Osprey, FL Homes

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  /49

  $1,495,000

  • 3 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  360 N Point Rd, Osprey, FL 34229

  Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger.

  Steve Abbe COLDWELL BANKER REALTY

  360 N Point Rd, Osprey, FL 34229
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  /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
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  /2

  $155,000

  Sold Apr 14, 2026

  316 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft
  • Built 1979

  Last Sold Summary

  • 16% Below List Price
  • $135/SF
  • 36 Days On Market

  Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

  316 Tropic Dr, Osprey, FL 34229
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  /2

  Est $479,710

  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
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  /52

  $2,100,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,768 Sq Ft

  448 E MacEwen Dr, Osprey, FL 34229

  Under contract-accepting backup offers. **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a

  Mark Lyda GENEROUS PROPERTY

  448 E MacEwen Dr, Osprey, FL 34229
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  $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

  $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 $359,079

  Last Listing Agent James Briley COLDWELL BANKER REALTY

  124 Revolution Way, Osprey, FL 34229
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  /2

  Est $305,379

  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
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  /62

  $769,000

  $196K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,310 Sq Ft

  13 Bayhead Ln, Osprey, FL 34229

  **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

  Mark Lyda GENEROUS PROPERTY

  13 Bayhead Ln, Osprey, FL 34229
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  /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

  $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
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  /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
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  /71

  $699,000

  $36K PRICE DROP

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

  5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229

  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 through the living room, dining area,

  Suki Scollo COLDWELL BANKER REALTY

  5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229
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  /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
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  /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
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  /62

  Est $575,446

  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.
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  /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
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  /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 $1,274,411

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
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  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
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  /45

  $799,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,607 Sq Ft

  Unlisted Address

  Under contract-accepting backup offers. MODERN COASTAL MASTERPIECE | OVER $200,000 IN LUXURY UPGRADES | NEW ROOF | HEATED SALTWATER POOL | PINE VIEW SCHOOL DISTRICTWelcome to one of Park Trace Estates’ finest fully renovated homes, where sophisticated design, exceptional craftsmanship, and the Florida lifestyle come together in perfect harmony. This spectacular 4-bedroom, 3-bath residence has

  Claudia Dybala DALTON WADE INC

  Unlisted Address
• 

  /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
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  /44

  Est $1,038,668

  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
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  /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
• 

  /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 $207,276

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  480 Blackburn Point Rd Unit 4, Osprey, FL 34229
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  /65

  Est $1,037,453

  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
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  /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
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  /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 $978,447

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

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

  

  /22

  Est $276,096

  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
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  /45

  $525,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft

  1361 New Forest Ln, Osprey, FL 34229

  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 bike to one of Florida’s most acclaimed

  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
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  /40

  Est $294,895

  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
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  /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
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  /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 $347,199

  Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, Osprey, FL 34229
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  Not Listed For Sale

  201 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1980

  201 Palm Air Dr, Osprey, FL 34229

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Roxane Solowey BERKSHIRE HATHAWAY HOMESERVICE
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  /39

  $317,000

  $3K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  4213 Expedition Way Unit 107, Osprey, FL 34229

  Under contract-accepting backup offers. "Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability.

  Yunfei Liu DALTON WADE INC

  4213 Expedition Way Unit 107, 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 $351,263

  Last Listing Agent Monica Moss KELLER WILLIAMS ON THE WATER S

  2141 Cordes St, Osprey, FL 34229
• 

  

  /46

  Est $540,179

  Not Listed For Sale

  2007 Cordes St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • Built 2023

  2007 Cordes St, Osprey, FL 34229

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP
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  /4

  $36,000

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

  This slip will house a boat with the maximum dimensions of 35.5' length, 10' width and 6' height 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

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
• 

  /2

  $1,385,000

  Sold Jun 23, 2026

  434 E MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,414 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $574/SF
  • 6 Days On Market

  Current Estimated Value $1,371,072

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  434 E MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $728,775

  Not Listed For Sale

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229

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

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

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