Siesta Key Real Estate

Siesta Key Real Estate

Welcome to Siesta Key, Florida – a stunning barrier island nestled in Sarasota County, renowned for its pristine beaches, vibrant culture, and laid-back charm. Just a short drive from the bustling city of Sarasota, Siesta Key offers a perfect blend of relaxation and adventure, making it an ideal destination for those seeking a slice of paradise.

One of the crown jewels of Siesta Key is its world-famous Siesta Beach, celebrated for its powdery white sand that remains cool underfoot, even on the hottest days. This beach has consistently ranked among the best in the United States, drawing sunbathers, families, and water sports enthusiasts alike. Whether you’re looking to soak up the sun, swim in the crystal-clear Gulf waters, or indulge in beach volleyball, Siesta Beach has something for everyone.

Beyond its breathtaking beaches, Siesta Key boasts a lively community filled with charming boutiques, eclectic dining options, and vibrant nightlife. The village area is a hub of activity, where you can enjoy fresh seafood, local art, and live music. Don’t miss the opportunity to explore the unique shops and galleries that showcase the island's artistic spirit.

Outdoor enthusiasts will appreciate the numerous parks and nature reserves, offering opportunities for kayaking, paddleboarding, and fishing in the tranquil waters of the Gulf and Sarasota Bay. With its stunning sunsets and welcoming atmosphere, Siesta Key is not just a destination; it’s a lifestyle.

Whether you’re considering a vacation home or a permanent residence, Siesta Key promises a unique blend of coastal living and community spirit. Come experience the magic of Siesta Key, where every day feels like a vacation!

Newest Listings in Siesta Key

617 Siesta Drive, Sarasota
$849,900
Bay Island SubDv. ⋅ 34242 Zip Code
A rare 0.30-acre homesite on Bay Island, the coveted gateway to Siesta Key, where homes seldom change hands and buildable land is almost impossible to find. This intimate, established neighborhood of tree-lined streets, deepwater canals, and beautiful new custom homes sits at the northern tip of Siesta Key, with the downtown Sarasota skyline just across the bay. Siesta Key Beach and Siesta Village are minutes away, and downtown Sarasota, St. Armands Circle, and Lido Key are a quick drive over the north bridge. The lot is framed by mature trees and tropical landscaping, with a circular brick paver drive and an existing in-ground pool already in place. The existing structure is offered for land value only and is ready to make way for something new. Clear the site and build the custom coastal home you've always envisioned. Located within the City of Sarasota limits, where short-term rentals are permitted, this property is ideal for a primary residence, seasonal retreat, or investment build. Public water and sewer available, no HOA. On an island where nearly every lot is built out, opportunities like this simply do not come along often. Bring your architect and your vision. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify.

617 Siesta Drive, Sarasota
809 Idlewild Way, Sarasota
$3,850,000
4 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Completely remodeled from top to bottom and expanded with a new 1,200-square-foot, two-level addition, 809 Idlewild Way is a one of one contemporary waterfront residence offering the look, feel and comfort of a new home in a prime Siesta Key location. The comprehensive renovation includes new electrical and plumbing, new HVAC systems, impact windows and doors, premium interior finishes and extensively redesigned outdoor living spaces. Set on a high elevation homesite along a coveted cul de sac with more than 100 feet of waterfrontage, the home combines excellent craftsmanship with beautiful water views throughout. Extensive structural improvements opened the living room, kitchen and covered patio toward the water, removing obstructing columns and preserving uninterrupted views across the pool and waterfront. Expansive sliders surrounding the primary suite bring in natural light and further connect the room to the water. The renovation carries through the exterior, where lush landscaping, integrated architectural lighting, a distinctive pergola entry, standing seam metal roof and stone fascia reinforce the home’s modern architectural character. Inside, premium engineered hardwood flooring, custom tray ceilings with integrated designer lighting, meticulous level 5 drywall and masterfully executed finish carpentry create a sophisticated interior. The gourmet kitchen features custom cabinetry and natural quartzite surfaces, complemented by additional custom bar cabinetry and entertaining space in the dining area. Beautifully appointed bathrooms are extensively wrapped in tile with dramatic glass shower enclosures. The home is offered furnished and move-in ready. Resort style outdoor living, created with entertaining in mind, centers around a new saltwater pool with a sun shelf, integrated fire and water features, a sealed paver deck, outdoor kitchen and gathering spaces overlooking the waterfront. A custom U shaped dock with a 24,000 pound boat lift, power, softened water and lighting completes the boating experience, with Sarasota Bay just a short boat ride away. The seller’s Formula boat is also available for purchase separately. An elevated seawall cap and reinforcing wall, 500 gallon underground propane tank and whole home generator add comfort and resilience. All of this is complemented by the beaches, dining and relaxed island lifestyle that make Siesta Key such a distinctive place to call home.

