Siesta Key Homes with Community Mailbox Community Features

Siesta Key Homes with Community Mailbox Community Features

Welcome to Siesta Key, a picturesque barrier island nestled off the southwestern coast of Florida in Sarasota County. Renowned for its stunning white sandy beaches and vibrant turquoise waters, Siesta Key is a tropical paradise that offers an idyllic lifestyle for residents and visitors alike. With a laid-back atmosphere, this charming community is perfect for those who appreciate both relaxation and adventure, from sunbathing on the beach to exploring local boutiques and dining at exquisite seaside restaurants.

One of the most appealing aspects of living in Siesta Key is the sense of community that thrives here. Homes with community mailbox features foster a friendly neighborhood atmosphere, encouraging residents to connect and engage with one another. Imagine greeting your neighbors during your daily stroll to collect your mail or exchanging pleasantries while enjoying the beautiful Florida weather. These community mailboxes not only serve as a convenient hub for postal services but also create a welcoming environment that enhances the overall living experience.

Siesta Key is not just about stunning beaches; it also boasts a diverse range of recreational activities, including water sports, fishing, and biking along scenic trails. The area is rich in culture and offers a variety of events throughout the year, from art festivals to live music performances. Whether you’re seeking a permanent residence or a vacation getaway, Siesta Key’s charming homes and vibrant community spirit make it an exceptional choice for those looking to embrace the Florida lifestyle. Come discover the magic of Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Community Mailbox Community Features

$1,495,000
2 Beds ⋅ 2 Baths ⋅ A4703277 MLS ⋅ 6144 BLDG.
Welcome to effortless beachfront living at Island House on iconic Siesta Key, where spectacular Gulf views, a premier location, and relaxed coastal style come together beautifully. Located on the second floor of one of the community’s most desirable beachfront buildings, this condo enjoys truly unobstructed views of the beach and Gulf with no neighboring building blocking the scenery. The water views are visible throughout the main living spaces, as well as from both the primary and guest bedrooms, creating a constant connection to the beauty of Siesta Key. On the beach residence with natural light while showcasing the turquoise Gulf and famous shoreline. Just steps from the beach, this location offers the convenience of true beachfront living while the elevated second-floor position provides added privacy and peace of mind. The unit has experienced no prior water intrusion or storm damage, and a convenient ramp makes transporting luggage and beach gear easy. Inside, the condo is move-in ready with tile flooring throughout, an updated kitchen featuring solid-surface and granite countertops, and beautifully renovated bathrooms with stylish tiled showers. The comfortable, low-maintenance interior makes it equally appealing as a personal vacation retreat or an income-producing property. With a flexible three-night minimum rental policy, this residence offers excellent investment potential while still giving owners the opportunity to enjoy their own Siesta Key getaway. Island House provides an impressive collection of amenities, including on-site management, beautifully refreshed landscaping, a heated community pool, beach chairs and chaise lounges, shaded beach cabanas, outdoor dining areas, shuffleboard, cornhole, and a clubhouse with billiards, foosball, board games, and puzzles. When you are ready to explore beyond the beach, take advantage of the free Siesta Key trolley or local ride services to Siesta Key Village for dining, shopping, and entertainment. Turtle Beach, downtown Sarasota, boating, fishing charters, museums, performing arts venue

