of mind and crafted for coastal living, this three-story, 3-bedroom home with den/guest room celebrates time on the water from the moment you arrive. The main level opens to a large canal-view balcony and features a bright living room with a 22 ft ceiling, a defined dining area, and a chef’s oasis kitchen anchored by a center island—offering abundant storage, wood cabinetry, stainless-steel appliances, and expansive prep surfaces for effortless entertaining. Upstairs, the private primary suite spans the top floor with an adjacent office, a generous walk-in closet, and a spacious bathroom with dual sinks, soaking tub, and walk-in shower. Sliders open to your own third-floor balcony with beautiful canal views. The ground level offers a 2-car garage plus 700 sq ft of air-conditioned flex space (not included in main living area) with sliders to the pool and boat dock—ideal for a gym, rec lounge, or entertaining space. A private elevator connects all three levels—from the garage to the main living space and top-floor suite. Outside is a boater’s dream: deep-water frontage on the Grand Canal with quick access to Roberts Bay, Sarasota Bay, and the Gulf; composite decking, a 10,000-lb lift, and a seawall with turn-backs (all new as of Nov 2021). A clever two-level dock allows easy tide-height boarding and effortless kayak launches. This elevated Grand Canal home is perfect for boating, kayaking, paddle boarding, and daily dolphin/manatee watching. Lush, mature landscaping (on an irrigation well) wraps the property in privacy. All a short bike ride or walk to Siesta Key Village dining/shopping and world-famous Siesta Beach.

4929 Oxford Drive, Sarasota

$2,800,000
4 Beds 3 Baths Sarasota Beach SubDv. 34242 Zip Code
Certificate of Occupancy received 5/27/2026 *Call today to schedule your private showing! Welcome to 276 Island Circle, an exceptional waterfront retreat nestled on an oversized lot in the highly sought-after Palm Island neighborhood of Siesta Key. Perfectly positioned along the Grand Canal and just a half-mile from the world-famous shores of Siesta Key Beach, this beautifully designed 4-bedroom, 3-bathroom residence captures the essence of luxury coastal living. Thoughtfully crafted with both elegance and functionality in mind, the home offers an open and inviting floor plan highlighted by soaring tray ceilings, abundant natural light, and impressive zero-corner sliding glass doors that seamlessly blend indoor and outdoor living. Impact-rated windows and sliders provide peace of mind while framing picturesque views of the waterfront setting. The heart of the home is a stunning chef's kitchen designed for entertaining and everyday enjoyment alike. Exquisite quartz countertops and backsplash, dramatic waterfall edges, custom solid wood cabinetry, a Wolf range with custom hood, paneled Sub-Zero refrigerator, paneled Bosch dishwasher, Sharp microwave drawer, hidden outlets, and a showstopping glass-front pantry complete with a wine cooler combine to create a space that is as beautiful as it is functional. The primary suite offers a private sanctuary with custom-designed his-and-her closets and a spa-inspired bathroom featuring dual vanities, a curbless walk-in shower, and a freestanding soaking tub. Outdoor living is equally impressive. Overlooking the Grand Canal, the resort-style backyard was designed to embrace Florida's year-round sunshine. Relax in the saltwater PebbleTec pool and spa, unwind on the sun shelf, or entertain guests on the expansive leathered marble paver deck. Boaters will appreciate the impressive, brand new 107 feet of seawall frontage, offering direct access to the waterways that make Siesta Key such a coveted waterfront destination. Beyond the property, the Siesta Key lifestyle awaits. Spend your mornings walking Siesta Key Beach, consistently ranked among the finest beaches in the world for its powder-soft quartz sand and crystal-clear Gulf waters. Enjoy afternoons exploring Siesta Key Village's collection of boutique shops, waterfront restaurants, lively cafés, and local entertainment. Whether boating, dining al fresco, watching spectacular sunsets, or simply enjoying the laid-back island atmosphere, every day feels like a vacation. Rarely does a home combine a premier Palm Island location, exceptional waterfront setting, luxurious finishes, and close proximity to Siesta Key Beach so effortlessly. 276 Island Circle offers a unique opportunity to experience the very best of Sarasota's island lifestyle.

