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$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

$852,500
2 Beds 2 Baths Gulf N Bay SubDv. 34242 Zip Code
Enjoy the best of Siesta Key living in this bright and airy 2-bedroom, 2-bath condo located within the gated Gulf & Bay Club community. Surrounded by tropical landscaping and peaceful water views, this home offers the perfect mix of comfort and resort-style living just steps from the sand. The spacious floor plan features a welcoming living area that flows into a dedicated dining space and an extended sunroom lined with large windows. Flooded with natural light, this flexible area is ideal for reading, relaxing, or taking in the view of swaying palms and the shimmering Gulf beyond. Gulf & Bay Club spans 32 acres of beautifully maintained beachfront grounds with top-tier amenities including three heated swimming pools, tennis and pickleball courts, saunas, a modern fitness center, EV charging stations, and a clubhouse designed for social gatherings and events. The community also provides private access to Siesta Key’s iconic white-sand beach, recognized among the finest in the country. An elevator offers easy access, and the free island trolley is just outside, ready to take you to the shops, restaurants, and live music of Siesta Village. Whether you’re searching for a year-round residence or a seasonal escape, this home captures the essence of coastal comfort and island living.

5780 Midnight Pass Road Unit 303, Sarasota

$670,000
2 Beds 2 Baths Our House At The Bch SubDv. 34242 Zip Code
Price Drop of 20K - best price for a Tower Unit in Our House at the Beach !Strong Rental Income – Across from Siesta Beach! Totally updated 2 bed / 2 bath condo in the West Tower of “Our House at the Beach”, directly across from Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor in 2024. This second-floor unit offers incredible natural light and nearly 270 degrees of wraparound views thanks to 46 feet of sliding glass doors in the living and dining areas. This unit is turnkey furnished (excluding some artwork and personal items) and features luxury plank vinyl flooring throughout, with updated bathrooms and a gorgeous, remodeled kitchen with granite countertops, stainless steel appliances, and a pass-through to the main living area. The spacious primary bedroom offers abundant windows and a bright, airy feel. Both bathrooms have been tastefully upgraded. Enjoy two oversized balconies, perfect for relaxing after a day at the beach or hosting guests. This is not just a beach retreat—it’s a solid investment: • $32,900 gross rental income in 2023 • $28,000 in 2024 (despite storms) • Projected $40,000+ in 2025 with owner use! Weekly rentals allowed, boosting occupancy and revenue potential. The $45,000 special assessment (impact glass & more) is fully paid by the seller. Community amenities include: • Heated pool • 2 tennis courts • Grilling pavilion • Assigned covered parking • In-unit full-size washer/dryer • Pet-friendly (owners may have 1 pet up to 15 lbs) Units in the West Tower rarely come on the market—last year’s sale went for significantly more. This is your chance to own a beautifully maintained, income-producing condo across from one of the world’s most beautiful beaches!

1001 Beach Road Unit A203, 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

$865,000
3 Beds 2 Baths Sarasota Beach SubDv. 34242 Zip Code
Experience the best of island living in this beautifully maintained Turnkey FULLY FURNISHED, Key West-style home just moments from Siesta Key Public Beach and the vibrant Siesta Village. Offering 3 bedrooms, 2 bathrooms, and a 2-car garage with brand-new doors, this residence has been thoughtfully updated over the years with major recent improvements including a 2023 metal roof and all-new impact glass windows and doors for peace of mind. Head upstairs to the main living level where an open-concept layout welcomes you with luxury vinyl plank flooring, vaulted ceilings, and plantation shutters that fill the space with natural light. The kitchen features stainless steel appliances only a few years old, granite countertops, and a convenient connection to the dining area—ideal for hosting friends and family. Each bedroom showcases plantation shutters and crown molding for added charm. The primary suite is a true retreat, complete with a walk-in closet with built-in organization, an ensuite bathroom with a glass-enclosed shower tucked behind a stylish barn door, and direct access to the backyard deck through sliding glass doors. The two guest bedrooms share a tastefully updated full bathroom. Step outside to the elevated deck overlooking the private backyard, where a cozy fire pit area awaits in the corner—perfect for evening conversations and coastal breezes. An outdoor shower is the perfect spot to rinse off after a long day at the beach. Whether you’re seeking a full-time residence or the ideal vacation getaway, the flexibility of no HOA allows you to live as you please. Located just down the road from the powdery white sands of world-renowned Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home delivers the quintessential Siesta Key lifestyle.

