Osprey Homes with Trail(s) Amenities

Osprey Homes with Trail(s) Amenities

Welcome to Osprey, Florida – a hidden gem nestled in the heart of Sarasota County. This charming coastal town seamlessly blends the tranquility of a small community with the vibrancy of nearby urban life. Osprey is renowned for its picturesque landscapes, rich history, and proximity to some of the most beautiful beaches in the Sunshine State. With its lush greenery, serene waterways, and stunning sunsets, it’s no wonder that many choose to call this idyllic location home.

For those seeking a lifestyle enriched by nature, Osprey offers an array of homes with trail amenities. Imagine stepping out of your front door and onto scenic trails that wind through lush parks and along the waterfront. Whether you enjoy morning jogs, leisurely strolls, or biking adventures, these trails provide the perfect backdrop for an active lifestyle.

The community is also home to several parks, including the popular Oscar Scherer State Park, where residents can explore miles of trails, picnic areas, and wildlife viewing opportunities. The nearby Nokomis Beach, just a short drive away, offers pristine sands and inviting waters, perfect for a day of sun and relaxation.

With a variety of housing options, from charming single-family homes to luxurious waterfront properties, Osprey caters to diverse tastes and lifestyles. Living here means embracing a harmonious blend of outdoor adventure and community spirit, making it an ideal place for families, retirees, and anyone looking to enjoy the best of Florida living. Discover the enchanting lifestyle that awaits you in Osprey, where every day feels like a vacation!

Newest Osprey Homes with Trail(s) Amenities

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 ⋅ 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

2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code

Penthouse level residence with ALL NEW APPLIANCES, including washer and dryer, complemented by beautiful water views. From its sixth-floor penthouse setting, this waterfront residence at Hidden Bay opens to expansive views across Little Sarasota Bay and the Intracoastal Waterway, with the Gulf beyond Casey Key in the distance. High ceilings, tall interior doors, and abundant natural light create an open interior with water views throughout the main living spaces. The great room brings living and dining together and extends into the enclosed waterfront sunroom, adding comfortable living space overlooking the bay. The kitchen features ALL NEW APPLIANCES, including refrigerator, microwave, range and oven, and dishwasher, along with a counter-height breakfast bar, pantry storage, and adjacent dining nook. A separate den offers flexible space for an office, media room, or guests. The primary suite includes multiple closets and an en suite bath with dual vanities, soaking tub, walk-in shower, water closet, and dedicated makeup vanity area. The second bedroom has an adjoining bath and walk-in closet. Luxury vinyl flooring extends through the bedrooms and den, and a new washer and dryer are located within the residence. A private, fully enclosed two-car garage provides additional storage and convenience. Furnishings are included, allowing the residence to convey as presented, or they may be removed at the buyer’s preference. Hidden Bay is a gated waterfront community along Little Sarasota Bay with a clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, kayak storage and launch, and a mangrove boardwalk leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is positioned between Sarasota and Venice, with convenient access to area beaches, the Legacy Trail, shopping, dining, and the surrounding Gulf Coast communities.

242 Hidden Bay Drive Unit 602, Osprey

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