Osprey, FL Homes

• 

  

  

  /57

  Est $647,554

  Not Listed For Sale

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft
  • Built 2005

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Giuseppe Gambo CENTURY 21 SCHMIDT REAL ESTATE
• 

  

  

  /54

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  780 Sarabay Rd Unit 16, Osprey, FL 34229

  Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with

  Mark Segreto RMS ELITE PROPERTIES

  780 Sarabay Rd Unit 16, Osprey, FL 34229
• 

  

  /2

  $95,000

  Sold Apr 30, 2026

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Last Sold Summary

  • 4% Below List Price
  • 17 Days On Market

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
• 

  

  

  /13

  Est $1,123,319

  Not Listed For Sale

  3603 N Point Rd Unit 603, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft
  • Built 2007

  3603 N Point Rd Unit 603, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  

  /37

  $185,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,199 Sq Ft

  320 Tropic Dr, Osprey, FL 34229

  Virtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and

  Susan Retzke RE/MAX PALM

  320 Tropic Dr, Osprey, FL 34229
• 

  /2

  $215,000

  Sold Nov 12, 2025

  158 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 2014

  Last Sold Summary

  • 9% Below List Price
  • $145/SF
  • 12 Days On Market

  Last Listing Agent Renee Marquiss NEXTHOME IN THE SUN

  158 Edgewood Dr, Osprey, FL 34229
• 

  /2

  Est $1,447,791

  Not Listed For Sale

  639 Eagle Watch Ln, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 3,906 Sq Ft
  • Built 1989

  639 Eagle Watch Ln, Osprey, FL 34229

  Last Sold Summary

  • 212 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /70

  $2,199,900

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,236 Sq Ft

  180 Lookout Point Dr, Osprey, FL 34229

  Virtually Staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  180 Lookout Point Dr, Osprey, FL 34229
• 

  /2

  $1,500,000

  Sold Aug 12, 2026

  893 MacEwen Dr, Osprey, FL 34229

  • Land
  • 28,749 Sq Ft
  • $2,272,727 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  893 MacEwen Dr, Osprey, FL 34229
• 

  

  /25

  Est $548,368

  Not Listed For Sale

  543 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • Built 2001

  543 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Mary Jo Violett WHITE SANDS REALTY GROUP FL
• 

  

  /92

  $789,000

  $136K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,246 Sq Ft

  21 Bayhead Ln, Osprey, FL 34229

  Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing...what

  Steve Abbe COLDWELL BANKER REALTY

  21 Bayhead Ln, Osprey, FL 34229
• 

  /2

  $730,000

  Sold May 13, 2026

  1019 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $292/SF
  • 10 Days On Market

  Current Estimated Value $731,906

  Last Listing Agent Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

  1019 Scherer Way, Osprey, FL 34229
• 

  

  /64

  Est $240,647

  Not Listed For Sale

  224 Woodland Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1980

  224 Woodland Dr, Osprey, FL 34229

  Last Sold Summary

  • 133 Days On Market

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC
• 

  

  /7

  $289,999

  $30K PRICE INCREASE

  • Land
  • 5,662 Sq Ft
  • $2,230,762 per Acre

  456 Washington Ave, Osprey, FL 34229

  Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the

  Mike Vo FLOTACAL

  456 Washington Ave, Osprey, FL 34229
• 

  /2

  $4,700,000

  Sold Jun 17, 2026

  730 Sarabay Rd, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 6,308 Sq Ft
  • Built 2011

  Last Sold Summary

  • 14% Below List Price
  • $745/SF
  • 174 Days On Market

  Current Estimated Value $4,777,011

  Last Listing Agent Debbie Baraona JASON MITCHELL REAL ESTATE FLO

  730 Sarabay Rd, Osprey, FL 34229
• 

  

  /59

  Est $1,214,520

  Not Listed For Sale

  384 S Creek Ct, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,811 Sq Ft
  • Built 1982

  384 S Creek Ct, Osprey, FL 34229

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Brandi Furlan KW COASTAL LIVING III
• 

  

  /34

  $109,900

  Open Sun 11AM - 4PM $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  348 Tropic Dr, Osprey, FL 34229

  Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

  John Alexander FINE PROPERTIES

  348 Tropic Dr, Osprey, FL 34229
• 

  /2

  $1,500,000

  Sold Dec 12, 2025

  325 Osprey Point Dr, Osprey, FL 34229

  • 3 Beds
  • 4.5 Baths
  • 3,905 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Below List Price
  • $384/SF
  • 12 Days On Market

  Current Estimated Value $1,524,384

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  325 Osprey Point Dr, Osprey, FL 34229
• 

  

  /99

  Est $656,645

  Not Listed For Sale

  801 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,330 Sq Ft
  • Built 2004

  801 Oak Briar Ln, Osprey, FL 34229

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Christopher Costello RE/MAX PALM
• 

  

  /19

  $510,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  4429 Conchfish Ln, Osprey, FL 34229

