(941) 356-1054 williamgladerealtor@gmail.com William Glade Real Estate
    Traffic Dashboard
    Home
    • HOME
    • SEARCH
    • COMMUNITIES
      • Sarasota County
      • Manatee County
      • Pinellas County
      • Charlotte County
      • Hillsborough County
    • RENTALS
      • SEARCH RENTALS
    • BUYING
      • SEARCH HOMES
      • FEATURED LISTINGS
      • MORTGAGE CALCULATOR
    • SELLING
      • LIST WITH US
    • PROPERTY MANAGEMENT
    • MEET THE TEAM
    • CONTACT
    Traffic Dashboard
    William Glade
    (941) 356-1054 williamgladerealtor@gmail.com
    • Sarasota, FL
    Explore
    • Property Search
    • Communities
    • Buying
    • Selling
    About
    • About
    • Contact Us
    • Testimonials
    • Home
    Legal
    • Privacy
    • Terms
    • DMCA
    • Accessibility
    • Fair Housing
    Account
    • Dashboard
    • Logout
    • Login
    William Glade | William Glade Lic. Real Estate - Footer Logo
    ©2026 William Glade Real Estate. All rights reserved.
    Website built by CloseHack.
    Miami Association of REALTORS®

    MIAMI ASSOCIATION OF REALTORS® All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than Marjo Realty Co. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS.

    My Florida Regional MLS DBA Stellar MLS

    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: William Glade | William Glade Lic. Real Estate

    Back

    Little Sarasota Bay Waterfront

    Condos & Apartments in Osprey, FL

    Welcome to Osprey, a waterfront community on Little Sarasota Bay in Sarasota County, Florida, set between Sarasota and Venice and minutes from Casey Key.

    Osprey is an unincorporated community in Sarasota County, Florida, situated on Little Sarasota Bay along the Gulf Coast between Sarasota and Venice. Its history stretches back to the late nineteenth century, when the Osprey post office was established in 1884, and the area has long been defined by its waterfront setting, its early pioneer families, and, more recently, a collection of established residential neighborhoods and country-club communities. With a population of roughly 6,700, Osprey offers a low-density, bay-oriented way of life. Waterfront and boating communities such as Sorrento Shores and Osprey Harbor Village sit along the bay, while the master-planned neighborhoods of The Oaks wrap around championship golf courses. Casey Key, a narrow barrier island with Gulf-front homes, lies just across the bay to the west, placing the open Gulf beaches within a few minutes' drive of most Osprey addresses. Osprey is also notable for its natural and historic assets, which set it apart from the purely residential stretches of the Sarasota County coast. Historic Spanish Point, a peninsula operated by Marie Selby Botanical Gardens, preserves archaeological and pioneer history along the bay, while Oscar Scherer State Park protects scrub habitat and the threatened Florida scrub-jay, with hiking trails and Lake Osprey drawing hundreds of thousands of visitors each year. Day-to-day life in Osprey is quiet and car-dependent, typical of the Gulf Coast's established residential communities. Residents boat and paddle on the bay, play golf, and take short drives to the arts, dining, and healthcare of Sarasota to the north or the beaches and shops of Venice and Nokomis to the south. The community's own commercial scene is modest—marinas, restaurants, and neighborhood services—so much of daily shopping and entertainment happens in the neighboring cities. These anchors, combined with a settled, low-density housing stock and direct access to the Gulf shoreline, make Osprey a distinctive coastal address for people seeking quiet, established living along the water.

    Population 6,690
    County Sarasota County
    Active Listings 160
    Browse by Listing Type
    attach_moneyFor Sale editFor Rent
    Browse by Property Type
    homeHouses apartmentCondos & Apartments holiday_villageTownhouses & Duplexes crop_landscapeLots & Land parkFarms & Ranches

    Frequently Asked Questions

    Where is Osprey, Florida?

    Osprey is an unincorporated community in Sarasota County, Florida, on Little Sarasota Bay along the Gulf Coast. It sits between the cities of Sarasota and Venice, with Casey Key and the Gulf beaches immediately to the west.

    What is Historic Spanish Point?

    Historic Spanish Point is a waterside archaeological and historic site on a peninsula in Little Sarasota Bay at Osprey. Operated by Marie Selby Botanical Gardens, it preserves pioneer and prehistoric history alongside botanical gardens and a short trail network.

    What school district serves Osprey?

    Osprey is served by Sarasota County Schools, the public school district covering all of Sarasota County, with neighborhood schools in the surrounding area plus private and charter options in nearby Sarasota and Venice.

    Is Osprey close to the beach?

    Yes. Osprey sits on the mainland side of Little Sarasota Bay, with Casey Key, Nokomis, and the Gulf of Mexico beaches just across the water to the west, typically a short drive across Blackburn Point Road.

    MARKET SNAPSHOT

    The Market at a Glance

    How homes have been selling here over the last 90 days.

    home_work New This Week 3
    Went Under Contract 0
    trending_down Price Reductions 0
    payments Median Sale Price $645,000 -4.8%
    square_foot Price per Sq Ft $254
    schedule Avg Days on Market 92
    sell Homes Sold 57
    percent Sale-to-List Ratio 95.0%
    inventory_2 Months of Inventory 6.4

    Price & Sales History

    Market data reflects closed sales over the last 90 days and is provided for informational purposes.

    BROWSE BY ZIP

    Zip Codes

    Browse listings by postal code in this area.

    010 homes for saleMedian sale$295K1 sale in the last 90 days
    003 homes for saleMedian sale$295K
    0001 home for saleMedian sale$295K
    00006 homes for saleMedian sale$295K
    0000029 homes for saleMedian sale$370KPer sq ft$199 sales in the last 90 days
    0060225 homes for saleMedian sale$417.5KPer sq ft$3124 sales in the last 90 days
    0060322 homes for saleMedian sale$235KPer sq ft$7273 sales in the last 90 days
    0061228 homes for saleMedian sale$160KPer sq ft$1685 sales in the last 90 days
    0062359 homes for saleMedian sale$240KPer sq ft$19214 sales in the last 90 days
    006418 homes for saleMedian sale$262KPer sq ft$1762 sales in the last 90 days
    00646141 homes for saleMedian sale$1.5MPer sq ft$59625 sales in the last 90 days
    0066239 homes for saleMedian sale$463KPer sq ft$2939 sales in the last 90 days
    View All Zip Codes
    Get Alerts Advanced Search
    • Grid
    • Map
    • List
    409 POINT ROAD #803 For Sale
    $985,000
    409 POINT ROAD #803Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2423 sqft
    • Built 2004
    • MFRA4703407
    260 HIDDEN BAY DRIVE #402 For Sale
    $775,000
    260 HIDDEN BAY DRIVE #402Osprey, FL 34229
    • 3 bd
    • 2.5 ba
    • 2109 sqft
    • Built 2019
    • MFRA4701000
    14041 BELLAGIO WAY #214 For Rent
    $6,000
    14041 BELLAGIO WAY #214Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 2089 sqft
    • Built 2006
    • MFRA4700702
    701 PINE RUN DRIVE #701 For Sale
    $172,000
    701 PINE RUN DRIVE #701Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 658 sqft
    • Built 1973
    • MFRA4700416
    108 WOODLAND PLACE #108 For Sale
    $285,000
    108 WOODLAND PLACE #108Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1474 sqft
    • Built 1979
    • A4699279
    2309 JESSIE HARBOR DRIVE #2402 For Sale
    $497,000
    2309 JESSIE HARBOR DRIVE #2402Osprey, FL 34229
    • 3 bd
    • 2.5 ba
    • 2446 sqft
    • Built 2006
    • A4698434
    6100 JESSIE HARBOR DRIVE #202 For Rent
    $5,500
    6100 JESSIE HARBOR DRIVE #202Osprey, FL 34229
    • 3 bd
    • 3.5 ba
    • 4209 sqft
    • Built 2005
    • A4698732
    7204 JESSIE HARBOR DRIVE #7204 For Sale
    $395,000
    7204 JESSIE HARBOR DRIVE #7204Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1410 sqft
    • Built 1985
    • A4697473
    110 WOODLAND PLACE #110 For Sale
    $215,000
    110 WOODLAND PLACE #110Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1400 sqft
    • Built 1979
    • A4696738
    401 POINT ROAD #504 For Sale
    $795,000
    401 POINT ROAD #504Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 3106 sqft
