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For sale
    • Price cut: $155K (6/13)
    $2,995,000

    14401 MASTHEAD DRIVE, OSPREY, FL 34229

    3beds
    2,665sqft
    : 
    $20,046/mo
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    Single Family Residence
    Built in 2017
    0.44 Acres Lot
    $-- Zestimate®
    $1,124/sqft
    $643/mo HOA

    What's special

    Private dock with liftWraparound windowsExpansive covered lanaiTwo additional en-suite bedroomsPocketing impact slidersDramatic great roomDen or office
    Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
    63 days
    |
    580
    |
    31
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Mackenzie Longueuil 941-961-4023,

    MICHAEL SAUNDERS & COMPANY 941-951-6660

    Source: Stellar MLS,MLS#: A4684834MLS LogoOriginating MLS: Sarasota - Manatee

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Den/Library/Office
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 285 Square Feet
      • Dimensions: 15x19
      Bedroom 2
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 180 Square Feet
      • Dimensions: 12x15
      Bedroom 3
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 195 Square Feet
      • Dimensions: 15x13
      Primary bathroom
      • Features: Dual Sinks
      • Level: First
      • Area: 150 Square Feet
      • Dimensions: 15x10
      Balcony porch lanai
      • Level: First
      • Area: 570 Square Feet
      • Dimensions: 19x30
      Den
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 11x12
      Dining room
      • Level: First
      • Area: 165 Square Feet
      • Dimensions: 11x15
      Great room
      • Features: Built-In Shelving
      • Level: First
      • Area: 494 Square Feet
      • Dimensions: 19x26
      Kitchen
      • Features: Kitchen Island, Pantry
      • Level: First
      • Area: 240 Square Feet
      • Dimensions: 15x16
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: Bar Fridge, Oven, Convection Oven, Cooktop, Dishwasher, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)
      • Flooring: Marble, Tile
      • Doors: French Doors, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors
      • Has fireplace: Yes
      • Fireplace features: Electric, Living Room
      Interior area
      • Total structure area: 3,984
      • Total interior livable area: 2,665 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      • Details: Garage Dimensions: 21x20
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Screened
      • Exterior features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, Boat Slip
      • Has private pool: Yes
      • Pool features: Deck, Heated, In Ground, Lap, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Solar Heat
      • Has spa: Yes
      • Spa features: Heated
      • Has view: Yes
      • View description: Water, Bay/Harbor - Full
      • Has water view: Yes
      • Water view: Water,Bay/Harbor - Full
      • Waterfront features: Bay/Harbor, Bay/Harbor Access, Lift
      • Body of water: LITTLE SARASOTA BAY
      Lot
      • Size: 0.44 Acres
      • Features: Cul-De-Sac, Flood Insurance Required
      • Residential vegetation: Trees/Landscaped
      Details
      • Parcel number: 0148150048
      • Zoning: RSF1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Stem Wall
      • Roof: Metal
      Condition
      • Completed
      • New construction: No
      • Year built: 2017

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Solar, Water Connected

      Community & HOA

      Community
      • Features: Dock, Water Access, Buyer Approval Required, Deed Restrictions, Golf Carts OK, Sidewalks
      • Security: Closed Circuit Camera(s), Gated Community, Security System
      • Pet fee: $0 monthly
      • Subdivision: BAYSIDE
      HOA
      • Has HOA: Yes
      • Amenities included: Gated
      • Services included: Common Area Taxes, Reserve Fund, Maintenance Grounds, Manager, Private Road
      • HOA fee: $643 monthly
      • HOA name: Bayside Community Association, Inc.
      • HOA phone: 941-460-5560
      Location
      • Region: Osprey

      Financial & listing details

      • Price per square foot: $1,124/sqft
      • Tax assessed value: $2,501,700
      • Annual tax amount: $874
      • Date on market: 3/5/2026
      • Cumulative days on market: 128 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/13/2026Price change$2,995,000-4.9%$1,124/sqft
        Source: Stellar MLS #A4684834 Report a problem
        5/27/2026Listed for sale$3,150,000$1,182/sqft
        Source: Stellar MLS #A4684834 Report a problem
        5/8/2026Listing removed$3,150,000$1,182/sqft
        Source: Stellar MLS #A4684834 Report a problem
        5/1/2026Price change$3,150,000-3.1%$1,182/sqft
        Source: Stellar MLS #A4684834 Report a problem
        3/6/2026Listed for sale$3,250,000+16.3%$1,220/sqft
        Source: Stellar MLS #A4684834 Report a problem
        6/16/2021Listing removed--
        Source: Stellar MLS #A4499155 Report a problem
        5/17/2021Price change$2,795,000-1.9%$1,049/sqft
        Source: Stellar MLS #A4499155 Report a problem
        4/30/2021Listed for sale$2,850,000+375%$1,069/sqft
        Source: Stellar MLS #A4499155 Report a problem
        12/30/2016Sold$600,000$225/sqft
        Source: Stellar MLS #A4170759 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$874 +11.8%$1,295,472 +2.9%
        2024$782 +12.2%$1,258,962 +3%
        2023$697 +5.1%$1,222,293 +3%
        2022$664 +22.6%$1,186,692 +3%
        2021$541 +4%$1,152,128 +1.4%
        2020$520 +7.4%$1,136,221 +2.3%
        2019$484 $1,110,675 +1.9%
        2018$484 +6.5%$1,089,966 +131.1%
        2017$455 $471,700 -15.5%
        2016-- $558,200
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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

        13 / 100
        Car-Dependent
        36 / 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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