Siesta Key Homes with Gated Amenities

Siesta Key Homes with Gated Amenities

Welcome to Siesta Key, Florida, a stunning barrier island renowned for its powdery white sand beaches and vibrant coastal lifestyle. Nestled in Sarasota County, Siesta Key offers an idyllic blend of relaxation and recreation, making it a coveted destination for both residents and visitors alike. With its picturesque sunsets, crystal-clear waters, and a charming village atmosphere, Siesta Key captures the essence of Florida living.

Siesta Key is not just about its breathtaking beaches; it also boasts a diverse array of dining, shopping, and entertainment options. From casual beachside cafes to upscale restaurants, you’ll find culinary delights that cater to every palate. The island is also home to a variety of boutiques and art galleries, perfect for those looking to explore local culture and craftsmanship.

For those seeking a slice of paradise with added security and luxury, Siesta Key features an impressive selection of homes with gated amenities. These exclusive residences offer not only peace of mind but also a sense of community and privacy. Picture yourself living in a beautifully designed home surrounded by lush landscapes, where you can enjoy resort-style amenities such as swimming pools, fitness centers, and private access to the beach.

Whether you’re looking for a vacation getaway, a permanent residence, or an investment opportunity, Siesta Key’s gated communities provide an unparalleled lifestyle. Embrace the charm of island living while enjoying the comfort and security of a gated home in this enchanting Florida paradise. Explore the possibilities and make Siesta Key your next home sweet home!

Newest Siesta Key Homes with Gated Amenities

1350 Siesta Bayside Drive Unit 1350B, Sarasota
$899,000
3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in nearby Building 1328 on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multigenerational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddleboarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.

1350 Siesta Bayside Drive Unit 1350B, Sarasota

1328 Siesta Bayside Drive Unit 1328C, Sarasota
$699,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the second floor, a townhome layout. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.

1328 Siesta Bayside Drive Unit 1328C, Sarasota

9397 Midnight Pass Road Unit 506, Sarasota
$665,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
LIVE WHERE THE GULF MEETS THE BAY. Discover an extraordinary island lifestyle at The Pointe on Midnight Pass, a private, gated, waterfront community at the southernmost tip of Siesta Key, uniquely positioned at the convergence of The Gulf of America, Little Sarasota Bay, and Blind Pass Lagoon. This beautifully renovated 2-bedroom, 2-bath residence captures the rare magic of both sides of the island—wake to spectacular sunrises over Little Sarasota Bay and the Jim Neville Nature Preserve, then watch the sky transform at sunset over The Gulf. Thoughtfully updated, the residence features elegant tray ceilings and recessed lighting, solid-wood cabinetry, granite countertops, stainless-steel appliances, breakfast bar and pantry, contemporary baths with floor-to-ceiling tile, ceramic tile flooring throughout, sleek white interior doors, and sun-control shades on the lanai. A spacious lanai extends the living space outdoors, creating the perfect setting for morning coffee, sunset cocktails, or watching dolphins, manatees, seabirds and boats move through the surrounding waters. A private utility room houses the washer and dryer, while ground-level storage provides coveted space for beach, boating and golf gear. And then there is The Pointe—more than five acres of waterfront living, surrounded by water on three sides and embraced by an extensive seawall, with pathways winding throughout lush, mature tropical vegetation. Enjoy a heated pool and spa, lighted tennis and pickleball courts, fitness center, sauna, clubhouse, private island pavilion with grills, kayak and canoe storage and launches, fishing areas, boat docks, and on-site management—with a vibrant social calendar during season that brings neighbors together and makes it easy to connect, participate, or simply enjoy the island lifestyle at your own pace. The newly reopened Midnight Pass adds another extraordinary dimension, reconnecting the Gulf and Intracoastal waters and enhancing the boating, fishing and wildlife experience right outside your door. Walk or bike to Turtle Beach, enjoy nearby restaurants, or take the trolley to explore more of Siesta Key. This is not simply a condominium—it is the rare opportunity to own a front-row seat to the natural beauty, wildlife and ever-changing waters of southern Siesta Key.

