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
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On average, homes in Osprey, FL sell after 93 days on the market compared to the national average of 53 days. The median sale price for homes in Osprey, FL over the last 12 months is $747,850, down 10% from the median home sale price over the previous 12 months.
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
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A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses.Conveniently positioned one mile East of US 41, within a mile of the Legacy Trail and the nationally-ranked Pine View School. Situated at the end of a
New listing alert 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. Residents also enjoy a waterfront park
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
***AVAILABLE NOVEMBER 2025 THRU JANUARY 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 &
Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West side of Tamiami Trail, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances, and two refrigerators—perfect for
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