Osprey, FL Homes

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  /13

  Est $350,705 Not Listed For Sale

  316 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2002

  316 Pennsylvania Ave, Osprey, FL 34229

  Last Sold Summary

  • 7% Below List Price
  • $363/SF
  • 376 Days On Market

  Last Sold Price $377,500

  Last Listing Agent Miranda Platt, PA RELAX PROPERTY GROUP, LLC
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  /51

  $449,000

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  107 Sorrento Dr, Osprey, FL 34229

  This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  107 Sorrento Dr, Osprey, FL 34229
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  /2

  $1,200,000 Sold Oct 24, 2025

  1484 Seafarer Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,479 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $345/SF
  • 82 Days On Market

  Current Estimated Value $1,183,606

  Last Listing Agent Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
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  /22

  Est $552,287 Not Listed For Sale

  743 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 2000

  743 Anna Hope Ln, Osprey, FL 34229

  Last Sold Summary

  • $256/SF
  • 177 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
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  /100

  $3,995,000 Pending

  • 4 Beds
  • 7 Baths
  • 6,705 Sq Ft

  691 Eagle Watch Ln, Osprey, FL 34229

  Under contract-accepting backup offers. Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.2 of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  691 Eagle Watch Ln, Osprey, FL 34229
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  /2

  $1,275,000 Sold Sep 30, 2025

  364 Renoir Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,241 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $393/SF
  • 7 Days On Market

  Current Estimated Value $1,289,032

  Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229
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  /2

  Est $1,785,470 Not Listed For Sale

  165 Sugar Mill Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,912 Sq Ft
  • Built 1989

  165 Sugar Mill Dr, Osprey, FL 34229

  Last Sold Summary

  • 1% Above List Price
  • $454/SF
  • 152 Days On Market

  Last Sold Price $1,775,000

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  /4

  $32,500

  570 Blackburn Point Rd Unit 38, Osprey, FL 34229

  Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Plus, HOA is prepaid thru the end of 2025! Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 38, Osprey, FL 34229
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  /2

  $945,000 Sold Apr 15, 2025

  128 Sea Anchor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,677 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $353/SF
  • 4 Days On Market

  Current Estimated Value $928,717

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  128 Sea Anchor Dr, Osprey, FL 34229
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  /24

  Est $1,032,632 Not Listed For Sale

  228 Windward Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,850 Sq Ft
  • Built 1981

  228 Windward Dr, Osprey, FL 34229

  Last Sold Summary

  • 14% Below List Price
  • $421/SF
  • 1 Day On Market

  Last Sold Price $1,200,000

  Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC
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  /39

  $1,099,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,374 Sq Ft

  14041 Bellagio Way Unit 218, Osprey, FL 34229

  Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers 2,374 sq ft of well-appointed living space, with water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a DEEDED 40' wet slip—providing immediate access to boating, fishing, and the

  Kelli Eggen COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 218, Osprey, FL 34229
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  /2

  $2,625,000 Sold Sep 16, 2025

  478 Oriskany Ct, Osprey, FL 34229

  • 4 Beds
  • 7 Baths
  • 5,778 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $454/SF
  • 10 Days On Market

  Current Estimated Value $2,588,179

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  478 Oriskany Ct, Osprey, FL 34229
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  /78

  Est $734,397 Not Listed For Sale

  522 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft
  • Built 2003

  522 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $355/SF
  • 48 Days On Market

  Last Sold Price $825,000

  Last Listing Agent David Cyr WILLIAM RAVEIS FLORIDA LLC
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  /42

  $829,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,876 Sq Ft

  1211 Lost Creek Ct, Osprey, FL 34229

  Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s

  Mark Lyda GENEROUS PROPERTY

  1211 Lost Creek Ct, Osprey, FL 34229
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  /2

  $1,325,000 Sold Nov 07, 2025

  402 Walls Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,464 Sq Ft
  • Built 2014

  Last Sold Summary

  • 22% Below List Price
  • $383/SF
  • 187 Days On Market

  Current Estimated Value $1,401,967

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  402 Walls Way, Osprey, FL 34229
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  /2

  Est $711,020 Not Listed For Sale

  520 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft
  • Built 2003

  520 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $333/SF
  • 4 Days On Market

  Last Sold Price $774,500

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /60

  $10,750,000

  • 5 Beds
  • 8 Baths
  • 8,050 Sq Ft

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /2

  $625,000 Sold Oct 10, 2025

  644 Rivendell Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,298 Sq Ft
  • Built 2001

  Last Sold Summary

  • 16% Below List Price
  • $272/SF
  • 260 Days On Market

  Current Estimated Value $629,871

  Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  /41

  Est $690,466 Not Listed For Sale

  675 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 2003

  675 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 12% Below List Price
  • $338/SF
  • 37 Days On Market

  Last Sold Price $783,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /48

  $200,000

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

  244 Woodland Dr Unit 244, Osprey, FL 34229

  Tranquil Coastal Living in Pine Run244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  244 Woodland Dr Unit 244, Osprey, FL 34229
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  /2

