Osprey Homes with Pickleball Court(s) Amenities

Osprey Homes with Pickleball Court(s) Amenities

Welcome to Osprey, Florida—a charming gem nestled in Sarasota County, where the sun-drenched shores meet a vibrant community spirit. This picturesque town, conveniently located just south of Sarasota, offers a unique blend of coastal living and suburban tranquility. With its lush landscapes, stunning waterfront views, and rich cultural heritage, Osprey is the perfect place to call home.

One of the standout features of Osprey is its commitment to an active lifestyle, particularly for those who love pickleball. Imagine waking up to sunny skies and stepping outside to your very own pickleball court! Many homes in Osprey come equipped with these fantastic amenities, allowing you to enjoy this fast-growing sport right in your backyard. Whether you’re a seasoned player or just starting out, having a pickleball court at home makes it easy to gather friends and family for a fun and engaging game.

In addition to pickleball, Osprey boasts a wealth of outdoor activities. With nearby beaches, parks, and nature preserves, residents can indulge in everything from kayaking in the Gulf of Mexico to leisurely strolls along scenic trails. The vibrant local community is also filled with charming shops, delightful eateries, and cultural attractions, ensuring there’s always something to explore.

Whether you’re seeking a family-friendly neighborhood or a peaceful retreat, Osprey offers a variety of homes tailored to your lifestyle. Embrace the best of Florida living and discover your dream home in Osprey, where pickleball courts and coastal charm await!

Newest Osprey Homes with Pickleball Court(s) Amenities

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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 and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, Osprey

3 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities and driving ranges. The member-owned Oaks Club features a 34,000-square-foot clubhouse with multiple dining venues, tennis courts, pickleball courts,a resort-style pool, and a 7,500-square-foot fitness center. Beyond the community gates, this location provides convenient access to Gulf Coast beaches, scenic trails including The Legacy Trail, local parks, as well as the cultural offerings of Sarasota and Venice. Schedule a private tour to explore the property and experience the distinct lifestyle of The Oaks Club.

226 Saint James Park, Osprey

2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of Little Sarasota Bay and the Gulf immediately take center stage. Thoughtfully designed with an impressive array of upgrades, the residence features high ceilings, crown molding, hardwood and tile flooring, and a beautifully appointed kitchen with a large island and seating area, granite countertops, stainless steel appliances, solid-wood cabinetry, and ample storage. The spacious Owner’s Suite is a peaceful retreat, complete with a generous walk-in closet, custom-tiled shower, relaxing soaking tub, and dual vanities. Step outside onto the expansive balcony and enjoy a serene setting surrounded by spectacular water views, abundant wildlife, and unforgettable Gulf sunsets. Hurricane-impact windows and sliding doors provide added peace of mind. Climate-controlled storage is conveniently located on the second floor. Residents of Meridian enjoy an array of private amenities, including a heated pool and spa, fitness center, and outdoor grilling area, along with access to the exceptional amenities of The Oaks Club’s main campus. Experience elevated coastal living, spectacular views, privacy, and resort-style amenities—all from this remarkable penthouse at The Oaks. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional residence is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location.

409 N Point Road Unit 803, Osprey

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

1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code

Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a balcony, creating a seamless indoor-outdoor living experience. Master bedroom with en-suite bath, vaulted ceiling and another balcony! The updated kitchen boasts beautiful butcher block countertops and you’ll enjoy peace of mind that comes with a NEW TANKLESS HOT WATER HEATER. THE ROOF WAS INSTALLED IN 2019, A/C APROX. 7-8 YEARS OLD, ELECTRIC WAS COMPLETELY INSPECTED IN 2025 BY GRAHAM ELECTRIC WITH CORRECTION MADE TO CODE., NEW APPLIACNES, EXTERIOR OF BUILDING WAS PAINTED 12/2025. Pine Run is a vibrant, amenity-rich community offering tennis and pickleball courts, two swimming pools, a clubhouse with a fitness room and over 20 acres of mature trees, lush landscaping and a scenic pond with water feature. Ideally located between Sarasota and Venice, you’ll be just minutes from the beautiful beaches of Siesta Key and Nokomis Beach. Shopping, dining and everyday conveniences along with the Intracoastal Waterway and one of the area’s favorite waterfront restaurants, Casey Key Fish House & Tiki Bar are all just a walk away! Come take a look - your new lifestyle is waiting - make it your own!

701 Pine Run Drive Unit 701, Osprey

3 Beds ⋅ 3 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code

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 doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

2309 Jessie Harbor Drive Unit 2402, Osprey

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

206 Four Knot Lane, Osprey

2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code

Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!

116 Woodland Place Unit 116, Osprey

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey

Oaks The SubDv. ⋅ 34229 Zip Code

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

216 Osprey Point Drive, Osprey

Start Your Search