    • Built 2003
    • A4696459
    116 WOODLAND PLACE #116 For Sale
    $249,900
    116 WOODLAND PLACE #116Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1483 sqft
    • Built 1979
    • A4696616
    51 MAC EWEN DRIVE #8 For Rent
    $1,600
    51 MAC EWEN DRIVE #8Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 675 sqft
    • Built 1990
    • A4695928
    184 EXPLORER DRIVE For Rent
    $2,150
    184 EXPLORER DRIVEOsprey, FL 34229
    • 2 bd
    • 2 ba
    • 1430 sqft
    • Built 2016
    • A4695420
    4296 EXPEDITION WAY #104 For Sale
    $299,990
    4296 EXPEDITION WAY #104Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1219 sqft
    • Built 2017
    • A4694926
    260 HIDDEN BAY DRIVE #401 For Rent
    $4,850
    260 HIDDEN BAY DRIVE #401Osprey, FL 34229
    • 3 bd
    • 2.5 ba
    • 2433 sqft
    • Built 2019
    • A4693277
    280 HIDDEN BAY DRIVE #302 For Sale
    $749,000
    280 HIDDEN BAY DRIVE #302Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 2241 sqft
    • Built 2024
    • A4690813
    4219 FRONTIER WAY #105 For Rent
    $2,200
    4219 FRONTIER WAY #105Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1560 sqft
    • Built 2017
    • N6144275
    51 MACEWEN DRIVE #12 For Sale
    $275,000
    51 MACEWEN DRIVE #12Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 623 sqft
    • Built 1990
    • A4690540
    184 EXPLORER DRIVE For Sale
    $294,900
    184 EXPLORER DRIVEOsprey, FL 34229
    • 2 bd
    • 2 ba
    • 1397 sqft
    • Built 2016
    • A4692249
    6100 JESSIE HARBOR DRIVE #202 For Sale
    $850,000
    6100 JESSIE HARBOR DRIVE #202Osprey, FL 34229
    • 3 bd
    • 3.5 ba
    • 4209 sqft
    • Built 2005
    • A4690969
    14021 BELLAGIO WAY #404 For Sale
    $1,100,000
    14021 BELLAGIO WAY #404Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2526 sqft
    • Built 2006
    • N6144070
    5100 JESSIE HARBOR DRIVE #304 For Sale
    $699,000
    5100 JESSIE HARBOR DRIVE #304Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 2304 sqft
    • Built 2004
    • A4690942
    409 NORTH POINT ROAD #401 For Sale
    $560,000
    409 NORTH POINT ROAD #401Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2837 sqft
    • Built 2004
    • A4690812
    51 MACEWEN DRIVE #5 For Sale
    $235,000
    51 MACEWEN DRIVE #5Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 675 sqft
    • Built 1990
    • A4689838
    51 MAC EWEN DRIVE #14 For Sale
    $285,000
    51 MAC EWEN DRIVE #14Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 595 sqft
    • Built 1990
    • A4690371
    14041 BELLAGIO WAY #214 For Sale
    $700,000
    14041 BELLAGIO WAY #214Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 2089 sqft
    • Built 2006
    • A4689731
    4271 EXPEDITION WAY #103 For Sale
    $260,000
    4271 EXPEDITION WAY #103Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1219 sqft
    • Built 2017
    • A4689541
    4226 FRONTIER LANE #103 For Sale
    $299,000
    4226 FRONTIER LANE #103Osprey, FL 34229
    • 2 bd
    • 2 ba
    • 1219 sqft
    • Built 2018
    • A4687965
    51 MACEWEN DRIVE #12 For Rent
    $2,250
    51 MACEWEN DRIVE #12Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 623 sqft
    • Built 1990
    • A4686127
    14021 BELLAGIO WAY #309 For Sale
    $899,995
    14021 BELLAGIO WAY #309Osprey, FL 34229
    • 3 bd
    • 2.5 ba
    • 2430 sqft
    • Built 2006
    • A4681589
    3621 N POINT ROAD #301 For Sale
    $525,000
    3621 N POINT ROAD #301Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2968 sqft
    • Built 2006
    • A4681290
    409 POINT ROAD #601 For Sale
    $1,250,000
    409 POINT ROAD #601Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2837 sqft
