5,060

Homes in ZIP Code 34229

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  • /51

    $749,000

    $241K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    678 Faith Ave, Osprey, FL 34229

    Under contract-accepting backup offers. Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient location—just minutes from Pine View School, shopping, restaurants, and the Intracoastal Waterway—yet offering the privacy and space of a true country setting. This combination of acreage and accessibility makes the home

    Troy Sacco GENEROUS PROPERTY

    678 Faith Ave, Osprey, FL 34229
  • /15

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    2068 Preymore St, Osprey, FL 34229

    Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

    Kenia Rivas PREFERRED SHORE LLC

    2068 Preymore St, Osprey, FL 34229
  • /2

    $362,500

    Sold Apr 09, 2026

    124 Revolution Way, Osprey, FL 34229

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

    Last Sold Summary

    • 9% Below List Price
    • $230/SF
    • 47 Days On Market

    Current Estimated Value $355,874

    Last Listing Agent James Briley COLDWELL BANKER REALTY

    124 Revolution Way, Osprey, FL 34229
    • /2

      Est $1,355,795

      Not Listed For Sale

      5345 Trails Bend Ct, Sarasota, FL 34238

      • 3 Beds
      • 3 Baths
      • 3,071 Sq Ft
      • Built 2020
      5345 Trails Bend Ct, Sarasota, FL 34238

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

  • /71

    $699,000

    $36K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229

    Under contract-accepting backup offers. Experience effortless coastal living in this stunning third-floor waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing

    Suki Scollo COLDWELL BANKER REALTY

    5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229
  • /34

    $2,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft
    • Condo for Rent

    4219 Frontier Ln Unit 105, Osprey, FL 34229

    Welcome to this immaculate 2-bedroom, 2-bathroom condo with a private 1-car garage, offering beautiful pond views from every window and a peaceful, resort-style setting.Ideally located just minutes from some of Florida’s most beautiful Gulf Coast beaches:10 minutes to Nokomis Beach and Casey Key15 minutes to the world-famous Siesta Key BeachOutdoor enthusiasts will love

    Tim Weller EXIT KING REALTY

    4219 Frontier Ln Unit 105, Osprey, FL 34229
  • /2

    $2,100,000

    Sold May 14, 2026

    479 S Creek Dr, Osprey, FL 34229

    • 5 Beds
    • 5.5 Baths
    • 4,261 Sq Ft
    • Built 1995

    Last Sold Summary

    • 34% Below List Price
    • $493/SF
    • 135 Days On Market

    Current Estimated Value $2,102,307

    Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    479 S Creek Dr, Osprey, FL 34229
    • /2

      Est $272,265

      Not Listed For Sale

      153 Navigation Cir Unit 106, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,135 Sq Ft
      • Built 2014
      153 Navigation Cir Unit 106, Osprey, FL 34229

      Last Sold Summary

      • 150 Days On Market

      Last Listing Agent Peggy Olson PREMIER SOTHEBYS INTL REALTY

  • /13

    $525,000

    $74K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,861 Sq Ft

    4428 Conchfish Ln, Osprey, FL 34229

    Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

    Mariana Georgieva HORIZON REALTY INTERNATIONAL

    4428 Conchfish Ln, Osprey, FL 34229
  • /31

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,367 Sq Ft
    • House for Rent

    1355 Southbay Dr, Osprey, FL 34229

    Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the

    Sharon Lewis GOLF & BAY PROPERTIES LLC

    1355 Southbay Dr, Osprey, FL 34229
  • /2

    $635,000

    Sold Aug 31, 2026

    816 Shadow Bay Way, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft
    • Built 1998

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 24 Days On Market

    Current Estimated Value $651,603

    Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

    816 Shadow Bay Way, Osprey, FL 34229
    • /2

      Est $485,909

      Not Listed For Sale

      19 Westview Dr, Osprey, FL 34229

      • 2 Beds
      • Built 1990
      19 Westview Dr, Osprey, FL 34229

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /45

    $824,900

    $26K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,607 Sq Ft

    Unlisted Address

    Back on the market — this is a new opportunity to own this beautiful home. The previous contract fell through, and the property has successfully passed all inspections and appraisal. It is ready for a quick and smooth closing.MODERN COASTAL MASTERPIECE | OVER $200,000 IN LUXURY UPGRADES | NEW ROOF | HEATED SALTWATER POOL | PINE VIEW SCHOOL DISTRICT.Welcome to one of Park Trace Estates’ finest

