Osprey, FL Homes

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  $1,197,000 Sold May 30, 2025

  223 Saint James Park, Osprey, FL 34229

  • 3 Beds
  • 5 Baths
  • 3,321 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $360/SF
  • 20 Days On Market

  Current Estimated Value $1,192,734

  Last Listing Agent John Hockenberry RE/MAX ALLIANCE GROUP

  223 Saint James Park, Osprey, FL 34229
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  Est $761,782 Not Listed For Sale

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1999

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229

  Last Sold Summary

  • 15% Below List Price
  • $426/SF
  • 50 Days On Market

  Last Sold Price $895,000

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /65

  $6,475,000

  • 4 Beds
  • 5.5 Baths
  • 4,096 Sq Ft

  121 N Casey Key Rd, Osprey, FL 34229

  Directly on the turquoise waters of the Gulf, this newly remodeled Spanish Mediterranean estate on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
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  $520,000 Sold Nov 14, 2025

  708 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 8 Days On Market

  Current Estimated Value $528,946

  Last Listing Agent Julien Collet PINEYWOODS REALTY LLC

  708 Anna Hope Ln, Osprey, FL 34229
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  /42

  Est $915,783 Not Listed For Sale

  1108 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,106 Sq Ft
  • Built 2002

  1108 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $330/SF
  • 20 Days On Market

  Last Sold Price $1,025,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /88

  $650,000

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  571 Pine Ranch Rd E, Osprey, FL 34229

  One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

  571 Pine Ranch Rd E, Osprey, FL 34229
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  /62

  $560,000 Sold May 29, 2025

  221 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $289/SF
  • 68 Days On Market

  Current Estimated Value $559,358

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  221 Sorrento Dr, Osprey, FL 34229
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  /44

  Est $667,909 Not Listed For Sale

  858 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,228 Sq Ft
  • Built 1999

  858 Oak Briar Ln, Osprey, FL 34229

  Last Sold Summary

  • 5% Below List Price
  • $314/SF
  • 47 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Jill French REAL BROKER, LLC
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  $1,200,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  385 N Point Rd Unit 304, Osprey, FL 34229

  **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 304, Osprey, FL 34229
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  $640,000 Sold Jan 06, 2026

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft
  • Built 2004

  Last Sold Summary

  • 12% Below List Price
  • $258/SF
  • 130 Days On Market

  Current Estimated Value $640,522

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
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  /2

  Est $445,679 Not Listed For Sale

  393 N Point Rd Unit 302, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 2001

  393 N Point Rd Unit 302, Osprey, FL 34229

  Last Sold Summary

  • 2% Above List Price
  • $212/SF
  • 106 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  /42

  $275,000

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft

  51 MacEwen Dr Unit 11, Osprey, FL 34229

  Rarely available Windsor Lodge efficiency condominium located within The Oaks Club. This second-floor, maintenance-free, lakeside unit features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership

  Sabine Spycher 342 REAL ESTATE

  51 MacEwen Dr Unit 11, Osprey, FL 34229
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  $640,000 Sold Jun 04, 2025

  519 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $286/SF
  • 15 Days On Market

  Current Estimated Value $638,665

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  519 Habitat Blvd, Osprey, FL 34229
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  /3

  Est $647,085 Not Listed For Sale

  812 Foothill Ct, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft
  • Built 2002

  812 Foothill Ct, Osprey, FL 34229

  Last Sold Summary

  • 9% Below List Price
  • $313/SF
  • 0 Days On Market

  Last Sold Price $714,000

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /86

  $655,000

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  57 Bishops Court Rd Unit 121, Osprey, FL 34229

  Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architecturally designed, this classic Georgian style townhouse features two bedrooms, two full ensuite baths, one half bath, a spacious great room, and a large terrace overlooking a lake. A welcoming foyer leads to the expansive great room where high ceilings,

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  57 Bishops Court Rd Unit 121, Osprey, FL 34229
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  $910,000 Sold Nov 19, 2025

  766 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $265/SF
  • 132 Days On Market

  Current Estimated Value $933,702

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  Est $836,272 Not Listed For Sale

  995 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,933 Sq Ft
  • Built 2004

  995 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • $290/SF
  • 33 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Ellen Ross BRIGHT REALTY
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  /43

  $639,000

  • 4 Beds
  • 2 Baths
  • 2,145 Sq Ft

  819 Shadow Bay Way, Osprey, FL 34229

  Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include 2026 irrigation valves, 2025 roof replacement, 2024 pool pump and a 2017 air

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  819 Shadow Bay Way, Osprey, FL 34229
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  $325,000 Sold Jul 24, 2025

  4236 Expedition Way Unit 106, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2016

  Last Sold Summary

  • 10% Below List Price
  • $213/SF
  • 90 Days On Market

  Current Estimated Value $312,405

  Last Listing Agent Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
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  /35