221 Island 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

$240,000
1 Beds 1 Baths Siesta SubDv. 34242 Zip Code
LOWEST PRICE ON SIESTA KEY FOR A ONE BR CONDO OFFERING SHORT TERM RENTALS! Siesta Key Beach is calling you…experience the allure of coastal living at the quaint Sea Winds complex, conveniently located along Midnight Pass Rd., just a short walk to the world-renowned Siesta Key beach! This prime beach investment offering the opportunity to rent with a 2-week minimum and also use for yourself. This condo has an excellent rental history with bookings in place currently and into high season 2026. Average gross rental income is $20K/year with more upside potential. This delightful 2nd floor, generously sized 1 bedroom condo sustained NO damage from storms and comes fully furnished turn key offering desirable features such as a fully updated & equipped kitchen in on trend design, updated bathroom with new granite top vanity, tub/shower with new high end glass door, tile flooring, fresh bright paint colors, room for guests with convertible sofa, inviting dining space, open floor plan, AC 5 years new, H2O heater 2 years new, well maintained and move in ready! Easy parking with your own assigned space in front of your condo, plus guest parking. The Sea Winds is a small community of 35 units with amenities designed for year-round enjoyment, including bicycle rooms, a social room, shared laundry, pet friendly, and a heated pool complete with lounge chairs, umbrellas, and convenient bathroom facilities. Community pool had a complete upgrade in summer 2025. All buildings had new roofs in 2024 and experienced no major storm damage. The vibrant South Village is nearby, offering a variety of restaurants, boutiques, lively beach bars, ice cream shops, groceries, pharmacies and rental options for everything from fishing and boating to biking and kayaking. Plus, a daily trolley service stops right in front of the Sea Winds Condominium complex, providing easy access to all of Siesta Key's attractions. See this well priced condo today that is ready to go and a great investment on the Key!

6703 Midnight Pass Road Unit 208, Sarasota

$7,950,000
6 Beds 9 Baths Hidden Harbor SubDv. 34242 Zip Code
Pre-Construction. To be built. Welcome to this newly imagined Siesta Key residence, a world curated for those with a sophisticated palate for modern architecture at the edge of the sea. Here, light dances across water and peers through your windows blending luxury, privacy and resort-style living within the exclusive enclave of Hidden Harbor. The journey begins as you approach this designer estate—a vision of coastal modernism, 4,900 square feet under air and meticulously crafted by TDI Coastal Homes, celebrated for precision, integrity, and elegance. Clean lines and natural textures blend with lush tropical surroundings, setting the stage for a life that lives like an endless retreat. The lower level invites you to linger outdoors surrounded by the scent of the saltwater breeze and the sounds of the cascading waters of the 65-foot infinity pool and spa. A covered living space blurs the line between home and horizon. A custom waterslide arcs playfully into the pool, while beyond, your private dock with a 20,000-pound lift awaits spontaneous voyages to Roberts Bay. Ascend by elevator or sculpted staircase to the heart of the home—spaces that feel both expansive and intimate. Walls of glass reveal shimmering water views, while the Meile appliance suite anchors a chef’s kitchen made for creating fine cuisine and lasting memories. Every detail and finish bears the signature of master craftsmanship. The home’s six bedrooms include two primary suites, each a retreat of its own with spa-inspired baths. Six full and three half baths offer both comfort and convenience for family and guests alike. A 700-square-foot bonus space stands ready to become whatever your imagination allows—a golf simulator, game lounge, or wellness studio. A three-car garage, new seawall, whole-home generator, and zero water intrusion during the 2024 storms provide unmatched peace of mind. As evening settles, the home transforms. Ambient lighting glows across the infinity edge and the hush of the bay replaces the day’s energy. You can almost hear the future stories unfolding here—laughter by the pool, sunrise swims, quiet coffee on the terrace. 5179 Hidden Harbor Road isn’t just a home; it’s a state of being—modern, effortless, and deeply connected to the water.

