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For sale
    • Price cut: $100 (2/20)
    $819,900

    14039 Hampshire Bay Cir, Winter Garden, FL 34787

    4beds
    3,801sqft
    : 
    Single Family Residence
    Built in 2006
    0.4 Acres Lot
    $827,300 Zestimate®
    $216/sqft
    $141/mo HOA

    What's special

    Extended loftOversized paved courtyardSolid surface countertopsHigh ceilingsAmple parkingSurround sound systemIrrigation system
    Fully Renovated 4BR Luxury Home | Bay Isle Gated | Private Cinema | Grand Primary Suite | Corner Lot Fully renovated 4-bedroom, 3.5-bath plus additional upstairs half bath, home located in the desirable Bay Isle gated community in Winter Garden. Residents enjoy access to a private lake, park, sidewalks, and gated security. HOA covers landscaping, private roads, amenities, and security. This premium corner-lot property features an oversized paved courtyard with ample space for a future pool and custom outdoor living area, ample parking, irrigation system, rain gutters, and a whole-house water filtration system (owned, no lease). Spacious layout includes open kitchen/family room, living/dining room combo, extended loft, private cinema room with reclining theater seating, 120” screen, short-throw projector, and surround sound system, and enclosed lanai ideal for entertaining. Interior features include porcelain tile flooring in main living areas and kitchen, high ceilings, crown molding, solid wood cabinetry, solid surface countertops, walk-in closets, and showers in all full bathrooms. The grand primary suite on the main level features a spa-style bathroom with jetted soaking tub and dual shower, along with two walk-in closets and an exceptional bonus area with three separate rooms and independent entrance, currently used as additional closets, offering flexible potential for a home office, gym, studio, or private retreat. Recent updates include roof replaced in 2021 and three A/C units (one brand new) for enhanced efficiency and reliability. The floor plan offers: • Primary suite on the main level • Upstairs private suite with bathroom and walk-in closet • Two additional upstairs bedrooms with shared full bathroom • Additional upstairs half bath (powder room) Prime location near Winter Garden Village, new hospital, and just minutes from charming Downtown Winter Garden, with easy access to major highways, theme parks, and Orlando International Airport.
    40 days
    |
    2,510
    |
    88
    |

    Likely to sell faster than

    Zillow last checked: 7 hours ago

    Listing updated: March 11, 2026 at 08:06am

    Listing Provided by:

    Kelly De Lima Perez 407-501-3896,

    SUMMERHILL REALTY GROUP LLC 407-963-8083

    Source: Stellar MLS,MLS#: O6274785MLS LogoOriginating MLS: Orlando Regional

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    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 5
    • Full bathrooms: 3
    • 1/2 bathrooms: 2
    Primary bedroom
    • Features: Walk-In Closet(s)
    • Level: First
    Bedroom 2
    • Features: Built-in Closet
    • Level: Second
    Bedroom 3
    • Features: Built-in Closet
    • Level: Second
    Bedroom 4
    • Features: Built-in Closet
    • Level: Second
    Primary bathroom
    • Level: First
    Bathroom 2
    • Level: Second
    Bathroom 3
    • Level: Second
    Kitchen
    • Level: First
    Living room
    • Level: First
    Media room
    • Level: Second
    Heating
    • Central
    Cooling
    • Central Air
    Appliances
    • Included: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator
    • Laundry: Laundry Room
    Features
    • Attic Fan, Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Walk-In Closet(s)
    • Flooring: Porcelain Tile, Vinyl
    • Doors: French Doors
    • Windows: Window Treatments
    • Has fireplace: No
    Interior area
    • Total structure area: 4,590
    • Total interior livable area: 3,801 sqft
    Video & virtual tour

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage - Attached
    • Attached garage spaces: 2
    Features
    • Levels: Two
    • Stories: 2
    • Exterior features: Irrigation System, Lighting, Rain Gutters
    Lot
    • Size: 0.4 Acres
    Details
    • Parcel number: 342227016200420
    • 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: 2006

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Cable Available, Cable Connected, Sewer Available, Sewer Connected, Water Available, Water Connected

    Community & HOA

    Community
    • Features: Water Access, Gated Community - Guard, Park, Playground, Sidewalks
    • Subdivision: BAY ISLE 48 17
    HOA
    • Has HOA: Yes
    • Services included: Maintenance Grounds, Private Road, Recreational Facilities, Security
    • HOA fee: $141 monthly
    • HOA name: SINDI KLEIN-HAMIL
    • Pet fee: $0 monthly
    Location
    • Region: Winter Garden

    Financial & listing details

    • Price per square foot: $216/sqft
    • Tax assessed value: $706,188
    • Annual tax amount: $11,068
    • Date on market: 1/24/2025
    • Cumulative days on market: 354 days
    • Listing terms: Cash,Conventional,FHA,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Road surface type: Asphalt
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    Estimated market value

