Osprey, FL Homes

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  $569,000

  • 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
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  /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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  $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 $934,774

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  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

  • $160/SF
  • 57 Days On Market

  • Last Sold Price $179,000
  • Apr 28, 2025

  Last Listing Agent Michelle Ward COMPASS FLORIDA LLC
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  /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, & finishes

  

  Andrea Stultz

  ENGEL + VOELKERS SARASOTA

  (941) 231-5436

  401 Walls Way, 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 JUNE 15 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 &

  (941) 845-6331

  236 Woodland Dr, 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 $246,784

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
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  Est $419,115 Not Listed For Sale

  418 Sarabay Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft
  • Built 1960

  418 Sarabay Rd, Osprey, FL 34229

  Last Sold Summary

  • 6% Above List Price
  • $224/SF
  • 81 Days On Market

  • Last Sold Price $395,000
  • Apr 30, 2025

  Last Listing Agent Tracey Fiedler DALTON WADE INC
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  /78

  $850,000 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

  (941) 208-4807

  1486 Landview Ln, 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

  (941) 207-5680

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229
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  $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 $423,422

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  Est $337,259 Not Listed For Sale

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2001

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  Last Sold Summary

  • 1% Below List Price
  • $217/SF
  • 166 Days On Market

  • Last Sold Price $340,000
  • May 08, 2025

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /41

  $299,900

  • 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
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  /18

  $3,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  260 Hidden Bay Dr Unit 204, Osprey, FL 34229

  Property Id: 18124583 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large

  (270) 813-2485

  260 Hidden Bay Dr Unit 204, Osprey, FL 34229
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  $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 $853,022

  Last Listing Agent Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
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  Est $172,989 Not Listed For Sale

  235 Woodland Dr Unit 235, Osprey, FL 34229

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

  235 Woodland Dr Unit 235, Osprey, FL 34229

  Last Sold Summary

  • 5% Above List Price
  • $135/SF
  • 53 Days On Market

  • Last Sold Price $165,000
  • Apr 28, 2025

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC
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  $1,099,000

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

  353 S Shore Dr, Osprey, FL 34229

  Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned 4 houses from the Open waters of the Intercoastal waterway on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway! A true boater’s dream, your private dock provides quick and easy access to some of the

  

  Phyllis Coviello

  COLDWELL BANKER SARASOTA CENT.

  (941) 420-6389

  353 S Shore Dr, Osprey, FL 34229
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  $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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  $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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  Est $1,750,274 Not Listed For Sale

  916 MacEwen Dr, Osprey, FL 34229

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

  916 MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 9% Above List Price
  • $267/SF
  • 1 Day On Market

  • Last Sold Price $1,600,000
  • May 01, 2025

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  $699,000 Pending

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

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229

  BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of

  

  Scott Swonger

  HOMESMART

  (941) 304-4466

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229
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  /20

  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,371 Sq Ft
  • House for Rent

  253 Glenwood Ave, Osprey, FL 34229

  Welcome to your new oasis in Osprey! This charming 3-bedroom, 2-bathroom house offers a perfect blend of comfort and convenience, making it an ideal place to call home. With a spacious 1,371 square feet, there's plenty of room for you to spread out and enjoy life.Step inside to discover a bright and inviting living space, complete with modern amenities that make daily living a breeze. The

  (941) 335-5525

  253 Glenwood Ave, Osprey, FL 34229
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  $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 $1,836,267

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  Est $309,972 Not Listed For Sale

  115 Villa Dr Unit 115, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1972

  115 Villa Dr Unit 115, Osprey, FL 34229

  Last Sold Summary

  • 3% Below List Price
  • $225/SF
  • 125 Days On Market

  • Last Sold Price $318,000
  • Apr 30, 2025

  Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S
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  $1,599,000

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

  480 Oriskany Ct, Osprey, FL 34229

  Positioned on a premium golf course lot within the Oaks Club in Osprey, Florida, this Toll Brothers-built residence offers a rare combination of scenic beauty, privacy and practical upgrades (newer roof and pool cage 2023) that set it apart from other homes in the community. Overlooking the Heron 14 fairway, and paired with a tranquil preserve across the street, this property enjoys a unique

  

  Susan Pelton

  MICHAEL SAUNDERS & COMPANY

  (941) 491-3516

  480 Oriskany Ct, 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 EXCEPTIONSLanlord require 1st, last month rent and $450 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and background

  (914) 281-2489

  8 Bay Ave, Osprey, FL 34229
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  $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 $699,833

  Last Listing Agent Maria Rocha KELLER WILLIAMS ON THE WATER S

  146 Willow Bend Way, Osprey, FL 34229
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  Est $730,758 Not Listed For Sale

  710 Shadow Bay Way, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,533 Sq Ft
  • Built 2002

  710 Shadow Bay Way, Osprey, FL 34229

  Last Sold Summary

  • 3% Above List Price
  • $280/SF
  • 117 Days On Market

  • Last Sold Price $710,000
  • May 09, 2025

  Last Listing Agent Veronica Manes Michael Saunders
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  $3,690,000

  • 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
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  $2,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,857 Sq Ft
  • House for Rent

  531 Latitude Ln, Osprey, FL 34229

  Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink.

  Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

  531 Latitude Ln, Osprey, FL 34229
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  $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 $496,806

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
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  Est $757,612 Not Listed For Sale

  779 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft
  • Built 2002

  779 Fordingbridge Way, Osprey, FL 34229

  Last Sold Summary

  • 3% Below List Price
  • $362/SF
  • 6 Days On Market

  • Last Sold Price $780,000
  • May 08, 2025

  Last Listing Agent Leonard Giarrano RE/MAX
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  $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

  (941) 347-0413

  14041 Bellagio Way Unit 214, Osprey, FL 34229
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  $1,800

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  1847 Highland Rd Unit 1839 Highland Rd, Osprey, FL 34229

  Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.

  1847 Highland Rd Unit 1839 Highland Rd, Osprey, FL 34229
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  $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 $1,061,092

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  Est $364,054 Not Listed For Sale

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2018

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  Last Sold Summary

  • 17% Below List Price
  • $280/SF
  • 91 Days On Market

  • Last Sold Price $440,000
  • May 16, 2023

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  $1,100,000

  • 5 Beds
  • 3 Baths
  • 3,912 Sq Ft

  674 Clear Creek Dr, Osprey, FL 34229

  Looking for a house within #1 US public school within a short distance? Discover this expansive 5-bedroom, 3-bathroom home with an oversized flex room, office, and almost 4,000 sq. ft. of living space, perfectly situated on a 9,017 sq. ft. lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2025), HVAC units (2019 & 2023), a new water heater (2022), fresh

  

  Arkadiy Abdurakhmanov

  United Realty Group Inc.

  (941) 390-3801

  674 Clear Creek Dr, Osprey, FL 34229
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  $5,600 Per Month

  • 3 Beds
  • 2 Baths
  • 2,306 Sq Ft
  • House for Rent

  124 Turquoise Ln, Osprey, FL 34229

  Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key and the Gulf of Mexico.

  Cody Smith RENT SARASOTA

  124 Turquoise Ln, Osprey, FL 34229
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  $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 $499,668

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

  570 Crane Prairie Way, Osprey, FL 34229
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  Est $1,093,154 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

  • 5% Below List Price
  • $490/SF
  • 213 Days On Market

  • Last Sold Price $1,150,000
  • May 21, 2024

  Last Listing Agent Lee Brewer RE/MAX

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