Osprey, FL Homes

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  /41

  $330,000

  • 2 Beds
  • 2 Baths
  • 1,165 Sq Ft

  1801 Highland Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and

  

  Kimberly Werla

  RE/MAX ALLIANCE GROUP

  (941) 757-8192

  1801 Highland Rd, Osprey, FL 34229
• Explore Osprey

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  /10

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft
  • Condo for Rent

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229

  ***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 207-5680

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229
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  /2

  $900,000 Sold Jan 16, 2026

  3957 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,328 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $387/SF
  • 35 Days On Market

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
• 

  

  /2

  Est $299,731 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  128 Navigation Cir Unit 103, Osprey, FL 34229

  128 Navigation Cir Unit 103, Osprey, FL 34229
• 

  

  

  /98

  $970,000

  • 3 Beds
  • 3.5 Baths
  • 3,771 Sq Ft

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood

  

  Cynthia Brock

  GULF SANDS REALTY, LLC

  (941) 698-6279

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
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  /47

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Condo for Rent

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229

  RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &

  

  Alba Lange

  WAGNER REALTY

  (941) 207-9375

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229
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  /2

  $1,600,000 Sold May 01, 2025

  916 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 7.5 Baths
  • 5,987 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Below List Price
  • $267/SF
  • 1 Day On Market

  Current Estimated Value $1,713,049

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $1,290,436 Not Listed For Sale

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

  639 Eagle Watch Ln, Osprey, FL 34229

  639 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /65

  $1,025,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  701 Eaglenook Way, Osprey, FL 34229

  Under contract-accepting backup offers. A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses. Conveniently positioned one mile East of US 41, within a mile of the Legacy Trail and the nationally-ranked Pine View School.

  

  Michael Ballantyne

  COLDWELL BANKER SARASOTA CENT.

  (941) 883-9471

  701 Eaglenook Way, Osprey, FL 34229
• 

  /2

  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • House for Rent

  557 Crane Prairie Way, Osprey, FL 34229

  Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

  

  Craig McCoy

  PREFERRED SHORE LLC

  (941) 392-7290

  557 Crane Prairie Way, Osprey, FL 34229
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  /69

  $265,000 Sold May 15, 2025

  360 Pine Run Dr Unit 360, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $192/SF
  • 74 Days On Market

  Current Estimated Value $262,687

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
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  /2

  Est $1,469,353 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,614 Sq Ft

  738 N MacEwen Dr, Osprey, FL 34229

  738 N MacEwen Dr, Osprey, FL 34229
• 

  

  /93

  $700,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft

  14041 Bellagio Way Unit 414, Osprey, FL 34229

  Price Improvement offered on this Luxury waterfront penthouse with deep water marina access. Discover Osprey Harbor Village, an exclusive gated condo community of only 53 residences perfectly positioned along Florida’s sparkling Intracoastal Waterway. This stunning 3 bedroom, 2 bath penthouse offers nearly 2,000 square feet of thoughtfully designed living space plus a generous 290 square foot

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 297-4970

  14041 Bellagio Way Unit 414, Osprey, FL 34229
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  /40

  $5,000 per month

  • 2 Beds
  • 3 Baths
  • 1,709 Sq Ft
  • House for Rent

  716 Sarabay Rd, Osprey, FL 34229

  Experience Waterfront Luxury at 716 Sarabay Road, Osprey, FL. Welcome to your private waterfront retreat on Little Sarasota Bay. This stunning 2-bedroom, 3-bath residence offers over 100 feet of direct bay frontage and has been meticulously renovated throughout, combining modern luxury with timeless coastal charm. The open-concept living space is bright and inviting, featuring designer finishes

  

  Mitchell Roberts

  PARADISE REALTY OF VENICE INC

  (941) 241-3260

  716 Sarabay Rd, Osprey, FL 34229
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  /2

  $452,500 Sold Aug 29, 2025

  784 Sarabay Rd, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1981

  Last Sold Summary

  • 38% Below List Price
  • $287/SF
  • 257 Days On Market

  Current Estimated Value $442,005

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  /2

  Est $1,746,154 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,399 Sq Ft

  676 Eagle Watch Ln, Osprey, FL 34229

  676 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /90

  $1,125,000

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft

  1218 Yacht Harbor Dr, Osprey, FL 34229

  Attention water lovers... take a look at this home in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage.

