Osprey Real Estate for Sale, $400,000 - $500,000

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Image 0: TB8443161

1811 Highland Road, OSPREY, FL - $417,000

Residential, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,725 SQFT
  • 286 DOM
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Private Neighborhood - Fully Furnished 2 Bedroom Townhouse In The Casey Key Area, Quaint, Spacious 2-car Tandem Garage + Carport, Modern, High Ceilings, Kitchen Upgrades, Screened Balcony, 2 Beds + Den; 2 Baths; Living Area And Kitchen Open Plan; ...

Image 1: A4699464

329 Bay Vista Avenue, OSPREY, FL - $419,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 1,346 SQFT
  • 35 DOM
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Welcome To 329 Bay Vista Ave., Osprey, Fl 34229—a Rare Opportunity To Own A Beautifully Renovated 2-bedroom, 2-bathroom Home On An Expansive Lot (0.47 Acre!!!) With No Hoa, No Deed Restrictions, And Endless Possibilities. Inside, You'll Find A ...

524 Sarabay Road, OSPREY, FL - $419,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,760 SQFT
  • 194 DOM
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Location, Location. In The Heart Of Osprey, Centrally Located In The Highly Sought-after Well-established Bay Acres Community. Lowest Priced Home West Of The Taril. These 3 Bedrooms 2 Bath Ranch Home Is West Of 41 Within 10-minute Commutes To Down...

Image 3: O6404307

212 Washington Avenue, OSPREY, FL - $420,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,478 SQFT
  • 63 DOM
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Virtually Staged. Welcome To Your Private Poolside Retreat In The Desirable Coastal Community Of Osprey— Perfectly Situated On A Premium Corner Lot With No Hoa And No Cdd Fees! This Beautiful 3-bedroom, 2-bath Home Offers A Bright, Open-concept ...

Image 4: N6143210

107 Sorrento Drive, OSPREY, FL - $425,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 1,284 SQFT
  • 163 DOM
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This Beautifully Updated, 1,284-square-foot, Mid-century Home Sits On Over One-third Of An Acre And Has Been Thoughtfully Renovated With Distinctive Sarasota Modern Flair By Hgtv Design Team. Go Through The Vibrant Turquoise Door Into A Light-fill...

Image 5: TB8528486

780 Sarabay Road 16, OSPREY, FL - $425,000

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 1,574 SQFT
  • 30 DOM
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Waterfront Villa W/boat Slips - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single Story Home-like Living. Fish Off The Pier Or Sit On The Dock & Enjoy The Sunsets! New Dock & Pier Welcome To Heron Bay Club, An Exclusive Enc...

Image 6: A4603773

401 N Point Road 301, OSPREY, FL - $459,900

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 691 DOM
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Virtually Staged. Short Sale. Enter Through The Secure Foyer And Take The Private Elevator To The Third Floor Where You Will Find This Charming 3 Bedroom, 3 Bath Residence. Situated At Treetop Level, Overlooking The Preserve And Surrounding Lush F...

Image 7: A4684009

447 N Shore Drive, OSPREY, FL - $474,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,874 SQFT
  • 161 DOM
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Classic And Cool, This Sorrento Shores Beauty Blends True Old Florida Charm With All The Modern Updates You Actually Want, Perfectly Positioned West Of The Trail Near The Sparkling Intracoastal Waterway. What’s Been At The Top Of Your List — Move-...

2309 Jessie Harbor Drive 2402, OSPREY, FL - $497,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,006 SQFT
  • 43 DOM
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West-facing Canal Views In Gated Blackburn Harbor. This Second-floor, 3-bedroom, 2.5-bath Condo In Blackburn Harbor Waterfront Villas Puts You Directly On The Canal With West-facing Views That Make Sunsets A Daily Event Worth Watching. At 2,006 Sq...

Image 9: A4666421

742 Harms Drive, OSPREY, FL - $499,900

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,293 SQFT
  • 300 DOM
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Beautifully Renovated And Move-in Ready, This Exceptional Property Offers The Perfect Blend Of Privacy, Comfort, And Investment Potential. Situated On Over Half An Acre Along A Private, Tree-lined Street, The Home Is Surrounded By Lush Tropical La...

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on August 14th, 2026 at 9:37pm EDT.