Casey Key Homes with Two Story Style

Casey Key Homes with Two Story Style

Welcome to the prestigious subdivision of Casey Key, located in beautiful Osprey/Nokomis, Sarasota County, Florida. Known for its luxurious waterfront estates and pristine beaches, Casey Key offers a truly exclusive and serene setting for those seeking a sophisticated coastal lifestyle.

One of the unique features of the homes in Casey Key is the prevalence of the two-story style. These elegant residences often boast stunning views of the Gulf of Mexico or the Intracoastal Waterway, providing residents with breathtaking sunsets and a true sense of tranquility.

Living in a two-story home in Casey Key allows for spacious living areas, multiple bedrooms, and versatile floor plans to accommodate various lifestyles. Whether you're looking for a vacation retreat or a permanent residence, the homes with two-story style in Casey Key offer the perfect blend of comfort and sophistication.

Imagine waking up to the sound of waves gently crashing on the shore, enjoying your morning coffee on a private balcony overlooking the water, and ending your day with a leisurely stroll along the sandy beaches just steps from your doorstep. This is the lifestyle that awaits you in Casey Key.

If you're ready to experience luxury coastal living in a stunning two-story home, Casey Key is the perfect place to find your dream property. Contact us today to explore the available listings and start living the life you've always imagined in this exclusive waterfront community.

Newest Casey Key Homes with Two Story Style

$1,995,000
4 Beds ⋅ 4 Baths ⋅ A4693377 MLS
Welcome to your private coastal retreat on the barrier island of Casey Key. Nestled along charming Sandspur Lane, this exceptional home is ideally positioned between the Gulf of Mexico and Little Sarasota Bay, just three homes from private deeded beach access. Offering the perfect blend of island charm and resort-style living, this property captures the essence of Florida’s coveted salt life lifestyle. The beautifully remodeled kitchen flows seamlessly into the spacious family and dining areas, creating an inviting space for entertaining and everyday living. The main residence features two generously sized bedrooms along with two versatile bonus rooms ideal for a home office, fitness studio, game room or additional guest accommodations. An attached one-bedroom in-law guest suite provides privacy and flexibility for extended family or visiting guests, making this home perfectly suited for multigenerational living or hosting. Outside, the lush tropical backyard feels like a private botanical oasis centered around a stunning 2017-built swimming pool, expansive decks and multiple outdoor living and dining spaces designed for relaxation and entertaining. Moments away, the community dock offers easy access to Little Sarasota Bay for kayaking and paddleboarding, and the beach access is perfect for enjoying breathtaking sunsets. Within Casey Key’s protected conservation district, this rare island community preserves its timeless character with no high-rise development and exclusively single-family homes. Conveniently located near downtown Venice and just a short drive to Sarasota, you’ll enjoy easy access to dining, shopping, marinas and local waterfront favorites. Experience the best of coastal living in one of Southwest Florida’s treasured island communities.

3708 Sandspur Lane, Osprey/Nokomis
$6,400,000
5 Beds ⋅ 5 Baths ⋅ A4680110 MLS
Experience true Florida coastal living in this impeccably maintained Key West–style home on Casey Key, offering the rare and coveted Gulf-to-Bay lifestyle. Thoughtfully designed with high ceilings and a bright, open feel, this residence blends relaxed island charm with modern updates throughout. Step outside to a beautifully landscaped, fenced, and gated backyard—your own private oasis. Enjoy the Pebble Tec resurfaced pool, perfect for entertaining or unwinding after a day on the water. Boaters will love the new composite dock with covered lift, providing effortless access to the bay and Gulf beyond. The dune walkover and 100 feet of private sandy beachfront is perfect for afternoons by the shore and evening sunsets. Adding exceptional flexibility, the separate guest house features one bath and two bedrooms (or one bedroom plus a den)—ideal for guests, extended family, or a home office retreat. This home has been extensively updated for peace of mind, including hurricane shutters, newer HVAC systems, water heaters, well pump, and a whole-house replumb. Every detail reflects pride of ownership and careful maintenance. Whether you’re seeking a full-time residence or a luxurious island escape, this exceptional Casey Key property delivers privacy, comfort, and the ultimate waterfront lifestyle.

3240 Casey Key Road, Osprey/Nokomis
$6,475,000
5 Beds ⋅ 6 Baths ⋅ A4667263 MLS
Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.

