Homes in ZIP Code 34229

• 

  

  

  /75

  $2,300,000

  • 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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  /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

  $760,000 Sold Jul 16, 2025

  790 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $246/SF
  • 158 Days On Market

  Current Estimated Value $761,557

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  790 Shadow Bay Way, Osprey, FL 34229
• 

  

  

  /4

  Est $53,437 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

  570 Blackburn Point Rd Unit 1-SIES, 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
• 

  

  /35

  $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 a WATERFRONT 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

  $227,000 Sold Dec 15, 2025

  111 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $172/SF
  • 81 Days On Market

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  111 Woodland Place, Osprey, FL 34229
• 

  

  /12

  Est $24,182 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
• 

  

  /24

  $925,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,328 Sq Ft

  3957 Waypoint Ave, Osprey, FL 34229

  A beautiful story book home of Coastal living with mainland conveniences is ready for your discovery. Come see Bayside on Little Sarasota Bay a peaceful and friendly gated Intracoastal community of 49 landscape maintenance-free residences. Bayside residents enjoy access to a private waterfront park overlooking the intracoastal waterway view of Casey Key...oh the sunsets we have for you. Under

  Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  /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
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  /2

  $835,000 Sold May 21, 2025

  14021 Bellagio Way Unit 410, Osprey, FL 34229

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

  Last Sold Summary

  • 12% Below List Price
  • $377/SF
  • 42 Days On Market

  Current Estimated Value $828,788

  Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE

  14021 Bellagio Way Unit 410, Osprey, FL 34229
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  /50

  Est $540,328 Not Listed For Sale

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

  2006 Preymore St, Osprey, FL 34229

  2006 Preymore St, Osprey, FL 34229
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  /68

  $2,299,000

  • 4 Beds
  • 4 Baths
  • 2,572 Sq Ft

  312 Yacht Harbor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  312 Yacht Harbor Dr, 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
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  /2

  $747,850 Sold Aug 08, 2025

  424 Cezanne Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 16% Below List Price
  • $254/SF
  • 128 Days On Market

  Current Estimated Value $762,586

  Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

  424 Cezanne Dr, Osprey, FL 34229
• 

  

  /17

  Est $308,470 Not Listed For Sale

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

  4247 Expedition Way Unit 103, Osprey, FL 34229

  4247 Expedition Way Unit 103, Osprey, FL 34229
• 

  

  /60

  $899,000

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft

  38 W Bay St, Osprey, FL 34229

  Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen with solid wood cabinets, stainless

  Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, 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

  $2,300,000 Sold Nov 05, 2025

  264 Saratoga Ct, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,857 Sq Ft
  • Built 1992

  Last Sold Summary

  • $596/SF
  • 9 Days On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  264 Saratoga Ct, Osprey, FL 34229
• 

  

  /39

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  169 Edgewood Dr, Osprey, FL 34229

  169 Edgewood Dr, Osprey, FL 34229
• 

  

  /13

  $599,000

  • 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
• 

  

  /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

  $4,250,000 Sold Feb 28, 2025

  2509 Bayshore Rd, Nokomis, FL 34275

  • 5 Beds
  • 4.5 Baths
  • 4,712 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $902/SF
  • 43 Days On Market

  Current Estimated Value $3,965,177

  Last Listing Agent Andrea Blackwell KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  2509 Bayshore Rd, Nokomis, FL 34275
• 

  

  /27

  Est $357,609 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  4260 Expedition Way Unit 4260, Osprey, FL 34229

  4260 Expedition Way Unit 4260, Osprey, FL 34229
• 

  

  /78

  $1,899,000 Pending

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

  453 E MacEwen Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Set an appointment to experience this thoughtfully designed Arthur Rutenberg home, where craftsmanship and details are truly on display. Upon entering through the double door entrance, the quality and attention to detail are immediately evident. Situated on a 1/2 acre + "premium" golf course lot strategically positioned on the Heron Course (hole 5). This

  William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
• 

  /2

  $358,000 Sold Nov 13, 2025

  115 Green St, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Above List Price
  • $238/SF
  • 5 Days On Market

  Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

  115 Green St, Osprey, FL 34229
• 

  

  /24

  Est $594,620 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  2001 Cordes St, Osprey, FL 34229

  2001 Cordes St, Osprey, FL 34229
• 

  

  /49

  $544,700

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft

  827 Placid Lake Dr, Osprey, FL 34229

  This lot and location really stands out! Set back on a quiet street, on a beautifully landscaped oversized lot, and a huge lawn in the backyard with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, and Florida lifestyle. This is a rare opportunity... one of the least expensive

  Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $540,000 Sold Nov 24, 2025

  813 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $273/SF
  • 121 Days On Market

  Last Listing Agent Jeremy Egglefield PREFERRED SHORE LLC

  813 Oak Pond Dr, Osprey, FL 34229
• 

  

  /48

  Est $360,878 Not Listed For Sale

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

  123 Revolution Way Unit 101, Osprey, FL 34229

  123 Revolution Way Unit 101, Osprey, FL 34229
• 

  

  /37

  $789,000

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

  Move-in Ready | Turnkey Furnished | Gulf & Intracoastal Views + Glorious Sunsets3 Bed | 2.5 Bath | Den w/ Custom Queen Murphy Bed | 2,168 Sq Ft | End Unit Bright, breezy, and beautifully maintained, this move-in ready End Unit at Edgewater at Hidden Bay is offered fully Turnkey Furnished by the original owners and designed for effortless coastal living. Plantation shutters throughout,

  Cathy Rustin FIRST LIGHT REAL ESTATE

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
• 

  

  /32

  $335,000 Sold Mar 12, 2025

  738 Harms Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 1986

  Last Sold Summary

  • 15% Below List Price
  • $197/SF
  • 26 Days On Market

  Current Estimated Value $353,447

  Last Listing Agent Warren McGregor MCGREGOR INTERNATIONAL REAL ESTATE CO

  738 Harms Dr, Osprey, FL 34229
• 

  

  /61

  Est $370,305 Not Listed For Sale

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

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  4185 Frontier Ln Unit 102, Osprey, FL 34229
• 

  

  /61

  $474,900

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

  PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

  Toy Coxey KW COASTAL LIVING

  7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
• 

  /2

  $179,000 Sold Apr 28, 2025

  312 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 57 Days On Market

  Last Listing Agent Michelle Ward COMPASS FLORIDA LLC

  312 Tropic Dr, Osprey, FL 34229
• 

  

  /59

  Est $355,831 Not Listed For Sale

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

  99 Explorer Dr Unit 102, Osprey, FL 34229

  99 Explorer Dr Unit 102, Osprey, FL 34229
• 

  

  /48

  $936,000

  • 3 Beds
  • 3 Baths
  • 2,283 Sq Ft

  172 Sea Anchor Dr, Osprey, FL 34229

  At last- the home you've been looking for! This updated 3-bedroom 3 bath retreat is tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout, saltwater pool, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball and

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  172 Sea Anchor Dr, Osprey, FL 34229
• 

  /2

  $999,500 Sold Feb 14, 2025

  146 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,627 Sq Ft
  • Built 1986

  Last Sold Summary

  • $380/SF

  Current Estimated Value $973,320

  Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

  146 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /42

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft

  36 Siesta Cir W, Osprey, FL 34229

  36 Siesta Cir W, Osprey, FL 34229
• 

  

  /77

  $850,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  123 Windward Dr, Osprey, FL 34229

  This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant

  David Cyr WILLIAM RAVEIS REAL ESTATE

  123 Windward Dr, Osprey, FL 34229

Showing Results 121 - 160, Page 4 of 18