Siesta Key Homes with Two Story Property Description

Siesta Key Homes with Two Story Property Description

Welcome to Siesta Key, Florida, a stunning barrier island nestled off the coast of Sarasota County. Renowned for its pristine white sandy beaches and vibrant local culture, Siesta Key is a tropical paradise that offers an unparalleled lifestyle. With an average year-round temperature of 75°F, residents and visitors alike enjoy outdoor activities, from sunbathing and swimming to kayaking and paddleboarding in the crystal-clear waters of the Gulf of Mexico. The island is also home to charming boutiques, gourmet restaurants, and lively beach bars, creating a perfect blend of relaxation and entertainment.

For those seeking the ideal home in this idyllic setting, Siesta Key boasts an array of stunning two-story properties. These homes are designed to maximize both space and comfort, providing the perfect backdrop for family gatherings and entertaining friends. Imagine waking up to breathtaking views of the ocean from your master suite, or hosting summer barbecues on spacious balconies that overlook lush tropical landscapes. The architectural styles range from modern coastal designs to classic Florida charm, ensuring there’s a perfect fit for every taste.

Living in a two-story home on Siesta Key means more than just a beautiful residence; it’s about embracing a lifestyle filled with sunshine, sea breezes, and a strong sense of community. Explore the local parks, take leisurely strolls along the beach, or simply enjoy the serenity of your own private oasis. Siesta Key is not just a place to live; it’s a destination where cherished memories are made. Discover your dream two-story home in this enchanting paradise today!

Newest Siesta Key Homes with Two Story Property Description

$22,000,000
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

$2,799,000
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

$2,690,000
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

$6,300,000
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

$4,190,000
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

$4,150,000
4 Beds 6 Baths Siesta Beach SubDv. 34242 Zip Code
Completed in 2025, this exceptional residence offers a rare opportunity to step into a brand-new partially furnished home without the wait. As opportunities to purchase newly built homes on Siesta Key become increasingly limited, this home delivers the quality, craftsmanship, and peace of mind of new construction in one of the island's most desirable neighborhoods, just moments from Siesta Beach. Spanning more than 5,200 sq ft, the home has been thoughtfully designed with a floor plan that feels as good as it looks. Natural light fills the interiors through expansive PGT impact-rated windows and sliding glass doors, while soaring cathedral and coffered ceilings, wide-plank wood flooring, and clean architectural detailing create a timeless backdrop throughout. The spaces flow naturally from one to the next, striking the right balance between openness and definition. At the center of the home, the kitchen anchors the main living spaces. An oversized quartz island, custom cabinetry, Sub-Zero refrigeration, a Wolf gas range, and generous prep space combine beauty with everyday practicality. Overlooking the great room and dining area, it's where family naturally comes together, while a beautifully appointed wet bar adds another gathering place when entertaining friends. Like any great Florida home, the living spaces don't stop at the back door. Walls of sliding glass open to a covered lanai with a wood-paneled ceiling, leading to a heated pool and spa surrounded by lush tropical landscaping. An outdoor kitchen, pool bath, and outdoor shower complete a backyard designed to be enjoyed year-round, whether hosting family and friends or simply enjoying the privacy of your own home. The thoughtful layout continues with a privately positioned primary suite on the first floor, offering cathedral ceilings, dual walk-in closets, and a beautifully finished bath with a freestanding soaking tub, oversized walk-in shower, and dual vanities. A dedicated office, mudroom, and laundry room complete the main level. Upstairs, three additional en-suite bedrooms, each with walk-in closets and private baths, are joined by a den overlooking the pool, a spacious bonus room with its own Romeo and Juliet balcony, and a second laundry room, providing flexibility as your needs evolve. Built with concrete block construction, a standing seam metal roof, and impact-rated windows and doors throughout, the home reflects the lasting quality buyers expect from a newly completed residence. A split three-car garage and generous paver driveway reinforce the home's thoughtful design and everyday functionality. The location is every bit as compelling as the home itself. Just moments from Siesta Key Beach, you'll have one of the country's most celebrated stretches of coastline practically at your doorstep, while Siesta Village's restaurants, boutiques, and cafés are just minutes away. Downtown Sarasota is an easy drive across the bridge, offering exceptional dining, waterfront parks, galleries, marinas, and the performing arts. It's a location that strikes a rare balance between the relaxed pace of island living and the conveniences of the city. For buyers considering building on Siesta Key, this presents an increasingly rare opportunity. Instead of spending years acquiring land, designing, permitting, and building, you can enjoy a brand-new home from day one, with the home being offered furnished. Beautifully executed and ready now, this is a home built for the next chapter.

656 Tropical Circle, Sarasota

$3,690,000
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

$17,650,000
4 Beds 6 Baths Bay Island SubDv. 34242 Zip Code
Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

3799 Flamingo Avenue, Sarasota

$2,800,000
4 Beds 4 Baths Sarasota Beach SubDv. 34242 Zip Code
Privately set on Palm Island in the heart of Siesta Key, this residence offers an exceptional combination of generous living space, thoughtful design and effortless access to the island’s most celebrated destinations. Just a short distance from the powdery, white quartz sands of Siesta Beach and the boutiques, dining and lively atmosphere of Siesta Village, this beautifully reimagined waterfront residence presents a rare opportunity to enjoy a relaxed coastal lifestyle without compromising comfort, privacy or quality. Nearly every aspect of the home was transformed, creating a fresh, modern interior, designed for both everyday living and gracious entertaining. Soaring ceilings, abundant natural light, a contemporary custom staircase and impact-rated windows and doors establish an open, airy atmosphere, while luxury vinyl and engineered hardwood flooring, recessed lighting and thoughtfully integrated storage add warmth and architectural interest. The expansive kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, upgraded stainless steel appliances, wine storage and an oversized quartz island with generous seating. Designed to accommodate everything from casual mornings to larger gatherings, the kitchen flows naturally into the surrounding living and dining spaces and continues outdoors to the pool, lawn and waterfront beyond. The main-level primary suite provides a serene private retreat with direct access to the pool area, a spacious custom-fitted closet and a beautifully appointed spa-inspired bathroom. Three additional bedrooms offer comfortable accommodations for family and guests, while an upstairs, separate flex space is ideally suited for a private office, exercise room or personalized retreat. A sunroom and conveniently positioned pool bath further enhance the home’s easy indoor-outdoor connection. Outside, the property reveals one of its most distinctive features: an unusually spacious backyard for Siesta Key. A broad lawn surrounds the heated pool, creating room for outdoor dining, recreation, pets and relaxed afternoons beneath the Florida sun. Beyond the pool, peaceful canal views and a private dock provide a tranquil waterfront setting with boating access. A well supplies the irrigation system, helping maintain the lush tropical landscape. A detached two-car garage offers valuable parking and additional storage for beach equipment, bicycles, paddleboards and other island essentials to enjoy the Siesta Key lifestyle. Morning walks along Siesta Beach, afternoons beside the pool and evenings dining in Siesta Village can all become part of everyday life. Spacious, extensively remodeled, and ideally positioned near the beach, Village and boating water, 430 Island Circle is a sophisticated yet wonderfully comfortable island retreat designed for those who want to experience the very best of Siesta Key.

430 Island Circle, Sarasota

$1,150,000
4 Beds 3 Baths Roberts Point SubDv. 34242 Zip Code
Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive luxury residences. The primary living spaces are positioned on the upper level, where vaulted ceilings and an open layout create a bright, comfortable setting for everyday living and entertaining. Multiple decks extend the living areas outdoors, offering peaceful views of the water and surrounding tropical landscape. A hot tub overlooking the bayou provides a relaxing place to unwind at the end of the day. The legal ground level (non-conforming) adds valuable versatility with a private bedroom and bath, bonus room, screened lanai and two-car garage, well suited for guests, extended family, a home office or a recreational space. A new roof completed in August 2023, hurricane shutters and completed storm remediation provide added peace of mind. The property offers direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards, making it easy to enjoy Siesta Key’s natural surroundings from your own backyard. Ideally located near Siesta Beach, Siesta Village, shopping, dining, and entertainment, and easy access to mainland Sarasota, this is a distinctive opportunity to live, renovate or rebuild in a coveted North Siesta Key setting.

4114 Roberts Point Circle, 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

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