Homes in ZIP Code 34229

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  $2,925,000 Sold Sep 23, 2025

  550 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $373/SF
  • 63 Days On Market

  Current Estimated Value $2,858,187

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
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  /68

  Est $982,797 Not Listed For Sale

  501 Velasquez Dr, Osprey, FL 34229

  • 3 Beds
  • 4 Baths
  • 3,028 Sq Ft
  • Built 1975

  501 Velasquez Dr, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • $330/SF
  • 56 Days On Market

  • Last Sold Price $1,000,000
  • May 04, 2023

  Last Listing Agent Randy Owens COLDWELL BANKER REALTY
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  /36

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  4226 Frontier Ln Unit 103, Osprey, FL 34229

  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 exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage

  Kate Kwiecinski COLDWELL BANKER REALTY

  4226 Frontier Ln Unit 103, Osprey, FL 34229
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  $280,000 Sold Feb 04, 2026

  232 Explorer Dr Unit 15, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2019

  Last Sold Summary

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

  Current Estimated Value $281,338

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
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  /40

  Est $511,925 Not Listed For Sale

  510 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 2001

  510 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 12% Below List Price
  • $324/SF
  • 19 Days On Market

  • Last Sold Price $580,000
  • Dec 22, 2023

  Last Listing Agent Mary Jo Violett Michael Saunders
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  /27

  $429,900 Pending

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  328 E Bay St, Osprey, FL 34229

  Welcome to this beautifully updated home on a half acre lot. Presenting a modern comfort in a county-like setting. Only 10 minutes from Siesta Key Beach, 8 minutes from Nokomis Beach, within a mile from a highly sought-after Pine View Elementary School, and close to shopping and dining! Inside you will find a fully remodeled interior featuring a custom kitchen with shaker cabinets, subway tile

  Steven Koleno BEYCOME OF FLORIDA LLC

  328 E Bay St, Osprey, FL 34229
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  $1,500,000 Sold Jul 08, 2025

  269 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft
  • Built 1997

  Last Sold Summary

  • 16% Below List Price
  • $420/SF
  • 76 Days On Market

  Current Estimated Value $1,486,245

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
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  /41

  Est $559,437 Not Listed For Sale

  506 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft
  • Built 1995

  506 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 15% Below List Price
  • $337/SF
  • 10 Days On Market

  • Last Sold Price $655,000
  • Sep 27, 2023

  Last Listing Agent Sharon Morea EXIT KING REALTY
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  /78

  $1,699,000

  • 3 Beds
  • 3.5 Baths
  • 3,565 Sq Ft

  402 E MacEwen Dr, Osprey, FL 34229

  Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that

  Steven Kepecz, PA COLDWELL BANKER REALTY

  402 E MacEwen Dr, Osprey, FL 34229
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  $335,000 Sold Mar 27, 2026

  172 Explorer Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $343,493

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  172 Explorer Dr, Osprey, FL 34229
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  /45

  Est $2,857,910 Not Listed For Sale

  349 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,202 Sq Ft
  • Built 1978

  349 Yacht Harbor Dr, Osprey, FL 34229

  Last Sold Summary

  • 5% Below List Price
  • $937/SF
  • 6 Days On Market

  • Last Sold Price $3,000,000
  • Apr 27, 2023

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /35

  $280,000

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  4271 Expedition Way Unit 103, Osprey, FL 34229

  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 offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar

  Toni Zarghami KW COASTAL LIVING III

  4271 Expedition Way Unit 103, Osprey, FL 34229
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  $995,000 Sold Mar 05, 2026

  105 Turquoise Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,606 Sq Ft
  • Built 2001

  Last Sold Summary

  • $382/SF
  • 162 Days On Market

  Current Estimated Value $956,263

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  105 Turquoise Ln, Osprey, FL 34229
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  /50

  Est $349,103 Not Listed For Sale

  1821 Highland Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1998

  1821 Highland Rd, Osprey, FL 34229

  Last Sold Summary

  • 10% Below List Price
  • $329/SF
  • 53 Days On Market

  • Last Sold Price $390,000
  • Apr 16, 2024

  Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S
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  /34

  $427,000

  • 3 Beds
  • 2 Baths
  • 1,478 Sq Ft

  212 Washington Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey—perfectly situated on a premium corner lot with NO HOA and NO CDD fees!This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed forboth everyday comfort and effortless entertaining. The spacious living area features

  Jeff Jones MARK SPAIN REAL ESTATE

  212 Washington Ave, Osprey, FL 34229
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  $3,050,000 Sold Aug 15, 2025

  5 N Casey Key Rd, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,380 Sq Ft
  • Built 1969

  Last Sold Summary

  • 27% Below List Price
  • $1,282/SF
  • 278 Days On Market

  Current Estimated Value $2,989,261

  Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229
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  /86

  Est $1,628,307 Not Listed For Sale

  435 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,087 Sq Ft
  • Built 1998

  435 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 9% Above List Price
  • $367/SF
  • 268 Days On Market

  • Last Sold Price $1,500,000
  • Dec 29, 2023

  Last Listing Agent Candy Swick CANDY SWICK & COMPANY
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  /4

  $1,500

  • 1 Bed
  • 1 Bath
  • 480 Sq Ft

  124 Happy Haven Dr Unit 10, Osprey, FL 34229

  Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 10, Osprey, FL 34229
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  $660,000 Sold Aug 26, 2025

  463 Park Trace Blvd, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $307/SF
  • 63 Days On Market

  Current Estimated Value $666,463

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  463 Park Trace Blvd, Osprey, FL 34229
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  /2

  Est $3,811,811 Not Listed For Sale

  2509 Bayshore Rd, Nokomis, FL 34275

  • 5 Beds
  • 4.5 Baths
  • 4,712 Sq Ft
  • Built 2016

  2509 Bayshore Rd, Nokomis, FL 34275

  Last Sold Summary

  • 10% Below List Price
  • $902/SF
  • 43 Days On Market

  • Last Sold Price $4,250,000
  • Feb 28, 2025

  Last Listing Agent Andrea Blackwell KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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  /23

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,947 Sq Ft

  437 S Shore Dr, Osprey, FL 34229

  Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about.

