Homes in ZIP Code 34229

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  /74

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,066 Sq Ft

  25 Sugar Mill Dr, Osprey, FL 34229

  METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

  Mark Lyda GENEROUS PROPERTY

  25 Sugar Mill Dr, Osprey, FL 34229
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  /53

  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Condo for Rent

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

  Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French

  Henry Rossi RENT SARASOTA

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
• 

  

  /2

  $340,000 Sold May 08, 2025

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2001

  Last Sold Summary

  • 20% Below List Price
  • $217/SF
  • 166 Days On Market

  Current Estimated Value $348,719

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229
• 

  

  /2

  Est $387,091 Not Listed For Sale

  • 2 Beds

  19 Westview Dr, Osprey, FL 34229

  19 Westview Dr, Osprey, FL 34229
• 

  

  

  /49

  $1,175,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  219 Keel Way, Osprey, FL 34229

  Under contract-accepting backup offers. **IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout,

  Mark Lyda GENEROUS PROPERTY

  219 Keel Way, Osprey, FL 34229
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  /44

  $6,500 per month

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

  521 Habitat Blvd, Osprey, FL 34229

  REDUCED FOR THE SEASON! Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 60 Day minimum stay in Peak Season at $8,900/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees. 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

  $235,000 Sold Jun 13, 2025

  109 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $192/SF
  • 144 Days On Market

  Current Estimated Value $232,016

  Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

  109 Woodland Place, Osprey, FL 34229
• 

  /2

  Est $43,328 Not Listed For Sale

  • Studio

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

  570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
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  /82

  $1,295,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  /87

  $6,000 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! AVAILABLE JAN/FEB/MAR/APR 2026 $6,000/MONTH. Beautiful 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 converted from a den) and

  Chrissie Cummings JENNETTE PROPERTIES INC

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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  /55

  $480,000 Sold May 14, 2025

  564 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 2003

  Last Sold Summary

  • 15% Below List Price
  • $265/SF
  • 57 Days On Market

  Current Estimated Value $484,128

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  564 Meadow Sweet Cir, 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
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  /67

  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  /33

  $2,995 per month

  • 2 Beds
  • 3.5 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  60 Bishops Court Rd Unit 114, Osprey, FL 34229

  This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

  Heidi Thompson STRINGER MANAGEMENT INC

  60 Bishops Court Rd Unit 114, 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 $342,961

  Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, Osprey, FL 34229
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  /44

  Est $1,091,294 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3925 Waypoint Ave, Osprey, FL 34229

  3925 Waypoint Ave, Osprey, FL 34229
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  /75

  $2,100,000

  • 4 Beds
  • 5.5 Baths
  • 4,346 Sq Ft

  538 Dove Pointe, Osprey, FL 34229

  **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

  Mark Lyda GENEROUS PROPERTY

  538 Dove Pointe, Osprey, FL 34229
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  /39

  $6,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft
  • Townhouse for Rent

  101 Woodland Place, Osprey, FL 34229

  Price Reduction and Now AVAILABLE FOR LEASE for FEBRUARY through APRIL 2026 at PINE RUN Condominiums in OSPREY, Florida! One month availability. 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of

  Patrice Ivan WAGNER REALTY

  101 Woodland Place, Osprey, FL 34229
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  /2

  $1,285,000 Sold Jun 30, 2025

  393 N Point Rd Unit 801, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft
  • Built 2001

  Last Sold Summary

  • 22% Below List Price
  • $424/SF
  • 204 Days On Market

  Current Estimated Value $1,278,209

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 801, Osprey, FL 34229
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  /65

  Est $1,071,315 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,314 Sq Ft

  3937 Waypoint Ave, Osprey, FL 34229

  3937 Waypoint Ave, Osprey, FL 34229
• 

  

  /56

  $5,000,000

  • 4 Beds
  • 5.5 Baths
  • 5,087 Sq Ft

  101 Osprey Point Dr, Osprey, FL 34229

  A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances

  Joel Schemmel DOUGLAS ELLIMAN

  101 Osprey Point Dr, Osprey, FL 34229
• 

  