276 Island Circle, Sarasota

$2,695,000
3 Beds 4 Baths Bay Island SubDv. 34242 Zip Code
548 Siesta Drive is more than just a home—it’s a gateway to the best of Siesta Key living with unmatched flexibility, location, and waterfront luxury. Welcome to this luxury coastal retreat on North Siesta Key, perfectly positioned inside Sarasota city limits, making it a rare short-term rental–friendly opportunity. With deep water access just seconds from the Bay, two boat lifts, and a jet ski lift, this home is tailor-made for boaters, water enthusiasts, and investors seeking a strong rental return. Property Highlights • 3 bedrooms | 3.5 bathrooms | Bonus room • Over 4,300 sq. ft. of living space • Nearly 5,000 sq. ft. total under roof • Prime North Siesta Key location in city limits • Quick drive to Downtown Sarasota and Siesta Key Village • Short-term rental potential in one of Sarasota’s hottest markets Interior Features As you step inside, you’re greeted by soaring vaulted ceilings and gleaming oversized porcelain white tile floors that set the tone for the home’s regal, modern style. • Living Room: Expansive and open with dramatic volume ceilings • Bonus Room: Hidden retreat above the garage ideal for a quiet office, playroom, or guest space • First Suite: Convenient en suite bedroom on the main floor • Primary Suite: Oversized retreat with a private screened lanai, spacious walk-in closets, and a beautifully remodeled spa-style shower • Third Bedroom: Private en suite with direct access to the pool deck The chef’s kitchen and entertaining area have been fully remodeled with high-end finishes, blending function and style for both everyday living and gatherings. Outdoor Living Step outside to your large lap pool with water views, framed by paver decking and multiple lounging areas. With direct boating access, two boat lifts, and a jet ski lift, the water is truly an extension of your backyard. Key Upgrades This home has been renovated from top to bottom, ensuring a move-in-ready experience with timeless finishes and thoughtful design details.

548 Siesta Drive, Sarasota

$1,550,000
5 Beds 4 Baths Siesta Beach SubDv. 34242 Zip Code
Exceptional Investment Opportunity on Siesta Key – Turnkey 5-Bedroom Home with Strong Rental Income Potential Unlock the full potential of coastal luxury with this expansive 5-bedroom, 4-bathroom residence offering over 3,700 square feet of casually refined living space. Perfectly situated on an oversized, private lot just minutes from the world-famous Siesta Key Beach, this property is a rare find for savvy investors or those seeking a dual-purpose personal retreat and income-generating asset. Designed with both comfort and functionality in mind, the home features flexible living spaces, an abundance of natural light, a home office, and luxuriously updated kitchen and bathrooms. The kitchen is equipped with high-end stainless steel appliances, custom cabinetry, and ample prep space—ideal for entertaining guests or catering to vacationing families. Step outside to your own tropical oasis: a heated pool and spa, expansive patio, and lush, mature landscaping provide the perfect backdrop for relaxation and outdoor gatherings. The detached 3-car garage offers generous storage for vehicles, beach equipment, and water sports gear—an essential amenity for short-term rental guests. With a 7-night minimum rental policy, this property is perfectly positioned to generate premium vacation rental income year-round. The home's size, layout, and resort-style features make it an ideal choice for large families or groups, significantly increasing its desirability and earning potential in Siesta Key’s thriving short-term rental market.

185 Faubel Street, Sarasota

$10,500,000
5 Beds 7 Baths Sandy Hook SubDv. 34242 Zip Code
Welcome to this extraordinary Gulf-front estate located in one of Siesta Key’s most exclusive enclaves. Situated on a full acre in the private Sandy Hook community, this fully renovated, turnkey residence offers over 5,000 square feet of refined living space and more than 3,000 square feet of covered outdoor areas, all just a short stroll from Siesta Key Village and with direct access to a private community beach. Inside, the layout features five en-suite bedrooms, two powder baths, a dedicated office, and a three-car garage with beach cruisers and kayaks included. Floor-to-ceiling Andersen impact windows frame panoramic Gulf views, while rich finishes like Sapele mahogany siding, IPE hardwood decking, and a custom Pecky Cypress entertainment system reflect the home’s elevated craftsmanship. The chef’s kitchen is a showpiece, centered around a Labradorite Lumarian Blue granite island imported from Brazil, with Wolf, Miele, and Sub-Zero appliances throughout. The spa-inspired primary suite includes a waterfall feature wall, dual curbless shower, lighted soaking tub, and Toto smart toilets. A private elevator and full smart-home system ensure ease and efficiency. Outdoor living is exceptional, with a heated saltwater pool and Jacuzzi, a fully equipped summer kitchen, a covered outdoor living room with fireplace and TV, a poolside theater with dual fireplaces and TVs, and a sunset-facing gas fire pit. The professionally designed $1M+ tropical landscape includes advanced mosquito-misting and irrigation systems for effortless maintenance. With direct access to a private, resident-only beach and an ideal location just minutes from restaurants, shopping, and entertainment, this one-of-a-kind estate offers a rare opportunity to experience the best of coastal living on Siesta Key. Designed for elevated living and effortless enjoyment, 26 Sandy Hook Road S is more than a home—it is a fully realized Gulf-front sanctuary.

