Osprey Homes with Playground Amenities

Osprey Homes with Playground Amenities

Welcome to Osprey, Florida, a charming gem nestled within Sarasota County that perfectly blends serene living with vibrant community spirit. Known for its stunning coastal views and lush landscapes, Osprey is a haven for those seeking a peaceful yet engaging lifestyle. With its proximity to the beautiful Gulf of Mexico, residents can enjoy a plethora of outdoor activities, from sun-soaked beach days to scenic hikes in nearby nature preserves.

Osprey boasts a rich history and a warm, welcoming community, making it an ideal place for families and individuals alike. One of the standout features of this delightful area is its array of homes equipped with playground amenities, perfect for families with children. These properties not only offer a comfortable living space but also provide a safe and fun environment for kids to play and grow. Imagine watching your little ones explore, laugh, and make lifelong memories just steps from your backdoor!

In addition to the playgrounds, Osprey’s neighborhoods are designed with family-friendly features, including parks, walking trails, and community events that foster a strong sense of belonging. Whether you’re enjoying a weekend barbecue at the playground or taking a leisurely stroll through the scenic surroundings, Osprey offers a lifestyle that promotes connection and joy.

If you’re looking for a place where family values, natural beauty, and community spirit thrive, Osprey, Florida, is the perfect destination to call home. Come discover the charm of Osprey and find your dream home today!

Newest Osprey Homes with Playground Amenities

117 Bishops Court Road, Osprey
$850,000
3 Beds ⋅ 2 Baths ⋅ Bishops Court At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Enjoy the benefits of living in a three bedroom, two bath, maintenance free home in the ever popular Bishops Court in the Oaks Preserve. This desirable floor plan with rear southern exposure allows for easy living with landscape maintenance and irrigation included. The interior features beautiful wood cabinetry, a gas range, and granite countertops in the kitchen and baths. Attractive tile floors in most living areas are easy to maintain. The primary suite is spacious enough for a sitting area or a desk, and the guest suites are on the opposite side for privacy. The dining room has a custom built in buffet with abundant cabinetry for storage. The roof is 4 years new, and the lanai has a plunge pool to enjoy. Bishops Court is a quaint neighborhood, with canopied oak tress offering shade for strolling the neighborhood. Also, enjoy the community pool steps away for a quiet swim, or soaking up the sun. Being a member of The Oaks Country Club is an extraordinary experience offering the best of golf, dining, tennis, regulation croquet, and every social activity to keep you busy throughout the year. Choose either a social membership, or golf (two 18 hole courses) and begin your active and fun lifestyle in a beautiful community.

117 Bishops Court Road, Osprey
409 N Point Road Unit 601, Osprey
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Experience luxury living in this spacious, light-filled corner residence offering nearly 2,600 square feet of elegant living space. Featuring three bedrooms, a den/office, and three full baths, this exceptional condo also includes access to two elevator banks, two assigned second-level parking spaces, and a climate-controlled storage unit. Located behind the secure gates of The Oaks Preserve, this unit has a thoughtfully designed open floor plan showcasing beautiful flooring throughout, crown molding, two wine reserve refrigerators, and a smart Nest thermostat. The updated kitchen features granite countertops and premium stainless-steel appliances, including Bosch and GE Monogram. The spacious master suite offers private balcony access, a walk-in closet, and an updated spa-inspired bath with dual vanities, a custom-tiled shower, and a soaking tub. When you step out onto the screened balcony, equipped with Kevlar hurricane shutters, you will be taken with the expansive views over the Preserve and out to the Bay. And, as another perfect Florida day ends, this is the perfect place to take in breathtaking sunsets, as the sky is drenched with gorgeous color. Residents of the Meridian enjoy exclusive amenities, including a heated pool and spa, workout room and outdoor grilling area. Additionally, with mandatory club membership, you can take advantage of all that The Oaks offers: two championship 18-hole golf courses, an award-winning racquets program with 12 Har-Tru courts, pickleball courts, a junior Olympic community pool, state-of-the-art WellFit center and casual-to- refined dining options. There is currently no waiting list for either Golf or Sports/Social membership.

409 N Point Road Unit 601, Osprey
1474 Landview Lane, Osprey
$1,485,999
4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Welcome to 1474 Landview Ln, a charming single-family home located in the desirable Southbay Yacht & Racquet Club in Osprey, FL. This spacious property features and exceptional layout with a total finished area of 3,246 sq.ft. As you step inside, you'll be greeted by a warm and inviting atmosphere with plenty of natural light flowing through the home. Quality, attention to detail, and fine finishes surround you in every room. The interior features 3 bathrooms, providing convenience and privacy for all residents and guests. Premium upgrades throughout include a built-in coffee system, custom cabinetry, multiple living rooms- including a 6' fireplace! The gourmet kitchen flows into the hearth room and simultaneously opens to the pool counter. The lot size is an impressive 10,560 sq.ft. offering ample outdoor space for entertaining, gardening, or simply relaxing in serene privacy. Whether you're looking to host a BBQ with friends or enjoy a quiet evening under the stars, this property has plenty of room to accommodate your lifestyle. Southbay Yacht & Racquet Club has it's own PRIVATE MARINA with well maintained boat slips up to 55ft. Easy access to the ICW and Gulf passes make Southbay one of Florida's most unique neighborhoods. Southbay is conveniently located near a variety of amenities and attractions, including the Heritage Bicycle and Recreational Trail. Finally, shopping, dining, a micro brewery, coffee shop, Pilates studio, fitness center, beauty salon and more are accessible with your golf cart via a designated entrance to the adjacent shopping center. Don't miss your chance to make this wonderful property your new home. With its ideal location, ample space, and charming features, boat slip, racquet courts, and more, 1474 Landview Ln is the perfect place to create lasting memories and enjoy the Florida lifestyle to the fullest. Contact us today to schedule a showing and see all that this property has to offer.