  Dawn Barnett EXIT KING REALTY

  437 S Shore Dr, Osprey, FL 34229
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  /2

  $1,700,000 Sold Jun 12, 2025

  525 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,315 Sq Ft
  • Built 1972

  Last Sold Summary

  • 15% Below List Price
  • $734/SF
  • 108 Days On Market

  Current Estimated Value $1,652,487

  Last Listing Agent Andree Huffine COLDWELL BANKER REALTY

  525 S Shore Dr, Osprey, FL 34229
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  /2

  Est $952,301 Not Listed For Sale

  1321 Southbay Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,968 Sq Ft
  • Built 1978

  1321 Southbay Dr, Osprey, FL 34229

  Last Sold Summary

  • 6% Above List Price
  • $303/SF
  • 29 Days On Market

  • Last Sold Price $900,000
  • Oct 04, 2024

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $2,650,000

  • 4 Beds
  • 3.5 Baths
  • 5,287 Sq Ft

  449 Webbs Cove, Osprey, FL 34229

  A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views.Offering

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  449 Webbs Cove, Osprey, FL 34229
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  /2

  $750,000 Sold Dec 30, 2025

  523 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $324/SF
  • 122 Days On Market

  Current Estimated Value $745,010

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
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  /2

  Est $497,599 Not Listed For Sale

  629 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1996

  629 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • $268/SF
  • 250 Days On Market

  • Last Sold Price $500,000
  • Mar 21, 2025

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III
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  $735,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft

  1019 Scherer Way, Osprey, FL 34229

  Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window

  Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

  1019 Scherer Way, Osprey, FL 34229
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  /2

  $799,000 Sold Mar 09, 2026

  529 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,617 Sq Ft
  • Built 2003

  Last Sold Summary

  • $305/SF
  • 2 Days On Market

  Current Estimated Value $793,545

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  529 Habitat Blvd, Osprey, FL 34229
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  /2

  Est $1,837,082 Not Listed For Sale

  451 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,368 Sq Ft
  • Built 1998

  451 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 1% Below List Price
  • $424/SF
  • 3 Days On Market

  • Last Sold Price $1,850,000
  • Jul 29, 2024

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  $4,995,000

  • 4 Beds
  • 5.5 Baths
  • 6,308 Sq Ft

  730 Sarabay Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf

  Debbie Baraona ROBERT SLACK LLC

  730 Sarabay Rd, Osprey, FL 34229
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  /2

  $550,000 Sold Mar 23, 2026

  510 Latitude Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 125 Days On Market

  Current Estimated Value $600,651

  Last Listing Agent Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
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  /3

  Est $226,710 Not Listed For Sale

  110 Oak St, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 858 Sq Ft
  • Built 1983

  110 Oak St, Osprey, FL 34229

  Last Sold Summary

  • 26% Above List Price
  • $209/SF
  • 64 Days On Market

  • Last Sold Price $179,679
  • May 31, 2023

  Last Listing Agent Mark Corradetti VYLLA HOME
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  /26

  $535,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  1348 Thornapple Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Under contract- accepting backup offers. Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan

  Margot Vigar (Leonard) COLDWELL BANKER REALTY

  1348 Thornapple Dr, Osprey, FL 34229
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  $715,000 Sold Mar 17, 2026

  319 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,551 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $280/SF
  • 33 Days On Market

  Current Estimated Value $723,774

  Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

  319 Park Trace Blvd, Osprey, FL 34229
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  /11

  Est $899,421 Not Listed For Sale

  226 Saint James Park, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 1988

  226 Saint James Park, Osprey, FL 34229

  Last Sold Summary

  • 16% Above List Price
  • $299/SF
  • 0 Days On Market

  • Last Sold Price $775,000
  • Feb 05, 2024

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /64

  $794,000

  • 4 Beds
  • 3.5 Baths
  • 2,854 Sq Ft

  919 Tranquility Cir, Osprey, FL 34229

  *BRAND NEW BARREL TILE ROOF (APRIL 2026)* WOW! AND A TOTAL OF 55,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy

  Ann Winger TIDELINE REAL ESTATE BROKERS

  919 Tranquility Cir, Osprey, FL 34229
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  $645,000 Sold Jul 31, 2025

  673 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,223 Sq Ft
  • Built 2003

  Last Sold Summary

  • 13% Below List Price
  • $290/SF
  • 9 Days On Market

  Current Estimated Value $654,342

  Last Listing Agent Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

  673 Crane Prairie Way, Osprey, FL 34229
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  Est $1,775,625 Not Listed For Sale

  337 Passage Way, Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 4,551 Sq Ft
  • Built 1984

  337 Passage Way, Osprey, FL 34229

  Last Sold Summary

  • 32% Above List Price
  • $297/SF
  • 57 Days On Market

  • Last Sold Price $1,350,000
  • Jun 13, 2024

  Last Listing Agent Benjamin Moricz KELLER WILLIAMS ON THE WATER S
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  /11

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  110 Pine Ave, Osprey, FL 34229

  Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

  Marisa Marino BRIGHT REALTY

  110 Pine Ave, Osprey, FL 34229
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  $362,500 Sold Feb 23, 2026

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $227/SF
  • 58 Days On Market

  Current Estimated Value $378,063

  Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE INC

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229

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