Osprey, FL Homes

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  $200,000 Sold Dec 09, 2025

  201 Woodland Dr Unit 201, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  Last Sold Summary

  • 33% Below List Price
  • $152/SF
  • 346 Days On Market

  Last Listing Agent Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

  201 Woodland Dr Unit 201, Osprey, FL 34229
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  /46

  Est $978,250 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,107 Sq Ft

  423 S Creek Dr, Osprey, FL 34229

  423 S Creek Dr, Osprey, FL 34229
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  /41

  $424,000

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  524 Sarabay Rd, Osprey, FL 34229

  Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

  Ibetta Giannone SUN N SAND REAL ESTATE LLC

  524 Sarabay Rd, Osprey, FL 34229
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  $1,014,000 Sold Nov 12, 2025

  201 Eaglenook Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,379 Sq Ft
  • Built 1992

  Last Sold Summary

  • 16% Below List Price
  • $300/SF
  • 211 Days On Market

  Last Listing Agent Dawn Bear WILLIAM RAVEIS REAL ESTATE

  201 Eaglenook Way, Osprey, FL 34229
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  /54

  Est $831,095 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,575 Sq Ft

  216 Windward Dr, Osprey, FL 34229

  216 Windward Dr, Osprey, FL 34229
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  /85

  $595,000

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

  409 N Point Rd Unit 603, Osprey, FL 34229

  BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF! Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 full baths and a formal dining room/den. With this condo you have found a best-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private elevator to the sixth floor

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
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  $200,000 Sold Oct 06, 2025

  444 Washington Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $156/SF
  • 9 Days On Market

  Current Estimated Value $209,850

  Last Listing Agent Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  444 Washington Ave, Osprey, FL 34229
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  /82

  Est $950,402 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,900 Sq Ft

  682 Clear Creek Dr, Osprey, FL 34229

  682 Clear Creek Dr, Osprey, FL 34229
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  /70

  $899,995

  • 3 Beds
  • 4 Baths
  • 3,561 Sq Ft

  616 Crane Prairie Way, Osprey, FL 34229

  Located in Willowbend, this expansive residence offers a rare blend of space, privacy, and long-term potential, set against tranquil water and preserve views with Oscar Scherer State Park as a stunning natural backdrop. Offering over 3,500 square feet of living space, the home provides exceptional flexibility for buyers looking to personalize a well-designed layout. High ceilings, architectural

  Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  616 Crane Prairie Way, Osprey, FL 34229
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  $745,000 Sold Mar 27, 2025

  401 N Point Rd Unit 401, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $287/SF
  • 17 Days On Market

  Current Estimated Value $735,627

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 401, Osprey, FL 34229
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  /45

  Est $656,550 Not Listed For Sale

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

  752 Sarabay Rd Unit 2, Osprey, FL 34229

  752 Sarabay Rd Unit 2, Osprey, FL 34229
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  /47

  $264,900

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

  232 Woodland Dr, Osprey, FL 34229

  This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within

  Pat Williams PAT WILLIAMS REALTY, LLC

  232 Woodland Dr, Osprey, FL 34229
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  $855,000 Sold May 30, 2025

  14021 Bellagio Way Unit 311, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,235 Sq Ft
  • Built 2006

  Last Sold Summary

  • 14% Below List Price
  • $383/SF
  • 211 Days On Market

  Current Estimated Value $850,381

  Last Listing Agent Kristin O'Connor GULF TO BAY SOTHEBY'S INTERNAT

  14021 Bellagio Way Unit 311, Osprey, FL 34229
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  /87

  Est $393,530 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,515 Sq Ft

  223 Hidden Bay Dr Unit 303, Osprey, FL 34229

  223 Hidden Bay Dr Unit 303, Osprey, FL 34229
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  /53

  $395,000

  • Land
  • 0.24 Acre
  • $1,645,833 per Acre

  51 N Tamiami Trail, Osprey, FL 34229

  Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and

  Betsy De Manio COLDWELL BANKER REALTY

  51 N Tamiami Trail, Osprey, FL 34229
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  $525,000 Sold Sep 30, 2025

  116 Villa Dr Unit 116, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1968

  Last Sold Summary

  • $430/SF
  • 2 Days On Market

  Current Estimated Value $505,022

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  116 Villa Dr Unit 116, Osprey, FL 34229
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  Est $259,065 Not Listed For Sale

