Siesta Key Homes with Buyer Approval Required Community Features

Siesta Key Homes with Buyer Approval Required Community Features

Welcome to Siesta Key, Florida—a picturesque gem nestled in Sarasota County, renowned for its stunning beaches and vibrant community. This tropical paradise is famous for its powdery white sands, crystal-clear waters, and breathtaking sunsets, making it a sought-after destination for both vacationers and those looking to call this enchanting island home.

Siesta Key offers a unique blend of relaxation and excitement, with an array of outdoor activities, including kayaking, paddleboarding, and fishing. The charming village area is brimming with delightful shops, eclectic dining options, and lively entertainment, ensuring that there’s always something to explore. Whether you’re taking a leisurely stroll along the beach or enjoying a night out at one of the local eateries, Siesta Key captures the essence of coastal living.

For those considering a move to this idyllic locale, the Homes with Buyer Approval Required community features provide a unique opportunity. These communities are designed to foster a sense of belonging and camaraderie among residents, with amenities that promote an active lifestyle and social engagement. From well-maintained parks and recreational facilities to organized community events, you'll find that living here not only offers a beautiful home but also a welcoming neighborhood atmosphere.

Siesta Key is not just a place to live; it’s a lifestyle. With its captivating scenery, vibrant community, and the allure of island life, it’s no wonder that so many are drawn to make this enchanting destination their forever home. Discover the magic of Siesta Key and find your dream home today!

Newest Siesta Key Homes with Buyer Approval Required Community Features

$729,500
2 Beds ⋅ 2 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code
Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gulf of America, with a 5-minute walk down community path. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. One bedroom has a 1 king bed and one with a 1 queen bed, queen sofa bed in living room. Cozy Electric Fireplace, Heated Pool, Area for lounging in the sun, dock area for fishing, Tiki Hut with chairs & charcoal grills. This fabulous property offers a comfortable and inviting space for guests- enclosed lanai and a large private deck overlooking the Bay with a gas grill and outdoor furniture. You'll find all the essentials you need, including 2 yr. old AC, hair dryer, Wi-Fi, an iron, coin laundry, beach chairs, wagon and umbrella, beach towels included in this turn-key sale! Move in and enjoy your new purchase. Laundry hook-ups but there are coin laundry machines on the 1st floor. Pets are not allowed. Minutes from Restaurants, Shopping, Entertainment, Grocery Store and Downtown Siesta Key Village. Public Stop for the Trolly is steps from the Condo Entrance! The views are exceptional of the ICW and bay as this the bayfront unit on the second floor, the only one with the large patio. This unit comes with a one car garage that only a few units are lucky enough to have. This two-bedroom unit has a deluxe bathroom and a half bathroom as well. Nice kitchen with granite tops and island L bar seating. Dinig table next to kitchen for those family dinners to make memories at. There is a community marina to bring your boat and enjoy this true Florida Beach and Bay lifestyle!!

5955 Midnight Pass Road Unit 21E, 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 od 8-10-2026

5770 Midnight Pass Road Unit 301, Sarasota
$299,000
1 Beds ⋅ 1 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code
Discover one of Siesta Key's best values at White Sands Village, where island living meets exceptional affordability. This beautifully furnished one-bedroom, one-bath condominium is ideally located just across the street from world-famous Siesta Key Beach and only a short stroll to the public beach access. One of the few pet-friendly communities on Siesta Key, White Sands Village welcomes well-behaved pets, making this an outstanding opportunity for full-time residents, seasonal owners, or investors seeking strong rental appeal. The community also offers an optional on-site rental management program, providing owners with flexibility to self-manage or utilize professional rental services. Residents enjoy a heated community pool, community boat docks available on a first-come, first-served basis, and convenient on-site laundry facilities. Siesta Key Public Beach is just moments away, offering tennis, pickleball, volleyball, nature trails, a playground, pavilion, and food concessions. Crescent Beach, Turtle Beach, Siesta Key Village, and downtown Sarasota's renowned dining, shopping, arts, and entertainment are all within easy reach. Whether you're searching for a personal beach getaway, a seasonal retreat, or an investment property with excellent rental potential, this furnished condominium delivers an exceptional combination of location, lifestyle, flexibility, and value at one of Siesta Key's most attractive price points.

5641 Midnight Pass Road Unit 902, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Virtually Staged. Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Welcome to Beach Way, where island living begins just steps from world-famous Siesta Key Beach! Perfectly positioned directly across from the powdery white quartz sands and turquoise Gulf waters, this spacious 2-bedroom, 2-bath condominium offers an incredible opportunity to enjoy one of Florida's most sought-after coastal lifestyles. Inside, you'll find a traditional floor plan with defined living and dining spaces, creating a comfortable layout for everyday living or seasonal enjoyment. The kitchen features quartz countertops and ample cabinet space, while tile flooring throughout offers easy maintenance and timeless appeal. The screened lanai overlooks the peaceful community pool, creating the perfect place to relax after a day at the beach. Additional features include PGT WinGuard Series 710 impact-resistant windows and PGT Series 700 impact-resistant sliding glass doors. The condo also includes assigned covered parking conveniently located directly in front of the building, elevator access, and private storage. Beach Way is a beautifully maintained community centered around a gorgeous pool, lush tropical landscaping, and ample guest parking. Owners enjoy the flexibility of one-month minimum rentals, up to 12 times per year, making this an excellent option as a primary residence, vacation retreat, or investment property. Ideally located just a short stroll from Siesta Key Village's restaurants, boutiques, and entertainment, this condo offers the best of island living with easy access to downtown Sarasota's dining, arts, and cultural attractions. Whether you're looking for a full-time residence, a winter escape, or an income-producing beach property, this Beach Way condo is ready for you to make it your own!

5600 Beach Way Drive Unit 111, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Virtually Staged. Rarely available 5th-floor residence in Siesta Gulf View’s coveted 08 stack. This exceptional beach retreat showcases an extended wrap balcony with unobstructed west and south panoramic views of Siesta Key’s white-sand beaches and glowing Gulf sunsets. Bathed in natural light, the spacious split-bedroom layout offers walk-in closets in both bedrooms, motorized storm shutters, an interior laundry room, and abundant flexibility to create a tailored coastal home—reimagine the breakfast nook as a den or keep the expansive office area. Offered for the first time in nearly 30 years, this is a rare opportunity to personalize a premier view property. Enjoy deeded beach access via the private community boardwalk, along with a pool, tennis, pickleball, fitness room, clubhouse with meeting room and kitchen, and beachside grilling and seating area—all within Siesta Gulf View’s intimate 59-residence setting, just two blocks to famous Siesta Key Village.

420 Beach Road Unit 508, Sarasota
$689,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. Experience the best of Siesta Key living in this beautifully renovated first-floor condominium at Beach Way. Located directly across from the world-famous Siesta Key Beach and just a short stroll to Siesta Key Village, this 2-bedroom, 2-bath residence offers the perfect combination of luxury, convenience, and investment potential. Inside, you'll find a thoughtfully updated interior featuring elegant quartz countertops, brand-new stainless steel appliances, durable Cali luxury vinyl plank flooring throughout, and a bright, open floor plan that flows seamlessly into the enclosed lanai. The lanai overlooks the tropical landscaping with a partial view of the community pool, creating the perfect place to relax after a day at the beach. Built for peace of mind, the unit features PGT WinGuard impact-resistant windows (Series 710) and PGT 700 Series impact-resistant sliding glass doors. Convenience continues outside with assigned covered parking located directly in front of the unit, along with ample guest parking for family and friends. Beach Way's desirable monthly rental policy makes this property an excellent option for a primary residence, vacation home, seasonal retreat, or income-producing investment. Enjoy resort-style coastal living just steps from the white quartz sand of world-famous Siesta Key Beach, with the Siesta Key Trolley stop conveniently located right in front of the community for effortless access to Siesta Key Village, shopping, dining, entertainment, and everything the island has to offer.

