Osprey Homes with No Truck/RV/Motorcycle Parking Community Features

Osprey Homes with No Truck/RV/Motorcycle Parking Community Features

Welcome to Osprey, Florida—a hidden gem nestled in the heart of Sarasota County. This charming coastal community offers a unique blend of serene living and vibrant local culture, making it an ideal place to call home. With its lush landscapes, stunning waterfront views, and proximity to the beautiful Gulf of Mexico, Osprey is perfect for those who seek both tranquility and adventure.

Osprey is known for its picturesque neighborhoods, where residents enjoy a peaceful lifestyle complemented by an array of recreational activities. Whether you’re exploring the scenic trails of the nearby Oscar Scherer State Park or indulging in the local dining scene, there’s always something to discover. The community is also home to a variety of shops, art galleries, and cultural events that showcase the rich heritage of the area.

For those seeking a home that promotes a harmonious living environment, Osprey offers communities with specific features, including homes that do not allow truck, RV, or motorcycle parking. These thoughtfully designed neighborhoods prioritize aesthetics and tranquility, ensuring that the community remains peaceful and visually appealing. This feature is especially attractive to families and individuals who appreciate a well-maintained environment and a sense of community spirit.

Whether you’re looking for a cozy bungalow or a spacious family home, Osprey has a diverse range of real estate options to suit your needs. Experience the charm and beauty of Osprey, where your dream home awaits amidst the sun-soaked beaches and vibrant local culture. Let us help you find your perfect slice of paradise in this delightful Florida community!

Newest Osprey Homes with No Truck/RV/Motorcycle Parking Community Features

250 Hidden Bay Drive Unit 301, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in January 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy-to-maintain tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area opens to a large, screened-in terrace with privacy screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, a makeup vanity and a walk-in shower. Additional features include a private den/office, an in-unit laundry room, two full baths and a powder room, and air conditioner from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with a kitchen and quartz bar, a heated pool and spa, a fitness center, a library, a tiki hut with grilling stations, pickleball and tennis courts, a kayak launch, a fishing pier, a dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey, just south of Sarasota, near area beaches, shopping and dining and only minutes from Venice.

250 Hidden Bay Drive Unit 301, 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
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
156 Bishops Court Road, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. An expansive double lot, a quiet cul-de-sac setting and preserve views with no rear neighbors make this Bishops Court residence an exceptional private retreat. Mature oaks and lush landscaping frame the property, creating a sense of space and seclusion within this intimate gated enclave of The Oaks Preserve. Designed by renowned architect Frank Folsom Smith, the home pairs timeless architectural character with thoughtfully curated updates. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths and inviting spaces that make the most of its natural surroundings. Hardwood floors, custom millwork, crown molding, vaulted ceilings, plantation shutters and two fireplaces bring warmth and character throughout. The great room flows into the screened Florida room and outdoor living areas, keeping the peaceful setting in view. A built-in serving bar and wine chiller enhance the dining room, while the updated kitchen features custom white cabinetry, granite countertops, stainless steel appliances, an oversized island and designer lighting. A Sonos sound system extends throughout the home. The primary suite offers its own quiet retreat, with vaulted ceilings, a bay-window sitting area and direct outdoor access. Renovated in 2023, the spa-inspired bathroom features marble-look tile, a frameless glass shower, dual vanities and a freestanding soaking tub beneath a skylight. The additional bathrooms have also been extensively renovated with designer fixtures and finishes. Custom storage, built-ins and shiplap detailing bring the same considered style to the laundry room. Upstairs, a spacious bonus room with a fireplace opens to a newly renovated second-story deck overlooking the treetops. Freshly painted in 2026 and complete with a full bathroom, this versatile level can serve as guest accommodations, a media room, home office, art studio or secluded lounge. Outside, the generous lot gives the pool area a remarkable sense of privacy. A seven-foot-deep heated pool and spa are surrounded by brick pavers and tropical landscaping, with tranquil preserve views beyond. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club, where Golf or Social Membership is required with homeownership. Club amenities include two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a fitness center, fine and casual dining, and a year-round social calendar. The Oaks Club has been recognized as a Platinum Club of America, a Distinguished Emerald Residential Country Club and an Audubon International Certified property. Located in Osprey between Sarasota and Venice, the home places Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota and historic Venice within easy reach.

156 Bishops Court Road, Osprey
51 Mac Ewen Drive Unit 14, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey
51 Macewen Drive Unit 5, Osprey
$235,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey
401 N Point Road Unit 1001, Osprey
$1,995,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
**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 designed to maximize the breathtaking vistas, with panoramic views from the great room, dining area, kitchen, owner’s suite, and expansive balcony. Interior highlights include 10ft ceilings, crown molding, engineered hardwood and tile flooring throughout, and plantation shutters. The well-appointed kitchen offers newer Cambria quartz countertops (2022), solid wood cabinetry, counter seating, and newer stainless-steel appliances (2023). The spacious primary suite features walk-in closets and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. 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 1001, Osprey
852 Macewen Drive, Osprey
$2,395,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**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 Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**

852 Macewen Drive, Osprey
909 Macewen Drive, Osprey
$1,595,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

909 Macewen Drive, Osprey
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