5,082

Osprey, FL Homes

Section Image Section Image
  • /53

    $1,100,000

    • 5 Beds
    • 3 Baths
    • 3,912 Sq Ft

    674 Clear Creek Dr, Osprey, FL 34229

    Looking for a house within #1 US public school within a short distance? Discover this expansive 5-bedroom, 3-bathroom home with an oversized flex room, office, and almost 4,000 sq. ft. of living space, perfectly situated on a 9,017 sq. ft. lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2025), HVAC units (2019 & 2023), a new water heater (2022), fresh

    Agent Photo

    Arkadiy Abdurakhmanov

    United Realty Group Inc.

    674 Clear Creek Dr, Osprey, FL 34229
  • /46

    $14,000 Per Month

    • 4 Beds
    • 6 Baths
    • 9,081 Sq Ft
    • House for Rent

    854 MacEwen Dr, Osprey, FL 34229

    Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round

    854 MacEwen Dr, Osprey, FL 34229
  • /2

    $727,500

    Sold Feb 12, 2026

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

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Built 2019

    Last Sold Summary

    • 17% Below List Price
    • $336/SF
    • 257 Days On Market

    Current Estimated Value $736,121

    Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE

    260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
    • /2

      Est $257,538

      Not Listed For Sale

      51 MacEwen Dr Unit 20, Osprey, FL 34229

      • 1 Bed
      • 1 Bath
      • 623 Sq Ft
      • Built 1990
      51 MacEwen Dr Unit 20, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

  • /35

    $270,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    4271 Expedition Way Unit 103, Osprey, FL 34229

    Virtually Staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an

    Agent Photo

    Toni Zarghami

    KW COASTAL LIVING III

    4271 Expedition Way Unit 103, Osprey, FL 34229
  • /48

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,306 Sq Ft
    • House for Rent

    124 Turquoise Ln, Osprey, FL 34229

    **RENT JUST LOWERED**Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key

    Cody Smith RENT SARASOTA

    124 Turquoise Ln, Osprey, FL 34229
  • /2

    $1,750,000

    Sold Oct 27, 2025

    627 N MacEwen Dr, Osprey, FL 34229

    • 4 Beds
    • 4.5 Baths
    • 3,857 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $454/SF
    • 1 Day On Market

    Current Estimated Value $1,736,825

    Last Listing Agent Mark Lyda GENEROUS PROPERTY

    627 N MacEwen Dr, Osprey, FL 34229
    • /2

      Est $619,419

      Not Listed For Sale

      610 Pine Ranch Rd E, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,431 Sq Ft
      • Built 1995
      610 Pine Ranch Rd E, Osprey, FL 34229

      Last Sold Summary

      • 113 Days On Market

  • /97

    $540,000

    • 4 Beds
    • 2 Baths
    • 2,399 Sq Ft

    523 Oak Bay Dr, Osprey, FL 34229

    Welcome home to this beautifully maintained 3-bedroom + den, 2-bath pool home nestled on a desirable corner lot, in a cul-de-sac, in Osprey. This home has been impeccably maintained and is an unbeatable location, this is the effortless Florida lifestyle you've been searching for.Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 21⁄2 years ago, and

    Agent Photo

    Karie Backman

    KELLER WILLIAMS ON THE WATER S

    523 Oak Bay Dr, Osprey, FL 34229
  • /27

    $2,599 Per Month

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • The Residences of Blackburn Bay

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229
  • /2

    $650,000

    Sold Jul 03, 2025

    236 Hidden Bay Dr Unit 301, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Built 1997

    Last Sold Summary

    • 13% Below List Price
    • $310/SF
    • 246 Days On Market

    Current Estimated Value $649,455

    Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

    236 Hidden Bay Dr Unit 301, Osprey, FL 34229
    • /2

      Est $238,891

      Not Listed For Sale

      51 MacEwen Dr Unit 13, Osprey, FL 34229

      • 1 Bed
      • 1 Bath
      • 595 Sq Ft
      • Built 1990
      51 MacEwen Dr Unit 13, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

  • /20

    $175,000

    $15K PRICE DROP
    • Land
    • 20,908 Sq Ft
    • $364,583 per Acre

    14 Old Venice Rd, Osprey, FL 34229

    **Pine View School** NO HOA** Custom House-Separate Guest House- Separate RV/Boat** Discover an exceptional opportunity to create your custom dream home in the heart of Osprey — one of Sarasota County’s most desirable coastal communities. This buildable vacant homesite offers the perfect canvas to design a private retreat tailored to your lifestyle, all while enjoying the charm, convenience, and

    Agent Photo

    Mousa Wakileh

    COLDWELL BANKER REALTY

    14 Old Venice Rd, Osprey, FL 34229
  • /36

    $3,775 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Condo for Rent

    280 Hidden Bay Dr Unit 201, Osprey, FL 34229

    Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! Sorry, no pets for renters. The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and

    Nancy Guerrero PMI SOUTHWEST FLORIDA

    280 Hidden Bay Dr Unit 201, Osprey, FL 34229
  • /2

    $635,000

    Sold May 15, 2026

    120 Candyce Dr, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,103 Sq Ft
    • Built 1962

    Last Sold Summary

    • 25% Below List Price
    • $302/SF
    • 155 Days On Market

    Current Estimated Value $651,646

    Last Listing Agent Michelle Ward COMPASS FLORIDA LLC

    120 Candyce Dr, Osprey, FL 34229
    • /2

      Est $830,002

      Not Listed For Sale

      124 Tina Island Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft
      • Built 1975
      124 Tina Island Dr, Osprey, FL 34229