9397 Midnight Pass Road Unit 506, Sarasota

6144 Midnight Pass Road Unit 4N, Sarasota
$1,495,000
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
Welcome to effortless beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, an exceptional beachfront setting, and relaxed coastal elegance come together in one very special residence. Perfectly positioned on the second floor of one of Island House’s highly desirable direct-beachfront buildings, Unit 4 North offers truly unobstructed views of the gorgeous sandy beach and sparkling Gulf of Mexico. With no neighboring building interrupting the panorama, the scenery takes center stage from the main living areas, filling the residence with natural light and creating the unmistakable feeling of being right on the water. Step outside and the beach is just moments away. The elevated second-floor location offers an appealing combination of privacy, convenience, and added peace of mind, while a convenient access ramp makes transporting luggage, groceries, and beach gear especially easy. The residence has experienced no prior water intrusion or storm damage. Inside, the condo is beautifully maintained and move-in ready, with tile flooring throughout for easy coastal living. The updated kitchen features solid-surface and granite countertops and opens comfortably to the living and dining areas, allowing the Gulf views to remain part of the experience whether you are entertaining or simply relaxing at home. Both bathrooms have been tastefully renovated with attractive tiled showers and updated finishes. Whether envisioned as a private Siesta Key retreat, a seasonal residence, or an income-producing investment, Unit 4 North offers outstanding versatility. Island House’s desirable three-night minimum rental policy provides excellent flexibility for owners who want to enjoy the property themselves while also taking advantage of strong vacation-rental potential. Island House offers an impressive collection of resort-style amenities designed for carefree island living, including professional on-site management, beautifully refreshed tropical landscaping, a heated community pool, beach chairs and chaise lounges, shaded beach cabanas, outdoor dining areas, shuffleboard, cornhole, and a welcoming clubhouse complete with billiards, foosball, board games, and gathering spaces. And when you are ready to explore beyond the beach, Siesta Key makes it effortless. Hop aboard the free Siesta Key trolley or use one of the island’s convenient local ride services to visit Siesta Key Village for restaurants, shopping, entertainment, and nightlife. Turtle Beach, boating, fishing charters, downtown Sarasota, museums, theaters, and Sarasota’s renowned arts and cultural attractions are all within easy reach. This is more than a beach condo—it is an opportunity to own a front-row seat to the Siesta Key lifestyle, where mornings begin with Gulf views, days unfold on one of Florida’s most celebrated beaches, and spectacular sunsets become part of everyday life.

6144 Midnight Pass Road Unit 4N, Sarasota

5855 Midnight Pass Road Unit 605, Sarasota
$719,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Harbor Towers 605 represents a unique opportunity to live on a high floor in the building with the coveted south-facing views looking over the pool. Welcome to Harbor Towers, your home at the beach- this perennial favorite building is now better than ever after undergoing massive exterior renovations which include strengthening and impact glass windows and sliding doors for all units! The unique and large grounds of Harbor Towers provide a spectacular setting with lots of space to enjoy the coastal lifestyle. You are not just buying a home, you're buying into a Yacht and Tennis Club, with har-tru tennis courts, a recently revamped marina with inexpensive boat mooring prices, a heated community pool, fitness center, meeting area, community kayak area and much much more. This unit has been renovated and lovingly cared for over the years. Besides the impeccable view down the Intracoastal Waterway, this unit offers well maintained luxury featuring tile floors throughout, kitchen update in 2021, in unit washer/dryer combo, full furniture package included- just to name a few. This unit must be seen to be appreciated. It is currently positioned in the rental program, but can be removed if desired. Pick your desired lifestyle- keep it all to yourself or earn some income to help pay for your investment. Harbor Towers is well taken care of and well managed. Onsite management, security and well funded reserves make this complex a true winner. This unit also has a covered carport spot that is included in the purchase. Don't wait on this opportunity- these types of units don't come to market very often. Schedule your private showing today!

5855 Midnight Pass Road Unit 605, Sarasota

6900 Bochi Circle, Sarasota
$2,175,000
4 Beds ⋅ 6 Baths ⋅ Coronas Park SubDv. ⋅ 34242 Zip Code
Architectural masterpiece tucked away in one of Siesta Key’s most coveted, private gated communities. Masterfully renovated, this executive estate seamlessly blends modern elegance with unparalleled coastal convenience. Positioned just one block from the water, the residence boasts beautiful views of the Gulf of Mexico and the glittering Sarasota skyline—offering front-row seats to world-class Florida sunsets every single evening. Built with peace of mind in mind, both the home and the community's ground level are significantly elevated to minimize flood risk, meaning this property has never flooded. Soaring high ceilings and impact-resistant windows and doors throughout. Convinent elevator providing effortless access to all levels. Chef’s kitchen equipped with premium Viking appliances, double convection ovens, and sleek quartz countertops.4 large bedrooms, each featuring private en-suite baths and spacious walk-in closets. Flexible bonus room perfect for a dedicated home office or a 5th bedroom. Extra-high ceilings throughout the entire house, creating an incredibly open, airy, and grand feel. Grand primary suite offering an extra-large layout, ocean and city views, and a spa-like bath. Convenient elevator servicing the living levels. Multiple private balconies that effortlessly expand your living space outdoors. Fully fenced backyard framed by lush, mature landscaping—ideal for pets. Outdoor oasis featuring a sparkling pool and a relaxing water fountain. Extra-large 3-car garage supplemented by a climate-controlled storage unit. Bonus ground-floor space, perfect for a secondary climate-controlled office or gym, complete with a half bath. Two nearly brand-new A/C units ensuring optimal climate comfort. Recently insulated attic with premium spray foam for maximum energy efficiency. Located just 5 minutes from the vibrant dining and shopping of Siesta Village and only 8 minutes from the sugar-white sands of world-famous Siesta Key Beach. This estate offers the ultimate balance of secluded privacy and immediate coastal accessibility.....Please Note-Some Photos Virtually Staged.