6144 Midnight Pass Road Unit 4N, Siesta Key
$865,000
2 Beds ⋅ 2 Baths ⋅ A4704645 MLS ⋅ Tivoli By The Sea BLDG.
This beautifully furnished turnkey, two-bedroom, two-bath condominium, will charm you with the luxury of direct access to world renown ‘’Siesta Key Beach. Embrace a rare opportunity to own at ‘Tivoli By The Sea’, the perfect combination of a desirable island location with resort-style amenities. You’ll savor vivid sunsets and panoramic views of the Gulf’s turquoise waters, all from your 26-by-6-foot private balcony. This condo is in immaculate condition, and perfect for year-round living, seasonally, or as an investment property. The modern open floor plan creates a seamless indoor-outdoor flow throughout the home. Sliders from the spacious Dining Room/Living Room area offers plenty of space for entertaining. The Primary Bedroom suite, which features a king-size bed, a vanity area and walk-in closet, also has its own set of sliders to the oversized balcony. The contemporary eat-in kitchen is bright and pristine, with thoughtful updates. The large Guest Bedroom, and nearby full Guest Bath, provides family and guests with their own quiet respite. There’s also a top-floor one bedroom Guest suite, available to owners at affordable weekly reservations for their visiting guests (see the photos). ‘Tivoli By The Sea’ offers an impressive collection of amenities including: a heated swimming pool, fitness center, recreation room, tennis/pickleball court, basketball court, putting green, and ping-pong table. You’ll be a short stroll to the sugary sands of Siesta Key Beach from your private gate. The rooftop Club Room features stunning 270-degree gulf views, and can be reserved for private parties. Each condo includes a storage unit, a covered parking space, and hurricane shutter protection. The building has benefited from numerous updates in recent years. Plumbing updates in 2014, electrical updates in 2017, replacement of catwalk railings in 2019, resurfacing of the tennis and pickleball courts in 2020, and a new roof in 2023. 'Tivoli By The Sea' boasts a strong track record for weekly & monthly rentals, all handled by the on-site company, 'Beachside Management'. Less than five minutes from Siesta Key Village, the home affords convenient access to an array of restaurants, shops and nightlife. Parasailing, paddle boarding, kayaking, boating rentals, and fishing, all provide endless opportunities to enjoy the surrounding waters. Downtown Sarasota is a simple drive with its vibrant arts and entertainment scene. Your social calendar will be filled with tons of culture to enjoy with the ‘Van Wezel Performing Arts Hall’, ‘Sarasota Opera House’, ‘Asolo Repertory Theatre’, ‘Florida Studio Theatre’ and the ‘Marie Selby Botanical Gardens’. Sarasota-Bradenton International Airport is a short drive away. This wonderful condo is vacant and easy to show!

625 Beach Road Unit 301, Siesta Key
$699,900
2 Beds ⋅ 4 Baths ⋅ A4706470 MLS ⋅ Midnight Sea BLDG.
Live the Siesta Key lifestyle just moments from the beach! This beautiful three-level townhome offers 2 spacious bedrooms, plus an additional room on the lower level, 2 full baths, 2 half baths, an oversized one-car garage, and two additional outdoor parking spaces. The extra lower-level room could be used as a third bedroom, study, home office, gym, media room, or private guest space. The main living level features hardwood flooring, abundant natural light, and a screened lanai directly off the living room - perfect for morning coffee, outdoor dining, or relaxing after a day at the beach. A second private lanai is located off the primary bedroom, creating a peaceful personal retreat. Recent improvements include a new roof (2024), new electrical panel (2024), HVAC (2024), tankless water heater (2024), washer and dryer (2025), all four new toilets (2025), updated flooring on the stairs and in both bedrooms, and a completely renovated lower level with an added shower. (2024). Popcorn ceilings have been removed throughout all three levels. Additional exterior improvements include new water lines (2026), new pavers (2026), new gutters, fresh exterior paint, and hurricane-impact sliding doors throughout, the entire house was repiped. Enjoy the community pool and deeded beach access located approximately 200 yards away. The townhome is also conveniently close to Siesta Key’s south beach area, Point of Rocks, 7-Eleven, restaurants, shops, grocery options, and bike and recreational rentals. Previously enjoyed by the owners as their own vacation retreat and also used as a rental property (during season this home can produce $9-11K, and off season months - $4-5K), this townhome offers wonderful flexibility. It could be an excellent primary residence, second home near the Gulf, or investment opportunity in one of Sarasota’s most desirable beach communities. Offered furnished, including beach equipment, for an easy transition into island living. Seller is offering up to $500 toward a one-year home warranty of the buyer’s choice at closing. Start enjoying Siesta Key!

6840 Midnight Pass Road, Siesta Key
$649,000
2 Beds ⋅ 2 Baths ⋅ A4706193 MLS ⋅ 8701 BLDG.
Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, this spacious condo blends modern coastal luxury with vibrant island living. Wake up to spectacular sunrises over the Intracoastal from your private, enclosed lanai, and wind down with sunsets via deeded beach access directly across the street. The generous primary suite features a walk-in closet, and a private entrance to the lanai. An in-unit laundry room includes a full-size washer/dryer and extra storage—a rare luxury on the Key! Additional upgrades include hurricane-impact windows to perfectly frame the water views. One of the most valuable features is the private, oversized 1-car garage providing secure parking and ample gear storage. Pet-friendly Turtle Bay offers premium amenities: brand-new boat docks/slips (just $300/year and you can add your own hoist), an updated fishing pier, kayak launch/storage, heated pool/spa, lighted tennis/pickleball courts, shuffleboard, clubhouse, and grilling area. Enjoy maintenance-free ease with on-site management, secure entry, and elevators. Leave your car behind and take the free trolley to nearby Siesta Village, South Village, or Point of Rocks snorkeling. Just minutes to Stickney Point Bridge and 20 minutes to downtown Sarasota. Perfect as a full-time residence, seasonal escape, or a great investment income opportunity.

