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For sale
    • Price cut: $15K (8/21)
    $870,000

    14411 HAMPSHIRE BAY CIRCLE, WINTER GARDEN, FL 34787

    4beds
    4,010sqft
    : 
    $5,940/mo
    Get pre-qualified
    Single Family Residence
    Built in 2005
    0.3 Acres Lot
    $-- Zestimate®
    $217/sqft
    $182/mo HOA

    What's special

    Private oasisAdditional half bathGenerous center islandCommanding gourmet kitchenTheater seatingBuilt-in microwaveDolby surround sound
    Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
    83 days
    3,845
    244

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Julie Bettosini, PA 321-689-9594,

    STOCKWORTH REALTY GROUP 407-909-5900

    Source: Stellar MLS,MLS#: O6413972MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 3
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Living Room, Utility Room, Loft, Media Room
      Primary bedroom
      • Features: Ceiling Fan(s), Dual Sinks, En Suite Bathroom, Exhaust Fan, Makeup/Vanity Space, Tub with Separate Shower Stall, Water Closet/Priv Toilet, Walk-In Closet(s)
      • Level: First
      • Area: 272 Square Feet
      • Dimensions: 17x16
      Bedroom 2
      • Features: Ceiling Fan(s), En Suite Bathroom, Tub With Shower, Walk-In Closet(s)
      • Level: Second
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Bedroom 3
      • Features: Ceiling Fan(s), En Suite Bathroom, Exhaust Fan, Jack & Jill Bathroom, Linen Closet
      • Level: Second
      • Area: 168 Square Feet
      • Dimensions: 14x12
      Bedroom 4
      • Features: Ceiling Fan(s), En Suite Bathroom, Jack & Jill Bathroom, Split Vanities, Tub With Shower, Walk-In Closet(s)
      • Level: Second
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Balcony porch lanai
      • Level: First
      • Area: 342 Square Feet
      • Dimensions: 19x18
      Balcony porch lanai
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 130 Square Feet
      • Dimensions: 13x10
      Dinette
      • Level: First
      • Area: 90 Square Feet
      • Dimensions: 10x9
      Dining room
      • Level: First
      • Area: 144 Square Feet
      • Dimensions: 12x12
      Family room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 288 Square Feet
      • Dimensions: 18x16
      Kitchen
      • Features: Breakfast Bar, Pantry, Kitchen Island, Stone Counters
      • Level: First
      • Area: 266 Square Feet
      • Dimensions: 19x14
      Laundry
      • Level: First
      • Area: 56 Square Feet
      • Dimensions: 8x7
      Living room
      • Level: First
      • Area: 176 Square Feet
      • Dimensions: 16x11
      Loft
      • Level: Second
      • Area: 252 Square Feet
      • Dimensions: 21x12
      Media room
      • Level: Second
      • Area: 273 Square Feet
      • Dimensions: 21x13
      Office
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 156 Square Feet
      • Dimensions: 13x12
      Heating
      • Central, Electric, Heat Pump
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Ceiling Fan(s), Crown Molding, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Carpet, Laminate, Tile
      • Doors: French Doors, Outdoor Shower
      • Has fireplace: No
      Interior area
      • Total structure area: 5,049
      • Total interior livable area: 4,010 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Side, Split Garage
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Patio, Rear Porch, Screened
      • Exterior features: Irrigation System, Outdoor Shower, Sidewalk
      • Has private pool: Yes
      • Pool features: Gunite, In Ground, Salt Water, Screen Enclosure, Tile
      • Has spa: Yes
      • Spa features: In Ground
      • Waterfront features: Lake Privileges, Fishing Pier
      • Body of water: BLACK LAKE
      Lot
      • Size: 0.3 Acres
      • Dimensions: 100 x 130
      • Features: City Lot, Level, Sidewalk
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Parcel number: 342227016200050
      • Zoning: R-1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2005
      Details
      • Builder name: Toll Orlando LP

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Street Lights, Underground Utilities, Water Connected

