Osprey, FL Homes

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  /37

  Est $628,375 Not Listed For Sale

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

  1353 Thornapple Dr, Osprey, FL 34229

  1353 Thornapple Dr, Osprey, FL 34229
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  /91

  $395,000 Pending

  • 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

  $505,000 Sold Jul 08, 2025

  622 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft
  • Built 1995

  Last Sold Summary

  • 26% Below List Price
  • $219/SF
  • 50 Days On Market

  Current Estimated Value $515,754

  Last Listing Agent Terri Persing PARADISE EXCLUSIVE INC

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

  Est $882,172 Not Listed For Sale

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

  919 Eagle Isle Ct, Osprey, FL 34229

  919 Eagle Isle Ct, Osprey, FL 34229
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  /65

  $739,000

  • 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

  $385,000 Sold Apr 16, 2025

  329 Bay Vista Ave, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1963

  Last Sold Summary

  • 14% Below List Price
  • $286/SF
  • 244 Days On Market

  Current Estimated Value $386,772

  Last Listing Agent Colette Jay HORIZON REALTY INTERNATIONAL

  329 Bay Vista Ave, Osprey, FL 34229
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  /74

  Est $657,016 Not Listed For Sale

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

  541 Luminary Blvd, Osprey, FL 34229

  541 Luminary Blvd, Osprey, FL 34229
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  /48

  $635,000

  • 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

  $640,000 Sold Sep 25, 2025

  6 Bay Acres Ave, Osprey, FL 34229

  • 1,887 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $339/SF
  • 48 Days On Market

  Current Estimated Value $641,176

  Last Listing Agent Bogdan Osipov OSIPOV GROUP REAL ESTATE

  6 Bay Acres Ave, Osprey, FL 34229
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  /2

  Est $701,993 Not Listed For Sale

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

  1228 Chalet Ct, Osprey, FL 34229

  1228 Chalet Ct, Osprey, FL 34229
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  /4

  $34,900

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 56, Osprey, FL 34229

  Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 418 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 56, Osprey, FL 34229
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  /2

  $315,000 Sold Apr 24, 2025

  214 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 2004

  Last Sold Summary

  • 17% Below List Price
  • $288/SF
  • 147 Days On Market

  Current Estimated Value $311,249

  Last Listing Agent Lisa Bouck, PA RE/MAX ALLIANCE GROUP

  214 Patterson Ave, Osprey, FL 34229
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  /2

  Est $764,537 Not Listed For Sale

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

  637 Crane Prairie Way, Osprey, FL 34229

  637 Crane Prairie Way, Osprey, FL 34229
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  /7

  $3,000

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 28, 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 28, Osprey, FL 34229
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  /2

  $489,000 Sold Jul 03, 2025

  328 Woods Point Rd, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1990

  Last Sold Summary

  • $263/SF

  Current Estimated Value $482,627

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  328 Woods Point Rd, Osprey, FL 34229
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  /25

  Est $892,697 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,027 Sq Ft

  1113 Millpond Ct, Osprey, FL 34229

  1113 Millpond Ct, Osprey, FL 34229
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  /39

  $899,995

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft

  14021 Bellagio Way Unit 309, Osprey, FL 34229

  Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy

  Tristin Hopler COMPASS FLORIDA, LLC

  14021 Bellagio Way Unit 309, Osprey, FL 34229
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  /2

  $425,000 Sold Oct 29, 2025

  264 Woods Point Rd, Osprey, FL 34229

  • 2 Beds
  • 3 Baths
  • 2,837 Sq Ft
  • Built 1992

  Last Sold Summary

  • 35% Below List Price
  • $150/SF
  • 368 Days On Market

  Current Estimated Value $441,195

  Last Listing Agent Mark Midyett KELLER WILLIAMS ON THE WATER S

  264 Woods Point Rd, Osprey, FL 34229
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  /53

  Est $966,045 Not Listed For Sale

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

  1064 Mallard Marsh Dr, Osprey, FL 34229

  1064 Mallard Marsh Dr, Osprey, FL 34229
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  /42

  $719,000

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229

  Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features

  Cathy Rustin FIRST LIGHT REAL ESTATE

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229
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  /2

  $665,000 Sold May 23, 2025

  123 Tina Island Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 1,922 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $346/SF
  • 125 Days On Market

  Current Estimated Value $706,054

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  123 Tina Island Dr, Osprey, FL 34229
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  /69

