Homes in ZIP Code 34229

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  $318,000 Sold Apr 30, 2025

  115 Villa Dr Unit 115, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1972

  Last Sold Summary

  • 16% Below List Price
  • $225/SF
  • 125 Days On Market

  Current Estimated Value $311,843

  Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S

  115 Villa Dr Unit 115, Osprey, FL 34229
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  /40

  Est $542,161 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  590 Oak Bay Dr, Osprey, FL 34229

  590 Oak Bay Dr, Osprey, FL 34229
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  /64

  $4,750,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft

  1049 N Casey Key Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies

  Courtney Green PREMIER SOTHEBYS INTL REALTY

  1049 N Casey Key Rd, Osprey, FL 34229
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  $1,855,000 Sold Feb 26, 2025

  533 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,794 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $489/SF
  • 9 Days On Market

  Current Estimated Value $1,808,001

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  533 N MacEwen Dr, Osprey, FL 34229
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  /49

  Est $170,528 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  701 Pine Run Dr, Osprey, FL 34229

  701 Pine Run Dr, Osprey, FL 34229
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  /78

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 4,781 Sq Ft

  1042 N Casey Key Rd, Osprey, FL 34229

  If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay breezes and water views, while majestic oaks and lush

  Brandy Sheldon COLDWELL BANKER REALTY

  1042 N Casey Key Rd, Osprey, FL 34229
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  /2

  $999,000 Sold Mar 21, 2025

  505 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,301 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $434/SF
  • 16 Days On Market

  Current Estimated Value $1,015,389

  Last Listing Agent Nancy Jordan COLDWELL BANKER REALTY

  505 S Shore Dr, Osprey, FL 34229
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  /60

  Est $578,155 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,363 Sq Ft

  104 Shoreland Dr, Osprey, FL 34229

  104 Shoreland Dr, Osprey, FL 34229
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  /62

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2251 Jessie Harbor Dr, Osprey, FL 34229

  **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

  Mark Lyda GENEROUS PROPERTY

  2251 Jessie Harbor Dr, Osprey, FL 34229
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  $1,150,000 Sold May 28, 2025

  327 Sea Anchor Dr, Osprey, FL 34229

  • 2 Beds
  • 3 Baths
  • 2,521 Sq Ft
  • Built 1981

  Last Sold Summary

  • 7% Below List Price
  • $456/SF
  • 20 Days On Market

  Current Estimated Value $1,122,884

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  327 Sea Anchor Dr, Osprey, FL 34229
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  /46

  Est $623,612 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  730 Fordingbridge Way, Osprey, FL 34229

  730 Fordingbridge Way, Osprey, FL 34229
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  /48

  $600,000

  • 4 Beds
  • 2 Baths
  • 2,133 Sq Ft

  711 Shadow Bay Way, Osprey, FL 34229

  Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the

  Susan Keal MICHAEL SAUNDERS & COMPANY

  711 Shadow Bay Way, Osprey, FL 34229
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  $640,000 Sold Jun 20, 2025

  455 Park Trace Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,590 Sq Ft
  • Built 1999

  Last Sold Summary

  • 15% Below List Price
  • $247/SF
  • 119 Days On Market

  Current Estimated Value $656,138

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  455 Park Trace Blvd, Osprey, FL 34229
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  /81

  Est $1,206,057 Not Listed For Sale

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

  385 N Point Rd Unit 604, Osprey, FL 34229

  385 N Point Rd Unit 604, Osprey, FL 34229
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  /46

  $545,000

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include:

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
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  $85,000 Sold May 23, 2025

  199 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1978

  Last Sold Summary

  • 15% Below List Price
  • $89/SF
  • 87 Days On Market

  Last Listing Agent Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  199 Palm Air Dr, Osprey, FL 34229
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  /40

  Est $782,493 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,830 Sq Ft

  672 Crane Prairie Way, Osprey, FL 34229

  672 Crane Prairie Way, Osprey, FL 34229
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  /41

  $193,000 Open Sat 2PM - 5PM

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  238 Palm Air Dr, Osprey, FL 34229

  AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more

  John Alexander FINE PROPERTIES

  238 Palm Air Dr, Osprey, FL 34229
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  /66

  $155,000 Sold May 15, 2025

  767 Pine Run Dr, Osprey, FL 34229

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1973

  Last Sold Summary

  • $211/SF
  • 4 Days On Market

  Current Estimated Value $158,950

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  767 Pine Run Dr, Osprey, FL 34229
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  /21

