Osprey, FL Homes

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  $300,000

  Sold Jun 15, 2026

  222 Glenwood Ave, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Above List Price
  • $315/SF
  • 3 Days On Market

  Current Estimated Value $292,839

  Last Listing Agent Zalysia Kaczmarczyk JAY ALAN REAL ESTATE

  222 Glenwood Ave, Osprey, FL 34229
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  /48

  Est $348,478

  Not Listed For Sale

  123 Revolution Way Unit 101, Osprey, FL 34229

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

  123 Revolution Way Unit 101, Osprey, FL 34229

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Tim Weller EXIT KING REALTY
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  /36

  $299,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  4226 Frontier Ln Unit 103, Osprey, FL 34229

  Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage

  Kate Kwiecinski COLDWELL BANKER REALTY

  4226 Frontier Ln Unit 103, Osprey, FL 34229
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  $2,035,000

  Sold Jun 18, 2026

  600 Eagle Watch Ln, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,681 Sq Ft
  • Built 1992

  Last Sold Summary

  • 7% Below List Price
  • $553/SF
  • 197 Days On Market

  Current Estimated Value $1,987,033

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  600 Eagle Watch Ln, Osprey, FL 34229
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  /2

  Est $356,050

  Not Listed For Sale

  4239 Expedition Way, Osprey, FL 34229

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

  4239 Expedition Way, Osprey, FL 34229

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP
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  $540,000

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  1140 Beachcomber Ct Unit 11, Osprey, FL 34229

  Virtually Staged. Welcome to Blackburn Point Marina Village, an intimate gated waterfront community of just 19 residences near Sarasota and Casey Key. This beautifully upgraded townhome delivers a relaxed coastal lifestyle with low-maintenance living—without the waterfront price tag. A bright, open floor plan features 9-foot ceilings, plantation shutters, ceiling fans, and new luxury vinyl

  Ralph Harvey LISTWITHFREEDOM.COM

  1140 Beachcomber Ct Unit 11, Osprey, FL 34229
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  /2

  $170,000

  Sold Mar 10, 2026

  238 Woodland Dr, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $197/SF
  • 126 Days On Market

  Current Estimated Value $167,780

  Last Listing Agent Kellie MacDonell COLDWELL BANKER REALTY

  238 Woodland Dr, Osprey, FL 34229
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  /2

  Est $827,415

  Not Listed For Sale

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $420,000

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,478 Sq Ft

  212 Washington Ave, Osprey, FL 34229

  Virtually Staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey—perfectly situated on a premium corner lot with NO HOA and NO CDD fees!This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed forboth everyday comfort and effortless entertaining. The spacious living area features slidingglass doors that lead

  Jeff Jones MARK SPAIN REAL ESTATE

  212 Washington Ave, Osprey, FL 34229
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  /2

  $430,000

  Sold May 19, 2026

  328 E Bay St, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1986

  Last Sold Summary

  • $486/SF
  • 2 Days On Market

  Current Estimated Value $420,102

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

  328 E Bay St, Osprey, FL 34229
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  Not Listed For Sale

  36 Siesta Cir W, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft
  • Built 1971

  36 Siesta Cir W, Osprey, FL 34229

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Tammie Pickard KW COASTAL LIVING III
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  /60

  $985,000

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

  409 N Point Rd Unit 803, Osprey, FL 34229

  ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 803, Osprey, FL 34229
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  $800,000

  Sold Mar 17, 2026

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $381/SF
  • 110 Days On Market

  Current Estimated Value $772,754

  Last Listing Agent Bart Tracy LASBURY-TRACY REALTY INC.

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229
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  Est $29,024

  Not Listed For Sale

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Moe Mossa SAVVY AVENUE, LLC
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  /2

  $1,800,000

  Pending

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

  222 Saint James Park, Osprey, FL 34229

  Beautifully maintained Arthur Rutenberg 3 bedroom, 3.5 bath home located on a quiet cul-de-sac. This architecturally inspired residence features crown molding, marble, tile and hardwood flooring, coffered ceilings, granite countertops, and a travertine pool deck. The first floor master suite includes a sitting area and private access to the lanai and pool. The outdoor living area offers an

  Steve Abbe COLDWELL BANKER REALTY

  222 Saint James Park, Osprey, FL 34229
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  $158,000

  Sold May 05, 2026

  166 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Below List Price
  • $165/SF
  • 17 Days On Market

  Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

  166 Edgewood Dr, Osprey, FL 34229
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  Est $785,416

  Not Listed For Sale

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $529,900

  • 2 Beds
  • 2 Baths
  • 1,704 Sq Ft

  432 S Shore Dr, Osprey, FL 34229

  Welcome to 432 S Shore Drive, where a complete interior renovation and an exceptional outdoor setting create the Florida lifestyle buyers are searching for. This beautifully updated 2-bedroom, 2-bath pool home offers 1,704 square feet with a freshly painted exterior and a 2023 roof for added peace of mind. Step inside to a bright, cohesive interior featuring updated living spaces, kitchen and

  Nicole Weiss KW COASTAL LIVING III

  432 S Shore Dr, Osprey, FL 34229
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  $169,000

  Sold Jan 09, 2026

  218 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $151/SF
  • 44 Days On Market

  Last Listing Agent Carlos Saramago EXIT KING REALTY

  218 Palm Air Dr, Osprey, FL 34229
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  Est $794,240

  Not Listed For Sale

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /95

  $695,000

  $205K PRICE DROP Pending

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

  401 N Point Rd Unit 304, Osprey, FL 34229

  Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 304, Osprey, FL 34229
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  $990,000

