Osprey, FL Homes

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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 $484,183

  Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  Est $961,089 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,420 Sq Ft

  184 Park Trace Blvd, Osprey, FL 34229

  184 Park Trace Blvd, Osprey, FL 34229
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  /96

  $1,500,000

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

  385 N Point Rd Unit 704, Osprey, FL 34229

  Experience breathtaking views of the Bay and Gulf from this spacious 3 bedroom, 3 bath end unit, featuring a separate dining room and den. Completely updated and meticulously maintained, this unit is beautifully appointed and custom features abound. A private elevator takes you to a majestic foyer which opens to the great room. Facing west the views are gorgeous from sunrise to sunset. The

  Steve Abbe COLDWELL BANKER REALTY

  385 N Point Rd Unit 704, 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 $243,295

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  Est $1,252,020 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,071 Sq Ft

  110 N Creek Ln, Osprey, FL 34229

  110 N Creek Ln, Osprey, FL 34229
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  /77

  $6,800,000

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

  121 N Casey Key Rd, Osprey, FL 34229

  Newly Remodeled Gulf-Front Mediterranean Villa on Casey KeyFramed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
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  $772,000 Sold Mar 04, 2025

  663 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 9 Days On Market

  Current Estimated Value $752,300

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  663 Crane Prairie Way, Osprey, FL 34229
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  Est $273,646 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  104 Woodland Place, Osprey, FL 34229

  104 Woodland Place, Osprey, FL 34229
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  $665,000

  • 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, 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 landscaping, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

  571 Pine Ranch Rd E, Osprey, FL 34229
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  $1,850,000 Sold Nov 07, 2025

  67 Sugar Mill Dr, Osprey, FL 34229

  • 4 Beds
  • 5 Baths
  • 4,020 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $460/SF
  • 240 Days On Market

  Current Estimated Value $1,820,252

  Last Listing Agent Paula Mapp MAPP REALTY & INVESTMENT CO

  67 Sugar Mill Dr, Osprey, FL 34229
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  /25

  Est $577,529 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft

  846 Oak Pond Dr, Osprey, FL 34229

  846 Oak Pond Dr, Osprey, FL 34229
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  $549,000

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft

  455 N Shore Dr, Osprey, FL 34229

  Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment. Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42 boat

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  455 N Shore Dr, Osprey, FL 34229
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  $130,000 Sold Jan 30, 2026

  106 Villa Dr Unit 106, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 1968

  Last Sold Summary

  • 48% Below List Price
  • $82/SF
  • 81 Days On Market

  Last Listing Agent Dan Ivanov KONA REALTY

  106 Villa Dr Unit 106, Osprey, FL 34229
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  Est $567,374 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,217 Sq Ft

  587 Meadow Sweet Cir, Osprey, FL 34229

  587 Meadow Sweet Cir, Osprey, FL 34229
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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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  $1,375,000 Sold Dec 05, 2025

  500 Shotgun Ln, Osprey, FL 34229

  • Land
  • 11.68 Acres
  • $117,723 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 45 Days On Market

  Last Listing Agent Ruediger Weiss CHARITY & WEISS INTERNATIONAL LLC

  500 Shotgun Ln, Osprey, FL 34229
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  Est $498,932 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,219 Sq Ft

  230 Burney Rd, Osprey, FL 34229

  230 Burney Rd, Osprey, FL 34229
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  $103,000 Pending

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229

  Under contract-accepting backup offers. The slip can hold a boat with the maximum dimensions of 30.5'L x 10'W x 9'H.This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229
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  $1,495,000 Sold Oct 31, 2025

  228 Saint James Park, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,425 Sq Ft
  • Built 1997

  Last Sold Summary

  • $616/SF
  • 0 Days On Market

  Current Estimated Value $1,451,898

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  228 Saint James Park, Osprey, FL 34229
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  Est $518,560 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  128 Villa Dr Unit 128, Osprey, FL 34229

  128 Villa Dr Unit 128, Osprey, FL 34229
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  $300,000

  • 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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  $95,000 Sold Jan 05, 2026

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229

  Last Sold Summary

  • 3% Below List Price
  • 7 Days On Market

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229
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  Est $629,271 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft

  433 S Shore Dr, Osprey, FL 34229

  433 S Shore Dr, Osprey, FL 34229
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  $685,000

  • 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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  $670,000 Sold Jun 10, 2025

  1426 Landview Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,513 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $267/SF
  • 72 Days On Market

  Current Estimated Value $715,560

  Last Listing Agent Stephanie Church COLDWELL BANKER REALTY

  1426 Landview Ln, Osprey, FL 34229
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  /2

  Est $793,087 Not Listed For Sale

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

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229
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  $875,000

  • 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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  $600,000 Sold Apr 18, 2025

  402 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,887 Sq Ft
  • Built 1995

  Last Sold Summary

  • 31% Below List Price
  • $208/SF
  • 24 Days On Market

  Current Estimated Value $745,236

  Last Listing Agent Ronnie Caron CARON REALTY INC

  402 Pine Ranch Rd E, Osprey, FL 34229
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  Est $952,956 Not Listed For Sale

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

  1108 Mallard Marsh Dr, Osprey, FL 34229

  1108 Mallard Marsh Dr, Osprey, FL 34229
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  $849,000 Pending

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

  327 Park Trace Blvd, Osprey, FL 34229

  Under contract-accepting backup offers. LOOK NO FURTHER! This immaculate, lake-view four-bedroom/ three-bath home is MOVE-IN READY. Completewith a NEW 60K Tile ROOF, PGT Impact Windows throughout and new A/C (2024)! Freshly painted interior fromtop to bottom with Regal select Benjamin Moore paint, sparkling epoxy garage floor, New GE 5 burner range withCrisp mode, walk in pantry,

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  327 Park Trace Blvd, Osprey, FL 34229
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  $700,000 Sold Apr 15, 2025

  521 Luminary Blvd, Osprey, FL 34229

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

  Last Sold Summary

  • 4% Below List Price
  • $280/SF
  • 69 Days On Market

  Current Estimated Value $694,054

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  521 Luminary Blvd, Osprey, FL 34229
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  Est $673,745 Not Listed For Sale

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

  858 Oak Briar Ln, Osprey, FL 34229

  858 Oak Briar Ln, Osprey, FL 34229
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  $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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  $145,000 Sold Jul 15, 2025

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • 23 Days On Market

  Current Estimated Value $143,419

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229
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  Est $656,553 Not Listed For Sale

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

  812 Foothill Ct, Osprey, FL 34229

  812 Foothill Ct, Osprey, FL 34229
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  $734,900 Open Sat 1PM - 3PM

  • 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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  $2,000,000 Sold Feb 09, 2026

  895 MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 4,828 Sq Ft
  • Built 1991

  Last Sold Summary

  • $414/SF
  • 0 Days On Market

  Last Listing Agent Maria Balaz EXIT KING REALTY

  895 MacEwen Dr, Osprey, FL 34229
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  Est $824,352 Not Listed For Sale

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

  995 Scherer Way, Osprey, FL 34229

  995 Scherer Way, Osprey, FL 34229
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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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  $85,000 Sold Jul 01, 2025

  570 Blackburn Point Rd Unit 7, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • 336 Days On Market

  Current Estimated Value $82,860

  Last Listing Agent Troy Gager BRIGHT REALTY

  570 Blackburn Point Rd Unit 7, Osprey, FL 34229

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