Siesta Key Homes with Two Story Property Description

Siesta Key Homes with Two Story Property Description

Welcome to Siesta Key, Florida – a sun-kissed paradise nestled within Sarasota County that offers a unique blend of laid-back coastal living and vibrant community spirit. Renowned for its powdery white sand beaches and crystal-clear turquoise waters, Siesta Key is not just a destination; it’s a lifestyle. With an abundance of outdoor activities, from kayaking and paddleboarding to biking along scenic paths, this idyllic island is perfect for those who cherish the great outdoors.

Siesta Key boasts a charming mix of quaint boutiques, delightful eateries, and lively nightlife, ensuring there’s always something to explore. Whether you’re enjoying a sunset at Siesta Beach or savoring fresh seafood at a local restaurant, the island's enchanting atmosphere captivates residents and visitors alike.

For those seeking a home that embodies this coastal charm, our stunning two-story properties offer the perfect blend of comfort and sophistication. These homes are designed with spacious layouts that maximize natural light and provide breathtaking views of the surrounding landscapes. Imagine entertaining guests in open-concept living spaces, enjoying family gatherings in beautifully landscaped backyards, or unwinding on private balconies that overlook the serene waters of the Gulf.

With the added benefit of multiple levels, these two-story homes provide ample room for families to grow and thrive. Whether you’re looking for a primary residence or a vacation retreat, Siesta Key’s two-story properties promise a perfect sanctuary where you can create lasting memories. Embrace the coastal lifestyle and discover your dream home in this picturesque paradise today!

Newest Siesta Key Homes with Two Story Property Description

3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Welcome to 5059 Commonwealth Drive, where relaxed Florida living meets one of Sarasota’s most desirable locations! This inviting home offers comfortable living spaces, abundant natural light, and a layout designed for easy everyday living and entertaining. Inside, the spacious living and dining areas provide plenty of room to gather with family and friends, while the kitchen is conveniently positioned at the heart of the home. Generously sized bedrooms offer comfortable private retreats, and the home’s flexible living spaces make it easy to create a space that fits your lifestyle. Outside, enjoy the tropical surroundings and year-round sunshine that make Sarasota living so special. Whether you're searching for a full-time residence, seasonal getaway, or your own piece of paradise near the coast, this property offers an outstanding opportunity. Located in the highly sought-after 34242 ZIP code, you'll enjoy convenient access to Siesta Key’s world-famous beaches, shopping, dining, entertainment, boating, and everything Sarasota has to offer. Spend the morning on the beach, enjoy dinner at one of Sarasota’s many restaurants, and come home to your own Florida retreat. Come discover the lifestyle waiting for you at 5059 Commonwealth Drive!

5059 Commonwealth Drive, Sarasota

2 Beds ⋅ 3 Baths ⋅ Gulf Haven SubDv. ⋅ 34242 Zip Code

RARELY AVAILABLE CONDO IN GULF HAVEN ON SIESTA KEY BEACH! This nicely updated 2-bedroom, 2.5-bath unit in the highly desirable Gulf Haven community won't be on the market for long. With limited availability in this intimate beachfront community, you have a special opportunity to be a part of the Siesta Key community. This unit offers comfortable coastal living with a practical layout and inviting spaces. With two bedrooms and two-and-a-half baths, there is plenty of room for owners and guests to relax and enjoy everything island living has to offer. Private beach access is one of the standout features of Gulf Haven, giving you the ability to enjoy the soft white sands and beautiful Gulf waters. After a day at the beach, take a refreshing dip in the inviting community pool. A covered carport that is connected to the unit provides convenient, protected parking—another valuable feature on Siesta Key. The location puts you close to the best of Siesta Key and Sarasota. Enjoy easy access to Siesta Key Village, local shops and restaurants, boating, and more. When you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering exceptional dining, shopping, arts, entertainment, and cultural attractions. Whether you're looking for a vacation home, seasonal retreat, investment property, or full-time residence, this rarely available Gulf Haven condo offers an exceptional way to enjoy the Sarasota Gulf Coast lifestyle. Updated interiors, private beach access, a community pool, covered parking, and a location close to it all make this a property worth seeing. Opportunities to own in Gulf Haven don't come along often—come experience the Siesta Key lifestyle for yourself.