809 Idlewild Way, Sarasota
4660 Ocean Boulevard Unit U2, Sarasota
$1,195,000
3 Beds ⋅ 2 Baths ⋅ Sea Village SubDv. ⋅ 34242 Zip Code
Experience the best of coastal living in this 3-bedroom gulf-front condo at 4660 Ocean Boulevard, Unit 2, on beautiful Siesta Key. Enjoy the unbeatable appeal of beachfront living, with the sparkling Gulf waters and world-famous silicon sand beaches just steps away. Ideally located near the charming Siesta Key Village, you'll have convenient access to popular restaurants, boutique shopping, and local entertainment. The community offers desirable amenities, including two swimming pools, perfect for relaxing and enjoying the Florida sunshine. Whether you're seeking a beachside retreat, a second home, or an investment opportunity, this exceptional Gulf-front location offers the perfect blend of coastal charm, convenience, and resort-style living.

4660 Ocean Boulevard Unit U2, Sarasota
4200 Shell Road, Sarasota
$25,500,000
6 Beds ⋅ 6 Baths ⋅ Fidder Bayou SubDv. ⋅ 34242 Zip Code
For the first time The Higel Estate presents a rare opportunity to acquire 4200, 4189, and 4185 Shell Road, creating a 2.64-acre Gulf-front estate on Siesta Key with approximately 290ft of frontage along Sarasota Big Pass with a private beach. Rooted in the island's Old Florida character, the property brings together a collection of residences and an expanse of Gulf-front land rarely found along Sarasota's coastline. Built in 1953, the original main residence and guest house remain nestled among mature tropical landscaping, just steps from the private beach. Across the three parcels, the scale of the assemblage creates the opportunity to envision something extraordinary. Architectural plans by MHK Architecture illustrate the potential for an approximately 14,000sqft residence, transforming the acreage into one grand coastal estate. Alternatively, the existing residence could become the centerpiece of a private multi-residence compound, with a separate conceptual plan envisioning an approximately 8,000sqft residence across the additional parcels. These plans offer a glimpse of what may be possible, while the combined acreage leaves the door open to an entirely different vision, shaped by the ambitions of its next owner. Named after Sarasota pioneer Harry Higel, Higel Avenue holds a distinctive place in the history of Siesta Key. Today, its Gulf-front corridor remains one of the area's most coveted settings, where assembling acreage of this scale has become increasingly difficult. The Higel Estate brings together the elements that define a truly exceptional coastal offering: a meaningful stretch of Gulf frontage, a private beach, historic island character, and the rare opportunity to shape what comes next.

4200 Shell Road, Sarasota
8212 Midnight Pass Rd Road Unit 1-10, Sarasota
$4,500,000
34242 Zip Code
Siesta Key Bungalows is a cozy island offering 10 one-bedroom bungalows, some over looking the tranquil pristine blue waters of Heron Lagoon, and others overlook the lush tropical courtyard of Siesta Key Bungalows. The Bungalows sit less than a mile away from Siesta Key's beaches and boast free kayaking and canoeing on Heron Lagoon as well as a sparkling, heated pool and affordable rates year round. Siesta Key Bungalows are located near all 3 beaches on Siesta Key. You will be able to view all the beauty Siesta Key has to offer. Siesta Key offers a free trolley that connects the entire island including Siesta Key Bungalows. Gross income in past years prior to the hurricane was just over $500,000.00. Net operating income was just over $200,000.00 for the year.

8212 Midnight Pass Rd Road Unit 1-10, Sarasota
1256 Riegels Landing Drive, Sarasota
$1,895,000
3 Beds ⋅ 4 Baths ⋅ Riegels Landing SubDv. ⋅ 34242 Zip Code
Designed by Sarasota School of Architecture.

1256 Riegels Landing Drive, Sarasota
5950 Midnight Pass Road Unit 201, Sarasota
$575,000
2 Beds ⋅ 2 Baths ⋅ Siesta Beach House SubDv. ⋅ 34242 Zip Code
Gulf-side living at its best! This charming, completely remodeled two bed, two bath ground-floor residence offers the perfect blend of coastal style, comfort, and convenience. Renovated from top to bottom, the home features new electrical and plumbing, impact windows and doors, stylish new flooring, beautifully updated bathrooms, and a stunning kitchen with quartz countertops, tile backsplash, breakfast bar, and stainless-steel appliances. This unit offers a comfortable living space with the primary bedroom with ensuite half bath, while the guest bedroom is conveniently located near the fully remodeled hall bath. With everything already beautifully updated, this inviting residence is ready to enjoy from day one! Step outside your door and enjoy the best of the Gulf-side lifestyle with private beach access, a sparkling community pool, and inviting outdoor seating areas with picnic tables. Assigned parking and additional guest spaces add everyday convenience, while short-term rentals are permitted, offering excellent rental potential. There are also bookings already in place that can be retained by the new owner, if desired. Ideally located close to the Village, you'll be just minutes from shops, restaurants, and entertainment, with the free trolley nearby providing easy access to both sides of the Key. Whether you're looking for your own beachside escape or an investment with income potential, this beautifully renovated coastal retreat offers an opportunity to enjoy the Florida lifestyle from day one.

5950 Midnight Pass Road Unit 201, Sarasota
6204 Midnight Pass Road Unit 205, Sarasota
$775,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Welcome to Siesta Dunes! This bright and airy second-floor end-unit condominium offers a wonderful combination of comfort, updates, and location, with peaceful garden views and a peek-a-boo view of the Gulf. High ceilings and an abundance of natural light create a spacious, open feel throughout the residence, while new hurricane-impact windows provide added peace of mind. The roof and air conditioning system are also newer. The two bed, two bath layout features an updated kitchen with ample counter space and a convenient dinette area. The spacious living room opens through sliding glass doors to the balcony, extending the living space outdoors and providing a pleasant spot to enjoy the surrounding views. The primary suite offers a walk-in closet and ensuite bath, while the additional guest bedroom and full bath provide comfortable accommodations for family and friends. The desirable gulf front community of Siesta Dunes offers a saltwater pool & spa, tennis and pickleball courts, a beach deck and pavilion, carports, additional storage and small pets are allowed. Weekly rentals are also permitted, making this an appealing opportunity for those looking for a vacation home with rental potential or an investment property. With easy access to the renown Siesta Key Village, where you can enjoy the tropical ambiance of dining, shopping, and entertainment as well as everything Sarasota has to offer including the arts and culture of downtown. Whether you're looking for a place to enjoy yourself or an opportunity to generate rental income, this Siesta Dunes residence offers the flexibility, updates, and location to enjoy the best of the Florida lifestyle.

6204 Midnight Pass Road Unit 205, Sarasota
797 Beach Road Unit 415, Sarasota
$850,000
2 Beds ⋅ 2 Baths ⋅ Crescent Royale SubDv. ⋅ 34242 Zip Code
Your Siesta Key beach getaway awaits! This two-bedroom, two-bath condo offers an exceptional location, convenience, and investment potential just steps from the world-famous white sands of Siesta Key Beach. Freshly painted and professionally cleaned, this unit is ready for its next owner to enjoy. One of the standout features of this condo is its prime location within the building, situated just steps from the elevator, with convenient parking located nearby. Whether you're bringing in groceries, unloading luggage, or heading out for a day at the beach, this desirable location makes coming and going effortless. Enjoy the Florida lifestyle with access to community amenities, including a heated swimming pool, fitness center, shuffleboard, and outdoor grilling areas. Located directly across from Siesta Key Beach and just minutes from the shopping, dining, and entertainment of Siesta Key Village, everything you need is within easy reach. With weekly rentals permitted, this property offers excellent flexibility as a personal beach retreat, seasonal residence, or income-producing investment. Whether you're looking to enjoy the island lifestyle yourself or take advantage of its rental potential, this condo offers an exciting opportunity to own a piece of paradise on Siesta Key!

797 Beach Road Unit 415, Sarasota
6005 Midnight Pass Road Unit S6, Sarasota
$839,000
2 Beds ⋅ 2 Baths ⋅ Provintial Gardens SubDv. ⋅ 34242 Zip Code
Escape the winter blues with this turnkey furnished free-standing villa ready for IMMEDIATE occupancy with DEEDED SIESTA KEY BEACH and BAY access steps away in a non age restricted community. No logistical headaches having to furnish a property in order to occupy or rent it. This beautifully decorated and extensively updated, maintenance-free, open floor plan, villa can be your very own piece of paradise. Offering two spacious bedrooms and bathrooms, a flex (den) space, a full size washer/dryer, and your very own lush private patio oasis, all designed with comfort and style in mind. Added peace of mind comes from no flooding or storm damage sustained from recent storms. Some of the many updates include an extensive renovation to replace the old 1960s cast iron drain lines under the property’s slab with all-new PVC lines. Once completed, designer selected wood look tile flooring was added throughout the majority of the home. This intrusive, time-consuming, and costly project has already been completed, putting a new owner at ease regarding future concerns and major costs. The roof and A/C are new as of 2025, exterior painting will be completed by December. The primary bathroom has been completely updated, along with new hardscaping and landscaping. Handpicked light fixtures and ceiling fans have been installed, along with brand new solid core doors throughout the home to reduce noise from room to room. New coastal colors and tones have been added to the interior, along with all new appliances within the past two years. For accessibility 36 inch doorways and grab bars are present, as well as smart home features such as keyless electronic front door entry, nest thermostat, and ring door bell. The residence invites plenty of natural light into the home, with multiple windows and sliding glass doors enhancing the appeal of the split floor plan. The primary and expansive guest suite are located on opposite sides of the villa, providing ample space and privacy for all. The kitchen features an abundance of soft close cabinets, granite countertops, a large pantry, water filter system, and stainless steel appliances. Throughout the villa, you will find plenty of built-in storage closets, crown molding, as well as both a walk-in shower (primary) and a soaking tub (guest). Open your three sliding glass doors to create a seamless extension of your living space into your private tropical sanctuary, complete with an outdoor shower. The guest suite includes its own private outdoor space with a water fountain. When you are ready to venture out and enjoy your surroundings, there is an endless list of options to keep you busy. Enjoy your morning coffee while watching the sunrise/wildlife at the community’s bay front park with a new seawall. Here, you will find a kayak launch with two storage racks specifically for your use. Head out on the water kayaking/paddle boarding among dolphins and manatees. The community’s bay front park includes a day dock for residents’ use. Choose between relaxing on the beach with the sand between your toes or reading a book by the pool, with deeded access to the beach and one of the largest heated pools on Siesta Key via Aloha Kai across the street. Catch the free trolley to enjoy a casual lunch or a fine dining dinner. Owners can rent their property on a monthly basis with three weekly rentals permitted a year (outside of Jan-March) and can have one pet. The monthly HOA fee is $1,113. Come enjoy winter on Siesta Key!

