Osprey, FL Homes

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  $685,000 Sold Jan 30, 2026

  866 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,434 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $281/SF
  • 182 Days On Market

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  866 Oak Briar Ln, Osprey, FL 34229
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  Est $410,090 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229
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  $5,495,000

  • 4 Beds
  • 5.5 Baths
  • 5,397 Sq Ft

  144 N Casey Key Rd, Osprey, FL 34229

  Located on the exclusive stretch of North Casey Key, this private waterfront estate offers a rare blend of resort-style living, protected boating water, and direct Gulf beach access in one of Sarasota County’s most coveted coastal enclaves. Set on over half an acre along Little Sarasota Bay, this durably constructed residence, engineered for strength and storm protection, delivers a private,

  Lisa Napolitano DOUGLAS ELLIMAN

  144 N Casey Key Rd, Osprey, FL 34229
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  $635,000 Sold Jan 29, 2026

  178 Willow Bend Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $336/SF
  • 8 Days On Market

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  178 Willow Bend Way, Osprey, FL 34229
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  /40

  Est $1,554,983 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  1787 S Creek Dr, Osprey, FL 34229

  1787 S Creek Dr, Osprey, FL 34229
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  /15

  $41,000

  570 Blackburn Point Rd Unit 42, Osprey, FL 34229

  Welcome to OSPREY HARBOR VILLAGE. This boat rackominium was built as a category 3 hurricane-rated building. Store your boat out of the sun and protected from the harsh Florida weather. This 3rd-level rack measures 28'L x 12'W x 8.5'H and can accommodate a boat with dimensions of 28'L x 11'W x ~6.5'H (measure height from the keel to the highest fixed point on the boat). This rackominium features

  Joe Cleary RE/MAX ALLIANCE GROUP

  570 Blackburn Point Rd Unit 42, Osprey, FL 34229
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  $395,000 Sold Jun 16, 2025

  109 Burney Rd, Osprey, FL 34229

  • 2 Beds
  • 1.5 Baths
  • 714 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $553/SF
  • 50 Days On Market

  Current Estimated Value $382,819

  Last Listing Agent Lori Madden MANGROVE REALTY ASSOCIATES

  109 Burney Rd, Osprey, FL 34229
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  /68

  Est $967,837 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,028 Sq Ft

  501 Velasquez Dr, Osprey, FL 34229

  501 Velasquez Dr, Osprey, FL 34229
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  $429,500

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  352 Glenwood Ave, Osprey, FL 34229

  Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the

  Kano Keller WHITE SANDS REALTY GROUP FL

  352 Glenwood Ave, Osprey, FL 34229
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  $700,000 Sold Oct 08, 2025

  826 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,589 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $270/SF
  • 160 Days On Market

  Current Estimated Value $705,053

  Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
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  /40

  Est $516,074 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  510 Meadow Sweet Cir, Osprey, FL 34229

  510 Meadow Sweet Cir, Osprey, FL 34229
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  $185,000

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft

  316 Tropic Dr, Osprey, FL 34229

  Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath mobile home offers generous space, some updates, and a vibrant 55+ lifestyle in one of the area’s most convenient locations. Step inside to find a formal living room accented with built-in features, plus a dedicated dining room perfect for entertaining or everyday meals. The home boasts spacious room sizes

  Karen Geiger COLDWELL BANKER SARASOTA CENT.

  316 Tropic Dr, Osprey, FL 34229
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  $245,000 Sold Apr 21, 2025

  225 Woodland Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 18% Below List Price
  • $186/SF
  • 103 Days On Market

  Current Estimated Value $240,405

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  225 Woodland Dr, Osprey, FL 34229
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  Est $2,381,384 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 5,521 Sq Ft

  134 Marys Chapel Ct, Osprey, FL 34229

  134 Marys Chapel Ct, Osprey, FL 34229
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  $399,000

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

  124 Revolution Way, Osprey, FL 34229

  The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this

  James Briley COLDWELL BANKER REALTY

  124 Revolution Way, Osprey, FL 34229
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  $832,750 Sold Apr 10, 2025

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2025

  Last Sold Summary

  • $430/SF
  • 27 Days On Market

  Current Estimated Value $821,257

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229
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  Est $576,515 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  506 Oak Bay Dr, Osprey, FL 34229

  506 Oak Bay Dr, Osprey, FL 34229
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  $2,795,000

  • 5 Beds
  • 5.5 Baths
  • 4,261 Sq Ft

  479 S Creek Dr, Osprey, FL 34229

  Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant

  Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  479 S Creek Dr, Osprey, FL 34229
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  $260,000 Sold Jan 23, 2026

  761 Pine Run Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  Last Sold Summary

  • 7% Below List Price
  • $189/SF
  • 31 Days On Market

  Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

  761 Pine Run Dr, Osprey, FL 34229
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  Est $1,332,779 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,521 Sq Ft

  1236 Yacht Harbor Dr, Osprey, FL 34229

  1236 Yacht Harbor Dr, Osprey, FL 34229
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  $645,000

  • 4 Beds
  • 2 Baths
  • 2,217 Sq Ft

  472 Park Trace Blvd, Osprey, FL 34229

  Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for

  Damon Zuchelli SUNDANCE REAL ESTATE SERVICES

  472 Park Trace Blvd, Osprey, FL 34229
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  $2,327,000 Sold Jun 18, 2025