1474 Landview Lane, Osprey
366 S Creek Court, Osprey
$1,049,000
4 Beds ⋅ 3 Baths ⋅ South Creek SubDv. ⋅ 34229 Zip Code
Welcome to 366 South Creek Court, located in the highly sought-after gated waterfront community of South Creek in Osprey, Florida. Nearly completely renovated, this beautiful 4-bedroom, 3-bathroom home offers 2,775 square feet of thoughtfully designed living space, combining elegant finishes, comfortable living spaces, and exceptional indoor-outdoor living. The open and bright floor plan features separate living and dining areas, a spacious family room, and a charming dinette overlooking the lanai and backyard. Luxury details throughout include tray ceilings, crown molding, rounded wall edges, plantation shutters, 8-foot doors, arched doorways, and engineered hardwood flooring. Fresh interior paint and expansive windows and doors fill the home with natural light. At the heart of the home is the beautifully renovated kitchen, featuring 42-inch shaker-style soft-close cabinetry with crown molding, deep drawers, stainless steel appliances, induction cooking, a hood vent, dual-bowl sink, and quality hardware. Vibrant quartz countertops and an oversized island with seating create an inviting space for everyday living and entertaining. The front living area provides a welcoming setting for conversation or relaxing with a book beside the electric fireplace with solid wood mantel. Adjacent to the living space is a dedicated dining area with a wet bar and wine chiller, ideal for entertaining family and guests. The spacious primary suite offers abundant natural light and direct access to the screened lanai. The ensuite features dual vanities, a dedicated makeup counter and seat, generous counter space, dual walk-in closets, and a brand-new oversized custom walk-in shower. Three additional guest bedrooms offer excellent closet space and natural light. The first guest bath combines a large walk-in shower with a conveniently located laundry area featuring a stackable washer and dryer. The second guest bath offers a dual vanity, tub/shower combination, and adjacent linen closet. Outdoor living takes center stage with a covered and screened paver lanai featuring a heated pool and spa. The lush, mature landscaping and areca palm-lined backyard provide a private and tranquil setting. An additional exterior patio has been designed to accommodate a 72-inch outdoor kitchen, creating an ideal space for entertaining. The home welcomes guests with a paver driveway and sidewalk leading to a charming country-style front porch. The oversized two-car extended garage features ceiling storage racks, a side-entry door, and a hurricane-rated garage door. Additional exterior improvements include fresh paint, new lighting, security cameras, beautiful landscaping, an irrigation system, and hurricane storm panels for every opening. South Creek offers a low HOA fee and an exceptional collection of amenities, including a kayak launch, tennis and pickleball courts, basketball court, and community boat and fishing dock on the South Creek saltwater canal. Ideally located near Casey Key, Nokomis and Siesta Key beaches, Pine View School, shopping, restaurants, a dog park, and the Legacy Trail. Located in an X flood zone, flood insurance is optional. This beautifully renovated South Creek home offers the perfect combination of style, privacy, amenities, and coastal Florida living.

366 S Creek Court, Osprey
401 N Point Road Unit 703, Osprey
$1,200,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Enjoy spectacular Gulf sunsets from this Move-In Ready, Fully Renovated 7th-floor condominium residence featuring 3-Bedrooms, 3-Full-Baths and over 2,200 square feet of beautifully designed living space with an open floor plan ideal for both everyday living and entertaining. The thoughtfully updated kitchen features quartz countertops, stainless steel appliances, Sub-Zero refrigeration, a wine refrigerator, and an Invisacook® invisible induction cooktop, creating a sleek and highly functional culinary space. The spacious private balcony offers tranquil preserve views and abundant opportunities for wildlife watching. Additional highlights include two assigned parking spaces and an exceptional combination of expansive views, privacy, modern finishes, and coastal living. A new HVAC system adds to the convenience and peace of mind. A must-see property! Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. Meridian Tower #3 also features a new roof (2025). THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

401 N Point Road Unit 703, Osprey
275 Lookout Point Drive, Osprey
$4,590,000
5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey
324 Osprey Point Drive, Osprey
$3,700,000
5 Beds ⋅ 5 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey
226 Saint James Park, Osprey
$1,350,000
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
409 N Point Road Unit 803, Osprey
$985,000
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
1036 Oak Meadow Lane, Osprey
$630,000
4 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

1036 Oak Meadow Lane, Osprey
360 N Point Road, Osprey
$1,445,000
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
216 Osprey Point Drive, Osprey
$695,000
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

How much is your home worth?

Get instant property value now!