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For sale
    • $4,790,000

    101 Osprey Point Dr, Osprey, FL 34229

    4beds
    5,087sqft
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    Single Family Residence
    Built in 1985
    0.93 Acres Lot
    $-- Zestimate®
    $942/sqft
    $950/mo HOA

    What's special

    Dramatic fireplacesLakefront terraceLakefront livingTranquil resort-style settingOversized granite-tiled circular driveUpdated guest bathsCorian countertops
    Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.
    45 days
    |
    357
    |
    10
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    Zillow last checked:

    Listing updated:

    Listed by:

    Joel Schemmel 941-587-4894,

    DOUGLAS ELLIMAN 941-867-6199

    Source: Stellar MLS,MLS#: A4694716MLS LogoOriginating MLS: Sarasota - Manatee

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Living Room
      Primary bedroom
      • Features: En Suite Bathroom, Walk-In Closet(s)
      • Level: First
      • Area: 550 Square Feet
      • Dimensions: 25x22
      Bedroom 2
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 180 Square Feet
      • Dimensions: 15x12
      Bedroom 3
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Bedroom 4
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Primary bathroom
      • Features: Bidet, Shower No Tub, Water Closet/Priv Toilet
      • Level: First
      Dining room
      • Level: First
      • Area: 375 Square Feet
      • Dimensions: 15x25
      Family room
      • Level: First
      • Area: 400 Square Feet
      • Dimensions: 20x20
      Kitchen
      • Level: First
      • Area: 368 Square Feet
      • Dimensions: 16x23
      Library
      • Features: Bar
      • Level: First
      • Area: 520 Square Feet
      • Dimensions: 20x26
      Living room
      • Level: First
      Heating
      • Central, Electric, Zoned
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Chair Rail, Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
      • Flooring: Brick/Stone, Ceramic Tile, Parquet
      • Doors: French Doors
      • Windows: Blinds, Window Treatments, Hurricane Shutters
      • Has fireplace: Yes
      • Fireplace features: Family Room, Living Room, Other Room, Master Bedroom, Wood Burning
      Interior area
      • Total structure area: 6,841
      • Total interior livable area: 5,087 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Off Street
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      • Details: Garage Dimensions: 22x35
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Front Porch, Rear Porch
      • Exterior features: Irrigation System, Lighting, Private Mailbox
      • Has private pool: Yes
      • Pool features: Gunite, In Ground
      • Has spa: Yes
      • Spa features: In Ground
      • Has view: Yes
      • View description: Water, Lake
      • Has water view: Yes
      • Water view: Water,Lake
      • Waterfront features: Lake Front
      Lot
      • Size: 0.93 Acres
      • Features: Cul-De-Sac, In County, Landscaped
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Parcel number: 0142050008
      • Zoning: RSF1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Custom,Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1985

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public, Well
      • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Well, Street Lights, Water Connected

      Community & HOA

      Community
      • Features: Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)
      • Security: Gated Community, Security System Owned, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: THE OAKS
      HOA
      • Has HOA: Yes
      • Amenities included: Clubhouse, Fitness Center, Gated, Handicap Modified, Pool, Recreation Facilities, Security, Tennis Court(s)
      • Services included: 24-Hour Guard, Community Pool, Manager, Private Road, Security
      • HOA fee: $950 monthly
      • HOA name: Asset Management/ Hope Root
      • HOA phone: 813-607-2220
      Location
      • Region: Osprey

      Financial & listing details

      • Price per square foot: $942/sqft
      • Tax assessed value: $2,008,500
      • Annual tax amount: $12,940
      • Date on market: 5/26/2026
      • Cumulative days on market: 46 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/26/2026Listed for sale$4,790,000-4.2%$942/sqft
        Source: Stellar MLS #A4694716 Report a problem
        3/25/2026Listing removed$5,000,000$983/sqft
        Source: Stellar MLS #A4664424 Report a problem
        9/17/2025Listed for sale$5,000,000-5.7%$983/sqft
        Source: Stellar MLS #A4664424 Report a problem
        6/11/2025Listing removed$5,300,000$1,042/sqft
        Source: Stellar MLS #A4639897 Report a problem
        3/23/2025Listed for sale$5,300,000+307.7%$1,042/sqft
        Source: Stellar MLS #A4639897 Report a problem
        2/26/2019Listing removed$1,300,000$256/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420459 Report a problem
        12/11/2018Pending sale$1,300,000$256/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420459 Report a problem
        11/30/2018Listed for sale$1,300,000$256/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker #A4420459 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$12,813 +4%$1,032,181 +2.9%
        2024$12,315 +3.3%$1,003,091 +3%
        2023$11,925 +3%$973,875 +3%
        2022$11,578 +0.9%$945,510 +3%
        2021$11,472 -0.6%$917,971 +1.4%
        2020$11,541 -13.5%$905,297 -11.4%
        2019$13,349 $1,021,600 +4.7%
        2018$13,349 +4.4%$976,000 +3.8%
        2017$12,784 -3.4%$940,500 +2.6%
        2016$13,237 $916,500 -6%
        2015$13,237 +13.3%$975,100 -4.8%
        2014$11,684 -19.6%$1,024,400
        2013$14,533 +4%$1,024,400 +3.4%
        2012$13,969 +12.5%$991,090 +11%
        2011$12,417 -12.2%$892,900 -10.2%
        2010$14,148 -19.9%$994,400 -14%
        2009$17,668 $1,156,000 -14.6%
        2008$17,668 -2.4%$1,353,200 -1.9%
        2007$18,109 $1,379,700 -16.5%
        2006-- $1,653,200 +15.9%
        2005-- $1,427,000 +10.9%
        2004$19,518 +1.9%$1,286,700 +5.3%
        2003$19,161 +13.1%$1,221,900 +12.7%
        2002$16,943 +19.1%$1,084,600 +13.6%
        2001$14,224 +25.8%$954,700 +23.9%
        2000$11,304 $770,533
        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

        3 / 100
        Car-Dependent
        33 / 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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