$879,024Average Value$357Average Price per Sq Ft78Homes For Sale
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 96 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 $654,000, down 13% from the median home sale price over the previous 12 months.
Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style
Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in
West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass
Priced to sell! 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,
Looking for a house within #1 US public school within a short distance? Discover this expansive 5-bedroom, 3-bathroom home with an oversized flex room, office, and almost 4,000 sq. ft. of living space, perfectly situated on a 9,017 sq. ft. lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2025), HVAC units (2019 & 2023), a new water heater (2022), fresh
Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village-3 Bedrooms | 2 Bathrooms | Direct Intracoastal FrontageRare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and
Welcome to 329 Bay Vista Ave., Osprey, FL 34229—a rare opportunity to own a beautifully renovated 2-bedroom, 2-bathroom home on an expansive lot (0.47 acre!!!) with no HOA, no deed restrictions, and endless possibilities.Inside, you'll find a thoughtfully updated interior that's move-in ready, offering the perfect blend of comfort and style. Whether you're looking for a full-time
Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and
**Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional
**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home
**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered
**MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer
**FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and features 3 bedrooms plus a study/den, 3 full baths, two elevator banks, two assigned second-level parking spaces, and climate-controlled storage. Located behind the secure gates of The Oaks Preserve Country Club, this residence
AVAILABLE 2027 SEASON. 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 & dryer
Property Id: 1524644 Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONS Landlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and
Virtually Staged. Welcome to paradise! Osprey's most desirable luxury community at the Villas at the Osprey Harbor Village with direct access to the Little Sarasota Bay is available for 3 months to 12 months lease. Residences will have direct access to the Interacoastal Waterways, 10 minute boat trips to famous Midnight Pass, Blackburn Point Park, and picturesque Casey Key for morning stroll.
The advertised rate of $11,037/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
***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.
The advertised rate of $7,500/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 31, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a
The advertised rate of $4,991/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
**RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank,
Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village! Experience comfortable Sarasota living in this well-appointed condo, featuring neutral paint, ceiling fans throughout, tile flooring in the main living areas, and carpeted bedrooms. The open-concept living and dining area flows seamlessly into the kitchen, complete with
Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the
Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round
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