  Est $718,149 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,069 Sq Ft

  188 Dory Ln, Osprey, FL 34229

  188 Dory Ln, Osprey, FL 34229
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  /43

  $369,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  177 Navigation Cir, Osprey, FL 34229

  Under contract-accepting backup offers. Wow! Rare opportunity to own one of only 11 townhomes with two separate one-car garages in Bay Street Village. This beautifully maintained 3-bedroom, 2.5-bath residence offers effortless, maintenance-free living in a prime location tucked between Sarasota and Venice with accessibility to all the perks. A charming front porch welcomes you inside to a bright,

  Kate Kwiecinski COLDWELL BANKER REALTY

  177 Navigation Cir, Osprey, FL 34229
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  /2

  $165,000 Sold Apr 28, 2025

  235 Woodland Dr Unit 235, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft
  • Built 1980

  Last Sold Summary

  • 17% Below List Price
  • $135/SF
  • 53 Days On Market

  Current Estimated Value $176,617

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  235 Woodland Dr Unit 235, Osprey, FL 34229
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  /2

  Est $1,441,045 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,526 Sq Ft

  491 E MacEwen Dr, Osprey, FL 34229

  491 E MacEwen Dr, Osprey, FL 34229
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  /2

  $643,749 New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 303, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 303, Osprey, FL 34229
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  /2

  $200,000 Sold Nov 24, 2025

  226 Woodland Dr, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • $231/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  226 Woodland Dr, Osprey, FL 34229
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  /73

  Est $1,577,793 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,201 Sq Ft

  419 E MacEwen Dr, Osprey, FL 34229

  419 E MacEwen Dr, Osprey, FL 34229
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  /2

  $514,999 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 202, 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 202, Osprey, FL 34229
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  /2

  $285,000 Sold May 30, 2025

  7102 Jessie Harbor Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft
  • Built 1985

  Last Sold Summary

  • 24% Below List Price
  • $227/SF
  • 112 Days On Market

  Current Estimated Value $280,612

  Last Listing Agent Chris Rankin RE/MAX PALM REALTY

  7102 Jessie Harbor Dr, Osprey, FL 34229
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  /67

  Est $889,797 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,491 Sq Ft

  236 Hidden Bay Dr Unit 601, Osprey, FL 34229

  236 Hidden Bay Dr Unit 601, Osprey, FL 34229
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  /69

  $697,500

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

  33 Bishops Court Rd Unit 118, Osprey, FL 34229

  **EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living

  Mark Lyda GENEROUS PROPERTY

  33 Bishops Court Rd Unit 118, Osprey, FL 34229
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  /2

  $410,000 Sold Sep 30, 2025

  321 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,541 Sq Ft
  • Built 1988

  Last Sold Summary

  • 17% Below List Price
  • $266/SF
  • 98 Days On Market

  Current Estimated Value $427,853

  Last Listing Agent Jim Comly LPT REALTY, LLC

  321 Sorrento Dr, Osprey, FL 34229
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  /37

  Est $943,501 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,917 Sq Ft

  77 Bayhead Ln, Osprey, FL 34229

  77 Bayhead Ln, Osprey, FL 34229
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  /76

  $1,089,000

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3936 Waypoint Ave, Osprey, FL 34229

  Discover the charm of coastal living with the convenience of a mainland location in this beautiful Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey, FL. The home can be sold either furnished or unfurnished. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal

  Angelic Tassos CORCORAN DWELLINGS REALTY

  3936 Waypoint Ave, Osprey, FL 34229
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  /2

  $896,148 Sold Apr 07, 2025

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $414/SF
  • 0 Days On Market

  Current Estimated Value $886,910

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  /18

  Est $431,517 Not Listed For Sale

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

  121 Burney Rd, Osprey, FL 34229

  121 Burney Rd, Osprey, FL 34229
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  /76

  $455,000

  • 2 Beds
  • 2 Baths
  • 1,604 Sq Ft

  508 Meadow Sweet Cir, Osprey, FL 34229

  PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in

  Bill Cantrell FLORIDA HOME TEAM LLC

  508 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  $650,000 Sold Nov 14, 2025

  866 Placid Lake Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $299/SF
  • 19 Days On Market

  Last Listing Agent Justin Brunswick KELLER WILLIAMS ON THE WATER S

  866 Placid Lake Dr, Osprey, FL 34229
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  /35

  Est $874,471 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,332 Sq Ft

  1069 Scherer Way, Osprey, FL 34229

  1069 Scherer Way, Osprey, FL 34229

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