Siesta Key Homes with City View

Siesta Key Homes with City View

Welcome to Siesta Key, Florida—a stunning barrier island off the southwestern coast of Sarasota County, renowned for its powdery white sand beaches and vibrant coastal lifestyle. With its laid-back charm and breathtaking views, Siesta Key is not just a vacation destination; it’s a place where you can truly call home.

Siesta Key boasts a unique blend of natural beauty and community spirit. The island is famous for its crystal-clear waters and the award-winning Siesta Beach, perfect for sunbathing, swimming, and beachcombing. Beyond the beach, you’ll find a lively village atmosphere filled with boutique shops, delightful restaurants, and vibrant nightlife, making it a perfect spot for both relaxation and recreation.

One of the most appealing aspects of Siesta Key is the availability of homes with stunning city views. Imagine waking up to panoramic vistas of the shimmering Gulf of Mexico or the picturesque Sarasota skyline. These homes offer not just a residence, but a lifestyle enriched by the beauty of nature and the vibrancy of urban living. Whether you’re looking for a cozy beach cottage or a luxurious waterfront estate, Siesta Key has an array of properties that cater to every taste and budget.

In addition to its beautiful homes, Siesta Key is also known for its friendly community and an array of outdoor activities, from kayaking and paddleboarding to fishing and biking along scenic trails. Embrace the Siesta Key lifestyle, where the sun shines bright, and the views are simply breathtaking. Discover your dream home in this coastal paradise today!

Newest Siesta Key Homes with City View

$899,900
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
**PANORAMIC GULF VIEWS**TURNKEY FURNISHED**STEPS FROM SIESTA KEY BEACH**A HISTORY OF STRONG RENTAL NUMBERS** Wake up to breathtaking panoramic views of the Gulf of Mexico and distant Sarasota skyline from this spacious sixth-floor, two-bedroom, two-bath condominium located directly across the street from world-famous Siesta Key Beach. Offered turnkey furnished, this exceptional vacation property is ready for immediate personal enjoyment or continued use as a rental investment. The spacious primary bedroom features a king-size bed, while the second bedroom comfortably accommodates guests with two queen-size beds. Enjoy spectacular sunsets, city skyline and coastal breezes from two large terraces, or relax in the quiet privacy of this intimate community with just the right amount of amenities. This unit also includes a rare under-building assigned parking space, one of only eight located under the building. Enjoy a quick walk to the beach, or cool off in the community pool! On-site gas grills and two tennis courts are also available for your enjoyment! The location is truly exceptional. Siesta Key Beach is renowned for its powdery white quartz sand and is consistently recognized among the nation’s finest beaches. The public beach area offers lifeguards, restrooms, concessions and beach amenities, making it especially appealing to families and vacationers. Inside, the residence is thoughtfully furnished and equipped for comfortable coastal living, continued rental income or a combination of both! The condo was extensively remodeled and has been enjoyed as a popular vacation destination. New impact windows and sliders give you the peace of mind and protect your investment. High-end finishes, stunning views and an inside laundry closet make this a guest favorite. Recent upgrades include impact windows and doors (2026), HVAC (2023), Water Heater (2026), Electrical Panel (2025) Beyond the beach, you’re just a short walk, bike ride or drive from Siesta Key Village, where you’ll find an array of restaurants, bars, shops and entertainment. Whether you’re looking for a personal beach retreat, a vacation home, or an income-producing investment, this turnkey Siesta Key condo offers an outstanding combination of location, Gulf views, privacy, covered parking and proven rental potential. Bring your suitcase and start enjoying the Siesta Key lifestyle! Very strong rental numbers - ask agent for more details. 2027 high season bookings are already in place!

1055 Beach Road Unit B602, 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
$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
$1,050,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome home to a fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring costal decor with modern neutral colors.This unit is nestled in B Building with direct beach access which is just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and car wash on grounds. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.

