Community known for its outdoor spaces and waterfront living opportunities
Osprey, a census-designated community, sits right on the Gulf Coast, offering residents vibrant outdoor spaces and ample activities on the water. It's a place where "locals here can start their morning off kayaking through mangroves," says Tamara Currey, a Realtor with Sotheby's International Realty who lives in the area. "They can relax at a waterfront restaurant for lunch and, at night, head to one of Casey Key's fun tiki bars," she adds. Shopping and dining establishments surround the Tamiami Trail, giving locals easy access to the area's fresh seafood flavors. Adding to the appeal are Osprey's many planned communities that foster a social lifestyle. Properties here range from condos to waterfront villas. While most of the residents in the community are retirees, Pine View School attracts people from all over the country who want to send their kids to one of the nation's top schools. With everything from historic places to plenty of green spaces to easy access to nearby beaches, Osprey offers residents a classic Florida lifestyle.
Wave runners, kayaks, and paddleboards can be rented on Casey Key.
Live music can be found on the sidewalks of the Shops at Casey Key in Osprey.
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Oscar Scherer State Park and Bay Preserve
For some time outside, locals can visit the Oscar Scherer State Park. Hikers walk on paths that meander through a forest of scrubby pine flatwoods, hoping to catch a glimpse of the blue and white Florida scrub jays. The Legacy Trail, which stretches from Venice to Sarasota, passes through the park, making it a popular destination among bikers. Canoers, kayakers and anglers alike head on South Creek to enjoy an experience surrounded by mangroves and giant leather ferns. In the summer, many dip in Lake Osprey to cool off. Bay Preserve is another popular spot. It's located right on Little Sarasota Bay, giving visitors access to activities like fishing and boating. Kayakers also enjoy exploring the bay's many mangrove islands. The preserve's 1931 Burrows-Matson House is a popular wedding venue.
Oscar Scherer State Park has many trails, perfect for walking and biking.
Osprey residents have many access points to the water, such as the Bay Preserve.
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The O Bar, Spanish Point Tiki Bar and other establishments
Situated around the Tamiami Trail are grocers like Publix and plenty of dining options, including Max’s Table, a favorite for breakfast. The restaurant features a menu ranging from pancakes to savory Greek-inspired dishes. Those wanting to enjoy classic American fare and live music flock to The O Bar. Locals can also check out waterfront restaurants like Casey Key Fish House, where patrons can come by boat or car to enjoy fresh seafood. For a night out, many people here head to Spanish Point Tiki Bar, which is known for its waterfront sunset views, live music and happy hour specials. Conveniently, the community is home to the Bay Street Town Center.
Osprey has a variety of local retail businesses and eateries at Bay Street Town Center.
Casey Key Fish House's Tiki Bar located on the water offers Adirondack chairs to relax in.
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Mediterranean-inspired properties and waterfront villas
Gated and subdivision communities are common here, meaning that many people here live in residences that have HOAs. These areas often feature palm-tree-lined sidewalks and specialized amenities. Residents of communities like the Oaks Club enjoy luxury coastal living with conveniences like expansive golf courses and a clubhouse. Houses here often have attached garages. Popular styles include contemporary subdivision properties, Mediterranean-inspired ranch-styles and stately villas situated on Little Sarasota Bay. Small ponds scattered throughout Osprey also offer residents waterfront views. Many homes have hurricane shutters because of Florida’s storm-prone weather, and Sarasota County encourages residents to purchase flood insurance. Condos are also typically readily available. Prices here typically range from around $180,000 for a condo to upwards of $3 million for a property on Little Sarasota Bay.
Aerial views of Osprey include planned subdivisions and the Gulf of Mexico.
Osprey features brightly colored homes, true to Floridan character.
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Historic spots in Osprey
At Historic Spanish Point, visitors can learn about the region's rich history. They can see a prehistoric mound or check out Webb Packing House to learn about the pioneers' citrus packing industry. Visitors can also take a boat tour to another section of the museum or spot butterflies at Marie Selby Botanical Gardens. Another nearby historic site is the one-lane Blackburn Point Bridge, which crosses over the Intracoastal Waterway. It's one of the only swing bridges remaining in Florida, and it is on the U.S. National Register of Historic Places.