121 N Casey Key Road, Osprey/Nokomis
$9,750,000
3 Beds ⋅ 4 Baths ⋅ A4664842 MLS
Pre-Construction. To be built. This is your chance to own a newly imagined Gulf-front estate on one of Sarasota’s most exclusive barrier islands. Positioned on 0.47 acres with 107 feet of direct Gulf frontage, this offering presents a 3,489 sq. ft residence designed by the renowned Stofft Cooney Architects in collaboration with Perrone Construction. The home’s architecture celebrates the Gulf at every turn, with walls of glass framing uninterrupted water views and inviting a seamless connection to the outdoors. Expansive terraces, a resort-style pool and spa, and a private beach pavilion create an atmosphere of relaxed sophistication, perfect for year-round enjoyment. Inside, an open-concept floor plan anchors the living spaces around a chef’s kitchen, ideal for both intimate gatherings and entertaining on a grand scale. Flow between indoor and outdoor living is effortless, encouraging a lifestyle defined by sunsets, sea breezes, and coastal luxury. Perfectly positioned near the Blackburn Point Bridge for easy access on and off the Key, this pre-construction opportunity is an exclusive chance to secure a design-driven Gulf retreat. For those interested in acquiring only the land, please refer to MLS#A4664853.

3761 Casey Key Road, Osprey/Nokomis
$1,999,000
3 Beds ⋅ 3 Baths ⋅ O6329570 MLS
IT'S ALWAYS ALL ABOUT THE LOCATION! Casey Key is a very private narrow barrier island located just North of Venice FL and South of Siesta Key; it separates the intracostal waterway and the Gulf of Mexico. The Key is home to some of the most luxurious waterfront Estates and Mansions in the Sarasota area. This large ½ acre Bayfront lot is peacefully set back from any traffic on Casey Key Road. The dock is on the North side of the property on a canal protected from wind and waves. From the living room or the Bay-side deck, views of the intracoastal waterway and its many traveling boats and yachts are stunning. Take a short 100 yard stroll down your deeded beach easement, to the pristine sands of the Gulf of Mexico. The beach is very private, ideal for swimming, snorkeling, sunbathing, shark tooth hunting, or just viewing the beautiful sunsets. The main floor houses 3 bedrooms and 2 full baths, the kitchen and the dining room. The first floor has one full bath and 3 rooms that can be used as bedrooms, rec room, den, etc. Other amenities include swimming pool, shuffle board court, elevator, and two single car garages. A new roof was installed in 2019. Live in the house "as is" or convert it to the home of your dreams located in paradise. Note: Some images have been virtually staged to better showcase the true potential of rooms and spaces in the home.

1210 Casey Key Road, Osprey/Nokomis
$3,650,000
2 Beds ⋅ 3 Baths ⋅ A4634851 MLS
Double your pleasure with two beaches and one extraordinary Gulf-to-Bay opportunity on exclusive Casey Key. This rare .58-acre waterfront parcel spans from the Gulf to Blackburn Bay, offering approximately 85 feet of private Gulf frontage plus a newly expanded sandy shoreline along the bay—creating a truly unique dual-beach setting. This property presents an exceptional opportunity for a future new build, the creation of a custom coastal estate, or continued use as an income-producing rental. Envision a bespoke architectural masterpiece designed to capture breathtaking sunrises over the bay and glowing sunsets over the Gulf, with panoramic water views from nearly every angle. The property includes a charming vintage 1951 beach cottage featuring pecky cypress siding, a brick fireplace, and an elevated split-level design reminiscent of classic Old Florida style. The home offers two bedrooms, two full baths, plus a third bath with shower located in the laundry room. A rooftop deck provides sweeping Gulf-to-Bay vistas. Recent improvements include two new AC units (2024), a roof replacement (2015), and new garage doors. The elevated structure remained dry during recent storms. Enjoy endless waterfront activities with private Gulf-front beach access, tranquil bay waters ideal for kayaking and paddleboarding, accessible from your private composite dock — complete with a boat lift. Situated near the desirable south bridge, this location offers convenient access to fine dining, boutique shopping, cultural attractions, and Venice Airport for private aviation. Surrounded by multi-million-dollar homes, this is a rare opportunity to secure one of Casey Key’s most dynamic and valuable Gulf-to-Bay parcels—perfect for building your dream beach home or investing in a legacy property on Florida’s west coast.

1620 Casey Key Road, Osprey/Nokomis
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