25 SUGAR MILL DRIVE
OSPREY FL $1,550,000

3 Beds /

3.5 Baths

/ 3,066 SqFt

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE ...

480 ORISKANY COURT
OSPREY FL $1,535,000

3 Beds /

3.5 Baths

/ 3,208 SqFt

Positioned on a premium golf course lot within the Oaks Club in Osprey, Florida, this Toll Brothers-built residence offers a rare combination of sceni...

360 N POINT ROAD
OSPREY FL $1,499,000

3 Beds /

3.5 Baths

/ 2,913 SqFt

**DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OA...

365 S SHORE DRIVE
OSPREY FL $1,349,000

3 Beds /

2 Baths

/ 1,824 SqFt

Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP W...

17 BAYHEAD LANE
OSPREY FL $1,295,000

3 Beds /

2 Baths

/ 2,850 SqFt

Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No de...

156 BISHOPS COURT ROAD
OSPREY FL $1,289,000

3 Beds /

3.5 Baths

/ 3,112 SqFt

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on ...

700 FAITH AVENUE
OSPREY FL $1,200,000

4 Beds /

3 Baths

/ 2,474 SqFt

One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of b...

1527 BUOY LANE
OSPREY FL $1,199,000

3 Beds /

2.5 Baths

/ 2,830 SqFt

Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile ro...

61 BAYHEAD LANE
OSPREY FL $1,185,000

3 Beds /

3 Baths

/ 3,180 SqFt

Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Featur...

296 PINE RANCH TRAIL
OSPREY FL $1,150,000

5 Beds /

3.5 Baths

/ 3,481 SqFt

**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** &' SELLER IS OFFERING A...

403 LONGBOW TRAIL
OSPREY FL $1,095,000

4 Beds /

3 Baths

/ 2,770 SqFt

Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Locate...

353 S SHORE DRIVE
OSPREY FL $1,060,000

3 Beds /

2 Baths

/ 1,840 SqFt

Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this...

204 WINDWARD DRIVE
OSPREY FL $1,050,000

3 Beds /

3 Baths

/ 2,486 SqFt

Spacious 3-bedroom, 3-bath home featuring high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. This h...

113 BURNEY ROAD
OSPREY FL $999,500

3 Beds /

2.5 Baths

/ 2,502 SqFt

**DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near t...

293 TURQUOISE LANE
OSPREY FL $910,000

3 Beds /

2 Baths

/ 2,271 SqFt

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offer...

664 CRANE PRAIRIE WAY
OSPREY FL $875,000

3 Beds /

3 Baths

/ 2,870 SqFt

It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with ...

21 BAYHEAD LANE
OSPREY FL $850,000

3 Beds /

2 Baths

/ 2,246 SqFt

Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath resi...

650 CRANE PRAIRIE WAY
OSPREY FL $799,990

4 Beds /

3 Baths

/ 3,183 SqFt

Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exception...

13 BAYHEAD LANE
OSPREY FL $799,000

2 Beds /

2 Baths

/ 2,310 SqFt

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan ...

127 PARK TRACE BOULEVARD
OSPREY FL $795,000

3 Beds /

2 Baths

/ 2,463 SqFt

Flawless from top to bottom, this beautifully maintained Florida home offers over 3,000 sq. feet of indoor and outdoor living space, perfect for casua...

919 TRANQUILITY CIRCLE CIRCLE
OSPREY FL $794,000

4 Beds /

3.5 Baths

/ 2,854 SqFt

*BRAND NEW BARREL TILE ROOF (APRIL 2026)* WOW! AND A TOTAL OF 55,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon mode...

759 FORDINGBRIDGE WAY
OSPREY FL $770,000

4 Beds /

3.5 Baths

/ 2,950 SqFt

Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural ...

678 FAITH AVENUE
OSPREY FL $749,000

3 Beds /

3 Baths

/ 2,583 SqFt

Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient locatio...

347 BAYSHORE DRIVE
OSPREY FL $739,000

3 Beds /

2.5 Baths

/ 2,216 SqFt

This is your chance to live West of the Trail in the coveted Bay Acres community. This waterfront community has no deed restrictions so you can keep ...

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Single Family listings in Osprey FL – Page 2