6005 Midnight Pass Road Unit S6, Sarasota
5012 Higel Avenue, Sarasota
$2,149,000
4 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Discover the best of Siesta Key waterfront living in this beautifully renovated canal-front residence, where modern comfort, thoughtful design, and an exceptional island lifestyle come together on nearly half an acre. Extensively renovated (2024 - 2025), this four-bedroom, three-bath home offers 3,541 square feet of inviting air-conditioned living space, a private dock and a west-facing backyard retreat designed for enjoying Florida's beautiful sunsets. The spacious open-concept interior features a beautifully updated kitchen with new appliances, generous living and dining areas, and expansive views of the pool and canal beyond. A thoughtfully designed split floor plan includes two private primary suites with ensuite baths, ideal for family and guests. The main primary retreat overlooks the water and features a luxurious bath with a soaking tub, walk-in shower, dual vanities, and access to an outdoor shower. Two additional bedrooms provide flexibility for guests, a home office or den, including one with a private courtyard entrance. Extensive improvements completed in 2024/2025 include beautifully updated interiors and major home systems, two HVAC systems, a replaced roof with storm-code strapping, impact-resistant windows, sliding doors and garage door. Outdoors, the heated pool, coral stone lanai and expansive fenced backyard create an inviting setting for entertaining or simply relaxing in the island sunshine. Boating enthusiasts will appreciate the private Trex dock, 112-foot seawall and canal access with just one higher fixed bridge to Sarasota Bay. A two-car garage and extended driveway add convenience. Ideally located just moments from Siesta Village's restaurants, boutiques and entertainment, and minutes from the world-renowned powdery white sands of Siesta Beach, this beautifully updated waterfront home offers the perfect balance of relaxed island living, boating adventures and modern coastal comfort. Your Siesta Key lifestyle awaits.

5012 Higel Avenue, Sarasota
5174 Sandy Cove Avenue, Sarasota
$5,100,000
5 Beds ⋅ 4 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Under Construction. Welcome to 5174 Sandy Cove Ave, a pinnacle of contemporary elegance nestled in the heart of Sarasota, Florida. Designed by architect Mark Sultana. This 3900 sq foot new construction home epitomizes the fusion of exquisite design and impeccable craftsmanship, promising an unparalleled sanctuary for its new owner. Positioned just minutes from Sarasota's pristine white sand beaches, dynamic city life, and a wealth of amenities, this residence seamlessly harmonizes tranquility with convenience. Its proximity to major thoroughfares, shopping districts, culinary delights, and recreational hubs ensures a lifestyle of unparalleled ease and accessibility. The expansive backyard, complete with an open pool area and 275 feet of corner canal lot, featuring a dock and 10,000 lb boat lift, offers endless opportunities for relaxation, recreation, and waterfront adventures, providing direct access to Sarasota's endless waterways. Thoughtfully designed with energy efficiency and cutting-edge smart home technology, this residence promises a lifestyle that transcends the ordinary, ensuring comfort and sophistication for generations to come. 5174 Sandy Cove Ave isn't just a home—it's a lifestyle, an embodiment of coastal living in one of Sarasota's most coveted neighborhoods. Seize the opportunity to make this exceptional property your own and embark on the ultimate Florida dream. Estimated time to complete is approximately 8 months

5174 Sandy Cove Avenue, Sarasota
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