Siesta Key Homes with Security Community Extras

Siesta Key Homes with Security Community Extras

Welcome to Siesta Key, Florida—a tropical paradise nestled along the stunning Gulf Coast in Sarasota County. Renowned for its powdery white sands and crystal-clear turquoise waters, Siesta Key is not just a beach lover’s dream; it’s a vibrant community filled with charm, culture, and a laid-back lifestyle that beckons both residents and visitors alike.

Living in Siesta Key means embracing a unique blend of coastal living and modern conveniences. The area boasts a variety of homes, many of which are nestled in secure communities that offer added peace of mind for families and individuals alike. These homes often feature luxurious amenities such as private pools, lush landscaping, and spacious outdoor areas perfect for entertaining. With security community extras, residents can enjoy a sense of safety and tranquility, allowing them to fully immerse themselves in the serene surroundings.

Siesta Key is not just about the breathtaking beaches; it’s also a hub for outdoor activities, with opportunities for kayaking, paddleboarding, and fishing right at your doorstep. The vibrant local dining scene offers everything from fresh seafood to international cuisine, ensuring there's something to satisfy every palate. With regular community events, art festivals, and live music, there's always something happening, making it easy to connect with neighbors and build lasting friendships.

Whether you are seeking a permanent residence or a vacation getaway, Siesta Key is a place where life feels like a never-ending holiday. Come discover the enchanting lifestyle that awaits you in this coastal gem!

Newest Siesta Key Homes with Security Community Extras

$1,099,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi, thermostat keyless entry! Your new condominium will be sold turnkey furnished, nothing to do except move in. Open floor plan great for entertaining. A super beverage cooler has been installed in the kitchen. You will find pull-outs and soft close doors & drawers. Two full sized beds in the guest room, and the main suite has gulf views, double vanities for convenience. Both bathrooms have walk-in showers. This is a split plan as well. What I really want you to see are the community grounds… the condo is fabulous, and this community is spectacular!!! You can search the state of Florida... no other community can compare itself to Gulf & Bay. Plus, END UNIT condos are the best - nothing compares to having an END UNIT. Gulf & Bay has 2 pools, new fitness center just steps away from the elevator plus saunas, tennis & PICKLEBALL courts, basketball, electric car charging stations, clubhouse, indoor hot tub. Another cool item is the complex is mapped out with its own app. Owners can easily navigate in and out of the grounds with your phone. No more fobs. Gulf & Bay is great for rental income. If you want rental income, this condo has it for 2027. Rentals must be a 30-day minimum 12 times a year. I know it just got better, right? Want to head to the village? Just hop on the free trolley out of the gates and head to the village for dinner and shopping. The condo is easy to show. Don’t miss seeing this community and condominium… the search is over... get here before this opportunity is gone! here are the dates booked for this coming season! Feb 1, 2027-Feb 28, 2027 27 nights $8,913.00 Mar 1, 2027-Mar 29, 2027 28 nights $10,052.00 Jan 1, 2027-Jan 31, 2027 30 nights $6,760.10 _____________ $25,725.10 As of 8-10-2026

5770 Midnight Pass Road Unit 301, Sarasota
$5,250,000
3 Beds ⋅ 4 Baths ⋅ Sunset Beach SubDv. ⋅ 34242 Zip Code
Introducing Residence #304 at Sunset Beach, Siesta Key's newest luxury address, where sophisticated coastal design and effortless living come together in an exclusive boutique beachfront community. One of only 11 private residences, this beautifully appointed home offers an exceptional blend of spacious interiors, elevated finishes, and timeless modern elegance. Designed to maximize comfort and functionality, the open-concept floor plan is filled with natural light through floor-to-ceiling hurricane-impact glass that seamlessly connects the living spaces to expansive outdoor terraces. The chef's kitchen is thoughtfully crafted with custom cabinetry, premium Wolf and Sub-Zero appliances, and designer finishes, while the spacious great room creates the perfect setting for entertaining or simply unwinding after a day on the beach. Luxurious bedroom suites provide a private retreat, each designed with comfort and sophistication in mind. Situated on 2.5 Gulf-front acres with 175 feet of private beachfront, Sunset Beach offers an unmatched collection of resort-style amenities, including a beachfront pool and spa, private cabanas, a fire pit, fitness center, grilling area, bicycles, and private owner storage. Just a short walk from Siesta Key Village, you'll enjoy boutique shopping, acclaimed restaurants, coffee shops, and live entertainment while returning home to the privacy and exclusivity of one of the island's most coveted new communities. Residence #304 offers the perfect combination of luxury, location, and exceptional design, making it an extraordinary opportunity to own at Siesta Key's newest luxury address.

