Homes in ZIP Code 34229

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  /2

  $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 $643,576

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

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

  Est $502,502 Not Listed For Sale

  230 Burney Rd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,219 Sq Ft
  • Built 1985

  230 Burney Rd, Osprey, FL 34229

  Last Sold Summary

  • 29% Above List Price
  • $175/SF
  • 2 Days On Market

  Last Sold Price $388,600

  Last Listing Agent Xiaoguang Ruan AAA GLOBAL VENTURES PA
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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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  $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 $623,212

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  519 Habitat Blvd, Osprey, FL 34229
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  /2

  Est $316,469 Not Listed For Sale

  208 Montana Ave, Nokomis, FL 34275

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • Built 1969

  208 Montana Ave, Nokomis, FL 34275

  Last Sold Summary

  • 5% Above List Price
  • $268/SF
  • 133 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Jeaneen Wiegand WIEGAND 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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  /2

  $324,000 Sold Mar 28, 2025

  76 Explorer Dr Unit 104, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Below List Price
  • $227/SF
  • 34 Days On Market

  Current Estimated Value $302,640

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

  76 Explorer Dr Unit 104, Osprey, FL 34229
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  /64

  Est $532,108 Not Listed For Sale

  128 Villa Dr Unit 128, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1978

  128 Villa Dr Unit 128, Osprey, FL 34229

  Last Sold Summary

  • 21% Below List Price
  • $480/SF
  • 67 Days On Market

  Last Sold Price $674,000

  Last Listing Agent Raphael Carlisi FINE PROPERTIES
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  /62

  $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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  /2

  $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 $926,161

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /70

  Est $623,565 Not Listed For Sale

  433 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 1984

  433 S Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 6% Below List Price
  • $353/SF
  • 72 Days On Market

  Last Sold Price $660,000

  Last Listing Agent Christine Pope Michael Saunders
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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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  /2

  $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 $314,084

  Last Listing Agent Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
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  /2

  Est $755,191 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

  • 16% 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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  /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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  $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 $100,076

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229
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  /42

  Est $900,257 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

  • 12% 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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  /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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  /2

  $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 $365,642

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
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  /44

  Est $662,248 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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  /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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  /2

  $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 $838,035

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  327 Park Trace Blvd, Osprey, FL 34229
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  /2

  Est $446,648 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

  • 3% 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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  /48

  $715,000

  • 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

  $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 $1,011,629

  Last Listing Agent Michael Ballantyne COLDWELL BANKER SARASOTA CENT.

  701 Eaglenook Way, Osprey, FL 34229
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  /3

  Est $629,423 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

  • 12% 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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  /16

  $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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  /2

  $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 $616,908

  Last Listing Agent Kim Klee COLDWELL BANKER REALTY

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

  Est $810,329 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

  • 5% Below List Price
  • $290/SF
  • 33 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Ellen Ross BRIGHT REALTY
• 

  

  /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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  /2

  $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 $477,472

  Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  /35

  Est $622,148 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

  • 13% 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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  /40

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  4284 Expedition Way, Osprey, FL 34229

  Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes

  Grace Bonaccorso PREFERRED SHORE LLC

  4284 Expedition Way, Osprey, FL 34229
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  /2

  $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 $241,138

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /37

  Est $615,932 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

  • 17% 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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  /65

  $720,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,395 Sq Ft

  851 Placid Lake Dr, Osprey, FL 34229

  Welcome to this stunning, recently remodeled 5-bedroom, 4-bath two-story residence nestled within the highly sought-after Woodlands at Rivendell in Osprey, Florida. Set on a prime corner lot with serene water and nature views, this expansive 3,400-square-foot home delivers a refined blend of elegance, comfort, and the very best of the Florida luxury lifestyle—where mornings begin with peaceful

  Peter LaSalle PREFERRED SHORE LLC

  851 Placid Lake Dr, Osprey, FL 34229
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  /2

  $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 $1,826,229

  Last Listing Agent Paula Mapp MAPP REALTY & INVESTMENT CO

  67 Sugar Mill Dr, Osprey, FL 34229
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  /2

  Est $862,996 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

  • 5% 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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  /48

  $599,000

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

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
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  /2

  $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

  Current Estimated Value $245,228

  Last Listing Agent Dan Ivanov KONA REALTY

  106 Villa Dr Unit 106, Osprey, FL 34229

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