Homes in ZIP Code 34229

• 

  

  /2

  Est $767,237

  Not Listed For Sale

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2006

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE
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  /50

  $2,199,999

  • 4 Beds
  • 3.5 Baths
  • 4,578 Sq Ft

  154 Lookout Point Dr, Osprey, FL 34229

  Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle.The heart of the home is a completely renovated kitchen featuring quartz

  Stephen Hachey FLAT FEE MLS REALTY

  154 Lookout Point Dr, Osprey, FL 34229
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  /2

  $585,000

  Sold Mar 27, 2026

  584 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,151 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $272/SF
  • 18 Days On Market

  Current Estimated Value $574,565

  Last Listing Agent Jack Keller JACK KELLER INC

  584 Meadow Sweet Cir, Osprey, FL 34229
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  /100

  Est $1,103,833

  Not Listed For Sale

  328 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,215 Sq Ft
  • Built 1991

  328 Pine Ranch Trail, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sally Green HOMESMART
• 

  

  

  /90

  $560,000

  $65K PRICE DROP

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

  409 N Point Rd Unit 401, Osprey, FL 34229

  Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown

  Steve Abbe COLDWELL BANKER REALTY

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

  /2

  $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

  Current Estimated Value $255,808

  Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

  761 Pine Run Dr, Osprey, FL 34229
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  /2

  Est $963,231

  Not Listed For Sale

  678 Clear Creek Dr, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 3,912 Sq Ft
  • Built 2002

  678 Clear Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Dena Dominiczak EXIT KING REALTY
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  /2

  $145,000

  Under Contract

  570 Blackburn Point Rd Unit 22, Osprey, FL 34229

  Under contract-accepting backup offers. The slip can hold a boat with the maximum dimensions of 35.5L x 10'W x 10.5'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 22, Osprey, FL 34229
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  /2

  $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 $2,943,791

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
• 

  

  /65

  Est $1,896,784

  Not Listed For Sale

  482 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft
  • Built 2001

  482 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 212 Days On Market

  Last Listing Agent David Butler Jr RE/MAX ALLIANCE GROUP
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  /50

  $1,690,000

  Open Sun 1PM - 3PM $160K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,411 Sq Ft

  206 Four Knot Ln, Osprey, FL 34229

  Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club/Marina

  Leighton Allenby Realty One Group MVP

  206 Four Knot Ln, Osprey, FL 34229
• 

  /2

  $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

  Current Estimated Value $276,987

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
• 

  /2

  Est $395,028

  Not Listed For Sale

  308 Kensey Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 1972

  308 Kensey Ln, Osprey, FL 34229

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Tracey Punzone UKEEPCOMMISSION REAL ESTATE
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  /4

  $39,500

  $3K PRICE DROP

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas 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 33L x 9.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
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  /2

  $335,000

  Sold Mar 27, 2026

  172 Explorer Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $329,418

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  172 Explorer Dr, Osprey, FL 34229
• 

  

  /30

  Est $122,922

  Not Listed For Sale

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft
  • Built 1973

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE
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  /2

  $1,250,000

  Pending

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

  401 N Point Rd Unit 903, Osprey, FL 34229

  This 3 bedroom, 3 bath 9th floor penthouse with PRIVATE 2 CAR GARAGE in Meridian at The Oaks Preserve offers the perfect living space for those who seek luxury and comfort in a country club community. Meticulously maintained, this residence’s open, spacious floor plan features a beautiful kitchen with stainless steel appliances. The master bedroom has ceiling-to-floor windows to enjoy views of

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 903, Osprey, FL 34229
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  /2

  $310,000

  Sold Aug 26, 2026

  2251 Jessie Harbor Dr Unit 2101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2006

  Last Sold Summary

  • 14% Below List Price
  • $221/SF
  • 17 Days On Market

  Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

  2251 Jessie Harbor Dr Unit 2101, Osprey, FL 34229
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  /50

  Est $535,739

  Not Listed For Sale

  529 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,789 Sq Ft
  • Built 2002

  529 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /61

  $320,000

  $25K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft

  89 Navigation Cir, Osprey, FL 34229

  Under contract-accepting backup offers. Virtually Staged. DISCOVER A LIMITED-TIME OPPORTUNITY! ?A SPECIAL OPPORTUNITY IS AVAILABLE FOR BUYERS WITH AN ACCEPTED PURCHASE CONTRACT ON OR BEFORE AUGUST 30, 2026. CONTACT THE LISTING AGENT FOR DETAILS.Experience the perfect blend of comfort, convenience, and Florida lifestyle in this beautifully maintained first-floor residence located in the

  Jozefina Polimirova KW COASTAL LIVING II

  89 Navigation Cir, Osprey, FL 34229
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  /2

  $995,000

  Sold Mar 05, 2026

  105 Turquoise Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,606 Sq Ft
  • Built 2001

  Last Sold Summary

  • $382/SF
  • 162 Days On Market

  Current Estimated Value $977,052

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  105 Turquoise Ln, Osprey, FL 34229
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  /2

