Osprey Homes with Trail(s) Amenities

Osprey Homes with Trail(s) Amenities

Welcome to Osprey, Florida, a charming gem nestled in Sarasota County, where the sun-kissed beaches meet the lush landscapes of the Gulf Coast. This vibrant community, straddling the picturesque towns of Osprey and Nokomis, offers an idyllic blend of serene living and outdoor adventure. With its rich history, friendly atmosphere, and breathtaking natural beauty, Osprey is a perfect place to call home.

One of the standout features of Osprey is its commitment to an active lifestyle, exemplified by the numerous homes that boast access to scenic trails and amenities. Residents can enjoy leisurely strolls or invigorating bike rides along the winding paths that meander through the area, offering stunning views of the lush greenery and tranquil waterways. Whether you’re an avid nature lover or simply looking to embrace a healthier lifestyle, these trails provide the perfect backdrop for your daily adventures.

In addition to the outdoor amenities, Osprey is home to a variety of charming shops, delightful dining options, and cultural attractions, including the renowned Oscar Scherer State Park and the historic Spanish Point. The community’s proximity to the vibrant city of Sarasota ensures that you are never far from world-class entertainment, art, and dining experiences.

With its unique blend of natural beauty, recreational opportunities, and a welcoming community spirit, Osprey is more than just a place to live; it’s a lifestyle waiting to be embraced. Explore the homes with trail amenities in this enchanting region, and discover the perfect setting for your next chapter in paradise.

Newest Osprey Homes with Trail(s) Amenities

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

Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.

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 Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior. The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use. The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence. The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference. Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.

242 Hidden Bay Drive Unit 602, Osprey

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Theresa Kimbrell

Theresa Kimbrell was Born in Chicago. She attended DeVry University of Arizona State and was a Graduate in business management and marketing as well as Computer Science programming and technology. She was also an English Major of Criminal Law and Forensic science. Theresa served in the United States Army and worked as a Corrections Officer and as A Deputy for the Maricopa County Sheriff's office. She is a devoted Mother and Daughter to her amazing family. She continuously gives back to her community, settling in Venice Florida In 2014. Theresa strives to bring out the best in people and deliver confidence and success, every step of the way. Theresa Kimbrell offers you, your best source for real-estate on Florida's Gulf Coast. It's not hard to recognize professionalism and strategic planning with great communication skills and knowledge. Theresa offers that and more on every level. Recognizing and understanding her client's goals and needs in every aspect on any scale is one of her many attributes. Her understanding of today's competitive market and performing the proper research and strategic marketing are your keys for success. Understanding the biggest decisions we make in life come in many forms, choosing the right home or property is one of the biggest decisions a person can make in a lifetime. Whether you are an investor, first time home buyer or have been down this road before we all know there can be obstacles in the way. With Theresa there is always a clear path to your goal. From protection to stability and great communication. This is what one should expect from their REALTOR. That is what Theresa Kimbrell delivers!

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