5860 Midnight Pass Road Unit 23, Sarasota

4 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Experience the relaxed Siesta Key lifestyle in this spacious Key West-inspired pool home, ideally located on a quiet street approximately one mile from Siesta Key Village and just minutes from the island’s world-famous beaches. Restaurants, shops, nightlife, and local favorites such as LeLu Coffee Lounge are all within an easy bike ride. Offering four bedrooms and two-and-a-half bathrooms, the home features a large, open living area and a generous kitchen with a breakfast bar—perfect for everyday living and entertaining. The main-level primary suite includes a private en-suite bathroom and direct access to the pool area. Upstairs, three additional bedrooms provide plenty of space for family, guests, or a home office. Outside, the private backyard and heated in-ground pool create a secluded tropical setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. With its desirable island location, flexible floor plan, and distinctive Key West character, this home offers an excellent opportunity to update and personalize a Siesta Key residence to your own style.

5157 Sandy Beach Avenue, Sarasota

4 Beds ⋅ 7 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Virtually Staged. Pre-Construction. To be built. Welcome to 3200 Higel Avenue, an extraordinary new waterfront residence by Pham Development, nearing completion on one of North Siesta Key’s most exceptional stretches of shoreline, with construction anticipated to be complete within the next few months. Commanding approximately 190 feet of sailboat-water frontage along two sides, this two-story contemporary estate overlooks Sarasota Bay and Big Pass, with sweeping views toward South Lido Beach Park, Bird Key, and the Downtown Sarasota Skyline. Encompassing approximately 5,453 square feet under air and 6,852 square feet under roof, the residence features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed to embrace its spectacular waterfront setting. Rare Big Pass dockage, protected access along Bayou Louise, and private boating infrastructure—including a 30,000-pound boat lift for deep-water boating and a separate 10,000-pound jet-ski/kayak lift—provide effortless access to Sarasota Bay and the Gulf. Designed with a refined contemporary aesthetic, the interiors pair dramatic scale with refined materials and meticulous attention to detail. Soaring ceilings and expansive walls of glass frame the water and skyline, while engineered hardwood flooring, level-five finishes, and custom built-in walk-in closets elevate the home throughout. A striking glass elevator offers water views as it connects the home’s living spaces and rooftop level. The chef’s kitchen is centered around an oversized island and complemented by a walk-in pantry, high-end finishes, a Sub-Zero refrigerator, and Wolf oven, creating a beautifully appointed space for living and entertaining. The primary suite is a private waterfront sanctuary, capturing panoramic views and featuring a spa-inspired bath with dual vanities, a rain shower, and separate soaking tub. The primary-suite level also features its own private secondary living room, creating an intimate retreat separate from the main entertaining spaces, while a dedicated indoor gym provides space for wellness and fitness. Multiple balconies and covered lanais extend the living spaces outdoors, while a private saltwater pool and spa create a resort-inspired setting at the water’s edge. Crowning the residence, an expansive rooftop deck offers breathtaking panoramic views across Sarasota Bay, Big Pass, Bird Key, South Lido, and the downtown Sarasota skyline—an unforgettable setting for sunset cocktails and evening entertaining. Dolphins, manatees, fish, and native coastal birds are part of the remarkable natural setting almost daily, while the surrounding waterways invite paddleboarding, fishing, snorkeling, windsurfing, and boating directly from home. The residence remains just minutes from the powder sand of Siesta Key Beach and the restaurants, boutiques, and energy of Siesta Village. Downtown Sarasota’s acclaimed dining, galleries, performing arts, and cultural attractions are also easily accessible, providing a rare combination of privacy and proximity to the best of Sarasota. With approximately 190 feet of waterfront, exceptional deep-water boating capabilities, dedicated lifts for boating and watersports, a glass elevator with water views, an incredible rooftop deck, private wellness and living spaces, panoramic views spanning some of Sarasota’s most iconic landmarks, and a newly constructed residence just months from completion, 3200 Higel Avenue represents a rare opportunity to experience an elevated level of waterfront living on Siesta Key.