70 Avenida Veneccia Unit 304, Sarasota
$4,950,000
3 Beds ⋅ 4 Baths ⋅ Sunset Beach SubDv. ⋅ 34242 Zip Code
Introducing Residence #204 at Sunset Beach, an extraordinary opportunity to own one of the largest residences at Siesta Key's newest luxury address. Offering more than 4,000 square feet of thoughtfully designed living space, this exceptional home combines the scale and comfort of a private residence with the effortless lifestyle of boutique beachfront condominium living. Designed with both everyday living and grand entertaining in mind, the expansive open-concept floor plan features soaring 10-foot ceilings, floor-to-ceiling hurricane-impact glass, generous gathering spaces, and seamless indoor-outdoor living. Every finish has been carefully curated, from the custom chef's kitchen with Wolf and Sub-Zero appliances to the beautifully appointed living spaces that showcase timeless modern coastal design. Spacious bedroom suites, luxurious baths, and oversized terraces provide the perfect balance of privacy and sophistication. As one of only 11 residences at Sunset Beach, owners enjoy an unmatched level of exclusivity along with resort-inspired amenities including a beachfront pool and spa, private cabanas, fire pit, fitness center, grilling area, bicycles, and private owner storage. Set on 2.5 Gulf-front acres with 175 feet of private beachfront, Sunset Beach is perfectly positioned just a short walk from the boutiques, acclaimed restaurants, coffee shops, and entertainment of Siesta Key Village, allowing you to enjoy the best of island living without ever getting in your car. Residence #204 is a rare opportunity to enjoy the spaciousness of a luxury home, the convenience of condominium living, and ownership at Siesta Key's newest luxury address

70 Avenida Veneccia Unit 204, Sarasota
$6,500,000
3 Beds ⋅ 4 Baths ⋅ Sunset Beach SubDv. ⋅ 34242 Zip Code
Virtually Staged. Welcome to Residence #202 at Sunset Beach, where timeless coastal luxury meets one of the most desirable floor plans on Siesta Key. Nestled within an exclusive collection of just 11 boutique beachfront residences, this exceptional home offers the rare opportunity to enjoy two Gulf-front bedroom suites, each perfectly positioned to capture spectacular water views and unforgettable sunsets. Thoughtfully designed for both relaxed everyday living and elegant entertaining, the spacious open-concept layout is framed by floor-to-ceiling hurricane-impact glass that fills the home with natural light and seamlessly extends onto an expansive Gulf-front terrace. The designer kitchen is appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and sophisticated finishes, while every space throughout the residence reflects a refined, modern coastal aesthetic. Set on 2.5 acres with 175 feet of private Gulf frontage, Sunset Beach delivers a true resort lifestyle with a beachfront pool and spa, private cabanas, fire pit, fitness center, outdoor grilling area, owner storage, and bicycles for exploring the island. Best of all, you're just a short walk from Siesta Key Village, where award-winning restaurants, boutique shopping, coffee shops, and vibrant island nightlife are all within easy reach. Residence #202 offers the perfect balance of beachfront serenity and walkable island living—a rare opportunity to own a brand-new luxury residence in one of Siesta Key's most exclusive communities.

70 Avenida Veneccia Unit 202, 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
$650,137
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Experience the ultimate island lifestyle in this beautifully appointed 2-bedroom, 2-bathroom condo on world-famous Siesta Key. Located just steps away from the powdery white quartz sands of Siesta Beach, this property grants you your own private deeded beach access where loungers are waiting for you. With the vibrant dining and shopping of the Village, this location cannot be beat. You can be picked up right at the front of the building with free transportation on the island. The split bedroom living space area features Italian porcelain tile flooring, crown molding, abundant natural light, hurricane impact windows throughout, NO popcorn ceilings here-smooth as butter, seamlessly flowing onto a private lanai where you can enjoy your morning coffee with a peaceful view of the courtyard, pool, pond, a peak of the Bay, and beautiful grounds. The community offers resort-style amenities, including two heated pools and hot tubs (one on the Bay side and one on the Gulf side), tennis courts, pickleball courts, a fitness center, shuffle board, fishing dock, grilling stations, library and a community room. You will have an assigned covered parking space under the building, ample additional parking for your guests and a storage unit for your beach toys. Excelsior Beach to Bay also has a management company on site to rent your unit while you are away for your convenience, if you choose to do so. You will love this close knit community and all the fun social events offered throughout the season. One week rentals now allowed outside of High Season! Call for your private showing today.