Burrows-Matson House in Osprey is a historical site and event space with beautiful grounds.
Marie Selby Botanical Gardens is located Historic Spanish Point on the Bay Preserve in Osprey.
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Pine View School in Osprey is designed for gifted students.
Highly ranked Pine View School and other schooling options
Children in Osprey can enroll in the Sarasota County School District. For kindergarten through fifth grade, students can attend Gulf Gate Elementary, which receives an A-minus rating from Niche. It serves 700 students and boasts a student-teacher ratio of 15-to-1. However, many parents move to Osprey for A-plus-rated Pine View School, which serves second-grade through 12th-grade students. Pine View students are admitted based on recommendations and a series of tests. It was selected as a National Blue Ribbon School in 2023. According to Niche, it is the nation's No. 2 public elementary school, No. 3 public middle school and No. 20 public high school. Another schooling option is A-rated Venice High, which offers career and technical education opportunities.
Osprey residents can find public transportation along Tamiami Trail.
Commutes, employers and more
Osprey is a primarily car-dependent area, but public transportation through the Breeze Transit is available. Locals here can head on the Tamiami Trail to nearby cities, airports, beaches and some of Sarasota County’s major employers. Locals are less than 10 miles from the Sarasota Memorial Hospital — the county’s largest employer — and PGT Innovations. On days off, folks can head to one of the area’s nearby beaches to relax by the water. Casey Key’s Nokomis Beach, known for its clear waters and white sand, is just 6 miles away, while Siesta Key Beach, known for its quartz-crystal sand and popularity among tourists, is just around 8 miles away. Travelers will be just 15 miles away from Sarasota Bradenton International Airport.
Photography Contributed By
Kristjan Veski
Interested in learning more about homes in this area?
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On average, homes in Osprey, FL sell after 102 days on the market compared to the national average of 55 days. The median sale price for homes in Osprey, FL over the last 12 months is $700,000, down 10% from the median home sale price over the previous 12 months.
Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant
Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom
Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exceptional scale, thoughtful architecture, and a preserve setting backing directly to Oscar Scherer State Park. With no rear neighbors and expansive natural views, the home offers privacy and tranquility while remaining minutes from beaches, dining, and
Attention water lovers... take a look at this home in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage.
One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the
Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble
Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, and
Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout,
One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and
One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood
BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of
Enjoy sweeping Intercoastal water views with peek-a-boo Gulf glimpses from this beautifully upgraded top-floor, end-unit residence filled with natural light, privacy, and coastal elegance. The interior features Luxury vinyl plank flooring, plantation shutters, crown molding, and higher ceilings unique to the top floor. The chef’s kitchen offers Bosch and JennAir appliances, a Liebherr split
Discover an exceptional opportunity to create your custom dream home in the heart of Osprey — one of Sarasota County’s most desirable coastal communities. This buildable vacant homesite offers the perfect canvas to design a private retreat tailored to your lifestyle, all while enjoying the charm, convenience, and natural beauty of Florida’s Gulf Coast. With over 7,000 square feet of buildable
CASEY KEY ISLAND OPPORTUNITY – Bring your preferred builder and create the coastal retreat of your dreams on one of Sarasota County’s most treasured barrier islands. Perfectly positioned on the coveted north end of Casey Key, this exceptional property offers over 100 feet of direct Gulf frontage and sweeping, unobstructed sunset views across shimmering turquoise waters. Your blank canvas awaits –
Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A
Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness
***AVAILABLE MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.
RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &
Now open for immediate move-ins, discover stunning one-, two-, and three-bedroom apartment homes in Sarasota, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that
For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A
Property Id: 310276AVAILABLE MAY 15 to SEP 30, 2026 Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal
Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target
Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,
Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School
Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage
Live the ultimate waterfront lifestyle in this beautifully maintained 2-bedroom, 2-bath canal-front home with direct boating access to the Intracoastal and the Gulf. Inside, you’ll find tile flooring throughout for a clean, cohesive look and easy maintenance. The beautifully updated kitchen features modern finishes, ample cabinetry, and generous counter space, all flowing seamlessly into the open
Impressive three-bedroom, two-bathroom home designed for both comfortable family living and grand-scale entertaining. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key and the Gulf of Mexico. This exceptional home showcases spacious,
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