Siesta Key Real Estate

Homes for Sale in Siesta Key, FL Between $1,500,000 to $2,000,000

Welcome to your dedicated resource for Homes for Sale Between $1,500,000 to $2,000,000 in Siesta Key, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Siesta Key, FL agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,500,000 to $2,000,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Siesta Key, FL Homes for Sale Between $1,500,000 to $2,000,000

$1,795,000
4 Beds ⋅ 3 Baths ⋅ TB8533327 MLS
Just bring your wardrobe! Welcome to this beautifully updated and fully furnished and equipped 4-bedroom, 3-bath cottage-style home in one of Siesta Key’s most sought-after neighborhoods - just a short stroll to public beach access at top-rated Siesta Key Beach. Meticulously renovated in 2025, this true turnkey entertainer's paradise offers a vacation-every-day lifestyle complete with thoughtful upgrades and everything you need to move right in. Inside you’ll find all-new tile flooring, fresh paint throughout, storm-rated windows, a new 310 Lennox air-conditioning system with a 10-year warranty, updated plumbing and electrical, a reverse-osmosis water system, a whole-house generator (gas or propane), and a newer roof (2021). The backyard oasis features a 50-foot saltwater pool, spa, and sundeck surrounded by elegant Italian marble, plus pool floats, basketball hoops, and a volleyball net for endless fun. Enjoy the outdoor shower, raised gardens, a Napoleon Prestige gas grill, fire table, electric vehicle charger, and a louvered pergola that opens or closes for perfect sun or shade, a 75-inch TV, and a Sonos outdoor surround sound system - ideal for outdoor movie nights. Ultimate privacy is provided by an 8-foot vinyl fence. The artificial turf in the front and backyard creates a clean and maintenance free living with a coastal feel. The gourmet kitchen is fully stocked and ready for entertaining, featuring 2025 Thermador appliances (refrigerator, stove top, dishwasher, and oven) plus a new LG washer and dryer. Practical extras include a Shark vacuum, clothes steamer, iron and board, and even towels, and washcloths already stocked in every bathroom. The home comes completely furnished with all shown décor, lamps, linens, and towels. Two of the bathrooms include bidets and large walk-in showers. Beach days are effortless thanks to the included beach chairs, towels, beach cart, and umbrella shade. A Ring camera system conveys with the home sale, offering peace of mind. Bonus: This home includes an assumable flood insurance policy for just under $4,700 annually. This is the fully equipped Siesta Key lifestyle you’ve been dreaming of. Call today to schedule your private showing!

5143 Sandy Beach Avenue, Siesta Key
$1,750,000
4 Beds ⋅ 3 Baths ⋅ A4703192 MLS
Discover a rare opportunity on Palm Island, one of Siesta Key’s most distinctive residential enclaves, where quiet island living meets exceptional access to the very best of Sarasota’s Gulf Coast lifestyle. Ideally located at 5334 Calle Florida, this custom-built residence offers privacy and character while remaining just moments from the white sands of Siesta Key Beach, the Village, boating, dining, and everything that makes this part of the island so desirable. Set on a generously sized lot and elevated approximately 10 feet above sea level, the home was thoughtfully constructed with island living in mind. The elevated Key West-inspired design provides an added sense of security, with the main residence having never experienced flooding during any storm. Inside, the home immediately makes an impression. Soaring 20-foot ceilings rise above the dramatic great room, while the open-concept design allows the kitchen, dining, and living spaces to flow naturally together. Abundant natural light and the impressive ceiling height create a bright, airy atmosphere that feels both sophisticated and relaxed. With 2,838 square feet of living space, four bedrooms, and three bathrooms, the home offers the scale and flexibility for full-time living, entertaining, or an exceptional Siesta Key retreat. The oversized primary suite provides a private escape with a custom-built window seat, two walk-in closets, and a spacious primary bath. Built-in speakers extend throughout the residence and onto the back porch, creating a seamless atmosphere for everyday living and entertaining. Outdoor living is equally impressive. The elevated heated pool and hot tub create a private resort-like setting complemented by an outdoor shower and generous areas for relaxing or gathering with friends and family. Thoughtful exterior details include landscape lighting and electrical power in the soffits for seasonal or year-round accent lighting. The home is also well equipped for coastal living with three-zone air conditioning, hurricane-rated Kevlar screens, a hurricane-rated front door and garage door, and a spacious two-car garage with ample storage. Recent improvements include a new roof in 2021, pool resurfacing in 2024, pool cage repainting and rescreening in 2025, and a new water heater in 2025. What truly sets 5334 Calle Florida apart is the combination of location and architecture: a custom, elevated residence with dramatic ceiling heights and open living spaces, tucked away on Palm Island yet remarkably close to the beach and Siesta Key lifestyle. It is a distinctive opportunity to enjoy privacy, elevation, and luxury in one of Sarasota’s most sought-after island settings.

5334 Calle Florida, Siesta Key
$1,700,000
N6145586 MLS
Rare Double-Lot Coastal Compound Opportunity on Siesta Key — Offered Together at $1,700,000 | 14,636 Total Sq. Ft. Embrace the quintessential Florida lifestyle on prestigious Palm Island—a peaceful, golf-cart-friendly sanctuary surrounded by deep-water canals, mature tropical canopies, and magnificent luxury residences. Combining Lot A (8,619 sq. ft.) and Lot B (6,017 sq. ft.), this rare joint offering creates an expansive 14,636-square-foot multi-parcel footprint, giving you the ultimate canvas to design a high-end, weather-resilient coastal estate. Are you looking for that legacy estate with a guest house where your family and friends gather for the holidays, one that will be passed down from generation to generation? Or perhaps these two parcels give the ultimate privacy you've been looking for? Or maybe you're a builder who could leverage the efficiency and convenience of building on side-by-side lots at the same time? Imagine never again having to time your beach visits around traffic, hunt for open spots, or compromise on your day because of a full parking lot. Instead, your coastal routine begins with the simple pleasure of stepping out your front door and taking a brief, effortless stroll down quiet, canopy-shaded streets. Within minutes, your toes sink into the pristine, powder-white quartz sands of Siesta Key Beach—consistently recognized among the top-ranked beaches in the world and repeatedly named the #1 beach in the United States. Whether you want to enjoy an early morning walk, take a spontaneous afternoon dip, or walk down to the water for an impromptu sunset cocktail, one of the globe's premier coastal treasures serves as a natural extension of your own backyard, completely free from the hassle of driving. Situated in the heart of Siesta Key, this prime parcel at 5323 Calle Florida offers an unbeatable location just 0.7 miles—a pleasant 15-minute stroll—from the vibrant dining, shopping, and nightlife of Siesta Key Village. Daily convenience and effortless island living are unmatched, with Sarasota Memorial Hospital just 5.6 miles away and Downtown Sarasota only 6.5 miles from your doorstep. Endless entertainment, boutique shopping, and world-class travel are all within easy reach, including St. Armands Circle (8 miles) and Sarasota-Bradenton International Airport (11.5 miles). Boating and water enthusiasts will love the proximity to nearby nautical hubs, with full-service facilities like Safe Harbor Siesta Key just 2.5 miles south, the free county-operated Turtle Beach Public Boat Ramp 5 miles down the key, and the iconic Marina Jack in downtown Sarasota under 7 miles away, making this property an extraordinary canvas for your dream coastal home or investment.

5323 Calle Florida, Siesta Key
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