Osprey, FL Homes

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  /3

  Est $231,118 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 858 Sq Ft

  110 Oak St, Osprey, FL 34229

  110 Oak St, Osprey, FL 34229
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  /48

  $184,900

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  238 Woodland Dr, Osprey, FL 34229

  GREAT NEW PRICE to live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding

  Kellie MacDonell COLDWELL BANKER REALTY

  238 Woodland Dr, Osprey, FL 34229
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  /2

  $510,000 Sold Jan 13, 2026

  12689 Promenade Estates Blvd, Osprey, FL 34238

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $249/SF
  • 38 Days On Market

  Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

  12689 Promenade Estates Blvd, Osprey, FL 34238
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  /11

  Est $899,055 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft

  226 Saint James Park, Osprey, FL 34229

  226 Saint James Park, Osprey, FL 34229
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  /4

  $1,500

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 10, 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 10, Osprey, FL 34229
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  /2

  $3,050,000 Sold Aug 15, 2025

  5 N Casey Key Rd, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,380 Sq Ft
  • Built 1969

  Last Sold Summary

  • 27% Below List Price
  • $1,282/SF
  • 278 Days On Market

  Current Estimated Value $2,972,202

  Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229
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  /70

  Est $1,564,600 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,551 Sq Ft

  337 Passage Way, Osprey, FL 34229

  337 Passage Way, Osprey, FL 34229
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  /33

  $164,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  216 Palm Air Dr, Osprey, FL 34229

  Under contract-accepting backup offers. This home is located in the sought-after 55+ community of The Arbors. It offers a blend of comfort, updates, and a prime location between Sarasota and Venice. Featuring 2 bedrooms, 2 bathrooms, and a newly built carport, this home is designed for easy and comfortable living. The bright and airy living room welcomes you with abundant natural light, while the

  Todd Goodman KELLER WILLIAMS ON THE WATER S

  216 Palm Air Dr, Osprey, FL 34229
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  /2

  $885,000 Sold Mar 31, 2025

  236 Hidden Bay Dr Unit 504, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $421/SF
  • 115 Days On Market

  Current Estimated Value $852,695

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  236 Hidden Bay Dr Unit 504, Osprey, FL 34229
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  /24

  Est $840,193 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  130 N Creek Ln, Osprey, FL 34229

  130 N Creek Ln, Osprey, FL 34229
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  /56

  $735,000 Pending

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

  1019 Scherer Way, Osprey, FL 34229

  Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window

  Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

  1019 Scherer Way, Osprey, FL 34229
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  /2

  $660,000 Sold Aug 26, 2025

  463 Park Trace Blvd, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $307/SF
  • 63 Days On Market

  Current Estimated Value $658,827

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  463 Park Trace Blvd, Osprey, FL 34229
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  /44

  Est $1,100,722 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,534 Sq Ft

  315 Sea Anchor Dr, Osprey, FL 34229

  315 Sea Anchor Dr, Osprey, FL 34229
• 

  

  /95

  $5,495,000

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

  730 Sarabay Rd, Osprey, FL 34229

  Premier Intracoastal Estate in Osprey4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront AcresA rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is aconvergence of residential luxury and unparalleled waterfront living. The two-story home sits atthe end of a long drive behind a gated entrance and tranquil pond. With approximately 100

  Debbie Baraona ROBERT SLACK LLC

  730 Sarabay Rd, Osprey, FL 34229
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  /2

  $615,000 Sold Feb 21, 2025

  242 Hidden Bay Dr Unit 403, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $318/SF
  • 86 Days On Market

  Current Estimated Value $606,324

  Last Listing Agent Tina Renta KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  242 Hidden Bay Dr Unit 403, Osprey, FL 34229
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  /46

  Est $1,611,410 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,740 Sq Ft

  345 S Shore Dr, Osprey, FL 34229

  345 S Shore Dr, Osprey, FL 34229
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  /8

  $750,000

  • Land
  • 0.47 Acre
  • $1,595,745 per Acre

  147 Osprey Point Dr, Osprey, FL 34229

  Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida‘s most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand and luxurious homes in the entire gulf coast region. The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of

  Mick Jordan BRIGHT REALTY

  147 Osprey Point Dr, Osprey, FL 34229
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  /2

  $1,700,000 Sold Jun 12, 2025

  525 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,315 Sq Ft
  • Built 1972

  Last Sold Summary

  • 15% Below List Price
  • $734/SF
  • 108 Days On Market

  Current Estimated Value $1,658,798

  Last Listing Agent Andree Huffine COLDWELL BANKER REALTY

  525 S Shore Dr, Osprey, FL 34229
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  /2

  Est $721,071 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,388 Sq Ft

  668 Clear Creek Dr, Osprey, FL 34229

  668 Clear Creek Dr, Osprey, FL 34229
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  /35

  $289,000

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

  2043 Cordes St, Osprey, FL 34229

  Charming & Versatile Home Near the Beaches!This cute and cozy, well-maintained 3-bedroom, 2-bath residence offers exceptional flexibility including a private-entrance 1-bedroom, 1-bath suite plus den—perfect for an in-law suite, guest quarters, extra bedroom or home office setup. The home features durable tile and vinyl flooring throughout, updated bathrooms with newer showers, and a bright,