8701 Midnight Pass Road Unit 304A, Siesta Key
$400,000
2 Beds ⋅ 2 Baths ⋅ N6145721 MLS ⋅ 116 BLDG.
Your Siesta Key Lifestyle Awaits — The Time to Own Is Now! Welcome to one of Sarasota’s most sought-after coastal destinations, where the beauty of Siesta Key is right outside your door. This completely updated ground-floor residence captures the true essence of coastal living with a soft, neutral palette and a relaxed, welcoming atmosphere. This property sets itself apart from all the others—it makes you feel right at home at the beach the minute you arrive. The spacious bedrooms provide plenty of room for family and guests, with the oversized guest bedroom large enough to accommodate two full-size beds, comfortably sleeping four. The beautifully refreshed kitchen features new appliances, quartz countertops, updated cabinetry, and a new tile backsplash that perfectly complements the home’s coastal-inspired design. Extend your enjoyment outdoors in the enclosed lanai, offering privacy and a comfortable space to enjoy year-round. There is also the possibility of adding a paver extension to the lanai, creating even more outdoor living space for relaxing and entertaining. A convenient in-unit laundry closet with washer and dryer adds to the ease of everyday living, while storm windows and doors provide added peace of mind. And then there’s the lifestyle! Spend your days enjoying the world-famous sands of Siesta Key Beach, explore the beauty of Selby Gardens, shop and dine at St. Armands Circle, or head into downtown Sarasota for its incredible restaurants, arts, culture, and waterfront attractions. And don’t miss one of the area’s most anticipated fall events—the Siesta Key Crystal Classic Sand Sculpting Festival. Come be part of the fun, experience the incredible artistry, and enjoy yet another reason why life on Siesta Key is so special. The time is now to make this coastal retreat your own and be ready for the 2027 season. Whether you’re looking for a full-time residence, a beach escape, or your own piece of the Siesta Key lifestyle, this beautifully updated home offers something truly special. Come see for yourself why this one feels different. Your beach lifestyle begins the minute you arrive.

116 Vista Hermosa Circle Unit 108C, Siesta Key
$875,000
1 Beds ⋅ 1 Baths ⋅ A4705633 MLS ⋅ N/A BLDG.
Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just steps from your private beach with plenty of beach chairs and five sun cabanas. Enjoy the crystal sands of Crescent Beach where the sand is always cool and you’ll never miss a sunset. This spacious 1-bedroom retreat boasts over 1,000 sq. ft. and has tiered ceilings up to 9 ½ feet. The west facing wall has oversized 6-foot-high impact windows that frame breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Perched above the lobby and mezzanine, use the elevator to enter this bright and cheerful end-unit with west and south facing windows in the living room. Enjoy an open, airy floor plan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. The generously sized bedroom has south and east facing windows and an en-suite bathroom with a beautifully tiled walk-in shower. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. This unit comes with private carport storage for all your beach toys. Hop on the free Siesta Key trolley for world-class dining and shopping. Come see why Siesta Key is ranked the #1 Beach in the USA and #4 in the world—your piece of paradise awaits!