  654 Trenton Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,582 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $650/SF
  • 86 Days On Market

  Current Estimated Value $2,242,224

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  654 Trenton Way, Osprey, FL 34229
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  Est $2,747,905 Not Listed For Sale

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

  349 Yacht Harbor Dr, Osprey, FL 34229

  349 Yacht Harbor Dr, Osprey, FL 34229
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  $699,000

  • Land
  • 0.55 Acre
  • $1,270,909 per Acre

  410 Blue Garden Ln, Osprey, FL 34229

  Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a

  Mark Grigoli ELITE PROPERTIES LLC

  410 Blue Garden Ln, Osprey, FL 34229
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  $2,925,000 Sold Sep 23, 2025

  550 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $373/SF
  • 63 Days On Market

  Current Estimated Value $2,862,689

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
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  Est $374,552 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft

  1821 Highland Rd, Osprey, FL 34229

  1821 Highland Rd, Osprey, FL 34229
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  /40

  $689,000

  • 4 Beds
  • 3 Baths
  • 2,661 Sq Ft

  162 Willow Bend Way, Osprey, FL 34229

  Impeccable 4 BR home plus office, located in the highly sought after Park Trace Estates, with HOA fees under 55$ a month. Proudly owned by the original owner, and built by Vison Homes, this property showcases meticulous care and quality upgrades, all offered at an unbeatable price. Freshly painted and filled with natural light, the home features PGT impact rated doors and windows throughout, in

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  162 Willow Bend Way, Osprey, FL 34229
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  $280,000 Sold Feb 04, 2026

  232 Explorer Dr Unit 15, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2019

  Last Sold Summary

  • 15% Below List Price
  • $247/SF
  • 220 Days On Market

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
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  Est $1,611,610 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,087 Sq Ft

  435 E MacEwen Dr, Osprey, FL 34229

  435 E MacEwen Dr, Osprey, FL 34229
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  $250,000 Pending

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  216 Glenwood Ave, Osprey, FL 34229

  Under contract-accepting backup offers. Nestled in the quietly coveted, underrated gem of Osprey, FL, this charming property offers the perfect blend of coastal living, privacy, and timeless Florida character. Situated on a maintained, fenced lot, this home is framed by mature greenery and ample outdoor space—ideal for gardening, play, pets, or serene evenings under the palms.The quaint,

  Kristen Wheat COMPASS FLORIDA LLC

  216 Glenwood Ave, Osprey, FL 34229
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  $2,100,000 Sold Mar 26, 2025

  703 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,641 Sq Ft
  • Built 2007

  Last Sold Summary

  • 16% Below List Price
  • $452/SF
  • 95 Days On Market

  Current Estimated Value $2,037,537

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  703 N MacEwen Dr, Osprey, FL 34229
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  Est $1,053,137 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,968 Sq Ft

  1321 Southbay Dr, Osprey, FL 34229

  1321 Southbay Dr, Osprey, FL 34229
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  $800,000

  • Land
  • 0.55 Acre
  • $1,454,545 per Acre

  0 Hidden Bay Dr, Osprey, FL 34229

  The Development Site is a lakefront parcel overlooking the community’s internal lake and clubhouse. The concept plan shows 24 2-3 bedroom units in 4 stories over parking, but the parcel has unprecedented zoning and entitlements for up to 42 units. All utilities and the roads are to the development site. The utilities, roads, and parking areas, the gated entrance and the resort-style amenities are

  Bob Morris SVN COMMERCIAL ADVISORY GROUP

  0 Hidden Bay Dr, Osprey, FL 34229
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  $1,500,000 Sold Jul 08, 2025

  269 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft
  • Built 1997

  Last Sold Summary

  • 16% Below List Price
  • $420/SF
  • 76 Days On Market

  Current Estimated Value $1,469,603

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
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  Est $661,702 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,144 Sq Ft

  521 Bayshore Dr, Osprey, FL 34229

  521 Bayshore Dr, Osprey, FL 34229
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  $549,900 Pending

  • 3 Beds
  • 3 Baths
  • 2,384 Sq Ft

  315 Bayshore Dr, Osprey, FL 34229

  Under contract-accepting backup offers. NEW PRICE • REAL OPPORTUNITY • SELLER READY.This is your chance to secure a West of the Trail pool home in the coveted Bay Acres community at an exceptional value.Welcome to Bay Acres—a quiet coastal enclave where classic Florida charm meets everyday livability. Positioned on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath

  Norma Mladineo COLDWELL BANKER REALTY

  315 Bayshore Dr, Osprey, FL 34229
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  $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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  Est $1,890,638 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,368 Sq Ft

  451 E MacEwen Dr, Osprey, FL 34229

  451 E MacEwen Dr, Osprey, FL 34229
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  $530,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,559 Sq Ft

  566 Oak Bay Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Seller is motivated! Welcome to Bay Oaks Estates—your quiet Florida retreat! This 3-bed, 2-bath + den home offers a true indoor-outdoor lifestyle with a private pool featuring a beautiful ocean-inspired mosaic. With no houses in front and none behind, you’ll appreciate the peace and privacy. Enjoy cozy winter nights with your wood-burning fireplace, and

  Greg Walters SARABAY REAL ESTATE INC

  566 Oak Bay Dr, Osprey, FL 34229
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  $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

Showing Results 241 - 280, Page 7 of 18