$878,031Average Value$364Average Price per Sq Ft94Homes 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.
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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 56 days. The median sale price for homes in Osprey, FL over the last 12 months is $660,000, down 13% from the median home sale price over the previous 12 months.
Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property
Welcome to this beautifully cared-for 3-bedroom, 2.5-bath, plus office/den home nestled within the sought-after gated community of Promenade Estates in Palmer Ranch. Thoughtfully designed for both everyday comfort and entertaining, this home offers an open-concept layout with split bedrooms that provide both functionality and privacy. The spacious main living areas create a bright and inviting
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
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 lanai, where golf course views
One or more photo(s) has been virtually staged. Welcome to this light-filled, beautifully maintained 2-bedroom, 2-bath townhome in the highly desirable Town-End Shores community of Osprey. With LOW HOA FEES $150.00 PER MONTH and GROUND MAINTENANCE INCLUDED IN FEE this townhouse is designed for comfortable living and easy entertaining, the open-concept main level features a spacious living room,
FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed
One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar
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
Gulf-front vacant lot on Casey Key in Osprey. Buildable lot with County guidance. 107' Gulf frontage, cleared site ready for new construction. For buyers seeking to build a custom waterfront home, this Gulf-front vacant lot on Casey Key in Osprey offers a compelling opportunity in one of Sarasota County’s most sought-after coastal locations. The homesite is cleared and confirmed buildable based
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 residence,
Welcome to 480 Oriskany Court...Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14. This home sits on a Premium golf course lot with additional privacy view across the street . Designed by Toll Brothers, this one story, 3200 sq. Ft. home with 3 bedroom ( plus office ) offers gracious entertaining and
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
**Pine View School** NO HOA** Custom House-Separate Guest House- Separate RV/Boat** 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
**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers
***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.
Property Id: 2540106 Welcome to Osprey, FL! This 2 bed, 2 bath fully furnished unit with a fenced back yard is perfect for families and small pets. Relax in a private lanai or binge-watch Netflix; Whatever your past time, this home has what you need. You will be walking distance to a Breeze bus stop route 17, and situated in the middle of the best beaches in southwest Florida as well as
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
Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a designer pool and spa with lake and preserve views, located in the
The advertised rate of $7,371/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 6, 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 be
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.
Property Id: 2376171 Welcome to Osprey, FL! This 2 bed, 2 bath fully furnished unit with a fenced back yard is perfect for families and small pets. Relax in a private lanai or binge-watch Netflix; Whatever your past time, this home has what you need. You will be walking distance to a Breeze bus stop route 17, and situated in the middle of the best beaches in southwest Florida as well as
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
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,
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
Luxury Modern Home with Private Pool in Gated Promenade Estates | Palmer Ranch, Sarasota!Welcome to 12657 Promenade Estates Blvd, a stunning and sophisticated single-family home located in the highly prestigious and secure gated community of Promenade Estates on Palmer Ranch. This beautifully designed residence offers a spacious and bright living environment, highlighted by your very own
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