6140 Midnight Pass Road Unit 101, Siesta Key
$1,325,000
2 Beds ⋅ 2 Baths ⋅ A4705155 MLS ⋅ South Tower BLDG.
Welcome to the ultimate Siesta Key getaway at Unit 612 in Siesta Breakers! This beautifully updated penthouse is completely move-in ready and offered TURNKEY FURNISHED—just bring your sunglasses, swimsuit, and sense of adventure! Light, bright, and stylish, this fabulous residence offers gorgeous beach and pool views from the living room and screened-in patio. Spacious rooms, two oversized walk-in closets, and the convenience of an interior washer and dryer add to the great layout. The open kitchen and well-designed floor plan create the perfect setting for entertaining family and friends or relaxing after a sun-filled day at the beach. And when you’re ready to let the property work for you, Siesta Breakers permits weekly rentals and features an on-site management and rental office to help maximize rental opportunities. This gated, beautifully landscaped beachfront community sits directly on world-famous Crescent Beach and offers a fabulous lineup of amenities, including a sparkling pool, lighted pickleball and tennis courts, updated clubhouse, and DEEDED BEACH ACCESS. Just across the street, enjoy dining, shopping, and a full-service marina with boat rentals. Popular Siesta Key South Village is only steps away with local favorites such as Captain Curt’s Crab & Oyster Bar and a full-service grocery store. Need to stay connected? The updated clubhouse provides a convenient space for an uninterrupted Zoom meeting or conference call. Current building renovations are enhancing the community and offering peace of mind. The free Siesta Key trolley provides easy access to everything the island has to offer and you may find yourself happily ditching the car altogether. This is coastal Florida living at its most carefree, convenient, and fun—come experience your own slice of paradise on Siesta Key!

6480 Midnight Pass Road Unit 612, Siesta Key
$3,995,000
4 Beds ⋅ 3 Baths ⋅ A4704110 MLS ⋅ Ten35 Seaside BLDG.
Welcome to Ten35 Seaside Drive, a newer mid-rise community at the south end of world-renowned Siesta Key Beach, where turquoise Gulf waters meet pristine quartz sand. Ten35 Seaside elevates island living with luxurious residences designed to highlight the area’s natural beauty. Gulf-view residence 502 offers four bedrooms, three baths and 2,385 square feet of thoughtfully designed living space. Floor-to-ceiling glass, an open-concept interior, and expansive terraces frame sweeping views of the sea, sand and sky. Refined finishes include porcelain tile floors, premium cabinetry, top-of-the-line appliances and a spacious primary suite with a spa-inspired bath. The main terrace is ideal for enjoying spectacular sunsets, while a second terrace off the en-suite guest bedroom captures beautiful sunrises. The kitchen features solid-wood cabinetry, Wolf and Sub-Zero appliances, a gas cooktop and a wine refrigerator. Additional highlights include solid-core entry and interior doors, floor-to-ceiling, hurricane-resistant balcony doors with laminated solar-tinted glass, sound-reducing laminated windows with solar-tinted glass, a recirculating hot-water system, high-efficiency heating and air conditioning, stained tongue-and-groove cypress terrace ceilings, tiled terrace floors and two covered parking spaces. Ten35 Seaside offers amenities that complement its beachfront setting, including a swimming pool and spa, fire pit, beach lounge chairs and umbrellas, kayaks, paddleboards, concierge-arranged water activities, fitness center and Gulf-front barbecue area. Daily beach chairs and umbrellas are also available. Residence 502 presents a rare opportunity to own a fully operational, potential income-producing property on Siesta Key’s Crescent Beach, one of Florida’s desirable vacation rental destinations. The residence is enrolled in the community’s on-site professional rental management program, providing immediate revenue while eliminating the setup time and day-to-day demands of vacation-rental ownership. Marketing, guest services, housekeeping and operations are managed on-site, allowing owners to potentially earn income while reserving time for personal use. Rental terms permit one-week minimum stays during the off-season and two-week minimum stays during peak season, balancing revenue potential with property preservation. Just moments from the dining and shopping of Siesta Key’s South Village, the property consistently attracts repeat visitors, supporting strong occupancy. Whether you are expanding an investment portfolio, completing a 1031 exchange or seeking a vacation home that can offset ownership costs, Residence 502 offers a rare combination of a Gulf-front location, professional management and potential rental income from day one. A must-see opportunity.