5179 Hidden Harbor Road, Sarasota

$699,000
2 Beds 2 Baths Pointe On Midnight Pass SubDv. 34242 Zip Code
Also available as a seasonal rental! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Negotiable furnishings available. Schedule your private showing today.

9397 Midnight Pass Road Unit 905, 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

$1,000,000
2 Beds 2 Baths Siesta Breakers SubDv. 34242 Zip Code
Fabulous Siesta Beach Condo at the Siesta Breakers #403 — Where Paradise Meets Profit Some properties are nice. This one is life-changing. Welcome to Unit #403 at Siesta Breakers — a rare, true beachfront end-unit perched directly on Crescent Beach, one of the most celebrated stretches of coastline on the planet. This isn't just a condo. It's a front-row seat to the Gulf of Mexico, every single day. Siesta Key's world-famous quartz-crystal sand stays cool even in the Florida heat — and 340 linear feet of it belongs exclusively to you and your guests. Across 5.6 lush acres, this gated community delivers a resort lifestyle that most only dream about. Inside, everything is already perfect. Bright. Open. Elevated. The open-concept living space flows effortlessly from designer interiors to a private balcony where sweeping Gulf views and legendary Siesta Key sunsets steal the show — every evening, without fail. The primary suite is a true sanctuary: a generous walk-in closet, an updated bath, and serene water views to wake up to. The guest bedroom is smartly designed for comfort, making it ideal for family or high-paying renters alike. It's offered completely turnkey — furniture, décor, and everything in between. Walk in and start living. Or start earning. Speaking of earning, the numbers speak for themselves. Unit #403 consistently generates $85,000+ annually in rental income, is already booked weekly through July 2026, and plugs directly into Siesta Breakers' highly sought-after weekly rental program. This isn't speculative income potential — the bookings are already in place. The community matches the lifestyle. Heated resort-style pool with tropical landscaping, Lighted tennis & pickleball courts, Private clubhouse, Security Gated Entrance, Secure under-building parking, Steps to island dining, boutique shopping & the free Siesta Key Breeze Trolley. Why #403 is the one: ? Prime beachfront end-unit — panoramic Gulf, pool & sunset views ? 340 ft. of private beach on world-renowned Crescent Beach ? Turnkey furnished & rental-ready from day one ? $85,000+ proven annual rental income ? Bookings already in place through July 2026 ? Low-maintenance luxury in a treasured, gated community Whether you're seeking your forever escape, a luxury vacation retreat, or a high-performing investment — this is the rare opportunity where all three align perfectly. Siesta Breakers #403 isn't just a purchase. It's a decision you'll never regret. Showings are only available on Saturdays between 2pm-4pm. Property is rented weekly thru July 2026.

6480 Midnight Pass Road Unit 403, 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

$750,000
2 Beds 2 Baths Siesta Towers SubDv. 34242 Zip Code
Price Improvement! Your Coastal Paradise Awaits! Step into a world of elegance and tranquility in this stunning condominium, perfectly situated along the breathtaking coastline of Siesta Key. Featuring two lavish ensuite bedrooms, this residence offers you the ultimate in coastal living. The primary bedroom boasts full panoramic views of the crystal blue waters of the Gulf, complete with a beautifully remodeled bathroom and an expansive walk-in closet designed for the modern lifestyle. Embrace a split floor plan that promotes privacy and relaxation, all within a breezy coastal open-concept design that floods the space with an abundance of natural light. Indulge in the outdoors from two covered balconies, ideal for outdoor dining or savoring a glass of rosé as you watch the sun dip below the horizon in a stunning display of colors. Enter the building through a well-appointed lobby that exudes sophistication and class. Residents enjoy a host of resort-style amenities that include a beautifully remodeled community center for exclusive use, a newly refurbished workout facility, and a gulf-front pool to soak in the sun. The outdoor BBQ area is perfect for gathering with friends and family, while storage for beach accessories and bikes adds to the convenience of a coastal lifestyle. Enjoy the peace of mind that comes with covered parking. Perfectly located, this luxury community allows you to walk, bike, or cruise your golf cart to local restaurants, boutique shopping, live music venues, and the vibrant farmers market, all within minutes from your doorstep. Of course, the soft, white sands of Siesta Key Beach are just a short stroll away, ready to fulfill your beach daydreams. Don't miss your chance to experience luxury coastal living at its finest. Schedule your private tour today and discover your new home in paradise!

