Siesta Key Homes with City View

Siesta Key Homes with City View

Welcome to Siesta Key, Florida, a slice of paradise nestled in Sarasota County, renowned for its stunning beaches, vibrant culture, and laid-back lifestyle. This enchanting barrier island is celebrated for its powdery white sand beaches, particularly the world-famous Siesta Beach, which has been consistently ranked among the best in the United States. With its crystal-clear turquoise waters and breathtaking sunsets, Siesta Key is a haven for beach lovers and outdoor enthusiasts alike.

The charm of Siesta Key extends beyond its natural beauty; it boasts a lively community filled with delightful shops, gourmet restaurants, and lively nightlife. Whether you’re indulging in fresh seafood at a waterfront eatery or exploring the local art scene, there’s always something to discover in this vibrant locale.

For those seeking a home with a view, Siesta Key offers an array of stunning properties that showcase the breathtaking scenery of the Gulf of Mexico. Imagine waking up to panoramic vistas of shimmering waters and lush landscapes right from your balcony. Homes with city views here provide the perfect blend of coastal living and urban convenience, allowing you to enjoy the best of both worlds.

Whether you’re looking for a cozy beach cottage or a luxurious waterfront estate, Siesta Key’s real estate market has something for everyone. Embrace the serene lifestyle that comes with living in this picturesque community, where every day feels like a vacation. Come explore the charm of Siesta Key and discover your dream home with an unforgettable view!

Newest Siesta Key Homes with City View

3799 Flamingo Avenue, Sarasota
$17,650,000
4 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

3799 Flamingo Avenue, Sarasota
5400 Ocean Boulevard Unit 15 1-4, Sarasota
$4,000,000
2 Beds ⋅ 3 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create an extraordinary 2,365-SF home. Completely reimagined by award-winning architect Michael Halflants of Halflants + Pichette Studio for Modern Architecture, the residence received the prestigious AIA Florida/Caribbean Honor Award of Excellence in Interior Design and was featured in Sarasota Magazine's Dream Homes issue. Original interior walls were removed to reveal uninterrupted vistas that extend along the shoreline of Siesta Key, across Sarasota Bay, and to the downtown Sarasota skyline. The result is a flowing two-bedroom, two-and-a-half-bath residence where panoramic views, exceptional materials, and thoughtful design exist in perfect balance. At the center of the home, a sculptural Etimoe hardwood core houses the kitchen, storage, primary bath, and an expansive walk-in closet, bringing warmth and architectural definition to the open floor plan. Floor-to-ceiling, seven-panel bi-fold glass doors disappear completely at the corners, creating a seamless connection to the Gulf and inviting coastal breezes into the living spaces. Custom folding partitions provide privacy between the primary suite and main living areas without compromising the home's openness or visual continuity. Thoughtful custom details continue throughout the residence, including a custom steel desk overlooking the Gulf of Mexico, creating a work-from-home setting few could rival. The raw concrete ceiling from Smith's original 1969 design was scraped and clear-coated to a soft sheen, transforming a defining element of the building into a striking contemporary feature. Large-format porcelain tile, custom steel detailing, and carefully selected wood finishes complete a sophisticated material palette that feels both timeless and contemporary. Residents of The Terrace enjoy private access to Siesta Key's renowned beach and are just moments from the shops, restaurants, and energy of Siesta Village. More than a luxury beachfront residence, this is a rare opportunity to own an award-winning home within one of Sarasota's most recognizable waterfront landmarks, where exceptional architecture and Gulf-front living are seamlessly intertwined.