  Est $1,053,951 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,541 Sq Ft

  1108 Bayhead Ln, Osprey, FL 34229

  1108 Bayhead Ln, Osprey, FL 34229
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  /47

  $725,000 Pending

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

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet and offers stunning, unobstructed vistas of the intracoastal waterways and Gulf of Mexico. Located within a gated, amenity-rich community, this condo features an open floor plan with high ceilings, a spacious kitchen, and a living area that seamlessly blends indoor comfort with

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
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  $795,000 Sold Mar 21, 2025

  280 Hidden Bay Dr Unit 304, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2023

  Last Sold Summary

  • $367/SF
  • 0 Days On Market

  Current Estimated Value $805,954

  Last Listing Agent Bob Morris SVN COMMERCIAL ADVISORY GROUP

  280 Hidden Bay Dr Unit 304, Osprey, FL 34229
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  /50

  Est $1,749,238 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,970 Sq Ft

  280 Saratoga Ct, Osprey, FL 34229

  280 Saratoga Ct, Osprey, FL 34229
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  /100

  $1,750,000

  • 3 Beds
  • 4.5 Baths
  • 4,364 Sq Ft

  76 Osprey Point Dr, Osprey, FL 34229

  COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available

  Steve Abbe COLDWELL BANKER REALTY

  76 Osprey Point Dr, Osprey, FL 34229
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  /2

  $625,000 Sold Jul 26, 2025

  695 Rivendell Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,256 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Below List Price
  • $277/SF
  • 1 Day On Market

  Current Estimated Value $628,564

  Last Listing Agent Dan Henson DALTON WADE INC

  695 Rivendell Blvd, Osprey, FL 34229
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  /88

  Est $530,242 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  578 Meadow Sweet Cir, Osprey, FL 34229

  578 Meadow Sweet Cir, Osprey, FL 34229
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  /87

  $2,350,000

  • 3 Beds
  • 3.5 Baths
  • 2,473 Sq Ft

  140 N Casey Key Rd, Osprey, FL 34229

  LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibrant 3-bed, 3.5-bath waterfront retreat, perfectly positioned along the Intracoastal Waterway with dazzling, front-row views. Designed for unforgettable days on the water, this home features a stunning Aqua-Tech infinity edge heated pool with therapy jet ledge, where you can unwind while watching boats, jet

  Rhonda Carder EXP REALTY LLC

  140 N Casey Key Rd, Osprey, FL 34229
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  /2

  $2,100,000 Sold Jan 24, 2025

  627 Eagle Watch Ln, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,896 Sq Ft
  • Built 1989

  Last Sold Summary

  • 8% Below List Price
  • $539/SF
  • 140 Days On Market

  Current Estimated Value $1,966,054

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  627 Eagle Watch Ln, Osprey, FL 34229
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  /2

  Est $283,602 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft

  707 Pine Run Dr, Osprey, FL 34229

  707 Pine Run Dr, 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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  $559,500 Sold Apr 04, 2025

  1219 Chalet Ct, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 56 Days On Market

  Current Estimated Value $557,205

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1219 Chalet Ct, Osprey, FL 34229
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  /13

  Est $373,766 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  316 Pennsylvania Ave, Osprey, FL 34229

  316 Pennsylvania Ave, Osprey, FL 34229
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  /77

  $7,100,000

  • 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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  /2

  $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 $1,176,814

  Last Listing Agent John Hockenberry RE/MAX ALLIANCE GROUP

  223 Saint James Park, Osprey, FL 34229
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  /22

  Est $583,549 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft

  743 Anna Hope Ln, Osprey, FL 34229

  743 Anna Hope Ln, Osprey, FL 34229
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  /87

  $685,000

  • 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-bed, 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 light

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

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

  $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

  Last Listing Agent Julien Collet PINEYWOODS REALTY LLC

  708 Anna Hope Ln, Osprey, FL 34229
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  /2

  Est $1,710,065 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,912 Sq Ft

  165 Sugar Mill Dr, Osprey, FL 34229

  165 Sugar Mill Dr, Osprey, FL 34229
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  /37

  $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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  $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 $568,807

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  221 Sorrento Dr, Osprey, FL 34229

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