5600 Beach Way Drive Unit 109, Sarasota
$4,000,000
2 Beds ⋅ 3 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create an extraordinary 2,365-SF home. Completely reimagined by award-winning architect Michael Halflants of Halflants + Pichette Studio for Modern Architecture, the residence received the prestigious AIA Florida/Caribbean Honor Award of Excellence in Interior Design and was featured in Sarasota Magazine's Dream Homes issue. Original interior walls were removed to reveal uninterrupted vistas that extend along the shoreline of Siesta Key, across Sarasota Bay, and to the downtown Sarasota skyline. The result is a flowing two-bedroom, two-and-a-half-bath residence where panoramic views, exceptional materials, and thoughtful design exist in perfect balance. At the center of the home, a sculptural Etimoe hardwood core houses the kitchen, storage, primary bath, and an expansive walk-in closet, bringing warmth and architectural definition to the open floor plan. Floor-to-ceiling, seven-panel bi-fold glass doors disappear completely at the corners, creating a seamless connection to the Gulf and inviting coastal breezes into the living spaces. Custom folding partitions provide privacy between the primary suite and main living areas without compromising the home's openness or visual continuity. Thoughtful custom details continue throughout the residence, including a custom steel desk overlooking the Gulf of Mexico, creating a work-from-home setting few could rival. The raw concrete ceiling from Smith's original 1969 design was scraped and clear-coated to a soft sheen, transforming a defining element of the building into a striking contemporary feature. Large-format porcelain tile, custom steel detailing, and carefully selected wood finishes complete a sophisticated material palette that feels both timeless and contemporary. Residents of The Terrace enjoy private access to Siesta Key's renowned beach and are just moments from the shops, restaurants, and energy of Siesta Village. More than a luxury beachfront residence, this is a rare opportunity to own an award-winning home within one of Sarasota's most recognizable waterfront landmarks, where exceptional architecture and Gulf-front living are seamlessly intertwined.

5400 Ocean Boulevard Unit #15 1-4, Sarasota
$509,000
2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
Opportunities to own in Sandy Cove are rare—and this residence presents the perfect chance to create your own island retreat in one of Siesta Key's most sought-after waterfront communities. Bring your vision and transform this well-located residence into the coastal getaway you've always imagined. Whether you're looking for a winter escape from the cold, a seasonal home to enjoy for years to come, or an investment in one of Florida's premier beach destinations, the value here lies in the location, lifestyle, and potential. Designed by renowned Sarasota architect Frank Folsom Smith, Sandy Cove is a boutique waterfront community celebrated for its timeless mid-century architecture, lush tropical landscaping, private shell beach, fishing pier, heated pool, kayak launch, and Gulf-front sunsets. Best of all, you're just a short stroll from Siesta Key Village, where local restaurants, boutiques, live music, and island charm await. Unlike buying someone else's renovation, this home offers the rare opportunity to update the interior to reflect your own style while investing in a community where demand remains consistently strong. Enjoy the property today, renovate at your own pace, and own a piece of Siesta Key in a location that continues to attract vacationers, seasonal residents, and investors alike. When the address is this exceptional, the possibilities are endless. Schedule your private showing today!