  Travis Matthews PREFERRED SHORE LLC

  2043 Cordes St, Osprey, FL 34229
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  /2

  $1,160,000 Sold Apr 15, 2025

  131 Tina Island Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,787 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $649/SF
  • 10 Days On Market

  Current Estimated Value $1,144,481

  Last Listing Agent Sarah McGuire WHITE SANDS REALTY GROUP FL

  131 Tina Island Dr, Osprey, FL 34229
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  /100

  Est $1,161,928 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,215 Sq Ft

  328 Pine Ranch Trail, Osprey, FL 34229

  328 Pine Ranch Trail, Osprey, FL 34229
• 

  

  /19

  $129,500 Pending

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  26 Siesta Cir W, Osprey, FL 34229

  Under contract-accepting backup offers. Just Move In ... Affordable Fully furnished 2-bedroom home with central air is located in an active 55 and over community Located in the heart of Osprey with nearby shopping and dining and easy access to nearby Siesta Key Beach, Casey Key and Nokomis Beach along with The Legacy Bike trail and Oscer Scherer State Park. The Arbors Mobile Home Park with Low

  Gary Hoskins COLDWELL BANKER REALTY

  26 Siesta Cir W, Osprey, FL 34229
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  /2

  $645,000 Sold Jul 31, 2025

  673 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,223 Sq Ft
  • Built 2003

  Last Sold Summary

  • 13% Below List Price
  • $290/SF
  • 9 Days On Market

  Current Estimated Value $652,979

  Last Listing Agent Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

  673 Crane Prairie Way, Osprey, FL 34229
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  /54

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,168 Sq Ft

  871 MacEwen Dr, Osprey, FL 34229

  871 MacEwen Dr, Osprey, FL 34229
• 

  

  /57

  $825,000

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

  919 Tranquility Cir, Osprey, FL 34229

  WOW! 25,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle. This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy an open, spacious split-plan layout with Four bedrooms,

  Ann Winger TIDELINE REAL ESTATE BROKERS

  919 Tranquility Cir, Osprey, FL 34229
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  /2

  $390,000 Sold Apr 15, 2025

  441 N Shore Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft
  • Built 1970

  Last Sold Summary

  • 18% Below List Price
  • $292/SF
  • 21 Days On Market

  Current Estimated Value $389,667

  Last Listing Agent Dawn Barnett EXIT KING REALTY

  441 N Shore Dr, Osprey, FL 34229
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  /65

  Est $1,892,338 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft

  482 E MacEwen Dr, Osprey, FL 34229

  482 E MacEwen Dr, Osprey, FL 34229
• 

  

  /11

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  110 Pine Ave, Osprey, FL 34229

  Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

  Marisa Marino BRIGHT REALTY

  110 Pine Ave, Osprey, FL 34229
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  /2

  $2,315,000 Sold Oct 30, 2025

  112 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 8,635 Sq Ft
  • Built 1989

  Last Sold Summary

  • 41% Below List Price
  • $268/SF
  • 156 Days On Market

  Current Estimated Value $3,087,979

  Last Listing Agent Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
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  /64

  Est $297,897 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  112 Woodland Place, Osprey, FL 34229

  112 Woodland Place, Osprey, FL 34229
• 

  

  /13

  $170,000 Pending

  • Land
  • 0.42 Acre
  • $404,762 per Acre

  911 Tranquility Cir, Osprey, FL 34229

  Beautiful and Private Buildable Lot in desirable North Creek Estates. Formerly under PID 0142020069 is currently combined with Lot 9 with home on listing A4674201, 919 Tranquility Cir but seller will separate the lot and sell lot and home as two transactions. See A4678841 for home without adjoining lot. These lots are a rarity in an already completed in such a great location. This lot has

  Mike Winger TIDELINE REAL ESTATE BROKERS

  911 Tranquility Cir, Osprey, FL 34229
• 

  /2

  $665,000 Sold Nov 06, 2025

  563 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,346 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 5 Days On Market

  Current Estimated Value $662,899

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  563 Pine Ranch Rd E, Osprey, FL 34229
• 

  /2

  Est $387,793 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  308 Kensey Ln, Osprey, FL 34229

  308 Kensey Ln, Osprey, FL 34229
• 

  

  /47

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  104 Park Trace Blvd, Osprey, FL 34229

  Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms,

  Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

  104 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  $2,400,000 Sold Jun 02, 2025

  230 Osprey Point Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,586 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $669/SF
  • 42 Days On Market

  Current Estimated Value $2,377,772

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  230 Osprey Point Dr, Osprey, FL 34229
• 

  

  /30

  Est $140,905 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  751 Pine Run Dr Unit 751, Osprey, FL 34229
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  /47

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 2,850 Sq Ft

  17 Bayhead Ln, Osprey, FL 34229

  Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom

  Steve Abbe COLDWELL BANKER REALTY

  17 Bayhead Ln, Osprey, FL 34229
• 

  /2

  $1,500,000 Sold Sep 19, 2025

  462 E MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,611 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $574/SF
  • 29 Days On Market

  Current Estimated Value $1,470,147

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  462 E MacEwen Dr, Osprey, FL 34229
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  /50

  Est $530,173 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,789 Sq Ft

  529 Meadow Sweet Cir, Osprey, FL 34229

  529 Meadow Sweet Cir, Osprey, FL 34229

Showing Results 281 - 320, Page 8 of 18