Homes in ZIP Code 34229

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  /2

  $730,000

  Sold Oct 24, 2025

  1728 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $315/SF
  • 44 Days On Market

  Current Estimated Value $750,316

  Last Listing Agent Melanie Albaric MICHAEL SAUNDERS & COMPANY

  1728 S Creek Dr, Osprey, FL 34229
• 

  

  

  /86

  Est $1,585,977

  Not Listed For Sale

  435 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,087 Sq Ft
  • Built 1998

  435 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 268 Days On Market

  Last Listing Agent Candy Swick CANDY SWICK & COMPANY
• 

  

  

  /55

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  103 Bishops Court Rd, Osprey, FL 34229

  **LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added

  Mark Lyda GENEROUS PROPERTY

  103 Bishops Court Rd, Osprey, FL 34229
• 

  

  /2

  $950,000

  Sold Jun 11, 2026

  5313 Trails Bend Ct, Sarasota, FL 34238

  • 3 Beds
  • 3 Baths
  • 2,268 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $419/SF
  • 26 Days On Market

  Current Estimated Value $970,852

  Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

  5313 Trails Bend Ct, Sarasota, FL 34238
• 

  

  /2

  Est $3,576,561

  Not Listed For Sale

  2509 Bayshore Rd, Nokomis, FL 34275

  • 5 Beds
  • 4.5 Baths
  • 4,712 Sq Ft
  • Built 2016

  2509 Bayshore Rd, Nokomis, FL 34275

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Andrea Blackwell KELLER WILLIAMS ISLAND LIFE REAL ESTATE
• 

  

  /75

  $760,000

  $40K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 2,474 Sq Ft

  1495 Landview Ln, Osprey, FL 34229

  Under contract-accepting backup offers. Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room

  Pat Williams PAT WILLIAMS REALTY, LLC

  1495 Landview Ln, Osprey, FL 34229
• 

  /2

  $170,000

  Sold Apr 01, 2026

  911 Tranquility Cir, Osprey, FL 34229

  • Land
  • 18,295 Sq Ft
  • $404,762 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Mike Winger TIDELINE REAL ESTATE BROKERS

  911 Tranquility Cir, Osprey, FL 34229
• 

  /2

  Est $955,772

  Not Listed For Sale

  1321 Southbay Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,968 Sq Ft
  • Built 1978

  1321 Southbay Dr, Osprey, FL 34229

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  /2

  $1,590,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,565 Sq Ft

  402 E MacEwen Dr, Osprey, FL 34229

  Located behind the gates of The Oaks Clubside and within close proximity to the clubhouse, this 3-bedroom plus office, 3.5-bath residence offers over 3,500 square feet of refined, comfortable living. Positioned on the 4th hole of the Eagle Course, the home features expansive golf views enjoyed from the screened lanai with pool and spa. The interior includes an elegant formal living room with

  Steve Abbe COLDWELL BANKER REALTY

  402 E MacEwen Dr, Osprey, FL 34229
• 

  /2

  $545,000

  Sold Jul 10, 2026

  104 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft
  • Built 2002

  Last Sold Summary

  • 16% Below List Price
  • $213/SF
  • 180 Days On Market

  Current Estimated Value $573,832

  Last Listing Agent Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

  104 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  Est $1,131,332

  Not Listed For Sale

  327 Sea Anchor Dr, Osprey, FL 34229

  • 2 Beds
  • 3 Baths
  • 2,521 Sq Ft
  • Built 1981

  327 Sea Anchor Dr, Osprey, FL 34229

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN
• 

  

  /43

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft

  2046 Cordes St, Osprey, FL 34229

  Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The

  Susan Mondello MICHAEL SAUNDERS & COMPANY

  2046 Cordes St, Osprey, FL 34229
• 

  /2

  $249,000

  Sold Aug 21, 2026

  754 Pine Run Dr Unit 754, Osprey, FL 34229

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

  Last Sold Summary

  • 7% Below List Price
  • $181/SF
  • 82 Days On Market

  Current Estimated Value $261,254

  Last Listing Agent Sasha Volosevych CALL IT CLOSED INTL REALTY

  754 Pine Run Dr Unit 754, Osprey, FL 34229
• 

  /2

  Est $538,379

  Not Listed For Sale

  629 Oak Bay Dr, Osprey, FL 34229

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

  629 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 250 Days On Market

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III
• 

  /2

  $1,480,000

  Pending

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

  401 N Point Rd Unit 701, Osprey, FL 34229

  Enjoy luxury living at its finest in this beautiful 3 bedroom, 3 bath residence with a PRIVATE ONE CAR GARAGE plus one parking space under the building. Located in Meridian, behind the secure gates of The Oaks Preserve, you truly feel like you have found the perfect tropical hide-a-away. Situated on the 7th floor, above the treetops, you are treated to an amazing vista taking in Little Sarasota

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 701, Osprey, FL 34229
• 

  /2

  $534,000

  Sold Dec 11, 2025

  757 Placid Lake Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $289/SF
  • 3 Days On Market

  Current Estimated Value $535,925

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  757 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  Est $1,940,144

  Not Listed For Sale

  451 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,368 Sq Ft
  • Built 1998