5780 Midnight Pass Road Unit 407, Sarasota
$2,550,000
2 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code
The Newest Boutique Gulf-Front Community on South Siesta Key with Proven Rental Performance Experience luxury beachfront living with the added benefit of documented rental income at Ten35 Seaside. This beautifully appointed 2-bedroom, 2.5-bath Gulf-front residence has generated over $164,800 in gross rental income, with more than $101,000 already recorded in 2026, offering a rare opportunity to enjoy an exceptional coastal lifestyle while helping offset ownership costs. The open floor plan features Wolf and Sub-Zero appliances, custom cabinetry, designer finishes, and expansive sliding glass doors opening to a private terrace. The spacious primary suite includes a spa-inspired bath and walk-in closet, while the guest suite with custom built-in bunk beds adds flexibility for family, guests, or vacation rentals. Enjoy private beach access, a Gulf-front pool and spa, fitness center, private cabanas, and the convenience of being just minutes from Siesta Key Village, dining, shopping, and downtown Sarasota. Whether you're seeking a luxury beachfront residence, vacation home, second home, or income-producing investment property, Ten35 Seaside offers one of the strongest combinations of boutique Gulf-front living and proven rental performance on Siesta Key. Buyer to independently verify rental policies, income history, room dimensions, HOA information, and all property details.

1035 Seaside Drive Unit 308, 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
$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
$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
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Surf & Racquet SubDv. ⋅ 34242 Zip Code
Great Opportunity at Sarasota Surf & Racquet Club!! Beautifully turn-key furnished 2BR/2BA condo with a split bedroom floorplan for privacy in Tower 10 Unit 3 right on the beach with a gorgeous view of the Gulf and the beautiful quartz sand beach and shoreline. The onsite rental management team takes care of your investment. You use it when you want and enjoy the great revenue stream coming your way with a rare and great opportunity to take advantage of their 3 night rental minimum policy and managing all the reservations and taking care of the upkeep and cleaning of your unit. This is really exceptional beachfront living on Siesta Key with so many resort style amenities. You have direct access to private Crescent Beach, two heated swimming pools, rental options for tents, cabanas and umbrellas, beachside and poolside BBQ grills, four pickleball courts, three tennis courts (one hard court and two Har-Tru clay) – the only clay courts for a resort community on Siesta Key. There is a fitness center on the property and a recreation room where owners can come together for fun. The interior of this unit has been re-modeled with a lovely coastal look. Both bathrooms have been beautifully re-modeled. The primary bedroom features a king size bed, large walk-in closet and has its own private vanity area and a stunning tiled walk-in shower with a seat and gorgeous glass block. The second bedroom features two queen size beds and large walk-in closet. There is a lanai/room looking out to the beach and Gulf that is perfect for a quiet space for reading or computer work. Washer and Dryer located in laundry room just steps from the unit. This resort style property has it all! Catch the trolley or walk into the Siesta Key village for great shops and lots of great casual dining or more polished dining experiences. Coastal music flows out from the open air fun places for entertainment. Come enjoy Paradise!!!