6900 Bochi Circle, Sarasota

9393 Midnight Pass Road Unit 205, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
This beautifully renovated 2-bedroom, 2-bath condominium overlooking the bay was freshly painted on 9/8/2026 and is truly move-in ready. Turnkey furnished with an open kitchen featuring granite countertops, stainless-steel appliances, and solid-wood cabinets. The thoughtfully reconfigured layout is ideal for entertaining or relaxing while taking in spectacular views of the bay and nature preserve. Both bathrooms have been nicely remodeled, with tile flooring throughout, recessed lighting, and solid-wood interior doors. Wake each morning to breathtaking sunrises from your bed with a cup of coffee or tea. The spacious air-conditioned lanai, with full-width sliding glass doors, is perfect for watching dolphins and manatees, boaters and kayakers, or simply enjoying a good book. In-unit washer and dryer plus a separate lower-level storage area for beach chairs, fishing gear, golf equipment, and more. Simple paradise! *** THE POINTE is a pet-friendly gated community that offers the best of both worlds — activity and exercise alongside peace and tranquility. Surrounded by water on three sides and set on 5+ acres of prime waterfront, residents enjoy boat docks with electricity and water, outdoor walkways to each unit, a heated outdoor lap pool, spa, sauna, kayak/canoe/SUP launches, tennis and pickleball courts, dog walk, open-air gazebo with BBQ grills, clubhouse, entertaining/party rooms, fitness centers in each building, a non-smoking environment, butterfly garden, and more. Advantageously located near fine and casual dining, Turtle Beach, shopping, coffee shops, nightlife, entertainment, Siesta Key Beach, a full-service marina, public transportation, and everything else this island paradise has to provide A rare opportunity to own a true piece of Siesta Key.

9393 Midnight Pass Road Unit 205, Sarasota

7740 Sanderling Road, Sarasota
$22,000,000
6 Beds ⋅ 8 Baths ⋅ Siesta Properties Inc SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, nearly one acre of pristine beachfront offers an exceptional canvas for a world-class custom residence in one of Florida's most exclusive coastal communities. Positioned along the sugar-white sands of Siesta Key, this rare Gulf-front homesite presents an unparalleled opportunity to design a private waterfront retreat with sweeping panoramic views of the Gulf of Mexico, spectacular year-round sunsets, and direct access to one of the world's most celebrated beaches. With expansive frontage and generous dimensions, the property invites limitless architectural possibilities—from a contemporary coastal masterpiece to a timeless estate designed for generations to enjoy. Located within the prestigious Sanderling Club, this exceptional property enjoys the distinction of being part of Siesta Key's only private, gated Gulf-front community with 24-hour manned security. Originally envisioned by renowned Architect Paul Rudolph, Sarasota School of Architecture, Sanderling Club has long been recognized as one of Sarasota's most coveted residential enclaves, where privacy, natural beauty, and architectural excellence come together in a setting unlike any other on Florida's Gulf Coast. Residents enjoy an exclusive collection of amenities, including a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, scenic nature canopy roads , and beautifully maintained grounds that preserve the community's tranquil coastal character. The neighborhood's low density and commitment to preserving its natural environment have made Sanderling Club one of the region's most enduring luxury addresses. Beyond the gates, Siesta Key offers an internationally acclaimed lifestyle defined by its powder-soft quartz beaches, turquoise Gulf waters, and relaxed sophistication. From waterfront dining and boutique shopping in Siesta Key Village to boating, paddleboarding, fishing, and endless days on the water, the island offers an effortless blend of recreation and refinement. Just minutes away, downtown Sarasota provides a vibrant cultural scene that rivals much larger metropolitan destinations. Residents enjoy world-class performing arts, acclaimed restaurants, private clubs, championship golf, luxury shopping, art galleries, marinas, and exceptional healthcare. From evenings at the Sarasota Opera or the Van Wezel Performing Arts Hall to waterfront dining at Marina Jack and shopping at St. Armands Circle, Sarasota continues to rank among the nation's premier luxury lifestyle destinations. Large Gulf-front homesites of this caliber have become exceedingly rare. Combining nearly an acre of buildable beachfront, extraordinary privacy, direct Gulf frontage, and the prestige of Sanderling Club, 7740 Sanderling Road represents an opportunity to create an iconic waterfront estate in one of the most desirable addresses on Florida's Gulf Coast. This is more than a homesite—it is the foundation for a legacy.