  451 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /39

  $719,000

  New Construction $30K PRICE DROP

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

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229

  Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229
• 

  /2

  $511,500

  Sold Jun 17, 2026

  562 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,414 Sq Ft
  • Built 1995

  Last Sold Summary

  • 9% Below List Price
  • $212/SF
  • 22 Days On Market

  Current Estimated Value $517,650

  Last Listing Agent Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

  562 Oak Bay Dr, Osprey, FL 34229
• 

  

  /70

  Est $1,627,386

  Not Listed For Sale

  337 Passage Way, Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 4,551 Sq Ft
  • Built 1984

  337 Passage Way, Osprey, FL 34229

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Benjamin Moricz KELLER WILLIAMS ON THE WATER S
• 

  

  /38

  $165,900

  Open Sat 1AM - 3PM $6K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  701 Pine Run Dr, Osprey, FL 34229

  Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a

  Pat Williams PAT WILLIAMS REALTY, LLC

  701 Pine Run Dr, Osprey, FL 34229
• 

  /2

  $1,600,000

  Sold May 14, 2026

  228 Saint James Park, Osprey, FL 34229

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

  Last Sold Summary

  • 6% Below List Price
  • $660/SF
  • 33 Days On Market

  Current Estimated Value $1,563,379

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  228 Saint James Park, Osprey, FL 34229
• 

  

  /24

  Est $807,695

  Not Listed For Sale

  130 N Creek Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1997

  130 N Creek Ln, Osprey, FL 34229

  Last Sold Summary

  • 140 Days On Market

  Last Listing Agent Mariana Georgieva HORIZON REALTY INTERNATIONAL
• 

  

  /38

  $550,000

  $45K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,731 Sq Ft

  547 Meadow Sweet Cir, Osprey, FL 34229

  Discover one of Osprey's best-kept secrets-The Cottages of Rivendell. Tucked away within The Woodlands of Rivendell, offers a lifestyle that is becoming increasingly rare. Towering oak trees create a tranquil, park-like setting, while charming front porches, white picket fences, and classic Old Florida architecture give the neighborhood its unmistakable character. This beautifully maintained 3/2

  Zita Bowers MICHAEL SAUNDERS & COMPANY

  547 Meadow Sweet Cir, Osprey, FL 34229
• 

  /2

  $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

  Current Estimated Value $687,016

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  866 Oak Briar Ln, Osprey, FL 34229
• 

  /2

  Est $506,443

  Not Listed For Sale

  544 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 2001

  544 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Zita Bowers MICHAEL SAUNDERS & COMPANY
• 

  

  /4

  $99,500

  570 Blackburn Point Rd Unit 36, Osprey, FL 34229

  This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 9' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks,

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 36, Osprey, FL 34229
• 

  /2

  $845,000

  Sold Jul 01, 2026

  664 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $294/SF
  • 93 Days On Market

  Current Estimated Value $848,478

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  664 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  Est $1,922,213

  Not Listed For Sale

  703 N MacEwen Dr, Osprey, FL 34229

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

  703 N MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /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
• 

  /2

  $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

  Current Estimated Value $637,186

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  178 Willow Bend Way, Osprey, FL 34229
• 

  

  /60

  Est $500,782

  Not Listed For Sale

  455 N Shore Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft
  • Built 1966

  455 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Bo Fuller FULLER GROUP
• 

  

  /70

  $675,000

  $64K PRICE DROP Under Contract

  • 2 Beds
  • 2.5 Baths
  • 2,216 Sq Ft

  347 Bayshore Dr, Osprey, FL 34229

  Under contract-accepting backup offers. This custom built home is located in the Osprey subdivision Bay Acres, west of the trail, in an established neighborhood along Little Sarasota Bay between Sarasota and Venice. This location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Key Beaches, and all amenities of both cities. This home

  Sharon Sprow COLDWELL BANKER REALTY

  347 Bayshore Dr, Osprey, FL 34229
• 

  /2

  $335,000

  Sold May 14, 2026

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 2000

  Last Sold Summary

  • 16% Below List Price
  • $227/SF
  • 69 Days On Market

  Current Estimated Value $342,526

  Last Listing Agent Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229
• 

  /2

  Est $705,876

  Not Listed For Sale

  668 Clear Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,388 Sq Ft
  • Built 2002

  668 Clear Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Cheryl Guentner RE/MAX PALM
• 

  

  /19

  $285,000

  • 1 Bed
  • 1 Bath
  • 595 Sq Ft

  51 MacEwen Dr Unit 14, Osprey, FL 34229

  This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area

  Steve Abbe COLDWELL BANKER REALTY

  51 MacEwen Dr Unit 14, Osprey, FL 34229
• 

  /2

  $1,285,000

  Sold Apr 08, 2026

  137 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,303 Sq Ft
  • Built 1996

  Last Sold Summary

  • 10% Below List Price
  • $389/SF
  • 118 Days On Market

  Current Estimated Value $1,496,703

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  137 Osprey Point Dr, Osprey, FL 34229
• 

  

  /72

  Est $596,603

  Not Listed For Sale

  593 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 2005

  593 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 194 Days On Market

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.
• 

  

  /62

  $599,000

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft

  5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229

  Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence

  Stuart Lawrence MICHAEL SAUNDERS & COMPANY

  5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229
• 

  /2

  $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 $720,364

  Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229

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