3200 Higel Avenue, Sarasota

6 Beds ⋅ 8 Baths ⋅ Siesta Properties Inc SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, nearly one acre of pristine beachfront offers an exceptional canvas for a world-class custom residence in one of Florida's most exclusive coastal communities. Positioned along the sugar-white sands of Siesta Key, this rare Gulf-front homesite presents an unparalleled opportunity to design a private waterfront retreat with sweeping panoramic views of the Gulf of Mexico, spectacular year-round sunsets, and direct access to one of the world's most celebrated beaches. With expansive frontage and generous dimensions, the property invites limitless architectural possibilities—from a contemporary coastal masterpiece to a timeless estate designed for generations to enjoy. Located within the prestigious Sanderling Club, this exceptional property enjoys the distinction of being part of Siesta Key's only private, gated Gulf-front community with 24-hour manned security. Originally envisioned by renowned Architect Paul Rudolph, Sarasota School of Architecture, Sanderling Club has long been recognized as one of Sarasota's most coveted residential enclaves, where privacy, natural beauty, and architectural excellence come together in a setting unlike any other on Florida's Gulf Coast. Residents enjoy an exclusive collection of amenities, including a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, scenic nature canopy roads , and beautifully maintained grounds that preserve the community's tranquil coastal character. The neighborhood's low density and commitment to preserving its natural environment have made Sanderling Club one of the region's most enduring luxury addresses. Beyond the gates, Siesta Key offers an internationally acclaimed lifestyle defined by its powder-soft quartz beaches, turquoise Gulf waters, and relaxed sophistication. From waterfront dining and boutique shopping in Siesta Key Village to boating, paddleboarding, fishing, and endless days on the water, the island offers an effortless blend of recreation and refinement. Just minutes away, downtown Sarasota provides a vibrant cultural scene that rivals much larger metropolitan destinations. Residents enjoy world-class performing arts, acclaimed restaurants, private clubs, championship golf, luxury shopping, art galleries, marinas, and exceptional healthcare. From evenings at the Sarasota Opera or the Van Wezel Performing Arts Hall to waterfront dining at Marina Jack and shopping at St. Armands Circle, Sarasota continues to rank among the nation's premier luxury lifestyle destinations. Large Gulf-front homesites of this caliber have become exceedingly rare. Combining nearly an acre of buildable beachfront, extraordinary privacy, direct Gulf frontage, and the prestige of Sanderling Club, 7740 Sanderling Road represents an opportunity to create an iconic waterfront estate in one of the most desirable addresses on Florida's Gulf Coast. This is more than a homesite—it is the foundation for a legacy.

7740 Sanderling Road, Sarasota

4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Prime investment opportunity directly on prestigious Beach Road in Siesta Key. This fully renovated, raised multi unit property offers strong short term rental income potential in one of Florida's most desirable coastal markets. The side by side duplex features a spacious 2 bedroom, 2 bathroom unit and a 2 bedroom, 1 bathroom unit. Zoned RMF and legally permitted for nightly rentals, making it ideal for vacation rental investors. The current owner is available to continue managing the property for the next owner at only a 10 percent fee, with staff, cleaning crew, and maintenance vendors already in place. The property generated $393,000 in gross income in 2023, $323,000 in 2024 (with two months of downtime due to hurricane impact), and $291,000 in 2025 (still down from hurricane related effects), with 2026 year to date income of $192,000 through July. Recent updates include new AC systems in 2022, updated flooring in 2025, modernized plumbing in 2022, full electrical upgrades in 2022, and private hot tubs installed at each unit in 2022. Additional upside exists with completed engineering drawings to enclose the lower level, adding approximately 2,000 square feet and significant rental income potential. Just steps from the sand and close to Siesta Key Village shops and restaurants, this is a rare chance to own an income producing property in one of the top beach destinations in the country. Property is part of a very successful Airbnb portfolio consisting of three duplexes with cap rates exceeding 10 percent. Please inquire for details.

