Osprey, FL Homes

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  /100

  $1,535,000

  $160K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,208 Sq Ft

  480 Oriskany Ct, Osprey, FL 34229

  Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14. This home sits on a Premium golf course lot with additional privacy view across the street . Designed by Toll Brothers, this one story, 3200 sq. Ft. home with 3 bedroom ( plus office ) offers gracious entertaining and comfortable everyday living. A

  

  Susan Pelton

  MICHAEL SAUNDERS & COMPANY

  480 Oriskany Ct, 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

  AVAILABLE 2027 SEASON. 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 & dryer

  

  Alba Lange

  WAGNER REALTY

  293 Hidden Bay Dr Unit 203, 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

  Current Estimated Value $936,688

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  /2

  Est $664,592

  Not Listed For Sale

  455 Park Trace Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,590 Sq Ft
  • Built 1999

  455 Park Trace Blvd, Osprey, FL 34229

  Last Sold Summary

  • 119 Days On Market
• 

  

  

  /50

  $225,000

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

  110 Woodland Place, Osprey, FL 34229

  FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed

  

  Echo Belser PA

  COLDWELL BANKER REALTY

  110 Woodland Place, Osprey, FL 34229
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  /8

  $775 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  8 Bay Ave, Osprey, FL 34229

  Property Id: 1524644Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONSLandlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and

  8 Bay Ave, 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 $430,983

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  /70

  Est $1,050,494

  Not Listed For Sale

  3961 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • Built 2018

  3961 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • 213 Days On Market
• 

  

  /64

  $799,990

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

  650 Crane Prairie Way, Osprey, FL 34229

  Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exceptional scale, thoughtful architecture, and a preserve setting backing directly to Oscar Scherer State Park. With no rear neighbors and expansive natural views, the home offers privacy and tranquility while remaining minutes from beaches, dining, and

  

  Cheri Castro

  MICHAEL SAUNDERS & COMPANY

  650 Crane Prairie Way, Osprey, FL 34229
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  /45

  $3,150 Per Month

  • 3 Beds
  • 2 Baths
  • 1,897 Sq Ft
  • House for Rent

  341 Bayshore Dr, Osprey, FL 34229

  This fully renovated classic-style residence blends Old Florida charm with modern finishes and spacious living areas throughout. Featuring 3 Bedrooms and 2 Bathrooms, the home offers a functional layout designed for comfort and privacy. Conveniently located near Blackburn Boat Ramp with plenty of on-site parking. Just under 1900 sqft of living space, the kitchen flows seamlessly into the dining

  

  Jeremy Myers

  COMPASS PROPERTY MANAGEMENT LLC

  341 Bayshore Dr, Osprey, FL 34229
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  /2

  $600,000

  Sold May 26, 2026

  522 Luminary Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Below List Price
  • $259/SF
  • 88 Days On Market

  Current Estimated Value $637,162

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  522 Luminary Blvd, Osprey, FL 34229
• 

  

  /98

  Est $714,871

  Not Listed For Sale

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Built 2017

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  Last Sold Summary

  • 38 Days On Market
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  $3,690,000

  $260K PRICE DROP

  • 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

  854 MacEwen Dr, Osprey, FL 34229
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  /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 JULY 1 to AUGUST 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

  $865,000

  Sold Feb 10, 2026

  38 W Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $407/SF
  • 107 Days On Market

  Current Estimated Value $846,188

  Last Listing Agent Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
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  /50

  Est $1,072,380

  Not Listed For Sale

  3973 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft
  • Built 2018

  3973 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • 84 Days On Market
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  /51

  $1,775,000

  $25K PRICE DROP Pending

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

  401 Walls Way, Osprey, FL 34229

  Under contract-accepting backup offers. Accepting Backup Offers. 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

  

  Andrea Stultz

  ENGEL + VOELKERS SARASOTA

  401 Walls Way, Osprey, FL 34229
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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 MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 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

  51 Mac Ewen Dr Unit 1, 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
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  /53

  Est $585,232

  Not Listed For Sale

  4421 Conchfish Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2017

  4421 Conchfish Ln, Osprey, FL 34229

  Last Sold Summary

  • 38 Days On Market
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  /62

  $774,900

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

  919 Tranquility Cir, Osprey, FL 34229

  BEACH LOVERS & ADVENTUROUS NATURE LOVERS — YOUR FLORIDA DREAM HOME AWAITS! This STUNNING 4-BR/3.5 BATH POOL HOME offers an OPEN CONCEPT, SPLIT FLOOR PLAN designed for comfortable living and effortless entertaining. The luxurious Primary Suite is your private retreat, featuring Dual Walk-In Closets, 2 separate vanities, 2 private toilet closets, and a relaxing garden tub. The heart of the home is

  

