Osprey Vacation Homes for Sale

FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings.

Experience exceptional waterfront living at Osprey Harbor Village. This 3-bedroom, 2-bath residence offers 2,374 sq ft of well-designed space with direct west-facing views of Little Sarasota Bay from every main room.

New listing alert in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage.

RARE OPPORTUNITY to own this stunning former John Cannon model home PLUS the adjacent buildable lot on peaceful Tranquility Circle. This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise, with direct access to North Creek, which leads to Little Sarasota Bay, offering abundant wildlife and serene water views.

Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot.

Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal lifestyle.

A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses. Conveniently positioned one mile East of US 41, within a mile of the Legacy Trail and the nationally-ranked Pine View School.

Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room.

**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS.

**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”.

Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle. As you arrive, the mature tropical landscaping and stately curb appeal immediately set the tone.

Welcome to your Boater's Paradise! This well-maintained South Bay home is your key to enjoy one of the best neighborhoods in the area. This three-bedroom pool home has the perfect layout with the primary bedroom and en suite on one side of the home and the two additional bedrooms on the other.