  $675,000 Sold Jan 21, 2026

  409 N Point Rd Unit 501, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2004

  Last Sold Summary

  • 36% Below List Price
  • $260/SF
  • 575 Days On Market

  Current Estimated Value $693,761

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 501, Osprey, FL 34229
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  /40

  Est $1,147,299 Not Listed For Sale

  109 Tina Island Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,827 Sq Ft
  • Built 1988

  109 Tina Island Dr, Osprey, FL 34229

  Last Sold Summary

  • 6% Below List Price
  • $433/SF
  • 15 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Sherri Mills Michael Saunders
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  /60

  $519,000

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  786 Sarabay Rd Unit 19, Osprey, FL 34229

  Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  786 Sarabay Rd Unit 19, Osprey, FL 34229
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  /2

  $1,400,000 Sold May 07, 2025

  378 MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,094 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $452/SF
  • 0 Days On Market

  Current Estimated Value $1,397,129

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  378 MacEwen Dr, Osprey, FL 34229
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  /2

  Est $524,953 Not Listed For Sale

  502 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1995

  502 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 6% Above List Price
  • $234/SF
  • 88 Days On Market

  Last Sold Price $495,000

  Last Listing Agent Carey Beychok RE/MAX
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  /92

  $1,775,000 Pre-Foreclosure

  • 4 Beds
  • 4 Baths
  • 4,001 Sq Ft

  75 Osprey Point Dr, Osprey, FL 34229

  **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

  Mark Lyda GENEROUS PROPERTY

  75 Osprey Point Dr, Osprey, FL 34229
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  /2

  $744,800 Sold Apr 24, 2025

  448 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • Built 2002

  Last Sold Summary

  • 22% Below List Price
  • $243/SF
  • 145 Days On Market

  Current Estimated Value $770,063

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  448 Park Trace Blvd, Osprey, FL 34229
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  /65

  Est $950,909 Not Listed For Sale

  800 Eaglenook Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,632 Sq Ft
  • Built 1978

  800 Eaglenook Way, Osprey, FL 34229

  Last Sold Summary

  • $361/SF
  • 2 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY
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  /86

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  252 Sun Air Cir, Osprey, FL 34229

  Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz

  Karen Geiger COLDWELL BANKER SARASOTA CENT.

  252 Sun Air Cir, Osprey, FL 34229
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  /2

  $3,525,000 Sold Jun 06, 2025

  275 Lookout Point Dr, Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 5,279 Sq Ft
  • Built 2007

  Last Sold Summary

  • 26% Below List Price
  • $668/SF
  • 124 Days On Market

  Current Estimated Value $3,560,611

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  275 Lookout Point Dr, Osprey, FL 34229
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  /9

  Est $179,824 Not Listed For Sale

  242 Washington Ave, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft
  • Built 1950

  242 Washington Ave, Osprey, FL 34229

  Last Sold Summary

  • 6% Above List Price
  • $270/SF
  • 162 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Dan Miller PREFERRED SHORE LLC
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  /78

  $690,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  102 Windward Dr, Osprey, FL 34229

  NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers

  David Cyr WILLIAM RAVEIS FLORIDA LLC

  102 Windward Dr, Osprey, FL 34229
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  /2

  $318,000 Sold Mar 25, 2026

  116 Navigation Cir Unit 106, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Below List Price
  • $222/SF
  • 220 Days On Market

  Current Estimated Value $324,771

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

  116 Navigation Cir Unit 106, Osprey, FL 34229
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  /2

  Est $648,006 Not Listed For Sale

  385 N Point Rd Unit 602, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 2000

  385 N Point Rd Unit 602, Osprey, FL 34229

  Last Sold Summary

  • $316/SF
  • 174 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Matt Buttner LIST NOW REALTY, LLC
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  /24

  $600,000

  • Land
  • 0.34 Acre
  • $1,764,706 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

  Matthew Charland LLC GULF SHORES REALTY ERA POWERED

  458 N Shore Dr, Osprey, FL 34229
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  /2

  $1,900,000 Sold Feb 10, 2026

  340 Osprey Point Dr, Osprey, FL 34229

  • 5 Beds
  • 7 Baths
  • 6,001 Sq Ft
  • Built 1998

  Last Sold Summary

  • 24% Below List Price
  • $317/SF
  • 273 Days On Market

  Current Estimated Value $1,954,948

  Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

  340 Osprey Point Dr, Osprey, FL 34229
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  /2

  Est $514,158 Not Listed For Sale

  515 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft
  • Built 1995

  515 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • $259/SF
  • 116 Days On Market

  Last Sold Price $512,500

  Last Listing Agent Thomas Cail RE/MAX
• 

  

  /3

  $89,000

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
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  /2

  $2,000,000 Sold Apr 21, 2025

  1862 Island Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,598 Sq Ft
  • Built 1982

  Last Sold Summary

  • 18% Below List Price
  • $556/SF
  • 76 Days On Market

  Current Estimated Value $2,035,195

  Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1862 Island Way, Osprey, FL 34229
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  /34

  Est $593,309 Not Listed For Sale

  1358 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft
  • Built 2003

  1358 Thornapple Dr, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • $280/SF
  • 86 Days On Market

  Last Sold Price $605,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

Showing Results 401 - 440, Page 11 of 18