5400 Ocean Boulevard Unit 15 1-4, Sarasota
1035 Seaside Drive Unit 308, Sarasota
$2,550,000
2 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code
This version sells privacy, scarcity, design, and effortless service first. The rental history supports the value proposition without cheapening the residence. A rare opportunity within Ten35 Seaside, the newest boutique Gulf-front community on South Siesta Key. Residence #308 offers an elevated coastal lifestyle defined by contemporary design, exceptional amenities, private beach access, and the personalized atmosphere discerning buyers seek from an intimate luxury property. This beautifully appointed 2-bedroom, 2.5-bath residence pairs refined interiors with effortless lock-and-leave living. An open, light-filled floor plan features Wolf and Sub-Zero appliances, custom cabinetry, designer finishes, and expansive sliding glass doors that extend the living space onto a private terrace. The spacious primary suite is a serene retreat with a spa-inspired bath and walk-in closet, while the guest suite—enhanced by custom built-in bunk beds—provides stylish flexibility for family and guests. Ten35 Seaside delivers a resort-caliber experience with direct private beach access, a Gulf-front pool and spa, fitness center, private cabanas, and a more intimate alternative to Siesta Key’s larger condominium communities. Its coveted south-key location offers convenient access to Siesta Key Village, acclaimed dining, shopping, boating, and downtown Sarasota. Beyond its lifestyle appeal, the residence offers compelling financial flexibility. It generated more than $164,800 in gross rental income and has already recorded over $101,000 in 2026, providing documented performance that may help offset ownership expenses while preserving the opportunity for personal enjoyment. For the buyer seeking a beachfront retreat, second residence, or luxury property with established rental demand, Residence #308 presents a distinctive combination of newer construction, boutique exclusivity, Gulf-front amenities, and proven income performance in one of Florida’s most celebrated coastal destinations. Buyer shall independently verify rental policies and income history, association information, room dimensions, and all property details deemed material.

1035 Seaside Drive Unit 308, Sarasota
6006 Midnight Pass Road Unit 51, Sarasota
$575,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!

6006 Midnight Pass Road Unit 51, Sarasota
332 Avenida De Mayo, Sarasota
$4,995,000
9 Beds ⋅ 8 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!

332 Avenida De Mayo, Sarasota
5880 Midnight Pass Road Unit 704, Sarasota
$1,400,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
You will melt away on Crescent Beach's powder/sugary white sand and float away in the shimmering waters of the Gulf of Mexico. This residence has been beautifully renovated to provide the ultimate beach home for you to call your own. The kitchen area features a day bed and a custom wood top island. Enjoy your morning coffee or sunset drink on your private lanai. Residents enjoy the heated pool/spa with cabana and outdoor kitchen, two grilling areas, a sunset beachside deck and lighted pickle ball/tennis courts. You will appreciate the on-site management office, fitness room and large community center. Come see for yourself what Casarina offers for fine beachside living.

5880 Midnight Pass Road Unit 704, Sarasota
648 Beach Road, Sarasota
$8,500,000
3 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
**Siesta Key beachfront living, reimagined. A different story from every floor.** Set directly along the shores of Siesta Beach and overlooking the Gulf of Mexico, **648 Beach Road** is a one-of-a-kind waterfront residence where the view is constantly changing. From each level of the home, the Gulf reveals itself differently. The perspective shifts. The horizon changes. The colors deepen and soften with the light. From one floor, you feel closer to the movement of the water. From another, the view opens wider toward the horizon. **Every level tells a different story of the Gulf. And no two views are ever exactly the same.** Recently renovated, reimagined, and elevated throughout, the residence has been designed to embrace its extraordinary setting from every angle. Expansive living spaces and wraparound terraces on every floor create a seamless connection between indoors and out, allowing the water, sky, and ever-changing colors of Siesta Key to become part of everyday life. A private elevator connects every level, leading all the way to the rooftop, where a private pool becomes the ultimate vantage point over the Gulf of Mexico. From here, the horizon seems endless and Siesta Key’s legendary sunsets take center stage. A rare **four-car garage** adds exceptional space and functionality, completing a residence that offers privacy, flexibility, and amenities seldom found directly on the beach. **648 Beach Road is more than a beachfront home. It is an experience of the water from every level.** A different perspective. A different color. A different story. Every single day.

648 Beach Road, Sarasota
5880 Midnight Pass Road Unit 804, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
An unusual price for an unusual seaside residence. Completely renovated with stunning views from every window. Enjoy your morning coffee on the lanai and relish the downtown skyline as well as the Gulf of Mexico and Siesta Beach. Renovations include completely repainted, impact resistance windows, new interior doors, closet organizers and new front door. Casarina amenities include heated pool/spa, pickle ball/tennis courts, exercise room, gas grills, etc. This is worth a visit to see everything you can bring into your life.

5880 Midnight Pass Road Unit 804, Sarasota
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