      Community & HOA

      Community
      • Features: Dock, Water Access, Association Recreation - Owned, Deed Restrictions, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
      • Security: Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: BAY ISLE 48 17
      HOA
      • Has HOA: Yes
      • Amenities included: Gated, Park, Playground
      • Services included: Private Road, Recreational Facilities
      • HOA fee: $182 monthly
      • HOA name: Bay Isle at Black Lake Homeowners Assn: c/o HMI
      • HOA phone: 407-392-1533
      Location
      • Region: Winter Garden

      Financial & listing details

      • Price per square foot: $217/sqft
      • Tax assessed value: $785,145
      • Annual tax amount: $11,923
      • Date on market: 6/5/2026
      • Cumulative days on market: 84 days
      • Listing terms: Cash,Conventional,VA Loan
      • 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
        8/21/2026Price change$870,000-1.7%$217/sqft
        Source: Stellar MLS #O6413972 Report a problem
        7/24/2026Price change$885,000-1.1%$221/sqft
        Source: Stellar MLS #O6413972 Report a problem
        6/6/2026Listed for sale$895,000+5.3%$223/sqft
        Source: Stellar MLS #O6413972 Report a problem
        8/18/2022Sold$850,000-2.2%$212/sqft
        Source: Public Record Report a problem
        7/22/2022Pending sale$869,000$217/sqft
        Source: Stellar MLS #O6042992 Report a problem
        7/14/2022Listed for sale$869,000+47.3%$217/sqft
        Source: Stellar MLS #O6042992 Report a problem
        10/2/2020Sold$590,000-3.3%$147/sqft
        Source: Public Record Report a problem
        8/3/2020Pending sale$609,900$152/sqft
        Source: RE/MAX 200 REALTY #O5871496 Report a problem
        7/23/2020Price change$609,900-3.2%$152/sqft
        Source: RE/MAX 200 REALTY #O5871496 Report a problem
        6/16/2020Listed for sale$629,900+29.9%$157/sqft
        Source: RE/MAX 200 REALTY #O5871496 Report a problem
        8/17/2017Sold$484,999-2.8%$121/sqft
        Source: Public Record Report a problem
        5/3/2017Listing removed$499,000$124/sqft
        Source: FLORIDA IN MOTION REALTY INC #S4845537 Report a problem
        4/28/2017Listed for sale$499,000+24.8%$124/sqft
        Source: FLORIDA IN MOTION REALTY INC #S4845537 Report a problem
        12/11/2012Sold$400,000-9.3%$100/sqft
        Source: Public Record Report a problem
        2/28/2012Listed for sale$441,000-31.6%$110/sqft
        Source: Keller Williams Classic Realty #O5088197 Report a problem
        8/27/2007Sold$645,000+40.2%$161/sqft
        Source: Public Record Report a problem
        9/26/2005Sold$460,100$115/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$11,337 +3.5%$750,540 +3%
        2023$10,958 +46.6%$728,680 +43.4%
        2022$7,476 +1.3%$508,072 +3%
        2021$7,378 +18.1%$493,274 +17.3%
        2020$6,247 +0.9%$420,546 +2.3%
        2019$6,193 +0.8%$411,091 +1.9%
        2018$6,143 $403,426 +3%
        2017$6,143 +7.2%$391,665 +3.1%
        2016$5,730 +0.1%$379,944 -12.5%
        2015$5,723 -2.4%$434,155 +6.3%
        2014$5,863 +2.3%$408,536 +13.1%
        2013$5,732 -6.6%$361,180 -5.3%
        2012$6,137 -9.4%$381,572 -8.2%
        2011$6,773 -1.2%$415,735 -4%
        2010$6,853 $433,192 -5%
        2009-- $456,210 -14.5%
        2008$7,800 -0.3%$533,544 -13.3%
        2007$7,827 -7.9%$615,259 +20.7%
        2006$8,499 +1150.5%$509,764 +1259.4%
        2005$680 +8.4%$37,500 +7.1%
        2004$627 -1.9%$35,000
        2003$639 +0.1%$35,000
        2002$639 $35,000
        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.
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        Climate risks

        Neighborhood: 34787

        Getting around

        30 / 100
        Car-Dependent
        33 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: SunRidge Elementary
        • Middle: SunRidge Middle
        • High: West Orange 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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