  Virtually Staged. SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A spacious great room

  Jennifer Kenna EXP REALTY, LLC

  4429 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $285,000

  Sold Mar 24, 2026

  2043 Cordes St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,186 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $240/SF
  • 44 Days On Market

  Current Estimated Value $282,348

  Last Listing Agent Travis Matthews PREFERRED SHORE LLC

  2043 Cordes St, Osprey, FL 34229
• 

  

  /57

  Est $629,359

  Not Listed For Sale

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft
  • Built 2005

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  Last Sold Summary

  • 222 Days On Market

  Last Listing Agent Bernadette Caswell MICHAEL SAUNDERS & COMPANY
• 

  

  /49

  $1,750,000

  $600K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  18 N Casey Key Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $113,000

  Sold Feb 17, 2026

  26 Siesta Cir W, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Built 1968

  Last Sold Summary

  • 13% Below List Price
  • $188/SF
  • 55 Days On Market

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  26 Siesta Cir W, Osprey, FL 34229
• 

  /2

  Est $747,269

  Not Listed For Sale

  401 N Point Rd Unit 401, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2003

  401 N Point Rd Unit 401, Osprey, FL 34229

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /19

  $417,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,725 Sq Ft

  1811 Highland Rd, Osprey, FL 34229

  PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

  Stephen Hachey REALTY OF RIVERVIEW LLC

  1811 Highland Rd, Osprey, FL 34229
• 

  /2

  $1,700,000

  Sold Jan 15, 2026

  409 N Point Rd Unit 1003, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $612/SF
  • 0 Days On Market

  Current Estimated Value $1,625,251

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 1003, Osprey, FL 34229
• 

  

  /96

  Est $950,093

  Not Listed For Sale

  385 N Point Rd Unit 501, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2000

  385 N Point Rd Unit 501, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /61

  $1,950,000

  • 5 Beds
  • 5.5 Baths
  • 4,885 Sq Ft

  97 Sugar Mill Dr, Osprey, FL 34229

  Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed

  Maria 'Indy' Domenech PALM PARADISE REALTY GROUP

  97 Sugar Mill Dr, Osprey, FL 34229
• 

  /2

  $525,000

  Sold May 21, 2026

  1348 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $242/SF
  • 9 Days On Market

  Current Estimated Value $530,991

  Last Listing Agent Margot Vigar (Leonard) COLDWELL BANKER REALTY

  1348 Thornapple Dr, Osprey, FL 34229
• 

  

  /73

  Est $378,411

  Not Listed For Sale

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

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

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY
• 

  

  /55

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  103 Bishops Court Rd, Osprey, FL 34229

  **LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added

  Mark Lyda GENEROUS PROPERTY

  103 Bishops Court Rd, Osprey, FL 34229
• 

  /2

  $730,000

  Sold Oct 24, 2025

  1728 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $315/SF
  • 44 Days On Market

  Current Estimated Value $742,338

  Last Listing Agent Melanie Albaric MICHAEL SAUNDERS & COMPANY

  1728 S Creek Dr, Osprey, FL 34229
• 

  /2

  Est $1,015,433

  Not Listed For Sale

  247 Keel Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,871 Sq Ft
  • Built 1979

  247 Keel Way, Osprey, FL 34229

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC
• 

  

  /75

  $760,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,474 Sq Ft

  1495 Landview Ln, Osprey, FL 34229

  Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool

  Pat Williams PAT WILLIAMS REALTY, LLC

  1495 Landview Ln, Osprey, FL 34229
• 

  /2

  $120,000

  Sold Aug 29, 2025

  0 Cordes St Unit MFRN6137674, Osprey, FL 34229

  • Land
  • 7,840 Sq Ft
  • $666,667 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 153 Days On Market

  Last Listing Agent Zuzanna Kacprzak CENTURY 21 SCHMIDT REAL ESTATE

  0 Cordes St Unit MFRN6137674, Osprey, FL 34229
• 

  /2

  Est $3,578,721

  Not Listed For Sale

  275 Lookout Point Dr, Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 5,279 Sq Ft
  • Built 2007

  275 Lookout Point Dr, Osprey, FL 34229

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  

  /74

  $1,200,000

  $100K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  700 Faith Ave, Osprey, FL 34229

  Virtually Staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country.The peace and tranquility of the outdoor space is highlighted by a resort style swimming pool 40

  steve mularky LACEY REALTY INC

  700 Faith Ave, Osprey, FL 34229
• 

  /2

  $170,000

  Sold Apr 01, 2026

  911 Tranquility Cir, Osprey, FL 34229

  • Land
  • 18,295 Sq Ft
  • $404,762 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Mike Winger TIDELINE REAL ESTATE BROKERS

  911 Tranquility Cir, Osprey, FL 34229
• 

  

  /40

  Est $490,104

  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

  • 19 Days On Market

  Last Listing Agent Mary Jo Violett WHITE SANDS REALTY GROUP FL

Showing Results 201 - 240, Page 6 of 18