1035 Seaside Drive Unit 502, Siesta Key
$399,000
2 Beds ⋅ 1 Baths ⋅ A4704655 MLS ⋅ G-11 BLDG.
Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Siesta Key
$529,000
2 Beds ⋅ 2 Baths ⋅ A4703214 MLS ⋅ 8977 BLDG.
Experience true waterfront living at Sunrise Cove with spectacular Intracoastal Waterway views, breathtaking sunrises each morning, and beautiful moonrises each evening. This TURNKEY FURNISHED 2- bedroom, 2-bath condo is located on the second floor and offers the perfect blend of comfort, convenience, and resort-style amenities. The spacious living room features sliding glass doors that open to a screened-in lanai, creating the perfect setting to relax and enjoy panoramic Intracoastal views throughout the day. The primary bedroom offers a walk-in closet and en-suite bath, while the second bedroom also features a walk-in closet and beautiful views toward the Gulf of Mexico and the beach across the street. The hall bathroom includes a walk-in shower and tile flooring. The kitchen features a convenient pass-through to the dining and living areas, making entertaining effortless. Sunrise Cove offers an impressive array of amenities, including two heated swimming pools, an Olympicsize pool with restrooms and a covered lounge area, pickleball and tennis courts, a state-of-the-art fitness center, and a game room. On-site management and 30-day minimum rentals provide flexibility and excellent income-producing potential. Turtle Beach is directly across the street, while the free Siesta Key Breeze trolley stops nearby approximately every 15 minutes, making it easy to explore Siesta Key. Two popular waterfront restaurants, Turtles on the Bay and Ophelia’s on the Bay, are conveniently located right next door. Additional features include an extra storage closet conveniently located near the elevators in the laundry room. Recent community improvements include new roofs, new docks, and newly completed carports. Whether you’re looking for a vacation getaway, income-producing property, or full-time residence, this fabulous waterfront condo offers an exceptional opportunity to enjoy the best of Siesta Key living.

8977 Midnight Pass Road Unit 219, Siesta Key
$580,000
2 Beds ⋅ 2 Baths ⋅ A4704350 MLS ⋅ 4 BLDG.
Welcome to your Siesta Key getaway at Midnight Cove II! This desirable first-floor condominium offers a wonderful combination of coastal living, resort-style amenities, and investment potential. Conveniently located close to the heated community pool, the unit enjoys a peaceful canal view and easy access to all that this popular Siesta Key community has to offer. Midnight Cove II is a sought-after bayside community with weekly rentals allowed, making this an attractive opportunity for those seeking a vacation home, investment property, or both. The community offers on-site management and a rental office, providing convenience for owners who want professional support while maximizing their time enjoying the island. Residents and guests can take advantage of an impressive array of amenities, including a heated swimming pool, fitness center, tennis courts, and pickleball courts. The community also provides easy access to the beautiful beaches of Siesta Key, where you can enjoy the area's famous white quartz sand and spectacular Gulf sunsets. Whether you're looking for a place to escape to, a property to generate rental income, or your own piece of paradise on Siesta Key, this first-floor condo at Midnight Cove II is an opportunity worth seeing. Property Highlights First-floor location Beautiful canal view Conveniently located near the heated pool Weekly rentals allowed On-site management On-site rental office Heated community pool Fitness center Tennis courts Pickleball courts Desirable Siesta Key location Excellent vacation-home or investment opportunity Live the Siesta Key lifestyle and enjoy the flexibility of owning a property where you can relax, play, and potentially generate rental income.

1600 Cove Ii Place Unit 412, Siesta Key
$545,000
2 Beds ⋅ 2 Baths ⋅ A4703172 MLS
Welcome to your tropical retreat at Beachaven, a highly desirable beachfront community on Siesta Key! This turnkey charming 2-bedroom, 2-full-bathroom villa spans 813 sq. ft., offering the ultimate beach escape. Nestled just steps from the pristine powdery white sands and crystal-clear waters, this villa provides unparalleled access to sun-soaked beaches and breathtaking Gulf views. Enjoy your morning coffee or unwind in the evenings on your private lanai, where you can immerse yourself in the sounds of the ocean and the vibrant coastal atmosphere. Beachaven features a heated pool overlooking the ocean, perfect for relaxing while soaking in the sun or enjoying a refreshing dip. The community boasts a unique monthly rental program, allowing you to generate rental income with minimal fees while maintaining the flexibility of using your villa as a personal getaway. This property is ideal for investors or those looking to offset ownership costs. Experience a relaxed lifestyle in this serene community, with easy access to Siesta Key Village, where you can explore boutique shops, delightful restaurants, and lively farmers markets. This villa is more than just a home; it’s a gateway to a vibrant coastal lifestyle. Don’t miss your opportunity to own a piece of paradise in this sought-after location! **This villa offers new appliances and air conditioner installed in 2022. The roof was installed approximately 20 years ago, and the seller is willing to either replace it or provide a credit at closing for your convenience.**

5858 Midnight Pass Road Unit 13, Siesta Key
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