Osprey Real Estate for Sale, $200,000 - $300,000

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Image 0: A4696738

110 Woodland Place 110, OSPREY, FL - $215,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,325 SQFT
  • 62 DOM
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Furnished. Welcome To Pine Run, Where You'll Find The Perfect Combination Of Natural Beauty And Modern Living. This Two-bedroom, Two-bath Condo Is Nestled Within The Serene 20+ Acres Of Lush Native Florida Landscape. As You Step Inside, You'll Be ...

Image 1: A4689838

51 Macewen Drive 5, OSPREY, FL - $235,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 595 SQFT
  • 115 DOM
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Discover A Rare Opportunity To Own A Serene Retreat In The Oaks, One Of Sarasota’s Most Sought-after Private Golf And Country Club Communities. This Bright, Beautifully Updated Ground-floor Studio Is Offered Fully Turnkey Furnished, Making It Idea...

Image 2: A4696616

116 Woodland Place 116, OSPREY, FL - $254,900

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,325 SQFT
  • 63 DOM
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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 ...

Image 3: A4689541

4271 Expedition Way 103, OSPREY, FL - $260,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,135 SQFT
  • 119 DOM
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One Or More Photo(s) Has Been Virtually Staged. Live Where Everyday Life Feels Simple, Connected, And Close To Everything You Love. Located In The Gated Community Of Bay Street Village In Osprey, This Beautifully Maintained Second-floor Condo Offe...

51 Macewen Drive 12, OSPREY, FL - $275,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 623 SQFT
  • 100 DOM
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Situated In Windsor Lodge In The Oaks Clubside, This Updated Second Floor Condo Has A Kitchenette With Quartz Countertops, A Modern Bath, A Bonus Space Set Up As A Small Office Area And In-unit Laundry. An End Unit, It Has More Windows Than The Ty...

Image 5: A4690371

51 Mac Ewen Drive 14, OSPREY, FL - $285,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 595 SQFT
  • 115 DOM
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This Completely Updated 595 Sq Ft Second-floor Condominium Is Located In The Windsor Lodge Behind The Gates Of The Oaks. It Features Top-of-the-line Finishes And Is Accessible By Both Elevator And Stairs. Offered Turn-key Furnished, The Unit Inclu...

108 Woodland Place 108, OSPREY, FL - $285,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,316 SQFT
  • 34 DOM
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Bring Your Furniture And Move Right In To This Popular Pine Run Neighborhood. No Need To Worry About Remodeling This Condo! New Coastal Look Ceramic Tile Throughout The Entire Home! New Kitchen And Appliances, New Guest Bathroom, New Doors Throu...

Image 7: N6140508

1801 Highland Road, OSPREY, FL - $289,900

Residential, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,165 SQFT
  • 331 DOM
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One Or More Photo(s) Has Been Virtually Staged. Welcome To This Light-filled, Beautifully Maintained 2-bedroom, 2-bath Townhome In The Highly Desirable Town-end Shores Community Of Osprey. With Low Hoa Fees $150.00 Per Month And Ground Maintenance...

184 Explorer Drive, OSPREY, FL - $294,900

Residential, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,244 SQFT
  • 102 DOM
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Luxury Corner Residence In Osprey | Top-rated Pine View School District. Welcome To An Exceptional Opportunity In The Heart Of Osprey, One Of Sarasota County’s Most Desirable And Rapidly Growing Locations. This Beautifully Maintained Corner-unit ...

Image 9: A4687965

4226 Frontier Lane 103, OSPREY, FL - $299,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,135 SQFT
  • 128 DOM
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Coastal Convenience Meets Effortless Living, Just Minutes From Siesta Key, America’s #1 Beach. Welcome To 4226 Frontier Lane, A Beautifully Maintained 2-bedroom, 2-bath Walk-up Condo In The Gated Community Of Bay Street Village, Offering Exception...

4296 Expedition Way 104, OSPREY, FL - $299,990

Residential, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,135 SQFT
  • 75 DOM
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Welcome To Bay Street Village In Osprey, Gorgeous Gated Community Where Maintenance-free Living Awaits. This Immaculate End-unit Condo Freshly Painted With New Lvp Stairs And Flooring Features 2 Bedrooms, 2 Bathrooms, Garage, Located Beneath The ...

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

Listing information last updated on August 14th, 2026 at 10:07pm EDT.