Osprey/Nokomis Homes with Key West Architectural style

Osprey/Nokomis Homes with Key West Architectural style

Welcome to the enchanting coastal communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. With their lush landscapes and stunning waterfront views, these charming towns offer a unique blend of natural beauty and vibrant local culture. Osprey, known for its rich history and proximity to the renowned Oscar Scherer State Park, boasts an array of outdoor activities, from hiking trails to kayaking in serene waters. Just a stone's throw away, Nokomis enchants with its pristine beaches and warm, inviting atmosphere, making it a perfect haven for families and retirees alike.

One of the standout features of homes in this picturesque area is the delightful Key West architectural style. Characterized by their vibrant colors, spacious porches, and metal roofs, these homes exude a laid-back charm that perfectly complements the coastal lifestyle. Imagine sipping your morning coffee on a breezy porch, surrounded by lush tropical landscaping and the soothing sounds of the nearby ocean. Key West-style homes in Osprey and Nokomis not only provide a cozy retreat but also reflect the region’s rich cultural heritage and love for outdoor living.

Whether you’re looking for a seasonal getaway or a permanent residence, Osprey and Nokomis offer a diverse selection of Key West-style homes that cater to your every need. Embrace the allure of coastal living in these delightful communities, where the sun shines bright, and the lifestyle is nothing short of paradise. Discover your dream home in Osprey or Nokomis today, and start your journey to a more relaxed and fulfilling life by the sea!

Newest Osprey/Nokomis Homes with Key West Architectural style

18050 Wooden Skiff Court, Nokomis
$599,000
2 Beds ⋅ 2 Baths ⋅ Nokomis Sub SubDv. ⋅ 34275 Zip Code
Virtually Staged. Your own private dock, boat lift and Gulf access right in your backyard. Built in 2018, this Key West-style home brings together everything you want in Florida living: newer construction, a peaceful waterfront setting and the freedom to be on the water whenever you want. A private 25-foot dock and 7,000-pound boat lift make it easy to enjoy boating, jet skis, kayaks or paddleboards right from home. From Curry Creek, cruise into Roberts Bay and out to the Gulf of Mexico through the Venice Jetties. Native mangroves create a peaceful and private Old Florida setting along the water. With 1,952 square feet of living space, the home feels open and comfortable throughout. The open floor plan is perfect for relaxed Florida living and entertaining. The kitchen features granite countertops, KitchenAid stainless steel appliances, a breakfast bar and plenty of cabinetry, all open to the great room. Large sliders open fully to the covered lanai, bringing the indoor and outdoor living spaces together. The generous 14' x 11' den gives the floor plan the flexibility of a three-bedroom home, with plenty of room for guests, a home office or additional living space. The split floor plan offers privacy between the primary and guest bedrooms. The primary suite features a large bath with dual sinks, a soaking tub and separate shower, while the guest bedroom offers a comfortable and private space for family and friends. Quality construction sets this home apart, with concrete-block construction, fiber-cement siding, PGT hurricane-impact windows, a metal roof, reinforced two-car garage door and extensive foam insulation throughout the attic and walls. The home is elevated and has never experienced flooding. Located in Cottages on Curry Creek, a gated enclave of just 12 Key West-style homes, lawn care and irrigation are included for easy, maintenance-free living. Whether you're looking for a full-time residence, second home or Florida getaway, this home makes it easy to enjoy the Florida lifestyle. Located in a small gated community, the Legacy Trail is less than half a mile away, with Oscar Scherer State Park, Nokomis Beach, Venice Beach and historic downtown Venice all nearby. Schedule your private showing and come see what makes this home and its waterfront setting so special.

18050 Wooden Skiff Court, Nokomis
260 Hidden Bay Drive Unit 402, Osprey
$775,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy breathtaking sunsets from your private screened-in balcony as you look out across the bay to the barrier island of Casey Key. Inside the unit, you'll find a spacious living room and dining room featuring an open floor plan. The gourmet kitchen offers KitchenAid stainless steel appliances, quartz countertops, white shaker-style cabinetry, counter seating and plenty of storage cabinets. The primary bedroom is expansive with large walk-in closets, closet organization system and direct access to the outside balcony. Both guest bedrooms have dual purpose, as they both have built-in Murphy beds, desk workstations, plantation shutters and walk-in closets. If you're looking for a condominium with extra space for a den/office/sewing room/craft room or TV media room, this is the one that offers it all. More great features are impact-resistant windows and doors, a large laundry room with built-in cabinetry, a full-size washer and dryer and utility sink. One assigned parking space with a large storage unit with a roll-down door for all your extra gear. Some of the amenities include a new fishing pier, lit pickleball courts, kayaking and kayake racks for storage, clubhouse, swimming pool, spa and tiki hut with grilling barbeque stations. The location is walkable to many restaurants, shopping and the post office. Bike the Legacy Trail or head to the beach that's just a few miles away. There's so much to do just minutes away.

260 Hidden Bay Drive Unit 402, Osprey
3240 Casey Key Road, Nokomis
$6,400,000
5 Beds ⋅ 5 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
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, Nokomis
221 Lychee Road, Nokomis
$1,650,000
5 Beds ⋅ 4 Baths ⋅ 34275 Zip Code
Gorgeous private deepwater canal-front home with a rare double slip boathouse and seawall. You’ll be thrilled when you enter this spacious home that offers five bedrooms, 3.5 baths plus a separate bonus/game room for a total of 4,166 square feet under air and sits on over half an acre lot. This home has been extensively remodeled, replumbed/re-piped, concrete flood protection system added in 2025. All has been done for you. Enjoy outdoor living with an inviting gazebo, expansive deck along with a beautiful, heated saltwater lap pool. Loaded with closets everywhere and extra storage in the oversized garage. The fenced yard is great for pets, and the wide circular drive offers plenty of parking for a boat or R/V. The boater will appreciate the boathouse, and the quick access to the open water from the deep sailboat water canal with no bridges. The home is minutes from shopping and beaches. A one-year homeowner warranty will be provided to buyers at closing. Visit and you will not believe your eyes!

221 Lychee Road, Nokomis
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