4822 Ocean Boulevard Unit 2A, Sarasota

$735,000
2 Beds 2 Baths Our House At The Bch SubDv. 34242 Zip Code
Welcome to Our House on the Beach, one of Siesta Key’s most desirable communities located directly across from world-famous Siesta Key Public Beach. This well-maintained 2-bedroom, 2-bath weekly rental residence features a spacious layout with two oversized private patios overlooking the heated community pool and spectacular west-facing sunsets. Thoughtfully cared for over the years, this condo is move-in ready and offers an ideal opportunity for light updating to make it your own coastal retreat. A major upgrade is already underway—brand-new, storm-rated impact windows and sliding doors are being installed in the coming days, and are fully paid for by the seller, offering peace of mind, energy efficiency, and improved storm protection for years to come. Additional highlights include updated bathrooms and a rare covered parking space conveniently located and protected from the elements—a highly sought-after feature on Siesta Key. Residents enjoy resort-style amenities including a heated pool, two tennis courts, golf cart parking, elevators, and bike storage. Located on Siesta Key, known for its world-famous quartz sand beach, vibrant Village, outdoor recreation, and relaxed Gulf Coast lifestyle, this condo is centrally positioned on the island and just moments to Siesta Key Village, and a short drive to mainland shopping, groceries, healthcare, and the arts and dining scene of downtown Sarasota. A prime island location, strong community amenities, and outstanding value—this is the Siesta Key lifestyle you've been waiting for.

1055 Beach Road Road Unit B204, 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

$4,500,000
6 Beds 7 Baths Hidden Harbor SubDv. 34242 Zip Code
Majestic waterfront home nestled in one of Siesta Key's most exclusive neighborhoods. Prime waterfront location with direct access to the inter-coastal (no bridges) and features a 16,000 pound vertical lift and a jet ski lift. This Waterfront home features wraparound decks on multiple levels composed of Brazilian Ipe decking, wood ceilings, a private grill area with a dramatic view up the canal and a resort like swimming pool and spa featuring a rock waterfall and paver patio to fill your sun filled afternoons. Upon entering the home, you will see the amount of detail and craftsmanship that was put into this home. Hand-scraped wood flooring, coffered tongue-n-groove ceilings, huge baseboard and crown molding throughout. Expansive windows let the natural light in and an aquarium glass wall in the kitchen/family room overlooks your lower deck, swimming pool, spa and water view. The home has well over 6000 square feet of living area with the master suite occupying the first-floor level. This home affords 6 bedrooms, 5 full baths, 2 half baths, a private office with built-in cabinetry, 2 wet bars one on each level, 2 laundries with one on each level, a Sports room/ man cave with a built-in entertainment center. Upstairs has 4 bedrooms, two of which are suites, a second family room/playroom, theater/entertainment room which connects to your second level deck. The main level of the home incorporates your kitchen, family room, pantry, wet bar, dining room, private office, master suite and laundry. The kitchen features a huge walk-in pantry with entry door, a huge center island with a granite top, Subzero refrigerator, a Wolf 6 burner/griddle stove, a Wolf warming drawer, a Wolf microwave, 2 drawer Fisher Paykel dishwasher and a second Miele dishwasher for all your entertainment needs. Each level has a wet bar with the lower level having a subzero wine refrigerator and a drink refrigerator and the upstairs level has a Fisher Paykel dishwasher, an ice-maker, microwave, and a refrigerator. For the car enthusiast you have two 2 car garages with separate drives which provides additional parking as well. This spectacular home is hard to match, and you won't be disappointed. The home has an elevation of 15 feet and also has a home generator to provide comfort and a sense of security during any power outages that may occur. Schedule an appointment to see your future home!