220 Pass Key Road Unit 220, Sarasota
$649,900
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Ready to Enjoy the Great Life? Welcome to your own piece of paradise at Island Reef, one of Siesta Key's most sought-after Gulf-to-Bay Communities. Perfectly positioned in the desirable "A" Building, this beautifully maintained and furnished second-floor end unit offers breathtaking panoramic views of the Gulf of Mexico from the moment you walk through the door. Natural light pours into the residence, while expansive water views create a peaceful backdrop that defines true coastal living. Offering over 1,200 square feet, this two-bedroom, two-bath residence features a desirable split-bedroom floor plan that provides comfort and privacy for both owners and guests. Thoughtfully updated over the years and offered turnkey furnished, the condo is ready to enjoy immediately while still providing the opportunity to personalize over time. Whether you're preparing dinner with the Gulf as your backdrop, enjoying your morning coffee on the lanai, or ending the day with one of Siesta Key's unforgettable sunsets, every space is designed to embrace the waterfront lifestyle. Life at Island Reef extends well beyond your front door. Begin your mornings with a walk along the private beach at Turtle Beach, spend afternoons kayaking or paddleboarding through Little Sarasota Bay, or watch dolphins play in the Gulf from the community's beachfront pool. Boating enthusiasts will appreciate the community's bayside docks with lift capability and direct access to Sarasota Bay and the Intracoastal Waterway. Residents enjoy an impressive collection of resort-style amenities, including two heated pools, private beach access, tennis and pickleball courts, shuffleboard, a fitness center, clubhouse, library, fishing pier, kayak and bike storage, beautifully landscaped walking paths, on-site management, and covered parking. Ideally located on the quieter southern end of Siesta Key, Island Reef offers a relaxed coastal atmosphere while remaining just minutes from Siesta Key Village's dining, shopping, and entertainment. Don't forget to check out the complimentary trolley that goes directly to the village!! Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this is a Rare Opportunity to own a beautifully furnished & spacious Gulf-front Condominium in Island Reef one of Siesta Key's premier Gulf-to-Bay communities, where lush tropical landscaping, resort-style amenities, private beach access and unmatched Coastal lifestyle come together harmoniously to create the perfect place to feel at Home. Call today to Book a Private Showing - these opportunities don't last long!

8764 Midnight Pass Road Unit A201, Sarasota
$1,589,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Welcome to Dolphin Bay, one of Siesta Key's premier waterfront communities, where luxury coastal living meets breathtaking scenery. This beautifully maintained 2-bedroom, 2-bath residence offers 2,217 square feet of thoughtfully designed living space with panoramic views of the Intracoastal Waterway, downtown Sarasota, and beyond. Filled with natural light, the open-concept floor plan was designed to maximize the spectacular waterfront views. Floor-to-ceiling windows create an inviting atmosphere where you can relax, entertain, and watch boats glide by as the Sarasota skyline transforms from sunrise to sunset. The spacious kitchen offers abundant cabinetry, generous counter space, Thermador appliances, and a breakfast area that opens seamlessly to the main living spaces, making everyday living and entertaining effortless. Wake up each morning to stunning water views from the luxurious primary suite, complete with a spacious walk-in closet and a spa-inspired en-suite bath featuring a large walk-in shower. The generously sized guest suite also features a large walk-in closet and is conveniently located adjacent to a full bath, providing exceptional comfort and privacy for family and guests. Life at Dolphin Bay extends far beyond your residence. Enjoy resort-style amenities including a pool and spa, Har-Tru tennis courts, fitness center, elegant clubhouse, kayak launch, fishing pier, and day dock with direct access to Sarasota Bay and the Gulf. Perfectly positioned just minutes from the award-winning white quartz sands of Siesta Key Beach, this exceptional residence also places you close to the restaurants, boutiques, and vibrant atmosphere of Siesta Key Village. A short drive brings you to downtown Sarasota, home to the Van Wezel Performing Arts Hall, Sarasota Opera House, The John and Mable Ringling Museum of Art, waterfront parks, fine dining, galleries, shopping, and year-round cultural events. Whether you're searching for a full-time waterfront residence, a seasonal retreat, or the ultimate Florida lifestyle, this exceptional Dolphin Bay residence offers the rare opportunity to enjoy luxury, boating, world-class beaches, and breathtaking waterfront views—all in one of Siesta Key's most desirable communities.