  Est $691,621

  Not Listed For Sale

  521 Luminary Blvd, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,504 Sq Ft
  • Built 2004

  521 Luminary Blvd, Osprey, FL 34229

  Last Sold Summary

  • 69 Days On Market

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

  

  /96

  $2,850,000

  $400K PRICE DROP Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,665 Sq Ft

  14401 Masthead Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the

  Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  14401 Masthead Dr, Osprey, FL 34229
• 

  /2

  $285,900

  Sold Aug 17, 2026

  120 Woodland Place Unit 120, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $216/SF
  • 5 Days On Market

  Current Estimated Value $255,363

  Last Listing Agent Kim Kruysman EXP REALTY LLC

  120 Woodland Place Unit 120, Osprey, FL 34229
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  /2

  Est $2,570,825

  Not Listed For Sale

  388 Bunker Hill, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 4,937 Sq Ft
  • Built 1999

  388 Bunker Hill, Osprey, FL 34229

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /54

  $850,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,468 Sq Ft

  144 Park Trace Blvd, Osprey, FL 34229

  Beautiful 4-bedroom, 3-bath pool home with 3-car garage. This home offers the space, upgrades and features you've been looking for. Park Trace Estates is a well-established residential community in Osprey Florida. Perfectly positioned between Sarasota and Venice providing easy access to nearby beaches, restaurants, Tiki bars, biking trails, parks, great schools and so much more! This four-bedroom

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  144 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  $1,700,000

  Sold Jul 17, 2026

  401 Walls Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,387 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $388/SF
  • 138 Days On Market

  Current Estimated Value $1,718,788

  Last Listing Agent Andrea Stultz ENGEL + VOELKERS SARASOTA

  401 Walls Way, Osprey, FL 34229
• 

  /2

  Est $2,289,617

  Not Listed For Sale

  425 E MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 5,153 Sq Ft
  • Built 1999

  425 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Robert Anderson Jr RE/MAX ALLIANCE GROUP
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  /66

  $6,475,000

  $625K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,096 Sq Ft

  121 N Casey Key Rd, Osprey, FL 34229

  Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting.Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $540,000

  Sold Aug 07, 2026

  523 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,399 Sq Ft
  • Built 1998

  Last Sold Summary

  • $225/SF
  • 20 Days On Market

  Current Estimated Value $536,993

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  523 Oak Bay Dr, Osprey, FL 34229
• 

  /2

  Est $769,772

  Not Listed For Sale

  424 Cezanne Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 2,945 Sq Ft
  • Built 1975

  424 Cezanne Dr, Osprey, FL 34229

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY
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  /62

  $1,100,000

  $100K PRICE DROP

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

  385 N Point Rd Unit 304, Osprey, FL 34229

  **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 304, Osprey, FL 34229
• 

  /2

  $750,000

  Sold Dec 30, 2025

  523 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $324/SF
  • 122 Days On Market

  Current Estimated Value $747,489

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
• 

  /2

  Est $422,333

  Not Listed For Sale

  441 N Shore Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft
  • Built 1970

  441 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Dawn Barnett EXIT KING REALTY
• 

  /2

  $2,750,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,323 Sq Ft

  447 E MacEwen Dr, Osprey, FL 34229

  Experience refined living in this extraordinary, elegant home. With 3 bedrooms and 4.5 baths it offers expansive lake and golf course views from its premier position along the Heron Course. Designed for both grand entertaining and everyday comfort, the home features generous living spaces, a bright open kitchen overlooking the family room with wood burning fireplace, and a luxurious primary suite

  Steve Abbe COLDWELL BANKER REALTY

  447 E MacEwen Dr, Osprey, FL 34229
• 

  /2

  $799,000

  Sold Mar 09, 2026

  529 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,617 Sq Ft
  • Built 2003

  Last Sold Summary

  • $305/SF
  • 2 Days On Market

  Current Estimated Value $799,326

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  529 Habitat Blvd, Osprey, FL 34229
• 

  /2

  Est $1,032,327

  Not Listed For Sale

  434 N Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,932 Sq Ft
  • Built 1989

  434 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 254 Days On Market

  Last Listing Agent Victoria Stultz ENGEL + VOELKERS SARASOTA
• 

  

  /70

  $999,900

  $289K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  14021 Bellagio Way Unit 404, Osprey, FL 34229

  This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. Arrive in effortless luxury with an elevator that opens directly into this beautifully appointed condo, creating an exceptional sense of privacy and exclusivity. The residence features three

  Megan George PREMIER SOTHEBYS INTL REALTY

  14021 Bellagio Way Unit 404, Osprey, FL 34229
• 

  /2

  $550,000

  Sold Mar 23, 2026

  510 Latitude Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 125 Days On Market

  Current Estimated Value $562,358

  Last Listing Agent Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
• 

  

  /29

  Est $2,161,524

  Not Listed For Sale

  162 Puesta Del Sol, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 4,747 Sq Ft
  • Built 2003

  162 Puesta Del Sol, Osprey, FL 34229

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Drew Russell MICHAEL SAUNDERS & COMPANY

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