527 Beach Road, Sarasota

6 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Discover an exceptional income producing property in the heart of coveted Siesta Key. This fully renovated multi unit compound features two spacious 3 bedroom, 2 bathroom units, one upstairs and one downstairs, making it ideal for short term rental investors. The current owner is available to continue managing the property for the next owner at only a 10 percent fee, offering a seamless, turnkey transition. The property generated $393,000 in gross income in 2023, $350,000 in 2024 (with two months of downtime due to hurricane impact), and $308,977 in 2025 (still down from hurricane related effects), with 2026 year to date income of $214,000 through July, offering strong and proven cash flow. Recent improvements include new AC (2025), updated flooring (2024 to 2025), modernized plumbing (2024), electrical upgrades (2022), and refreshed hot tubs (2021). What truly sets this property apart is its Commercial General (CG) zoning with a special exemption allowing nightly rentals, a rare and highly valuable designation on Siesta Key that protects the short term rental use. This zoning also unlocks significant redevelopment potential, including the possibility to construct an approximately 85 foot building with ground floor parking, 11 two bedroom units, and a rooftop pool. Property is part of a very successful Airbnb portfolio consisting of three duplexes with cap rates exceeding 10 percent. Please inquire for details.

5228 Calle Menorca, Sarasota

5 Beds ⋅ 5 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

NEW 2026 MODERN TROPICAL ESTATE | 5 BEDROOMS | 2 PRIMARY SUITES | 3-CAR GARAGE | POOL CABANA | INTRACOASTAL VIEWS Completed in 2026 by CribbsCo Development, this modern tropical residence makes an architectural statement with an approximately 9.5' x 9' Sapele wood pivot entry door handcrafted in the U.S. Two primary suites feature custom finished walk-in closets. The upstairs main primary is separated from the additional bedrooms by a glass breezeway and offers a pool-view balcony, custom cabinetry with integrated wet bar and built-in writing desk. Its spa-inspired bath features a soaking tub, oversized walk-in shower, dual vanities, private water closet and custom solid-oak barn door. Bathrooms feature Biancatto leathered dolomite, Kohler and California Faucets fixtures, and TOTO toilets. The ground-floor primary opens to a private patio overlooking the garden and outdoor gym. Two additional upstairs bedrooms share a full bath; one offers a large balcony with Intracoastal Waterway views, while the other features a private pool-view balcony. A powder bath serves the living area. A pool cabana guest suite with full ensuite bath, built-in desk and custom cabinetry offers flexibility for guests or multigenerational living. Nearby is a laundry room with dual washers and dryers. At the heart of the home is an approximately 18-foot Biancatto leathered dolomite island comfortably seating six. The chef's kitchen features Sub-Zero refrigeration, Wolf microwave, six-burner range with flat-top, dual ovens, two Bosch dishwashers, wine/beverage refrigeration, 1,000-CFM ventilation, reverse-osmosis hot/cold water faucet and custom cabinetry fabricated in the USA from German-imported materials. Biancatto leathered dolomite is carried throughout the kitchen, bathrooms, bedroom suites and outdoor kitchen. Custom-made solid oak doors were commissioned for every bedroom and closet and high-end Emtek hardware. The home opens to a covered outdoor lounge and custom dolomite outdoor kitchen with built-in BBQ, refrigerator, ice maker and sink. Ceiling fans extend throughout the residence and covered outdoor space. A large limestone patio provides additional outdoor dining. Natural limestone finishes patios, terraces, balconies, poolside areas, the outdoor gym and an exterior wall. The limestone does not get hot underfoot in the Florida sun, ideal for barefoot poolside living. Real teak is used throughout all soffits, covered patios and exterior cladding, complemented by smooth stucco, aluminum Geolam and architectural trellises. The heated saltwater pool and spa feature PebbleTec and natural stone, Pentair smart controls, LED lighting and bubblers, creating a private resort setting with the covered lounge, outdoor kitchen, cabana, gardens and outdoor gym. The residence and pool are elevated approximately 10 feet for FEMA compliance, with a privacy wall, walking path and mature landscaping. A spacious 3-car garage is designed for the car enthusiast. Additional features include five independently air-conditioned zones, triple-pane high-efficiency glazing, triple-pane PGT sliders, low-voltage smart-home wiring, Sugar Oak Natural Luxe wood flooring, oversized 4' x 4' porcelain tile, imported Plyboo wall treatments and custom artisan lighting. Furniture is available separately. An optional boat package at Safe Harbor featuring a 2023 Yamaha 25' FSH fishing boat and boat slip is also available, with slip transfer subject to marina approval.