1280 Dolphin Bay Way Unit 402, Sarasota
$849,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Discover this one-of-a-kind unit in Excelsior, featuring two spacious bedrooms and two bathrooms, complemented by an added staircase leading to a spacious second-story LOFT. A structural beam has been expertly installed to support the loft, and ceilings have been RAISED, enhanced with foam insulation throughout the attic for improved energy efficiency. The kitchen boasts custom solid wood cabinetry, elegant crown molding, and solid core doors. BRAND NEW carpet installed throughout bedrooms, loft and staircase. Enjoy year-round comfort with a Newer HVAC system (2023). Looking out from your front door, take in the breathtaking Gulf views, perfect for watching gorgeous sunsets. The Gulf to Bay community offers private deeded beach access and a wealth of amenities, including two large heated swimming pools with poolside restrooms and hot water showers, shuffleboard, two heated whirlpools, two lighted tennis courts, and two pickleball courts. For fitness enthusiasts, a well-equipped fitness center awaits, along with a spacious Gulf side sun deck, beach loungers and chairs, and outdoor barbecues and picnic areas. 2 Week rental minimums for those seeking to generate some income. Additionally, enjoy the intercoastal fishing pier with a shaded viewing area, a welcoming community room, and engaging monthly community events. Don’t miss your opportunity to own this exceptional property with unparalleled amenities!

6263 Midnight Pass Road Unit 403, Sarasota
$799,000
1 Beds ⋅ 2 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Turnkey furnished and beautifully reimagined in 2024, this top-floor Gulf-front residence at Fisherman's Cove offers a rare opportunity to own one of Siesta Key's most distinctive beachfront retreats. Positioned at the quiet southern end of the island, this one-bedroom residence enjoys unobstructed panoramic views of the Gulf of Mexico from nearly every room, where turquoise waters, sugar-white sand, and breathtaking sunsets become part of everyday living. Thoughtfully renovated throughout, this residence is also the only one-bedroom floor plan in the community offering both a full bath and an additional half bath, providing added comfort and convenience for guests. Designed to maximize natural light and waterfront scenery, the open floor plan flows effortlessly from room to room. The Gulf-front terrace has been enclosed, expanding the living space while walls of impact-rated glass frame uninterrupted beach views. Soft coastal finishes, elegant tile flooring, and a fresh, contemporary palette create a relaxed yet refined atmosphere ideal for full-time living, seasonal enjoyment, or investment. The remodeled kitchen features custom cabinetry, stone countertops, newer appliances, generous storage, and an open design that overlooks the living and dining areas while keeping the Gulf as the focal point. Renovations completed in 2024 include impact windows and sliding glass doors, beautifully updated bathrooms, and quality finishes throughout, while a newer air-conditioning system installed in 2023 adds peace of mind. The spacious primary suite enjoys spectacular Gulf views through oversized windows and features an updated en-suite bath. The additional powder room is a rare feature within Fisherman's Cove, allowing guests the convenience of a separate bath while maintaining the privacy of the primary suite. Nestled between the Gulf of Mexico and Blind Pass Lagoon, Fisherman's Cove offers one of Siesta Key's most desirable waterfront settings. Residents enjoy direct beach access, a heated community pool, fishing pier, complimentary first-come boat slips, and easy access to kayaking, paddleboarding, and boating that leads to Sarasota Bay and the Gulf. The island's south end is also renowned for exceptional shelling and miles of unspoiled shoreline stretching toward Casey Key. Ideally located just minutes from Siesta Key Village, waterfront dining, marinas, and downtown Sarasota's renowned Cultural Coast, residents enjoy boutique shopping, acclaimed restaurants, theaters, galleries, Selby Gardens, and year-round entertainment. Whether you're searching for a luxurious beachfront escape, a high-demand investment with one-week rental flexibility, or a move-in-ready Gulf-front residence, this exceptional Fisherman's Cove offering delivers the very best of Siesta Key living.

9000 Blind Pass Road Unit 303, Sarasota
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