  /42

  $5,900 per month

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft
  • Condo for Rent

  3603 N Point Rd Unit 602, Osprey, FL 34229

  **FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 602, Osprey, FL 34229
• 

  /2

  $925,000 Sold Mar 03, 2025

  1200 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 2002

  Last Sold Summary

  • 21% Below List Price
  • $316/SF
  • 118 Days On Market

  Current Estimated Value $919,627

  Last Listing Agent Sharon Osborne, PA RESULTS REALTY GROUP LLC

  1200 Mallard Marsh Dr, Osprey, FL 34229
• 

  

  /22

  Est $291,255 Not Listed For Sale

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

  101 Navigation Cir Unit 101, Osprey, FL 34229

  101 Navigation Cir Unit 101, Osprey, FL 34229
• 

  

  /62

  $895,000

  • 2 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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  /74

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Condo for Rent

  14041 Bellagio Way Unit 316, Osprey, FL 34229

  *BOOKED DEC THROUGH JUNE 2026.* MINS TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon

  Chrissie Cummings JENNETTE PROPERTIES INC

  14041 Bellagio Way Unit 316, Osprey, FL 34229
• 

  /2

  $904,900 Sold May 30, 2025

  336 Pine Ranch Rd E, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,705 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $335/SF
  • 5 Days On Market

  Current Estimated Value $931,443

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  336 Pine Ranch Rd E, Osprey, FL 34229
• 

  

  /40

  Est $300,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  163 Explorer Dr Unit 103, Osprey, FL 34229

  163 Explorer Dr Unit 103, Osprey, FL 34229
• 

  

  /61

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft

  3603 N Point Rd Unit 702, Osprey, FL 34229

  **MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 702, Osprey, FL 34229
• 

  

  /25

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  152 Navigation Cir Unit 107, Osprey, FL 34229

  BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with

  Henry Rossi RENT SARASOTA

  152 Navigation Cir Unit 107, Osprey, FL 34229
• 

  /2

  $430,000 Sold Aug 01, 2025

  117 Villa Dr Unit 117, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1967

  Last Sold Summary

  • 22% Below List Price
  • $305/SF
  • 244 Days On Market

  Current Estimated Value $424,038

  Last Listing Agent Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft

  201 Palm Air Dr, Osprey, FL 34229

  201 Palm Air Dr, Osprey, FL 34229
• 

  

  /43

  $780,250 New Construction

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

  280 Hidden Bay Dr Unit 202, Osprey, FL 34229

  READY FOR IMMEDIATE OCCUPANCY!Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota BayStep into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space

  Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  280 Hidden Bay Dr Unit 202, Osprey, FL 34229
• 

  

  /21

  $2,300 per month

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

  184 Explorer Dr Unit 184, Osprey, FL 34229

  Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

  Claudia Dybala DALTON WADE INC

  184 Explorer Dr Unit 184, Osprey, FL 34229
• 

  /2

  $1,051,025 Sold Apr 04, 2025

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Above List Price
  • $543/SF
  • 2 Days On Market

  Current Estimated Value $1,034,152

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229
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  /46

  Est $638,412 Not Listed For Sale

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

  2007 Cordes St, Osprey, FL 34229

  2007 Cordes St, Osprey, FL 34229
• 

  

  /63

  $1,250,000

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

  409 N Point Rd Unit 601, Osprey, FL 34229

  **FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and features 3 bedrooms plus a study/den, 3 full baths, two elevator banks, two assigned second-level parking spaces, and climate-controlled storage. Located behind the secure gates of The Oaks Preserve Country Club, this residence

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 601, Osprey, FL 34229
• 

  /2

  $925,000 Sold Mar 25, 2025

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • $478/SF
  • 0 Days On Market

  Current Estimated Value $915,060

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229
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  /5

  Not Listed For Sale

  0 N Point Rd Unit A11454780, Osprey, FL 34229

  0 N Point Rd Unit A11454780, Osprey, FL 34229
• 

  

  /76

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 4,191 Sq Ft

  85 Sugar Mill Dr, Osprey, FL 34229

  **STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN

  Mark Lyda GENEROUS PROPERTY

  85 Sugar Mill Dr, Osprey, FL 34229

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