6267 Midnight Pass Road Unit 306, Sarasota
$2,795,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Discover a rare opportunity to build your dream estate within The Sanderling Club - Siesta Key’s premier and exclusive Gulf-front community known for its natural beauty, serenity, and unmatched coastal lifestyle. Set on 1.13 private acres overlooking the tranquil waters of Heron Lagoon, this cleared and ready-to-build homesite offers the perfect canvas to bring your architectural vision to life in a setting defined by timeless coastal elegance, Old Florida charm, and tropical surroundings - a true slice of paradise! Offering a rare amount of privacy, the property features no neighboring home on the left-hand side, creating an exceptionally secluded and peaceful setting. This expansive lot offers endless possibilities to create a one-of-a-kind residence tailored to your lifestyle. Stretching along the peaceful shoreline of Heron Lagoon, the setting is surrounded by calm water views, lush tropical scenery, and incredible natural beauty. Enjoy kayaking, paddleboarding, canoeing, fishing, birdwatching, or simply relaxing by the water while taking in the tranquil surroundings that make this opportunity so extraordinary. The Sanderling Club combines the beauty of Siesta Key’s coastal living with the privacy and security of an exclusive gated community. Residents enjoy private Gulf-front beach access where breathtaking sunsets over the Gulf of Mexico become part of everyday life, along with new Har-Tru tennis courts, pickleball courts, playground, marina access, and 24-hour staffed security. Boat slips, when available, provide direct access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico via the recently reopened Midnight Pass - a boater’s paradise. The community’s historic clubhouse is also entering an exciting new chapter, with newly released renderings envisioning a reimagined waterfront gathering space designed to further elevate The Sanderling Club lifestyle. Near Siesta Key’s world-renowned quartz sand beaches, Siesta Village, boutique shopping, fine dining, and Downtown Sarasota’s celebrated arts and cultural scene, this is an invitation to create your dream home in one of Florida’s most sought-after coastal destinations.

7825 Sanderling Road, Sarasota
$395,000
1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.

5830 Midnight Pass Road Unit 32, Sarasota
$100,000
2 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code
Fractional Ownership. Unique opportunity to own four consecutive weeks in March on Siesta Key Beach. Experience luxury beachfront living with this Winter Fractional Package, offering a 1/8th ownership share at The Residences on Siesta Key Beach. This rare offering provides the opportunity to own a piece of paradise on one of America’s most celebrated beaches while enjoying the comfort, convenience, and elevated service of a luxury resort. This expansive residence features a primary suite, a junior suite and beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen is appointed with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy the legendary hospitality and services of Hyatt Vacation Club, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy the best of Siesta Key beachfront living with resort-style amenities, full-service convenience, and luxury condominium ownership, all at a fraction of the cost.

915 Seaside Drive Unit 402, Weeks 10-13, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for multiple seating groups, while a wall of floor to ceiling sliders – treated with beautiful shades - provides an abundance of natural light. Meal prep is easy in your bright NEW kitchen featuring white cabinetry, subway tile backsplash, granite counters, stainless Whirlpool appliances, recessed lighting, fandelier, & vinyl plank flooring. Three sets of new hurricane impact sliders open from the kitchen, dining room, and 2nd bedroom into your private fenced brick paver patio which offers valuable outdoor space for sunny relaxation or effortless entertaining. Both newly carpeted bedrooms feature an extended living space to accommodate a small seating group, desk, or exercise equipment. The bathrooms have been refreshed with NEW granite countertops, cabinets, vanities & fixtures. NEW 2026 stacked W/D in garage. 2019 HVAC. Recent enhancements include exterior pressure washing and villa painting in February 2026. Newly updated brick paver driveway. New landscaping is being planned by the HOA starting in 2026. Whispering Sands is a premiere 55+ Gulf front property ideally located next to the colorful boutiques and dining options of Siesta Key Village, and offers 800’ of PRIVATE beach, 2 heated pools, new beachside Tiki Hut, grills, shuffleboard, canoe/kayak storage, security, & onsite management. The clubhouse is scheduled to be remodeled in 2026 and when completed will include fitness rooms, catering kitchen, and an elegant and comfortable space for social gatherings. Seller is willing to include 3 year new Kia SUV automobile with acceptable offer. Your coastal retreat awaits!

206 Hourglass Way Unit V10, Sarasota
$48,000
3 Beds ⋅ 2 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code
Fractional Ownership. Experience luxury beachfront living with this Winter Fractional Package offering a 1/16th share of ownership at The Residences on Siesta Key Beach. This is a rare opportunity to own a piece of paradise on one of America’s top-rated beaches while enjoying the comfort, convenience, and services of a luxury resort. This expansive residence features a primary suite, junior primary suite, and guest bedroom, along with beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen includes premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy legendary Hyatt Vacation Club hospitality services, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy everything you would expect from a luxury Siesta Key beachfront condominium with resort-style amenities and services, all at a fraction of the cost.

915 Seaside Drive Unit 312, Weeks 16-17, Sarasota
$510,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!

225 Hourglass Way Unit 202, Sarasota
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