26 Sandy Hook Road N, Sarasota

$985,000
3 Beds 3 Baths Twitchell Ralph S Siesta Key Prop SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Tucked away at the end of quiet Estrada De Costa, a single lane road with just three homes, this unique and spacious Siesta Key 3 bedroom/3 bath lakefront property offers rare privacy, flexibility, and charm. The home was expanded in 2001, the property includes a 2 bedroom/2 bath main house, and a fully equipped one bedroom/one bath separate suite with its own private entrance, cozy living room, kitchen, walk-in closet, and screened porch with tranquil water views. Ideal for multigenerational living, guest accommodations, or income potential. Saltillo(Mexican) tile flooring flows throughout both living spaces and adds character and charm to every room, while the open layout flows seamlessly for comfortable everyday living. Sliding glass doors on the water side fill the rooms with natural light. The house did have water in the home after Hurricane Helene, so the owner completed some thoughtful and stylish renovations such as Shaker cabinets, quartz counters, subway tile backsplash, all new LG stainless steel appliances, new AC, and hot water heaters in both living spaces, and solid paneled doors throughout. New roof in 2022, and drain pipes lines in 2024. Located on Lake Rittwood, a serene neighborhood pond teeming with tilapia, turtles, ducks and birds, this home is a retreat. Stroll into Siesta Key Village, or catch sunset views at the Big Pass/Gulf public access at the West end of Givens St. and Ocean Blvd. This home offers the end-of-the-road seclusion, but still close to the wonderful activities of Siesta Key and Sarasota. Whether you're hosting guests, housing extended family, or exploring rental potential, this unique layout offers flexible living options rarely found on the Key.

4830 Estrada De Costa, Sarasota

$1,200,000
2 Beds 2 Baths Bay Island SubDv. 34242 Zip Code
Welcome to your dream family home on Bay Island, located on the premier north end of Siesta Key. This inviting 2-bedroom, 2-bathroom residence is nestled among beautiful homes on Norsota Way, one of Sarasota's most coveted streets, offering a perfect blend of comfort and elegance. Located in an exclusive neighborhood with multimillion-dollar homes, this property presents an incredible value opportunity. This solidly built block construction home offers peace of mind and durability without sacrificing old school Florida charm. The main living level is elevated on the second story and features a spacious open floor plan designed for ease and relaxation, including partial water views of Sarasota Bay from the upstairs bedrooms and a wrap-around deck, perfect for enjoying your morning coffee. This home includes approximately 1,527 additional square feet on the first floor, which is not included in the main living space square footage. From here, step outside through the sliding doors to discover a recently resurfaced pool and spa with brand new pool and pump equipment (2025), set in a captivating garden oasis. This gem is adorned with numerous updates, including a new hot water heater (2024), upstairs and downstairs HVAC systems (2024), a new furnace (2024), a new refrigerator (2024), a new washer and dryer (2024) and fresh landscaping. Just steps away, you'll find a gorgeous park with unobstructed views of passing sailboats, friendly dolphins, breathtaking sunsets, the Ringling Bridge and Sarasota skyline. Shell Beach is only a short stroll away or hop on your bike or golf cart and ride to Siesta Beach, Siesta Village, Southside Village, or to the Field Club for family-friendly entertainment. Sarasota Memorial Hospital, Out of Door Academy, Southside Elementary School are also less than two miles away. Don’t miss your chance to own a piece of paradise in this exclusive enclave! Schedule your private tour today!

854 Norsota Way, Sarasota