7740 Sanderling Road, Sarasota

6300 Midnight Pass Road Unit 809, Sarasota
$1,795,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an impressive rental history—all within one of Siesta Key’s most recognizable beachfront communities. Beyond its appeal as a personal beachfront escape, #809 offers an established rental history. The residence averages more than $80,000 in annual gross rental income (2024 – 2026), with bookings extending through year-end, offering a compelling opportunity for buyers seeking to combine personal enjoyment with income potential. Inside, the 1,271-square-foot residence has been thoughtfully reimagined with a fresh coastal aesthetic, luxury vinyl wood-plank flooring throughout, custom architectural ceiling treatments, and an open floor plan that keeps the Gulf firmly in view. The designer kitchen is both polished and functional, featuring granite countertops, custom Shaker-style cabinetry, stainless steel appliances, and a refrigerator cleverly concealed behind coordinating custom cabinet panels. The kitchen opens naturally to the dining area, where a built-in banquette creates an inviting gathering space beneath a dramatic coffered ceiling accented by designer lighting and naturally stained solid-wood beams. Beyond, the Gulf-front living room is framed by walls of glass, drawing your eye directly toward the water and opening to the screened terrace. The terrace is where the Siesta Key lifestyle truly takes center stage. Stretching across the Gulf-facing side of the residence, this generous outdoor living space provides a front-row seat to turquoise water, passing boats, and spectacular Gulf sunsets. A desirable split-bedroom floor plan provides privacy for owners and guests, with both bedrooms positioned to enjoy Gulf views and direct access to the screened terrace. Each bedroom also features a walk-in closet with built-in organization. The primary suite is complemented by a beautifully renovated en-suite bath with dual sinks, granite countertops, extensive built-in linen storage, and an oversized walk-in shower with bench seating. The second bath is also well appointed with newer cabinetry, stone counters and a tub/shower combination. Crystal Sands is an iconic Siesta Key beachfront community distinguished by its classic architectural presence and exceptional location directly on the Gulf of Mexico. Residents and guests enjoy a heated community pool, gated entry, elevators, recreation facilities, covered and guest parking, and direct access to the beach and Gulf. The residence also includes one covered carport space. And when you are ready to venture beyond the beach, some of Siesta Key’s favorite destinations are close at hand. Head north to Siesta Key Village for its lively collection of restaurants, boutiques, cafés, and nightlife, or south toward Crescent Beach, Point of Rocks, and the restaurants and conveniences surrounding Stickney Point Road. The Siesta Key trolley makes exploring the island especially easy, with service along the Key connecting beaches, dining, shopping, and Siesta Key Village.

6300 Midnight Pass Road Unit 809, Sarasota

5855 Midnight Pass Road Unit 222, Sarasota
$620,000
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Turnkey and ready for its next chapter, this spacious residence in the curve of Harbor Towers Yacht & Racquet Club is one of the largest floor plans in the building, featuring a split layout with each bedroom offering its own private bathroom. Sold completely furnished, this unit makes it effortless to fly or drive down and start enjoying it immediately, or begin renting it out right away. A rare find: existing washer/dryer electric hookups are already in place beneath the kitchen counter, a feature the building no longer permits for new installations. There's also a washer and dryer room located on the second floor just a few doors down. Picture the perfect Florida day: morning coffee on your enclosed patio overlooking the peaceful pond, then a match on the on-site tennis courts before laying out by the beautiful pool, both with views over the dock and water. Hop the trolley or take a short drive to the rose quartz sand beaches of Siesta Key, then wind down with happy hour and live music in Siesta Key Village. This unit can be rented short-term with a two-week minimum, and owners have the flexibility to use the community's on-site property management or bring in their own. Just three minutes to Siesta Key's world-famous beaches and five minutes to the shops and restaurants of Siesta Key Village, this is the perfect Florida lifestyle. Schedule your private showing today. Buyer to verify HOA rules regarding laundry hookups, boat slip rental terms, property management options, and rental restrictions.

5855 Midnight Pass Road Unit 222, Sarasota

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