  Est $654,632 Not Listed For Sale

  801 Golden Pond Ct, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 2003

  801 Golden Pond Ct, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $335/SF
  • 37 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Susan Mitchell Michael Saunders
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  /92

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  393 N Point Rd Unit 604, Osprey, FL 34229

  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. Experience the epitome of

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  $95,000 Sold Feb 19, 2026

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • 58 Days On Market

  Current Estimated Value $100,328

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229
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  Est $631,926 Not Listed For Sale

  1353 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,173 Sq Ft
  • Built 2003

  1353 Thornapple Dr, Osprey, FL 34229

  Last Sold Summary

  • 15% Below List Price
  • $341/SF
  • 16 Days On Market

  Last Sold Price $740,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $540,749 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 302, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 302, Osprey, FL 34229
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  $400,000 Sold Apr 08, 2025

  4239 Expedition Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 115 Days On Market

  Current Estimated Value $361,728

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
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  /2

  Est $881,143 Not Listed For Sale

  919 Eagle Isle Ct, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft
  • Built 2004

  919 Eagle Isle Ct, Osprey, FL 34229

  Last Sold Summary

  • 3% Below List Price
  • $348/SF
  • 37 Days On Market

  Last Sold Price $910,000

  Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY
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  /44

  $679,900

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

  This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid

  Cindy Migone PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
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  $800,000 Sold Mar 02, 2026

  327 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,935 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 44 Days On Market

  Current Estimated Value $840,244

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  327 Park Trace Blvd, Osprey, FL 34229
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  Est $686,193 Not Listed For Sale

  541 Luminary Blvd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,403 Sq Ft
  • Built 2004

  541 Luminary Blvd, Osprey, FL 34229

  Last Sold Summary

  • 12% Above List Price
  • $256/SF
  • 90 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Susan Mitchell Michael Saunders
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  /88

  $2,700,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  $950,000 Sold Feb 10, 2026

  701 Eaglenook Way, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,533 Sq Ft
  • Built 1978

  Last Sold Summary

  • 17% Below List Price
  • $269/SF
  • 97 Days On Market

  Current Estimated Value $981,901

  Last Listing Agent Michael Ballantyne COLDWELL BANKER SARASOTA CENT.

  701 Eaglenook Way, Osprey, FL 34229
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  Est $692,961 Not Listed For Sale

  1228 Chalet Ct, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,336 Sq Ft
  • Built 2004

  1228 Chalet Ct, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $321/SF
  • 10 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $699,000 Open House 4/11

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  597 Oak River Ct, Osprey, FL 34229

  Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator,

  Mairead Smialek COLDWELL BANKER REALTY

  597 Oak River Ct, Osprey, FL 34229
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  $650,000 Sold Apr 18, 2025

  610 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,431 Sq Ft
  • Built 1995

  Last Sold Summary

  • 7% Below List Price
  • $267/SF
  • 113 Days On Market

  Current Estimated Value $632,696

  Last Listing Agent Kim Klee COLDWELL BANKER REALTY

  610 Pine Ranch Rd E, Osprey, FL 34229
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  /2

  Est $765,741 Not Listed For Sale

  637 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,504 Sq Ft
  • Built 2004

  637 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 10% Below List Price
  • $339/SF
  • 22 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Darrell Imbrosciano CENTURY 21 SCHMIDT REAL ESTATE
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  $1,400,000

  • Land
  • 2.51 Acres
  • $557,769 per Acre

  2099 S Tamiami Trail, Osprey, FL 34229

  2.51 Acre Lot directly on South Tamiami Trail in Osprey - where Sarasota is growing and expanding! This property is zoned OPI and would be a good fit for an office/medical center or retail with residential above. Great exposure with consistently heavy traffic from Sarasota to Ft. Myers on S. Tamiami Trail just minutes from Sarasota Bay, Oscar Scherer State Park, Legacy Trail and all that Sarasota

  Susan Repp COLDWELL BANKER REALTY

  2099 S Tamiami Trail, Osprey, FL 34229
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  $470,000 Sold Aug 22, 2025

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2005

  Last Sold Summary

  • 15% Below List Price
  • $217/SF
  • 80 Days On Market

  Current Estimated Value $469,417

  Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  Est $979,381 Not Listed For Sale

  1064 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,183 Sq Ft
  • Built 1998

  1064 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 15% Below List Price
  • $362/SF
  • 2 Days On Market

  Last Sold Price $1,152,250

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /91

  $475,000 Pre-Foreclosure

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  401 N Point Rd Unit 301, Osprey, FL 34229

  One or more photo(s) has been virtually staged. 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 foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
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  $250,000 Sold Oct 23, 2025

  207 Woodland Dr Unit 207, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1980

  Last Sold Summary

  • 18% Below List Price
  • $189/SF
  • 491 Days On Market

  Current Estimated Value $245,135

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229

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