5920 Midnight Pass Road Unit 1003, Sarasota
$1,495,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
This Rare Beachfront, Classic Coastal Modern extensively renovated 2/2 condo has your Dream View! Unobstructed Beach View of 400’ of private beach on 7 acres. Offering total building area for unit is 1568 sq ft. Modern appointed living area is 1316sq ft with additional 252 sq ft Modern Private Lanai. High demand all year Monthly (12) rentals for Investor, 2nd Home or Primary Home. Passed Structural Integrity. Strong, Fully Funded Reserves. Replaced cast iron to New “PVC” drains in entire building, New building roof, New clubhouse roof lowered insurance master policy. Stilted Building, Designated Parking underneath. Gated with 24 Hr Security. Condo has Brand New HVAC 2026 with R454B gov. required cooling & New Water Tank. Designed by Owner, Floor to Ceiling integrating a cohesive Classic Coastal Modern feel throughout. Enjoy your “private outdoor living” new screened 31’x8’ Beach Lanai (no houses/buildings in line of sight) Modern flooring, locking storage Door. Condo is insulated & extremely “Quiet” w/updated PGT impact Sliders and Windows. Solar Shades are see-through when down on sliders but front windows have see-through Solar Shades & Privacy Shades. The Front has Quiet Solid Core Impact Door. Wi-Fi Thermostat. Stunning Modern Polished Porcelain, Large Rectified 24” Tile for entire condo & closets. Modern Frosted Glass Framed Solid Wood 4 Interior Doors. Frosted Glass Framed Solid Wood Interior Bifolds for all 7 closets, continuing a clean line design with 8” Solid Wood, Mitered Baseboards throughout. Calming Lighting with all LED lighting dimmers throughout & all walk-in closets. All Closets designed w/Solid Wood Shelving & fitted w/thick satin nickel Rods and Brackets to All Studs for Heavy organization needs. Both Bathrooms have Moreno Gloss Floating Soft Close Drawer Vanities w/satin nickel Series Pfister Kenzo Waterfall Faucets/Shower Handel & 4 piece Towel bar set. Kohler Skirted “Chair-Height” Toilets for both. Main bath is Designed w/24” Italian Carrera Marble Tile, full size Bench & tall Niche. Guest bathroom Designed w/24” Ivory Glass Tile & Tall Abalone Tile Niche. With owners not being a chef/cook, kitchen is gently used in immaculate condition. ALL "SMART Wi-Fi" Stainless Appliance Suite, Largest Size features; “Double Oven” 5 burner w/Warming Drawer. Refrigerator “Showcase” Triple French Door, ice/water, Middle Flex Drawer, Bottom Freezer Double Drawer. Stainless “Triple Storm” Dishwasher. Kohler 36” Large Stainless Steel Apron Sink w/Kohler Pull down Stainless Faucet. Matching to Suite are Over Size Stainless "Wi-Fi" Front Load Washing Machine & Front Load Dryer on Stainless Pedestals in “walk-in” Laundry Room, stainless light, solid wood shelving w/nickel stainless rod/brackets designed for Heavy storage needs. Owner has variety remodeled Product in front closet. This beachfront condo has been gently lived in and all the Design Aspects/Appliances are in Immaculate Condition. Clubhouse w/ 25‘x40‘ Heated Swimming Pool, Tennis & Pickleball Courts, updated Fitness room, bathrooms, your private locked Storage Room. Private Beach gate to Boardwalk w/ picnic area, 2 grills & birdwatching benches. Pet friendly, designated large pet park w/bench. “Private ISLAND Style Living” A truly Coveted Opportunity awaits you- private, unobstructed view, full condo length beachfront lanai, 6 floor, 7 acre property & 400’ beachfront. Property is available for Same Day Showings.

420 Beach Road Unit 606, Sarasota
$8,500,000
3 Beds ⋅ 4 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Welcome back to 648 Beach Road, you’ve seen it before, but it’s better than ever. Reconstructed, reimagined, and elevated in every detail, this extraordinary residence delivers the same breathtaking, front-row views you remember… with an entirely new feel that’s fresh, refined, and built for the way you live now. This expansive three-bedroom retreat lives like a private resort, with the space to convert to a five-bedroom, perfect for hosting, creating office space, or adding guest suites without sacrificing flow. Step outside to a wraparound terrace on every floor, designed for sunrise coffees, sunset cocktails, and everything in between, because when your backdrop is this spectacular, indoor/outdoor living isn’t a feature, it’s a lifestyle. Ride your private elevator to the top and discover the ultimate luxury: a private rooftop pool where the horizon becomes your daily view and the sky feels like it belongs to you. Add in a rare four-car garage, and you have a true coastal statement home, spacious, secure, and effortlessly impressive. 648 Beach Road isn’t just a comeback. It’s a glow-up, with the views you loved, and the home you’ve been waiting for.

648 Beach Road, 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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