5309 Hidden Harbor Road, Sarasota

$1,270,000
2 Beds 2 Baths Whispering Sands SubDv. 34242 Zip Code
EXQUISITE GULF FRONT LUXURY! Just one floor from the top, this stunning, 11th floor, FULLY remodeled GULF FRONT tower residence offers a seamless blend of sophistication and coastal style against a background of breathtaking, unobstructed 180-degree views of the shimmering Gulf! A rare combination of sophistication, comfort, and coastal beauty, this residence defines modern Gulf front luxury living. Every detail of this 2022 remodel reflects the finest in contemporary design and craftsmanship. The open concept interior is graced with beautiful wide plank tile flooring, seamlessly connecting living, dining, and kitchen spaces to the endless blue horizon beyond. True floor-to-ceiling 2020 hurricane impact sliders open to mesmerizing Gulf vistas, enhanced by Hunter Douglas motorized light-filtering shades for effortless ambiance control. The gourmet kitchen is a showpiece featuring striking Cambria® quartz surfaces, a dramatic 8’ waterfall breakfast bar with dimmable pendant lighting, Bosch stainless appliances, 32 bottle wine refrigerator, fabulous under counter drawer microwave, and custom soft-close cabinetry. The serene primary suite is equally refined, featuring a spa-inspired ensuite tiled bath with Cambria® quartz dual vanity and glassed walk-in shower. The guest bath echoes the same refined elegance. FURNITURE AND FURNISHINGS including Robb & Stucky pieces are included with the sale of the property, minus a small exclusion list.

19 Whispering Sands Drive Unit 1105, 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

$464,000
2 Beds 2 Baths Midnight Cove Ii SubDv. 34242 Zip Code
Welcome to your slice of paradise on Siesta Key! This turnkey furnished 2 bedroom, 1.5 bathroom condo offers stunning canal views surrounded by mature tropical landscaping. With weekly rentals allowed and convenient in-house property management, it’s an ideal opportunity for both personal enjoyment and investment income. On-site property management provides professional oversight and streamlined rental operations. Positioned just steps from Siesta Key Beach, ranked the #1 beach in America, this property offers the ultimate coastal lifestyle in one of Sarasota’s most desirable locations. The unit is high and dry, and did not sustain flooding from recent hurricanes. Midnight Cove II conveniently features deeded beach access for effortless days in the sun. Resort-style amenities include a heated pool, tennis courts w/ pickleball nets, basketball hoop, car wash station, barbecue grills, fitness center, and covered carport parking. Enjoy the ultimate island lifestyle with Captain Curt’s, Daiquiri Deck, Anna’s Deli, and more right across the street, and Siesta Key Village is just minutes away for dining, shopping, and entertainment. With easy access to the mainland, downtown Sarasota’s vibrant arts, dining, and cultural scene is only minutes away. Rental income history is available upon request. Live on the #1 beach in the USA while your investment works for you - this is Siesta Key living at its finest.

1300 Cove Ii Place Unit 710, 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

$874,000
1 Beds 1 Baths Terrace SubDv. 34242 Zip Code
Rarely does an opportunity like this emerge on Siesta Key — priced below the last comparable 1-bedroom sale and reduced over $120,000, this is value that simply cannot be ignored. Welcome to Beach Terrace, one of Siesta Key's most sought-after Gulf-front addresses. Nestled at the end of the village in a gated community with direct Gulf frontage, this exceptional corner residence delivers the quintessential Siesta Key lifestyle — world-famous white quartz sand at your feet, the sparkling aqua Gulf stretching to the horizon, and the energy of Siesta Key Village just a short stroll away. The panoramic views here are genuinely extraordinary. From the pristine beach below to the glittering skylines of downtown Sarasota and Longboat Key in the distance, every glance outward is a postcard moment. At night, the twinkling lights of the village and city skyline transform the backdrop into something truly magical — widely regarded as one of the finest views on Siesta Key. Three private balconies ensure there is always a perfect perch for morning coffee, evening sunsets, or simply savoring the coastal scenery throughout the day. Inside, dual sliding glass doors flood the living area with natural light while framing those sweeping Gulf views. The tiled foyer flows seamlessly into a well-appointed kitchen, and the dining area offers ample space to entertain with a backdrop that will leave guests speechless. Resort-style amenities complete the picture: an elevated heated saltwater pool, community room, and the security of a gated community — all just steps from your private beach access. This is Siesta Key living at its finest — Gulf-front, gated, walkable, and priced to sell.

5400 Ocean Boulevard Unit 9-4, 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