    • Built 2004
    • A4679994
    401 POINT ROAD #1001 For Sale
    $1,995,000
    401 POINT ROAD #1001Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 3355 sqft
    • Built 2003
    • A4679998
    385 N POINT ROAD #304 For Sale
    $1,100,000
    385 N POINT ROAD #304Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 3106 sqft
    • Built 2000
    • A4678422
    401 N POINT ROAD #603 For Sale
    $629,000
    401 N POINT ROAD #603Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2423 sqft
    • Built 2003
    • A4671958
    1811 HIGHLAND ROAD For Sale
    $417,000
    1811 HIGHLAND ROADOsprey, FL 34229
    • 2 bd
    • 2 ba
    • 1725 sqft
    • Built 1997
    • TB8443161
    1801 HIGHLAND ROAD For Sale
    $289,900
    1801 HIGHLAND ROADOsprey, FL 34229
    • 2 bd
    • 2 ba
    • 2125 sqft
    • Built 1999
    • N6140508
    5100 JESSIE HARBOR DRIVE #504 For Rent
    $7,500
    5100 JESSIE HARBOR DRIVE #504Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 2304 sqft
    • Built 2004
    • A4651384
    101 WOODLAND PLACE For Rent
    $6,950
    101 WOODLAND PLACEOsprey, FL 34229
    • 3 bd
    • 2.5 ba
    • 2039 sqft
    • Built 1979
    • A4644465
    3603 POINT ROAD #702 For Sale
    $1,395,000
    3603 POINT ROAD #702Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2904 sqft
    • Built 2007
    • A4642397
    3603 POINT ROAD #602 For Rent
    $5,900
    3603 POINT ROAD #602Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2904 sqft
    • Built 2007
    • A4640065
    385 POINT ROAD #402 For Sale
    $615,000
    385 POINT ROAD #402Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2250 sqft
    • Built 2000
    • A4635708
    409 POINT ROAD #502 For Sale
    $599,000
    409 POINT ROAD #502Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2250 sqft
    • Built 2004
    • A4621353
    14041 BELLAGIO WAY #316 For Rent
    $8,000
    14041 BELLAGIO WAY #316Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 2386 sqft
    • Built 2006
    • A4622973
    401 N POINT ROAD #301 For Sale
    $459,900
    401 N POINT ROAD #301Osprey, FL 34229
    • 3 bd
    • 3 ba
    • 2837 sqft
    • Built 2003
    • A4603773
    51 MAC EWEN DRIVE #1 For Rent
    $2,500
    51 MAC EWEN DRIVE #1Osprey, FL 34229
    • 1 bd
    • 1 ba
    • 623 sqft
    • Built 1990
    • A4589608
    152 NAVIGATION CIRCLE #107 For Rent
    $4,500
    152 NAVIGATION CIRCLE #107Osprey, FL 34229
    • 3 bd
    • 2 ba
    • 1889 sqft
    • Built 2016
    • A4517611
    293 HIDDEN BAY DRIVE #203 For Rent
    $5,000
    293 HIDDEN BAY DRIVE #203Osprey, FL 34229
    • 2 bd
    • 2 ba
    • Built 2000
    • A4410764
    48

    Osprey Searches

    • All Osprey
    • For Sale in Osprey
    • Rentals in Osprey
    • Houses in Osprey
    • Townhouses & Duplexes in Osprey
    • Lots & Land in Osprey
    • Farms & Ranches in Osprey

    Featured Searches

    Advanced Search
    • $200k to $300k Homes
    • $300k to $400k Homes
    • $400k to $500k Homes
    • Acreage
    • Commercial Properties
    • Farms & Ranches
    • Golf Course Homes
    • Homes Listed this Week
    • Homes with 2+ Beds
    • Homes with Pools
    • Large Houses (2k+ sqft)
    • Luxury Condos ($400k+)
    • Multi-Family Homes
    • New Construction
    • Oceanfront Condos
    • Rentals Under $2k
    • Rentals with Pets
    • Under $200k Homes
    • Under $250k Homes
    • Water View Homes
    • Water View Homes

    Popular Cities

    All Cities
    • Miami8657 Listings
    • Orlando5530 Listings
    • ocala4757 Listings
    • Port Charlotte4756 Listings
    • Tampa4503 Listings
    • Kissimmee3841 Listings
    • Sarasota3472 Listings
    • North Port3050 Listings
    • St Petersburg2915 Listings
    • Port St. Lucie2758 Listings