  Sold Feb 10, 2026

  820 Placid Lake Dr, Osprey, FL 34229

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft
  • Built 2002

  Last Sold Summary

  • 29% Below List Price
  • $251/SF
  • 309 Days On Market

  Current Estimated Value $989,607

  Last Listing Agent Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
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  /79

  Est $626,899

  Not Listed For Sale

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2017

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  Last Sold Summary

  • 236 Days On Market

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY
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  /97

  $2,650,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 5,287 Sq Ft

  449 Webbs Cove, Osprey, FL 34229

  A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views.Offering

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  449 Webbs Cove, Osprey, FL 34229
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  /2

  $479,000

  Sold Sep 10, 2025

  26 Bay Acres Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft
  • Built 1971

  Last Sold Summary

  • $252/SF
  • 6 Days On Market

  Current Estimated Value $513,537

  Last Listing Agent Erica Giesler COMPASS FLORIDA LLC

  26 Bay Acres Ave, Osprey, FL 34229
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  Not Listed For Sale

  570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

  • Studio

  570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

  Last Sold Summary

  • 135 Days On Market

  Last Listing Agent Bob Stahlschmidt II BRIGHT REALTY
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  $825,000

  • Land
  • 10,454 Sq Ft
  • $3,437,500 per Acre

  3820 Parrot Bay Ct, Osprey, FL 34229

  Build your dream home in one of Osprey's most exclusive waterfront communities. Nestled on a premium cul-de-sac homesite in the private enclave of Parrot Bay, this exceptional property is one of only nine custom home sites, offering a rare opportunity to create a truly personalized coastal retreat with the builder of your choice. Included in the sale is a private boat dock that accommodates up to

  Mitch Helmuth HARRY ROBBINS ASSOC INC

  3820 Parrot Bay Ct, Osprey, FL 34229
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  $492,500

  Sold May 13, 2026

  437 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,947 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $253/SF
  • 15 Days On Market

  Current Estimated Value $497,818

  Last Listing Agent Dawn Barnett EXIT KING REALTY

  437 S Shore Dr, Osprey, FL 34229
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  /25

  Est $204,555

  Not Listed For Sale

  13 Bay Ave, Osprey, FL 34229

  13 Bay Ave, Osprey, FL 34229

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE
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  $649,000

  $80K PRICE DROP

  • 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

  $625,000

  Sold Nov 07, 2025

  594 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,298 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $272/SF
  • 51 Days On Market

  Current Estimated Value $624,262

  Last Listing Agent Dan Henson DALTON WADE INC

  594 Pine Ranch Rd E, Osprey, FL 34229
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  /2

  Est $844,484

  Not Listed For Sale

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $749,900

  • 3 Beds
  • 3 Baths
  • 2,621 Sq Ft

  1117 Millpond Ct, Osprey, FL 34229

  One or more photo(s) has been virtually staged, AI generated or rendered. ONE OF A KIND HOME LAKE FRONT HOME! Welcome to a home where timeless elegance meets the natural beauty of Florida's Gulf Coast. Nestled within the highly sought-after Rivendell community in Osprey, this beautifully refreshed residence offers an exceptional combination of comfort, privacy, and lifestyle. Perfectly positioned

  Brehna Hovland Hovland Realty, LLC

  1117 Millpond Ct, Osprey, FL 34229
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  /2

  $160,000

  Sold Mar 03, 2026

  216 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Below List Price
  • $152/SF
  • 71 Days On Market

  Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

  216 Palm Air Dr, Osprey, FL 34229
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  /2

  Est $1,006,980

  Not Listed For Sale

  84 Bishops Court Rd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,573 Sq Ft
  • Built 1989

  84 Bishops Court Rd, Osprey, FL 34229

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY
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  $3,100,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,122 Sq Ft

  321 Lookout Point Dr, Osprey, FL 34229

  Experience the epitome of waterfront living in the sought-after Southbay neighborhood. This 3 bedroom, 3.5 bath home is ideally positioned on a peninsula, providing sweeping panoramic water views. The moment you step inside, you will be mesmerized by the breathtaking bay views through a plethora of windows and sliding glass doors that flood the space with natural light. The open, main level is

  Steve Abbe COLDWELL BANKER REALTY

  321 Lookout Point Dr, Osprey, FL 34229
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  /2

  $745,000

  Sold Jan 16, 2026

  640 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,534 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $294/SF
  • 23 Days On Market

  Current Estimated Value $741,391

  Last Listing Agent Jay Mitchell COLDWELL BANKER REALTY

  640 Crane Prairie Way, Osprey, FL 34229
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  /2

  Est $504,723

  Not Listed For Sale

  619 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,222 Sq Ft
  • Built 1994

  619 Pine Ranch Rd E, Osprey, FL 34229

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent John Michailidis KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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  $700,000

  • 3 Beds
  • 3 Baths
  • 2,837 Sq Ft

  264 Woods Point Rd, Osprey, FL 34229

  Ideally located to enjoy all that Sarasota, Venice and Casey Key has to offer, this superbly remodeled maintenance-free home offers more than 2,800 square feet of thoughtfully redesigned living space and lives comfortably like a private, stand-alone residence. Nestled within an intimate enclave of just 44 homes, this property offers the ultimate lock-and-leave lifestyle, with the HOA taking care

  Mina Johnson MICHAEL SAUNDERS & COMPANY

  264 Woods Point Rd, Osprey, FL 34229
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  /2

  $533,000

  Sold Aug 04, 2026

  4424 Conchfish Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft
  • Built 2017

  Last Sold Summary

  • 13% Below List Price
  • $225/SF
  • 60 Days On Market

  Current Estimated Value $587,511

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  4424 Conchfish Ln, Osprey, FL 34229

Showing Results 161 - 200, Page 5 of 18