  Ro Palladino

  AYERS AND ASSOCIATES REAL ESTATE

  919 Tranquility Cir, Osprey, FL 34229
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  /15

  $2,800 Per Month

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Condo for Rent

  6 Bay Acres Ave Unit 6 Bay Acres Ave, Osprey, FL 34229

  Property Id: 2376171Welcome to Osprey, FL! This 2 bed, 2 bath fully furnished unit with a fenced back yard is perfect for families and small pets. Relax in a private lanai or binge-watch Netflix; Whatever your past time, this home has what you need. You will be walking distance to a Breeze bus stop route 17, and situated in the middle of the best beaches in southwest Florida as well as

  6 Bay Acres Ave Unit 6 Bay Acres Ave, 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

  Current Estimated Value $1,835,527

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  /15

  Est $741,796

  Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, Osprey, FL 34229

  Last Sold Summary

  • 375 Days On Market
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  /78

  $850,000

  $145K PRICE DROP Pending

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

  1486 Landview Ln, Osprey, FL 34229

  Under contract-accepting backup offers. 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

  

  Barbara Teyssier

  EXP REALTY LLC

  1486 Landview Ln, Osprey, FL 34229
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  /45

  $2,850

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • House for Rent

  4400 Conchfish Ln, Osprey, FL 34229

  Discover this unfurnished, exceptional 3-bedroom, 2-bathroom single-family home built in 2018 in the desirable Palms at Casey Key neighborhood. Offering approximately 2,004 sq ft of living space on a 6,193 sq ft lot, this modern home provides comfort, style, and convenience. It is not in a flood zone and features low HOA fees.Step onto the paved driveway and enter through the wide, elongated

  4400 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $669,000

  Sold Apr 07, 2026

  146 Willow Bend Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $263/SF
  • 26 Days On Market

  Current Estimated Value $677,277

  Last Listing Agent Maria Rocha KELLER WILLIAMS ON THE WATER S

  146 Willow Bend Way, Osprey, FL 34229
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  /41

  Est $1,125,058

  Not Listed For Sale

  3932 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,416 Sq Ft
  • Built 2017

  3932 Waypoint Ave, Osprey, FL 34229

  Last Sold Summary

  • 11 Days On Market
• 

  

  /41

  $289,900

  $60K PRICE DROP

  • 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

  1801 Highland Rd, Osprey, FL 34229
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  /14

  $1,995

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  188 Explorer Dr Unit 188, Osprey, FL 34229

  Location, Location, Location. Beautiful, quiet, safe & secure, Newer 2 Bed, 2 Bath, for rent annually, All amenities including all Stainless Steel Appliances, Washer, Dryer, Stove, Refrigerator. Gorgeous Pool, Exercise Room, Clubhouse, great area, five minutes to Sarasota Square Mall, Costco, shopping, and medical facilities. Close to Siesta Key Beach and fabulous restaurants. Special Hurricane

  188 Explorer Dr Unit 188, Osprey, FL 34229
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  /2

  $1,025,000

  Sold Apr 24, 2026

  1218 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft
  • Built 1980

  Last Sold Summary

  • 15% Below List Price
  • $311/SF
  • 203 Days On Market

  Current Estimated Value $1,043,903

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  Est $935,843

  Not Listed For Sale

  336 Pine Ranch Rd E, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,705 Sq Ft
  • Built 1989

  336 Pine Ranch Rd E, Osprey, FL 34229

  Last Sold Summary

  • 5 Days On Market
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  /55

  $999,000

  $201K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  353 S Shore Dr, Osprey, FL 34229

  Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated

  

  Phyllis Coviello

  COLDWELL BANKER SARASOTA CENT.

  353 S Shore Dr, Osprey, FL 34229
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  /18

  $1,850

  Total Monthly Price

  • 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

  $480,000

  Sold Mar 18, 2026

  827 Placid Lake Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 2002

  Last Sold Summary

  • 16% Below List Price
  • $256/SF
  • 202 Days On Market

  Current Estimated Value $489,679

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
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  /2

  Est $872,656

  Not Listed For Sale

  402 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,887 Sq Ft
  • Built 1995

  402 Pine Ranch Rd E, Osprey, FL 34229

  Last Sold Summary

  • 24 Days On Market
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  /52

  $700,000

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

  14041 Bellagio Way Unit 214, Osprey, FL 34229

  Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village-3 Bedrooms | 2 Bathrooms | Direct Intracoastal FrontageRare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and

  

  Veronica Lee

  COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 214, Osprey, FL 34229
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  /14

  $2,250 Per Month

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

  51 Mac Ewen Dr Unit 8, Osprey, FL 34229

  Available NOW! Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures

  Deserea Hardy ROSSI & COMPANY INC

  51 Mac Ewen Dr Unit 8, Osprey, FL 34229
• 

  /2

  $505,025

  Sold Mar 26, 2026

  570 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 2 Days On Market

  Current Estimated Value $506,227

  Last Listing Agent Mickey Schweitzer MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

  570 Crane Prairie Way, Osprey, FL 34229
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  /2

  Not Listed For Sale

  312 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1979

  312 Tropic Dr, Osprey, FL 34229

  Last Sold Summary

  • 57 Days On Market

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