    Claudia Dybala DALTON WADE INC

    Unlisted Address
  • /44

    $5,900 Per Month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    521 Habitat Blvd, Osprey, FL 34229

    Stylish 3BR Pool Home w/ Office – 10 Mins to Beach -- 90 Day minimum stay, Peak Season at $7,900/mo plus taxes and fees; Off Season at $5,900/mo plus taxes and fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

    Dave Holt PMI SOUTHWEST FLORIDA

    521 Habitat Blvd, Osprey, FL 34229
  • /2

    $2,100,000

    Sold Jan 30, 2026

    889 MacEwen Dr, Osprey, FL 34229

    • 4 Beds
    • 4 Baths
    • 3,235 Sq Ft
    • Built 1994

    Last Sold Summary

    • 9% Below List Price
    • $649/SF
    • 41 Days On Market

    Current Estimated Value $2,066,838

    Last Listing Agent Mark Lyda GENEROUS PROPERTY

    889 MacEwen Dr, Osprey, FL 34229
    • /2

      Est $305,480

      Not Listed For Sale

      76 Explorer Dr Unit 104, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,430 Sq Ft
      • Built 2017
      76 Explorer Dr Unit 104, Osprey, FL 34229

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

  • /2

    $2,600,000

    Pending
    • 4 Beds
    • 4 Baths
    • 4,450 Sq Ft

    794 Lytham Cir, Osprey, FL 34229

    This 4 bedroom, 4 bath gem will please the most discriminating buyer. You will be immediately intrigued when you pull into the pavered circular driveway. Once you enter though the double front doors, you will feel like you’ve stepped into the pages of a magazine. There is no end to the delightful touches you will find; bathrooms with designer tile, walls sanded to a smooth finish and expertly

    Steve Abbe COLDWELL BANKER REALTY

    794 Lytham Cir, Osprey, FL 34229
  • /15

    $2,245 Per Month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Condo for Rent

    4248 Expedition Way, Osprey, FL 34229

    Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village!Experience comfortable Sarasota living in this well-appointed condo, featuring neutral paint, ceiling fans throughout, tile flooring in the main living areas, and carpeted bedrooms. The open-concept living and dining area flows seamlessly into the kitchen, complete with

    Brandon Green PMI SOUTHWEST FLORIDA

    4248 Expedition Way, Osprey, FL 34229
  • /2

    $1,330,000

    Sold Jan 07, 2026

    401 N Point Rd Unit 901, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,594 Sq Ft
    • Built 2003

    Last Sold Summary

    • 24% Below List Price
    • $513/SF
    • 764 Days On Market

    Current Estimated Value $1,289,315

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    401 N Point Rd Unit 901, Osprey, FL 34229
    • /4

      Not Listed For Sale

      0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

      0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Jennifer Arciniegas CUADRA GROUP LLC

  • /44

    $235,000

    $65K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    51 MacEwen Dr Unit 5, Osprey, FL 34229

    Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental.Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly

    Sabine Spycher 342 REAL ESTATE

    51 MacEwen Dr Unit 5, Osprey, FL 34229
  • /41

    $3,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,077 Sq Ft
    • House for Rent

    534 Oak Bay Dr Unit 1, Osprey, FL 34229

    AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. Very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping

    Brian ODonnell,PLLC REALTY BY DESIGN LLC

    534 Oak Bay Dr Unit 1, Osprey, FL 34229
  • /2

    $110,000

    Sold May 14, 2026

    234 Palm Air Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $111/SF
    • 30 Days On Market

    Last Listing Agent Toni Zarghami KW COASTAL LIVING III

    234 Palm Air Dr, Osprey, FL 34229
    • /62

      Est $568,068

      Not Listed For Sale

      221 Sorrento Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,935 Sq Ft
      • Built 1984
      221 Sorrento Dr, Osprey, FL 34229

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  • /85

    $1,100,000

    • 4 Beds
    • 3 Baths
    • 3,984 Sq Ft

    907 Eagle Isle Ct, Osprey, FL 34229

    Luxury Living in Rivendell WoodlandsWelcome to this exceptional 3,984-square-foot estate in the highly sought-after Rivendell Woodlands community, where luxury, comfort, and convenience come together in a spectacular lakefront and preserve setting. Built in 2003, this meticulously maintained residence offers 4 bedrooms, 3 baths, a private office/den, expansive bonus room, formal living and