1355 Roberts Bay Lane, Sarasota

4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

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, Sarasota

6 Beds ⋅ 7 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. This luxurious grand canal-front estate offers direct deep-water boating to the Gulf, out of one of the most exclusive neighborhoods on north Siesta Key. This in progress New Construction property by Pham Development is on an expansive 17,842 SF and 0.41 acre lot, with a 4,769 SF traditional-style home to be built. Enjoy two separate guests suites on top of the two 2-car garages, for a total of 4 garage spaces, both with elevator access to the above suites. The master bedroom will have water views, and the grand entry home hosts a total of 6 bedrooms, 6 baths, and 1 powder bath. This property's deep-water grand canal with no bridges is ideal for yachts and boats, with up to a 13-foot draft. A new dock and boat lift is set to be installed. Inside, expansive living spaces boast high-end finishes and top-of-the-line appliances, blending timeless elegance with modern comfort. Enjoy the water, and a large backyard perfect for entertaining, a private pool, and new lush landscaping—making this the ultimate waterfront estate for family.

3441 Gulfmead Drive, Sarasota

5 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code

Currently under renovation. Welcome to an exceptional newly updated residence on he highly coveted Bay Island neighborhood on north Siesta Key, where timeless coastal architecture and modern luxury come together in one of Siesta Key’s most desirable locations. Situated on an expansive 0.48-acre homesite, this beautifully designed home offers 4,536 square feet of refined living space with a total of 5 bedrooms, 5 full bathrooms, and 1 half bath. Thoughtfully enhanced with new finishes, designer upgrades, and premium appliances throughout, the home also enjoys glimpses of the ocean water that complement its tranquil coastal setting. A private gated driveway leads to a detached 4-car garage, and guest suite with 2 bedrooms and 2 bathrooms, providing both privacy and convenience. At the center of the residence is a stunning chef’s kitchen designed for both everyday living and entertaining, complete with premium Sub-Zero refrigeration, professional-grade gas appliances, custom cabinetry, elegant stone surfaces, and a spacious center island. The adjoining great room and dining area seamlessly connect to the outdoor living spaces, while the luxurious primary suite provides a private retreat with a spa-inspired bathroom, generous walk-in closets, and peaceful views of the surrounding tropical landscape. Step outside to your own private coastal oasis, where a screened pool and expansive pool deck create the perfect setting for relaxation and entertaining year-round. Beautifully landscaped grounds and thoughtfully designed outdoor living areas enhance the home's resort-style atmosphere. Located just moments from Siesta Key’s world-renowned beaches, waterfront dining, boutique shopping, and Sarasota’s vibrant cultural amenities, this exceptional residence offers an unparalleled blend of privacy, sophistication, and convenience. A rare opportunity to own a luxury home on Norsota Way, where exceptional craftsmanship and the coveted island lifestyle come together. Photos and renderings may include virtual staging and virtual enhancements intended to illustrate the property's anticipated completion and design.

604 Norsota Way, Sarasota

4 Beds ⋅ 5 Baths ⋅ Tortoise Estates SubDv. ⋅ 34242 Zip Code

With gulf sunset views, and 3-minute walkable private beach access, this New Construction Modern Beach House on Siesta Key mixes a sought-after location with modern luxury. Experience the best of coastal living in this brand-new 4 bed, 4.5 bath home with walking access to Turtle Beach. With 3,676 SF of thoughtfully designed space, this home offers ocean views throughout, multiple outdoor patios and terraces, rooftop deck, and seamless indoor-outdoor flow. Feel the sea breeze in the spacious backyard, including a pool, hot tub, and outdoor kitchen. Enjoy light-toned engineered hardwood floors, a chef’s kitchen with top-tier appliances, and spacious en-suite bedrooms, including a stunning primary suite with a private terrace and spa-like bath. Additional features include a 3-car garage, and 6 covered carport spaces for recreational utility vehicles such as, jet skis, golf carts, or a boat, with easy gate access. Enjoy an elevator included layout, and high-end finishes throughout—all just minutes from Siesta Village’s shops and dining. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Whether for full-time living or a coastal getaway, this is Siesta Key luxury at its finest.

8800 Midnight Pass Road, Sarasota

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