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

  135 Woodland Place, Osprey, FL 34229

  135 Woodland Place, Osprey, FL 34229
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  /2

  Est $863,147 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft

  1251 Windward Dr, Osprey, FL 34229

  1251 Windward Dr, Osprey, FL 34229
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  /2

  Est $584,266 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft

  817 Placid Lake Dr, Osprey, FL 34229

  817 Placid Lake Dr, Osprey, FL 34229
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  /61

  Est $147,632 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  750 Pine Run Dr, Osprey, FL 34229

  750 Pine Run Dr, Osprey, FL 34229
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  Est $997,501 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft

  1762 Island Way, Osprey, FL 34229

  1762 Island Way, Osprey, FL 34229
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  /35

  Est $3,690,987 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 4,202 Sq Ft

  722 Sarabay Rd, Osprey, FL 34229

  722 Sarabay Rd, Osprey, FL 34229
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  /62

  Est $314,624 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  250 Glenwood Ave, Osprey, FL 34229

  250 Glenwood Ave, Osprey, FL 34229
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  /46

  Est $911,050 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,494 Sq Ft

  354 Tintoretto Dr, Osprey, FL 34229

  354 Tintoretto Dr, Osprey, FL 34229
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  /27

  Est $1,546,738 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,665 Sq Ft

  935 Blue Heron Overlook, Osprey, FL 34229

  935 Blue Heron Overlook, Osprey, FL 34229
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  /2

  Est $1,896,296 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,738 Sq Ft

  385 N Point Rd Unit 802, Osprey, FL 34229

  385 N Point Rd Unit 802, Osprey, FL 34229
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  /47

  Est $831,363 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,644 Sq Ft

  1440 Seafarer Dr, Osprey, FL 34229

  1440 Seafarer Dr, Osprey, FL 34229
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  /42

  Est $829,321 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  116 Bishopscourt Rd, Osprey, FL 34229

  116 Bishopscourt Rd, Osprey, FL 34229
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  /26

  Est $564,467 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,225 Sq Ft

  603 Pine Ranch East Rd, Osprey, FL 34229

  603 Pine Ranch East Rd, Osprey, FL 34229
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  /11

  Est $2,082,491 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,768 Sq Ft

  442 Webbs Cove, Osprey, FL 34229

  442 Webbs Cove, Osprey, FL 34229
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  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft

  854 N Casey Key Rd, Osprey, FL 34229

  854 N Casey Key Rd, Osprey, FL 34229
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  /42

  Est $250,777 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 626 Sq Ft

  473 Glenwood Ave, Osprey, FL 34229

  473 Glenwood Ave, Osprey, FL 34229
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  /40

  Est $306,148 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft

  437 Pennsylvania Ave, Osprey, FL 34229

  437 Pennsylvania Ave, Osprey, FL 34229
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  /65

  Est $2,048,637 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  453 Webbs Cove, Osprey, FL 34229

  453 Webbs Cove, Osprey, FL 34229
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  /6

  Not Listed For Sale

  • 8 Beds

  50 W Bay St, Osprey, FL 34229

  50 W Bay St, Osprey, FL 34229
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  /2

  Est $606,111 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,312 Sq Ft

  603 Oak Bay Dr, Osprey, FL 34229

  603 Oak Bay Dr, Osprey, FL 34229
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  /45

  Est $693,927 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,510 Sq Ft

  40 Webb St, Osprey, FL 34229

  40 Webb St, Osprey, FL 34229
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  /43

  Est $144,907 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  760 Pine Run Dr, Osprey, FL 34229

  760 Pine Run Dr, Osprey, FL 34229
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  /72

  Est $245,380 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  756 Pine Run Dr, Osprey, FL 34229

  756 Pine Run Dr, Osprey, FL 34229
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  510 Old Venice Rd, Osprey, FL 34229

  510 Old Venice Rd, Osprey, FL 34229

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