Osprey Vacation Homes for Sale

***carpet was professionally cleaned 3/26/25*** Discover this beautiful, expansive 5-bedroom, 4-bathroom home offering 3,938 sq. ft. of living space on a 10,548 sq. ft. lot.

Spacious Custom built home featuring an oversized corner yard, High Ceilings, Updated Kitchen and Bathrooms, Family Room with Wood Burning Fireplace, 3 Bedrooms, 3 Full Baths and a Bonus Room/ 4th Bedroom upstairs. Entertain in the Large Lanai with Outdoor Kitchen overlooking the Pool and wide Greenbelt view.

CASUAL, COASTAL ELEGANCE in this charming WATERFRONT community – BAYSIDE on LITTLE SARASOTA BAY! The Florida Lifestyle you’ve always dreamt of awaits you at Bayside on Little Sarasota Bay – a GATED ENCLAVE OF JUST 49 HOMES tucked away on the bay in Osprey Florida - one of our area’s best kept secrets ideally located between Sarasota & Venice! This delightful POOL HOME offers 3 BEDROOMS,

FULLY UPDATED ~ WATER VIEWS ~ PRIVATE 2 CAR GARAGE ~ OFFICE/4TH BEDROOM OPTION ~ The eye of an artist and perfected skill of a craftsman created this spacious, expertly designed residence.

Under contract-accepting backup offers. Looking for quality craftsmanship??? This exceptional home was built by US Homes, with a unique distinction — the original owner was the president of US Homes at the time of construction, personally overseeing every detail to ensure top-tier quality and craftsmanship throughout.

Newly Built-Out & Fully Furnished Move-In Ready Office Space at Baystreet Village! Located in the vibrant heart of Osprey, this beautifully designed office space at 3976 Destination Drive, Unit A-411, Osprey, FL 34229 is the perfect opportunity for your business to thrive.

Under contract-accepting backup offers. Welcome to Luxury Living in Rivendell! Nestled on a premium, private lot with serene lake and preserve views, this impeccably maintained, custom-built Arthur Rutenberg home offers elegance, comfort, and thoughtful design in every detail.

**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”.

Step into this beautifully renovated Rivendell home and discover a stunning pool and lanai area, thoughtfully designed for relaxation and enjoyment. Offering expansive lake views, this home provides a serene retreat in one of the area's most sought-after communities.

Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening relaxation.

This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers.

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve.