Osprey, FL Homes

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  /78

  Est $729,898 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft

  522 Habitat Blvd, Osprey, FL 34229

  522 Habitat Blvd, Osprey, FL 34229
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  /37

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft

  455 N Shore Dr, Osprey, FL 34229

  Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment. Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42 boat

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  455 N Shore Dr, Osprey, FL 34229
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  /2

  $910,000 Sold Nov 19, 2025

  766 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $265/SF
  • 132 Days On Market

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $728,867 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft

  520 Habitat Blvd, Osprey, FL 34229

  520 Habitat Blvd, Osprey, FL 34229
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  /4

  $103,000

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229

  The slip can hold a boat with the maximum dimensions of 30.5'L x 10'W x 9'H.This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 33, Osprey, FL 34229
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  /2

  $325,000 Sold Jul 24, 2025

  4236 Expedition Way Unit 106, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2016

  Last Sold Summary

  • 10% Below List Price
  • $213/SF
  • 90 Days On Market

  Current Estimated Value $323,714

  Last Listing Agent Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
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  /41

  Est $707,186 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,320 Sq Ft

  675 Crane Prairie Way, Osprey, FL 34229

  675 Crane Prairie Way, Osprey, FL 34229
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  /92

  $1,000,000

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

  393 N Point Rd Unit 604, Osprey, FL 34229

  Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome of

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  /2

  $500,000 Sold Mar 21, 2025

  629 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1996

  Last Sold Summary

  • 17% Below List Price
  • $268/SF
  • 250 Days On Market

  Current Estimated Value $492,296

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  629 Oak Bay Dr, Osprey, FL 34229
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  /44

  Est $523,992 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229
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  /40

  $879,000

  • 4 Beds
  • 3 Baths
  • 2,935 Sq Ft

  327 Park Trace Blvd, Osprey, FL 34229

  LOOK NO FURTHER! This immaculate, lake-view four-bedroom/ three-bath home is MOVE-IN READY. Completewith a NEW 60K Tile ROOF, PGT Impact Windows throughout and new A/C (2024)! Freshly painted interior fromtop to bottom with Regal select Benjamin Moore paint, sparkling epoxy garage floor, New GE 5 burner range withCrisp mode, walk in pantry, beautifully Updated landscaping, new modern

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  327 Park Trace Blvd, Osprey, FL 34229
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  /2

  $400,000 Sold Apr 08, 2025

  4239 Expedition Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 115 Days On Market

  Current Estimated Value $388,266

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
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  /40

  Est $1,190,035 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,827 Sq Ft

  109 Tina Island Dr, Osprey, FL 34229

  109 Tina Island Dr, Osprey, FL 34229
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  /88

  $2,700,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /2

  $650,000 Sold Apr 18, 2025

  610 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,431 Sq Ft
  • Built 1995

  Last Sold Summary

  • 7% Below List Price
  • $267/SF
  • 113 Days On Market

  Current Estimated Value $627,273

  Last Listing Agent Kim Klee COLDWELL BANKER REALTY

  610 Pine Ranch Rd E, Osprey, FL 34229
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  /65

  Est $943,813 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,632 Sq Ft

  800 Eaglenook Way, Osprey, FL 34229

  800 Eaglenook Way, Osprey, FL 34229
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  /66

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  238 Lookout Point Dr, Osprey, FL 34229

  This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious

  Susanne Losso COLDWELL BANKER REALTY

  238 Lookout Point Dr, Osprey, FL 34229
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  /2

  $470,000 Sold Aug 22, 2025

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2005

  Last Sold Summary

  • 15% Below List Price
  • $217/SF
  • 80 Days On Market

  Current Estimated Value $487,338

  Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  /9

  Est $174,866 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  242 Washington Ave, Osprey, FL 34229

  242 Washington Ave, Osprey, FL 34229
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  /13

  $199,000

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  106 Villa Dr Unit 106, Osprey, FL 34229

  Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and

  Dan Ivanov KONA REALTY

  106 Villa Dr Unit 106, Osprey, FL 34229
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  /2

  $250,000 Sold Oct 23, 2025

  207 Woodland Dr Unit 207, Osprey, FL 34229

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

  Last Sold Summary

  • 18% Below List Price
  • $189/SF
  • 491 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /38

