Siesta Key Homes with City View

Siesta Key Homes with City View

Welcome to Siesta Key, Florida, a stunning barrier island located in Sarasota County that epitomizes the essence of coastal living. Known for its powdery white sand beaches and crystal-clear turquoise waters, Siesta Key is not just a vacation destination; it's a vibrant community that offers a unique blend of relaxation and excitement.

This charming island is home to a variety of outdoor activities, from paddleboarding and kayaking to beach volleyball and sunset strolls along the shore. The village area boasts delightful shops, gourmet restaurants, and lively bars that create a perfect atmosphere for both residents and visitors alike. With its laid-back vibe and friendly locals, Siesta Key invites you to unwind and enjoy the beauty of nature.

For those seeking a home with a view, Siesta Key offers a remarkable selection of residences that provide breathtaking vistas of the Gulf of Mexico and the vibrant sunsets that paint the sky in hues of orange and pink. Imagine sipping your morning coffee on a balcony overlooking the shimmering waters, or hosting friends for an evening barbecue as the sun sets on the horizon. Homes here range from luxurious beachfront estates to charming cottages, all designed to embrace the island’s natural beauty.

Living in Siesta Key means embracing a lifestyle filled with sun, sand, and sea, complemented by the warmth of a close-knit community. Whether you’re looking for a permanent residence or a vacation getaway, Siesta Key is the perfect place to call home. Discover the magic of this coastal paradise and experience the allure of homes with breathtaking city and water views. Your dream home awaits!

Newest Siesta Key Homes with City View

1640 Summerhouse Lane Unit 40, Sarasota
$1,600,000
3 Beds ⋅ 3 Baths ⋅ Summer Cove On Siesta SubDv. ⋅ 34242 Zip Code
Rarely available at Summer Cove on Siesta Key, this exceptional 3-bedroom, 2.5-bath residence offers an elegant opportunity to enjoy the best of island living. Set within a gated Gulf-to-Bay community built in 2005, the residence features beautiful views from every window, abundant natural light, and deeded beach access. A private elevator opens directly to the residence, where comfort and coastal sophistication come together effortlessly. The thoughtfully designed kitchen serves as a beautiful centerpiece, while two expansive balconies extend the living space outdoors. Two tandem garage spaces provide secure, convenient parking. There is deeded beach access and a kayak launch for an easy way to enjoy the surrounding waterways and explore the coast. At the heart of the community is a beautifully renovated clubhouse. It was formerly the renowned Summerhouse Restaurant and a memorable part of Siesta Key history. Today, this distinctive gathering space features a new fitness center, game room, pool tables, library, and more—creating an inviting setting for recreation, entertaining, and relaxation. Outdoor amenities include a resort-style pool and spa, and a barbecue area. With its private elevator, generous outdoor spaces, secure garage parking, deeded beach access, and exceptional community amenities, this rarely offered residence presents a distinctive opportunity to experience Siesta Key in comfort and style. Siesta Key shops, restaurants, and beaches are just minutes away. Also, it’s just a short drive downtown Sarasota, St. Armand’s Circle, and Longboat Key. Schedule your private tour today!

1640 Summerhouse Lane Unit 40, Sarasota
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
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
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