    $827,300

    $786,000 - $869,000

    $4,576/mo

    Price history

    Price history
    DateEventPrice
    2/20/2026Price change$819,9000%$216/sqft
    Source: Stellar MLS #O6274785 Report a problem
    2/2/2026Listed for sale$820,000-3.3%$216/sqft
    Source: Stellar MLS #O6274785 Report a problem
    12/3/2025Listing removed$848,000$223/sqft
    Source: Stellar MLS #O6274785 Report a problem
    11/16/2025Price change$848,000-0.1%$223/sqft
    Source: Stellar MLS #O6274785 Report a problem
    10/21/2025Price change$849,000-0.1%$223/sqft
    Source: Stellar MLS #O6274785 Report a problem
    10/15/2025Price change$850,000+0%$224/sqft
    Source: Stellar MLS #O6274785 Report a problem
    10/1/2025Price change$849,900-1.3%$224/sqft
    Source: Stellar MLS #O6274785 Report a problem
    9/28/2025Price change$861,000+0.2%$227/sqft
    Source: Stellar MLS #O6274785 Report a problem
    9/18/2025Price change$859,000-0.1%$226/sqft
    Source: Stellar MLS #O6274785 Report a problem
    9/9/2025Price change$860,000-5.4%$226/sqft
    Source: Stellar MLS #O6274785 Report a problem
    8/20/2025Price change$909,000+4.6%$239/sqft
    Source: Stellar MLS #O6274785 Report a problem
    7/30/2025Price change$869,000-2.2%$229/sqft
    Source: Stellar MLS #O6274785 Report a problem
    7/29/2025Price change$889,000-1.1%$234/sqft
    Source: Stellar MLS #O6274785 Report a problem
    6/26/2025Price change$898,9000%$236/sqft
    Source: Stellar MLS #O6274785 Report a problem
    6/9/2025Price change$899,000-1.7%$237/sqft
    Source: Stellar MLS #O6274785 Report a problem
    5/14/2025Price change$914,900-1.1%$241/sqft
    Source: Stellar MLS #O6274785 Report a problem
    5/5/2025Price change$924,900-0.1%$243/sqft
    Source: Stellar MLS #O6274785 Report a problem
    4/16/2025Price change$925,900-0.5%$244/sqft
    Source: Stellar MLS #O6274785 Report a problem
    4/11/2025Price change$930,900-0.2%$245/sqft
    Source: Stellar MLS #O6274785 Report a problem
    4/7/2025Price change$932,900-0.1%$245/sqft
    Source: Stellar MLS #O6274785 Report a problem
    4/3/2025Price change$933,900-0.1%$246/sqft
    Source: Stellar MLS #O6274785 Report a problem
    3/21/2025Price change$934,900+1.6%$246/sqft
    Source: Stellar MLS #O6274785 Report a problem
    2/10/2025Price change$919,8000%$242/sqft
    Source: Stellar MLS #O6274785 Report a problem
    1/25/2025Listed for sale$920,000+22.7%$242/sqft
    Source: Stellar MLS #O6274785 Report a problem
    2/27/2024Listing removed$749,900+1.3%$197/sqft
    Source: Stellar MLS #A4516734 Report a problem
    1/3/2022Sold$740,000+89.3%$195/sqft
    Source: Public Record Report a problem
    6/28/2006Sold$390,900$103/sqft
    Source: Public Record Report a problem

    Public tax history

    Public tax history
    YearProperty taxesTax assessment
    2024$11,068 +8.6%$685,407 +10%
    2023$10,188 +12.6%$623,097 +10%
    2022$9,046 +25.8%$566,452 +28.1%
    2021$7,191 +2.1%$442,106 +2.9%
    2020$7,045 +3.6%$429,684 +6%
    2019$6,800 +9.5%$405,180 +10%
    2018$6,212 $368,345 +3.4%
    2017$6,212 +3.8%$356,328 +3.9%
    2016$5,987 +1.7%$343,075 -12.2%
    2015$5,887 -11.7%$390,641 +4.6%
    2014$6,668 +29.8%$373,531 +14%
    2013$5,138 -6.6%$327,717 -5.3%
    2012$5,503 -9.6%$346,081 -8.3%
    2011$6,089 -2.6%$377,559 -5.2%
    2010$6,250 $398,476 -4.7%
    2009-- $418,098 -14.5%
    2008$7,709 +5.4%$489,080 +5.2%
    2007$7,317 +391%$465,054 +447.1%
    2006$1,490 +119.3%$85,000 +126.7%
    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

    BuyAbility℠ payment

    Est. payment
    $5,595/mo
    Principal & interest
    $3999
    Property taxes
    $1455
    HOA Fees
    $141
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      Climate risks

      Neighborhood: 34787

      Getting around

      33 / 100
      Car-Dependent
      32 / 100
      Somewhat Bikeable

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