Siesta Key Homes with Security Community Extras

Siesta Key Homes with Security Community Extras

Welcome to Siesta Key, Florida, a picturesque barrier island nestled in Sarasota County, renowned for its pristine beaches, vibrant culture, and serene lifestyle. This charming coastal community is famous for its powdery white sands, which have been consistently ranked among the best in the nation. With a laid-back ambiance, Siesta Key offers an idyllic escape for families, retirees, and everyone in between.

Imagine waking up to the soothing sounds of waves lapping against the shore and basking in the warm Florida sun. Siesta Key is not just about stunning beaches; it boasts a lively village atmosphere filled with boutique shops, delightful restaurants, and a thriving arts scene. Whether you’re enjoying a sunset at Siesta Beach or indulging in fresh seafood at a local eatery, the island exudes a welcoming charm that captivates all who visit.

For those seeking a home in this coastal paradise, Siesta Key offers a range of properties that cater to diverse lifestyles. Many of these homes come with exceptional community extras, including enhanced security features to ensure your peace of mind. Imagine living in a community where safety is prioritized, allowing you to fully embrace the island lifestyle without worry.

From luxurious waterfront estates to cozy beach cottages, Siesta Key has something for everyone. With its stunning natural beauty and welcoming community, it’s no wonder that Siesta Key is not just a place to live, but a place to thrive. Come discover your dream home in this enchanting slice of Florida paradise!

Newest Siesta Key Homes with Security Community Extras

5855 Midnight Pass Road Unit 221, Sarasota
$634,900
2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code
Beautiful turnkey 2-bedroom 2 bath condo in Harbor Towers! All new hurricane windows, window shades, new plumbing for entire home and hot water heater 2025. Master bedroom has walk in closet, renovated bath with floating vanity and tub/ shower combo. Second bedroom is large with lots of windows and connected bath with tub / shower and floating vanity. Dining room and Living room combo with open floor plan. Hurricane windows across the entire front of condo give lots of sun and nice view of the lake. This unit includes a covered parking spot ($15.000 value). Rental income is very strong with on-site management. Unit currently rented Feb 13, 2027- March 20th, 2027. Great rental Income! This property features many amenities, including, heated pool with kiddie pool, 2 BBQ areas, social room with renovated kitchen, Har-Tru tennis courts, fitness room, kayak storage, harbor with boat slip rental. Close proximity to Siesta Key beach. Harbor Towers also offers one of the lower HOA fees on the key for all that is included.

5855 Midnight Pass Road Unit 221, 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
5770 Midnight Pass Road Unit 301, Sarasota
$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
70 Avenida Veneccia Unit 304, 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
70 Avenida Veneccia Unit 204, 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
70 Avenida Veneccia Unit 202, 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
6267 Midnight Pass Road Unit 306, Sarasota
$650,137
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Motivated Seller! 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
7825 Sanderling Road, 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
5830 Midnight Pass Road Unit 32, 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
915 Seaside Drive Unit 402, Weeks 10-13, Sarasota
$80,000
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
4822 Ocean Boulevard Unit 3D, Sarasota
$825,000
2 Beds ⋅ 2 Baths ⋅ Siesta Towers SubDv. ⋅ 34242 Zip Code
This condominium at Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask in the glowing light of the stunning sunsets. Includes gym, fishing pier, BBQ, club house, and bike storage. Located on Siesta Key on the water, close to public beach access and Siesta Key Village. Many local beaches, parks, nature preserves, and bird sanctuary's close by. This turnkey fully furnished condo offers serene personal space, ample storage, walk in closet, lots of natural light, brand-new hurricane doors, eat in kitchen, dining room, living room, and office area. Designated parking space.

4822 Ocean Boulevard Unit 3D, Sarasota
206 Hourglass Way Unit V10, 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
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