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For sale
    • Price cut: $101K (5/3)
    $2,399,000

    49 Osprey Point Dr, Osprey, FL 34229

    4beds
    3,953sqft
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    Single Family Residence
    Built in 1989
    0.4 Acres Lot
    $-- Zestimate®
    $607/sqft
    $475/mo HOA

    What's special

    Private oasisRetractable window wallsSparkling poolExpansive spaExquisite baths and fixturesTranquil water featuresSoaring vaulted ceilings
    Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.
    240 days
    |
    531
    |
    17
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jonathan Abrams, PLLC 941-232-2868,

    MICHAEL SAUNDERS & COMPANY 941-349-3444

    Source: Stellar MLS,MLS#: A4671762MLS LogoOriginating MLS: Sarasota - Manatee

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Living Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      Bedroom 3
      • Features: Built-in Closet
      • Level: First
      Great room
      • Level: First
      Kitchen
      • Level: First
      Heating
      • Central, Zoned
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Dishwasher, Range, Range Hood, Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Central Vacuum, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
      • Flooring: Concrete
      • Doors: Outdoor Shower, Sliding Doors
      • Windows: Hurricane Shutters/Windows
      • Has fireplace: Yes
      • Fireplace features: Family Room, Living Room
      Interior area
      • Total structure area: 5,227
      • Total interior livable area: 3,953 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Workshop in Garage
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Enclosed, Screened
      • Exterior features: Outdoor Shower, Storage
      • Has private pool: Yes
      • Pool features: Fiber Optic Lighting, In Ground, Salt Water
      • Has spa: Yes
      • Spa features: Heated, In Ground, Other
      • Has view: Yes
      • View description: Lake
      • Has water view: Yes
      • Water view: Lake
      • Waterfront features: Bay/Harbor Front, Lake Front, Lake Privileges, Fishing Pier
      Lot
      • Size: 0.4 Acres
      • Features: Landscaped, Oversized Lot, Above Flood Plain
      • Residential vegetation: Mature Landscaping
      Details
      • Parcel number: 0142060007
      • Zoning: RSF1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary,Custom
      • Property subtype: Single Family Residence
      Materials
      • Block, Concrete, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1989

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Connected, Public, Water Connected
      Green energy
      • Indoor air quality: Whole House Vacuum System

      Community & HOA

      Community
      • Features: Bay/Harbor Front, Dock, Fishing, Water Access, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Restaurant, Tennis Court(s)
      • Security: Gated Community
      • Pet fee: $0 monthly
      • Subdivision: OAKS
      HOA
      • Has HOA: Yes
      • Amenities included: Clubhouse, Fitness Center, Golf Course, Maintenance, Pickleball Court(s), Tennis Court(s)
      • HOA fee: $475 monthly
      • HOA name: The Oaks Club
      • HOA phone: 941-966-2161
      Location
      • Region: Osprey

      Financial & listing details

      • Price per square foot: $607/sqft
      • Tax assessed value: $1,354,900
      • Annual tax amount: $14,206
      • Date on market: 11/13/2025
      • Cumulative days on market: 191 days
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/3/2026Price change$2,399,000-4%$607/sqft
        Source: Stellar MLS #A4671762 Report a problem
        1/29/2026Price change$2,500,000-3.7%$632/sqft
        Source: Stellar MLS #A4671762 Report a problem
        11/13/2025Listed for sale$2,595,000-3.7%$656/sqft
        Source: Stellar MLS #A4671762 Report a problem
        9/1/2025Listing removed$2,695,000$682/sqft
        Source: Stellar MLS #A4642364 Report a problem
        7/24/2025Price change$2,695,000-1.8%$682/sqft
        Source: Stellar MLS #A4642364 Report a problem
        6/11/2025Price change$2,745,000-1.8%$694/sqft
        Source: Stellar MLS #A4642364 Report a problem
        4/3/2025Price change$2,795,000-6.7%$707/sqft
        Source: Stellar MLS #A4642364 Report a problem
        3/5/2025Listed for sale$2,995,000+274.4%$758/sqft
        Source: Stellar MLS #A4642364 Report a problem
        6/4/2019Sold$800,000-5.9%$202/sqft
        Source: Public Record Report a problem
        4/17/2019Pending sale$850,000$215/sqft
        Source: Coldwell Banker Residential Real Estate - Longboat Key #A4431344 Report a problem
        3/29/2019Listed for sale$850,000+49.1%$215/sqft
        Source: COLDWELL BANKER RES R E #A4431344 Report a problem
        7/15/1998Sold$570,000+14.6%$144/sqft
        Source: Public Record Report a problem
        7/5/1996Sold$497,500$126/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$14,702 +3.5%$997,918 +10%
        2024$14,206 +14.7%$907,198 +10%
        2023$12,389 +4.6%$824,725 +10%
        2022$11,844 +45%$749,750 +21.2%
        2021$8,167 +1.7%$618,500 +3.9%
        2020$8,028 +0.7%$595,200 -5.8%
        2019$7,970 $631,780 +1.9%
        2018$7,970 +2%$620,000 -0.9%
        2017$7,814 -4.9%$625,900 +2%
        2016$8,215 $613,500 -6.1%
        2015$8,215 +0.3%$653,300 +9.4%
        2014$8,187 +0%$597,081
        2013$8,187 +2.7%$597,081 +1.7%
        2012$7,971 +4.7%$587,100 +3%
        2011$7,616 -16.9%$570,000 -14.7%
        2010$9,162 +10.4%$668,265 +2.7%
        2009$8,298 $650,696 +0.1%
        2008$8,298 +0.6%$650,046 +3%
        2007$8,246 $631,113 +2.5%
        2006-- $615,720 +3%
        2005-- $597,786 +3%
        2004$8,709 -1.2%$580,375 +1.9%
        2003$8,815 +2.4%$569,553 +2.4%
        2002$8,606 +7.4%$556,204 +1.6%
        2001$8,014 +2.7%$547,445 +3%
        2000$7,805 $531,500
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34229

        Getting around

        5 / 100
        Car-Dependent
        34 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Laurel Nokomis Elementary
        • Middle: Sarasota Middle
        • High: Venice Senior High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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