    Becky Culp CENTURY 21 ROSEBAY

    907 Eagle Isle Ct, Osprey, FL 34229
  • /87

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

    CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $7,000/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was

    Chrissie Cummings JENNETTE PROPERTIES INC

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
  • /2

    $210,000

    Sold Oct 22, 2025

    480 Blackburn Point Rd Unit 4, Osprey, FL 34229

    • Built 2006

    Last Sold Summary

    • 7% Below List Price
    • 5 Days On Market

    Current Estimated Value $207,186

    Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

    480 Blackburn Point Rd Unit 4, Osprey, FL 34229
    • /2

      Not Listed For Sale

      570 Blackburn Point Rd Unit C2, Osprey, FL 34229

      • Built 2005
      570 Blackburn Point Rd Unit C2, Osprey, FL 34229

      Last Sold Summary

      • 234 Days On Market

      Last Listing Agent David Babel BRIGHT REALTY

  • /4

    $115,000

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

    This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'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 supplied with water and electric.

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229
  • /2

    $980,000

    Sold Dec 09, 2025

    385 N Point Rd Unit 903, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,778 Sq Ft
    • Built 2000

    Last Sold Summary

    • 11% Below List Price
    • $353/SF
    • 41 Days On Market

    Current Estimated Value $991,530

    Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

    385 N Point Rd Unit 903, Osprey, FL 34229
    • /44

      Est $1,076,070

      Not Listed For Sale

      3925 Waypoint Ave, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,323 Sq Ft
      • Built 2016
      3925 Waypoint Ave, Osprey, FL 34229

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Barry Bright BRIGHT REALTY

  • /45

    $525,000

    $25K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    1361 New Forest Ln, Osprey, FL 34229

    Under contract-accepting backup offers. PRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or

    Linh Pham NEXTHOME EXCELLENCE

    1361 New Forest Ln, Osprey, FL 34229
  • /2

    $780,000

    Sold Aug 25, 2026

    903 Tranquility Cir, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,622 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Above List Price
    • $297/SF
    • 4 Days On Market

    Current Estimated Value $743,222

    Last Listing Agent Carolyn Yates COLDWELL BANKER SARASOTA CENT.

    903 Tranquility Cir, Osprey, FL 34229
    • /65

      Est $1,064,619

      Not Listed For Sale

      3937 Waypoint Ave, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,314 Sq Ft
      • Built 2016
      3937 Waypoint Ave, Osprey, FL 34229

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Toni Turner MICHAEL SAUNDERS & COMPANY

  • /3

    $89,000

    $9K PRICE DROP

    570 Blackburn Point Rd Unit 23, Osprey, FL 34229

    Extra-wide indoor boat rack accommodating vessels up to 33' L x 11.1' W x 9.3' H, with quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash service, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Condo fees cover in and outs, insurance, marina and building maintenance, staff,

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit 23, Osprey, FL 34229
  • /2

    $350,000

    Sold Oct 16, 2025

    240 Patterson Ave, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,360 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $257/SF
    • 157 Days On Market

    Current Estimated Value $351,825

    Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

    240 Patterson Ave, Osprey, FL 34229
    • /22

      Est $271,640

      Not Listed For Sale

      101 Navigation Cir Unit 101, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,135 Sq Ft
      • Built 2014
      101 Navigation Cir Unit 101, Osprey, FL 34229

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Kimberly Stanford REALNET FLORIDA REAL ESTATE

  • /99

    $2,175,000

    • 4 Beds
    • 3.5 Baths
    • 4,117 Sq Ft

    362 MacEwen Dr, Osprey, FL 34229

    Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with

    Steve Abbe COLDWELL BANKER REALTY

    362 MacEwen Dr, Osprey, FL 34229
  • /2

    $350,000

    Sold May 29, 2026

    2141 Cordes St, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,126 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Below List Price
    • $311/SF
    • 4 Days On Market

    Current Estimated Value $351,324

    Last Listing Agent Monica Moss KELLER WILLIAMS ON THE WATER S

    2141 Cordes St, Osprey, FL 34229
    • /40

      Est $292,587

      Not Listed For Sale

      163 Explorer Dr Unit 103, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,244 Sq Ft
      • Built 2014
      163 Explorer Dr Unit 103, Osprey, FL 34229

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lita Sciturro Smith LITA SCITURRO-SMITH LIC. REAL ESTATE BROKER

Showing Results 81 - 120, Page 3 of 18

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