Homes in ZIP Code 34229

• 

  

  

  /25

  $189,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  218 Palm Air Dr, Osprey, FL 34229

  Under contract-accepting backup offers. You’ll be impressed with this delightful double wide from the moment you enter featuring 2 spacious bedrooms and 2 updated bathrooms with a total of 1120 Sq Feet built in 1979 with large shed and enclosed lanai. Being sold Furnished and Turnkey. The kitchen was totally remodeled in 2020 an island was added with new appliances in and it flows into the dining

  Carlos Saramago EXIT KING REALTY

  218 Palm Air Dr, Osprey, FL 34229
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  /49

  $2,995 per month

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

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

  Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

  127 Explorer Dr Unit 127 Explorer Dr, 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

  Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, 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
• 

  

  

  /78

  $1,095,000

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft

  820 Placid Lake Dr, Osprey, FL 34229

  Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh

  Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
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  /36

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,069 Sq Ft
  • House for Rent

  305 Bay Vista Ave, Osprey, FL 34229

  Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

  Jennifer . STOCKTON REALTY ADVISORS LLC

  305 Bay Vista Ave, Osprey, FL 34229
• 

  /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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  /44

  Est $1,096,966 Not Listed For Sale

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

  3925 Waypoint Ave, Osprey, FL 34229

  3925 Waypoint Ave, Osprey, FL 34229
• 

  

  /57

  $1,570,000 New Construction

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

  360 N Point Rd, Osprey, FL 34229

  **DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen

  Mark Lyda GENEROUS PROPERTY

  360 N Point Rd, Osprey, FL 34229
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  /38

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Condo for Rent

  409 N Point Rd Unit 802, Osprey, FL 34229

  **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 802, Osprey, FL 34229
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  /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 $911,268

  Last Listing Agent Sharon Osborne, PA RESULTS REALTY GROUP LLC

  1200 Mallard Marsh Dr, Osprey, FL 34229
• 

  

  /65

  Est $1,089,014 Not Listed For Sale

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

  3937 Waypoint Ave, Osprey, FL 34229

  3937 Waypoint Ave, Osprey, FL 34229
• 

  

  /39

  $879,000

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

  903 Tranquility Cir, Osprey, FL 34229

  **IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated living area plus a spacious screened lanai with Heated Pool/Spa and ample covered seating area, for the

  Mark Lyda GENEROUS PROPERTY

  903 Tranquility Cir, Osprey, FL 34229
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  /9

  $2,395 per month

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Townhouse for Rent

  1817 Highland Rd, Osprey, FL 34229

  Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.

  Steven Koleno BEYCOME OF FLORIDA LLC

  1817 Highland Rd, Osprey, FL 34229
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  /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 $912,720

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  336 Pine Ranch Rd E, Osprey, FL 34229
• 

  

  /22

  Est $293,880 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
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  /62

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 4,241 Sq Ft

  909 MacEwen Dr, Osprey, FL 34229

  **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious

  Mark Lyda GENEROUS PROPERTY

  909 MacEwen 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
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  /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 $418,288

  Last Listing Agent Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
• 

  

  /40

  Est $300,069 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
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  /73

  $2,550,000

  • 3 Beds
  • 3.5 Baths
  • 4,519 Sq Ft

  852 MacEwen Dr, Osprey, FL 34229

  **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

  Mark Lyda GENEROUS PROPERTY

  852 MacEwen Dr, 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

  $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 $1,013,232

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 502, 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
• 

  

  /99

  $545,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,688 Sq Ft

  447 Oak Point Rd, Osprey, FL 34229

  Prepare to be impressed as you enter this bright and spacious maintenance-free townhome with soaring ceilings, an abundance of natural light, and surrounded by nature in a wooded setting. Nestled near Casey Key, this coveted West of the Trail subdivision with only 44 single-family, attached homes, is walking distance to Casey Key, Blackburn Point Marina, and Blackburn Point Park, which features a

  Priscilla Adams COMPASS FLORIDA LLC

  447 Oak Point Rd, Osprey, FL 34229
• 

  

  /39

  $4,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
• 

  /2

  $495,000 Sold Dec 27, 2024

  502 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1995

  Last Sold Summary

  • 14% Below List Price
  • $234/SF
  • 88 Days On Market

  Current Estimated Value $493,530

  Last Listing Agent Carey Beychok RE/MAX ALLIANCE GROUP

  502 Oak Bay Dr, Osprey, FL 34229
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  /46

  Est $604,226 Not Listed For Sale

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

  2007 Cordes St, Osprey, FL 34229

  2007 Cordes St, Osprey, FL 34229
• 

  

  /49

  $1,175,000

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

  219 Keel Way, Osprey, FL 34229

  **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, Expansive Kitchen with Hardwood Cabinets,

  Mark Lyda GENEROUS PROPERTY

  219 Keel Way, Osprey, FL 34229
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  /9

  $2,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,173 Sq Ft
  • House for Rent

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
• 

  /2

  $1,222,500 Sold Jan 17, 2025

  14021 Bellagio Way Unit 201, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,020 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $405/SF
  • 25 Days On Market

  Current Estimated Value $1,171,671

  Last Listing Agent Brian Wood COMPASS FLORIDA LLC

  14021 Bellagio Way Unit 201, 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
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  /82

  $1,350,000

  • 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
• 

  

  /39

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR SEASONAL RENTAL – READY FOR IMMEDIATE OCCUPANCY AND FULLY FURNISHED!Modern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
• 

  /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 $896,984

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229
• 

  /2

  Est $307,824 Not Listed For Sale

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

  4219 Frontier Ln Unit 105, Osprey, FL 34229

  4219 Frontier Ln Unit 105, 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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  /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
• 

  /2

  $525,000 Sold Dec 04, 2025

  1313 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,082 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 8 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1313 Thornapple Dr, Osprey, FL 34229
• 

  

  /24

  Est $303,870 Not Listed For Sale

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

  4224 Expedition Way Unit 105, Osprey, FL 34229

  4224 Expedition Way Unit 105, Osprey, FL 34229

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