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 352-2028

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  /235

  $1,599 - $2,925 per month

  Alton Osprey

  1 - 3 Beds

  4000 Destination Dr, Osprey, FL 34229

  Now open for immediate move-ins, discover stunning one-, two-, and three-bedroom apartment homes in Osprey, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that works

  4000 Destination Dr, Osprey, FL 34229
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  /2

  $875,585 Sold Mar 27, 2025

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $452/SF
  • 13 Days On Market

  Current Estimated Value $854,615

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229
• 

  /2

  Est $493,974 Not Listed For Sale

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

  393 N Point Rd Unit 302, Osprey, FL 34229

  393 N Point Rd Unit 302, Osprey, FL 34229
• 

  

  /69

  $3,890,000

  • 4 Beds
  • 6 Baths
  • 9,081 Sq Ft

  854 MacEwen Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the

  

  Joe Murphy

  COLDWELL BANKER REALTY

  (941) 394-8350

  854 MacEwen Dr, Osprey, FL 34229
• 

  

  /13

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • House for Rent

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
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  /2

  $75,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • 17 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229
• 

  /2

  Est $951,686 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,855 Sq Ft

  201 Saint James Park, Osprey, FL 34229

  201 Saint James Park, Osprey, FL 34229
• 

  

  /55

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,203 Sq Ft

  583 Pine Ranch East Rd, Osprey, FL 34229

  Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble

  

  William Fortner

  GALLERY PROPERTIES INTERNATIONAL

  (941) 239-7527

  583 Pine Ranch East Rd, Osprey, FL 34229
• 

  

  /20

  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Condo for Rent

  236 Woodland Dr, Osprey, FL 34229

  Property Id: 310276AVAILABLE MAY 15 to SEP 15, 2026 Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal

  236 Woodland Dr, Osprey, FL 34229
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  /2

  $1,050,000 Sold Apr 16, 2025

  247 Keel Way, Osprey, FL 34229

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

  Last Sold Summary

  • 9% Below List Price
  • $366/SF
  • 70 Days On Market

  Current Estimated Value $1,033,828

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  247 Keel Way, Osprey, FL 34229
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  /39

  Est $378,062 Not Listed For Sale

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

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  4234 Frontier Ln Unit 101, Osprey, FL 34229
• 

  

  /51

  $1,800,000

  • 4 Beds
  • 3.5 Baths
  • 4,387 Sq Ft

  401 Walls Way, Osprey, FL 34229

  Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, and

  

  Andrea Stultz

  ENGEL + VOELKERS SARASOTA

  (941) 231-5436

  401 Walls Way, Osprey, FL 34229
• 

  

  /36

  $3,895 per month

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Condo for Rent

  280 Hidden Bay Dr Unit 201, Osprey, FL 34229

  Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and entertaining. Expansive windows

  MJ LoParco PMI SOUTHWEST FLORIDA

  280 Hidden Bay Dr Unit 201, Osprey, FL 34229
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  /2

  $1,850,000 Sold Jan 22, 2026

  453 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,191 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $441/SF
  • 19 Days On Market

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  /70

  Est $1,069,994 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft

  3961 Waypoint Ave, Osprey, FL 34229

  3961 Waypoint Ave, Osprey, FL 34229
• 

  

  /78

  $995,000 Open House 2/22

  • 3 Beds
  • 2 Baths
  • 1,869 Sq Ft

  1486 Landview Ln, Osprey, FL 34229

  Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout,

  

  Barbara Teyssier

  EXP REALTY LLC

  (941) 208-4807

  1486 Landview Ln, Osprey, FL 34229
• 

  

  /18

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  455 Pennsylvania Ave, Osprey, FL 34229

  Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

  455 Pennsylvania Ave, Osprey, FL 34229
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  /2

  $925,000 Sold Apr 10, 2025

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

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

  Last Sold Summary

  • $427/SF
  • 31 Days On Market

  Current Estimated Value $906,944

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229
• 

  

  /98

  Est $784,997 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229
• 

  

  /45

  $3,200,000

  • Land
  • 0.39 Acre
  • $8,205,128 per Acre

  141 N Casey Key Rd, Osprey, FL 34229

  CASEY KEY ISLAND OPPORTUNITY – Bring your preferred builder and create the coastal retreat of your dreams on one of Sarasota County’s most treasured barrier islands. Perfectly positioned on the coveted north end of Casey Key, this exceptional property offers over 100 feet of direct Gulf frontage and sweeping, unobstructed sunset views across shimmering turquoise waters. Your blank canvas awaits –

  

  Julie Larson

  WHITE SANDS REALTY GROUP FL

  (941) 263-0115

  141 N Casey Key Rd, Osprey, FL 34229
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  /24

  $6,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,570 Sq Ft
  • House for Rent

  32 Bayhead Ln, Osprey, FL 34229

  Stunning 3 bedroom, 3 1⁄2 bath professionally redesigned home in the Oaks Preserve. This exceptional property features a spacious chef’s kitchen with top-of-the-line appliances, a large prep island, quartz countertops throughout, and an open concept for ease in entertaining. The family/gathering has a panoramic view overlooking the lanai, lake and fountain. and lake with a fountain. The Owners’

  Christian Higgins ANDRE LECLAIR PROPERTIES LLC

  32 Bayhead Ln, Osprey, FL 34229
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  /2

  $1,750,000 Sold Oct 27, 2025

  627 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,857 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $454/SF
  • 1 Day On Market

  Current Estimated Value $1,771,803

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  627 N MacEwen Dr, Osprey, FL 34229
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  /50

  Est $1,056,851 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft

  3973 Waypoint Ave, Osprey, FL 34229

  3973 Waypoint Ave, Osprey, FL 34229

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