  Est $511,830 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  527 Meadow Sweet Cir, Osprey, FL 34229

  527 Meadow Sweet Cir, Osprey, FL 34229
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  /48

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  597 Oak River Ct, Osprey, FL 34229

  Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator,

  Mairead Smialek COLDWELL BANKER REALTY

  597 Oak River Ct, Osprey, FL 34229
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  /2

  $772,000 Sold Mar 04, 2025

  663 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 9 Days On Market

  Current Estimated Value $743,468

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  663 Crane Prairie Way, Osprey, FL 34229
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  /2

  Est $661,101 Not Listed For Sale

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

  385 N Point Rd Unit 602, Osprey, FL 34229

  385 N Point Rd Unit 602, Osprey, FL 34229
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  /4

  $98,000 Pending

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229

  Under contract-accepting backup offers. This high-end boat dockominium facility keeps your boat high and dry. With a phone call, have your boat fueled and placed in the water. Upon your return, They flush the engines on your boat, wash it around the waterline and then put her to bed. This highly desirable bottom boat rack will handle a boat 30.5' long, 10' wide and 9' tall. The property also

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 25, Osprey, FL 34229
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  /2

  $1,850,000 Sold Nov 07, 2025

  67 Sugar Mill Dr, Osprey, FL 34229

  • 4 Beds
  • 5 Baths
  • 4,020 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $460/SF
  • 240 Days On Market

  Last Listing Agent Paula Mapp MAPP REALTY & INVESTMENT CO

  67 Sugar Mill Dr, Osprey, FL 34229
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  /2

  Est $528,140 Not Listed For Sale

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

  515 Oak Bay Dr, Osprey, FL 34229

  515 Oak Bay Dr, Osprey, FL 34229
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  /91

  $500,000

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

  401 N Point Rd Unit 301, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
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  /2

  $1,375,000 Sold Dec 05, 2025

  500 Shotgun Ln, Osprey, FL 34229

  • Land
  • 11.68 Acres
  • $117,723 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 45 Days On Market

  Last Listing Agent Ruediger Weiss CHARITY & WEISS INTERNATIONAL LLC

  500 Shotgun Ln, Osprey, FL 34229
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  /32

  Est $250,415 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  237 Woodland Dr Unit 237, Osprey, FL 34229

  237 Woodland Dr Unit 237, Osprey, FL 34229
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  /48

  $685,000

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

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
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  /2

  $1,495,000 Sold Oct 31, 2025

  228 Saint James Park, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,425 Sq Ft
  • Built 1997

  Last Sold Summary

  • $616/SF
  • 0 Days On Market

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  228 Saint James Park, Osprey, FL 34229
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  /34

  Est $600,913 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft

  1358 Thornapple Dr, Osprey, FL 34229

  1358 Thornapple Dr, Osprey, FL 34229
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  /7

  $3,000

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 28, 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 28, Osprey, FL 34229
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  /2

  $670,000 Sold Jun 10, 2025

  1426 Landview Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,513 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $267/SF
  • 72 Days On Market

  Current Estimated Value $704,629

  Last Listing Agent Stephanie Church COLDWELL BANKER REALTY

  1426 Landview Ln, Osprey, FL 34229
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  /42

  Est $575,022 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,079 Sq Ft

  564 Crane Prairie Way, Osprey, FL 34229

  564 Crane Prairie Way, Osprey, FL 34229
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  /61

  $5,500,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 4,048 Sq Ft

  614 Bayshore Dr, Osprey, FL 34229

  New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water views and spectacular Casey Key sunsets, setting the stage for an extraordinary lifestyle. Designed for

  Inbal August DOUGLAS ELLIMAN

  614 Bayshore Dr, Osprey, FL 34229
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  /2

  $600,000 Sold Apr 18, 2025

  402 Pine Ranch Rd E, Osprey, FL 34229

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

  Last Sold Summary

  • 31% Below List Price
  • $208/SF
  • 24 Days On Market

  Current Estimated Value $638,358

  Last Listing Agent Ronnie Caron CARON REALTY INC

  402 Pine Ranch Rd E, Osprey, FL 34229
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  /3

  Est $669,385 Not Listed For Sale

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

  6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

Showing Results 441 - 480, Page 12 of 18