      Last Sold Summary

      • 244 Days On Market

  • /9

    $2,850,000

    $350K PRICE DROP
    • Land
    • 16,988 Sq Ft
    • $7,307,692 per Acre

    141 N Casey Key Rd, Osprey, FL 34229

    Gulf-front vacant lot on Casey Key in Osprey. Buildable lot with County guidance. 107' Gulf frontage, cleared site ready for new construction. For buyers seeking to build a custom waterfront home, this Gulf-front vacant lot on Casey Key in Osprey offers a compelling opportunity in one of Sarasota County’s most sought-after coastal locations. The homesite is cleared and confirmed buildable based

    Agent Photo

    Julie Larson

    WHITE SANDS REALTY GROUP FL

    141 N Casey Key Rd, Osprey, FL 34229
  • /45

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,290 Sq Ft
    • Annual Rental: Luxurious 4 Bedroom 3 bath POOL home in Woodlands of Rivendell! Just Blocks form P...

    919 Scherer Way, Osprey, FL 34229

    Moving Deal! Sign a lease by July 1st at a better price of $4,300! Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a

    919 Scherer Way, Osprey, FL 34229
  • /2

    $1,495,000

    Sold Apr 14, 2026

    554 Dove Pointe, Osprey, FL 34229

    • 4 Beds
    • 3.5 Baths
    • 3,501 Sq Ft
    • Built 2002

    Last Sold Summary

    • $427/SF
    • 2 Days On Market

    Current Estimated Value $1,500,658

    Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

    554 Dove Pointe, Osprey, FL 34229
    • /2

      Est $93,635

      Not Listed For Sale

      570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

      • Studio
      570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

      Last Sold Summary

      • 104 Days On Market

  • /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
  • /38

    $4,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,290 Sq Ft
    • House for Rent

    956 Scherer Way, Osprey, FL 34229

    Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School

    Chantelle Edalgo EXIT KING REALTY

    956 Scherer Way, Osprey, FL 34229
  • /2

    $163,000

    Sold Mar 06, 2026

    334 Tropic Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • Built 1978

    Last Sold Summary

    • 7% Below List Price
    • $143/SF
    • 2 Days On Market

    Last Listing Agent Laura Guess-Fox COLDWELL BANKER REALTY

    334 Tropic Dr, Osprey, FL 34229
    • /2

      Est $279,749

      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

  • /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
  • /45

    $4,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Coastal Luxury at Hidden Bay | 3BR Waterfront Condo with Bay Views

    260 Hidden Bay Dr, Osprey, FL 34229

    6 Month Minimum Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled

    260 Hidden Bay Dr, Osprey, FL 34229
  • /2

    $1,065,000

    Sold Feb 20, 2026

    1235 Yacht Harbor Dr, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,698 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $395/SF
    • 30 Days On Market

    Current Estimated Value $1,068,182

    Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

    1235 Yacht Harbor Dr, Osprey, FL 34229
    • /2

      Est $473,025

      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

  • /62

    $1,595,000

    $200K PRICE DROP
    • 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
  • /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

    $830,000

    Sold Jun 16, 2026

    6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,630 Sq Ft
    • Built 2005

    Last Sold Summary

    • 8% Below List Price
    • $316/SF
    • 82 Days On Market

    Current Estimated Value $827,335

    Last Listing Agent Andrea Stultz ENGEL + VOELKERS SARASOTA

    6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
    • /2

      Est $316,220

      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

  • /84

    $1,289,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 3,112 Sq Ft

    156 Bishopscourt Rd, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional

    Joel Schemmel DOUGLAS ELLIMAN

    156 Bishopscourt Rd, 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

    $4,000,000

    Sold Apr 09, 2026

    854 N Casey Key Rd, Osprey, FL 34229

    • 4 Beds
    • 4 Baths
    • 3,462 Sq Ft
    • Built 1975

    Last Sold Summary

    • 16% Below List Price
    • $1,155/SF
    • 27 Days On Market

    Last Listing Agent Charles Ruck POTTER TRINITY

    854 N Casey Key Rd, 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

  • /72

    $2,189,000

    Open Sun 1PM - 3PM $61K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,012 Sq Ft

    433 E MacEwen Dr, Osprey, FL 34229

    An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

    Mark Lyda GENEROUS PROPERTY

    433 E MacEwen Dr, Osprey, FL 34229
  • /39

    $3,900 Per Month

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

    409 N Point Rd Unit 802, Osprey, FL 34229

    Move right into this gorgeous remodeled turnkey furnished condo in desirable gated community of The Oaks Preserve. This community is waterfront on the Intercostal Waterway with soothing stunning views and sunsets to adore. Take the elevator directly up to your front foyer to your unit. This unit is filled with beaming natural light and upscaled furnishings through out. The new oak wood flooring,

    toyia Youtzy JENNETTE PROPERTIES, INC.

    409 N Point Rd Unit 802, Osprey, FL 34229
  • /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
    • /62

      Est $555,243

      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

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home