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Accepting backups
  • Price cut: $11K (8/29)
    $939,000

    434 VALLEY VIEW DRIVE, WINTER GARDEN, FL 34787

    3beds
    2,765sqft
    : 
    $6,426/mo
    Get pre-qualified
    Single Family Residence
    Built in 2000
    0.33 Acres Lot
    $-- Zestimate®
    $340/sqft
    $83/mo HOA

    What's special

    Center islandBeautifully renovated kitchenExpansive loftTwo-and-a-half bathsThree bedroomsCustom board-and-batten millworkSparkling pool
    Under contract-accepting backup offers. Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.
    56 days
    1,886
    159

    Zillow last checked:

    Listing updated:

    Listed by:

    Jennifer Coon 321-948-8056,

    LAKESIDE REALTY WINDERMERE INC 407-876-5575

    Source: Stellar MLS,MLS#: O6425087MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 280 Square Feet
      • Dimensions: 20x14
      Kitchen
      • Level: First
      • Area: 231 Square Feet
      • Dimensions: 21x11
      Living room
      • Level: First
      • Area: 434 Square Feet
      • Dimensions: 31x14
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
      • Laundry: Inside
      Features
      • Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
      • Flooring: Carpet, Tile, Hardwood
      • Doors: French Doors
      • Windows: Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 3,602
      • Total interior livable area: 2,765 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Driveway, Garage Door Opener, Garage Faces Side, Oversized
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Front Porch, Patio, Porch
      • Exterior features: Irrigation System, Lighting, Rain Gutters
      • Has private pool: Yes
      • Pool features: In Ground
      Lot
      • Size: 0.33 Acres
      • Features: Landscaped
      • Residential vegetation: Oak Trees, Trees/Landscaped
      Details
      • Parcel number: 142227194200410
      • Zoning: R-1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Wood Frame, Wood Siding
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2000

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected, Public, Street Lights, Underground Utilities

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: COURTLEA OAKS PH 01A
      HOA
      • Has HOA: Yes
      • HOA fee: $83 monthly
      • HOA name: Tracy Durham
      • HOA phone: 407-317-5252
      Location
      • Region: Winter Garden

      Financial & listing details

      • Price per square foot: $340/sqft
      • Tax assessed value: $565,706
      • Annual tax amount: $4,087
      • Date on market: 7/16/2026
      • Cumulative days on market: 48 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
        8/29/2026Price change$939,000-1.2%$340/sqft
        Source: Stellar MLS #O6425087 Report a problem
        7/31/2026Listed for sale$950,000$344/sqft
        Source: Stellar MLS #O6425087 Report a problem
        7/24/2026Contingent$950,000$344/sqft
        Source: Stellar MLS #O6425087 Report a problem
        7/16/2026Listed for sale$950,000+216.8%$344/sqft
        Source: Stellar MLS #O6425087 Report a problem
        8/15/2013Listing removed$299,900$108/sqft
        Source: Christy Clark-Weber #o5015334 Report a problem
        8/1/2013Listed for sale$299,900$108/sqft
        Source: Christy Clark-Weber #o5015334 Report a problem
        8/28/2011Listing removed$299,900+9.1%$108/sqft
        Source: Southern Heritage Realty, Inc. #o5007435 Report a problem
        5/26/2011Sold$275,000-8.3%$99/sqft
        Source: Stellar MLS #O5015334 Report a problem
        9/30/2010Listed for sale$299,900+33.3%$108/sqft
        Source: Southern Heritage Reatly, Inc. #o5007435 Report a problem
        9/20/2001Sold$225,000+379.7%$81/sqft
        Source: Public Record Report a problem
        3/26/1999Sold$46,900+17%$17/sqft
        Source: Public Record Report a problem
        9/25/1995Sold$40,078$14/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$3,881 +4.2%$283,163 +3.4%
        2023$3,723 +3.1%$273,945 +3%
        2022$3,610 +1.5%$265,966 +3%
        2021$3,555 +0.8%$258,219 +1.4%
        2020$3,527 +1%$254,654 +2.3%
        2019$3,492 +0.9%$248,929 +1.9%
        2018$3,459 $244,288 -16.5%
        2017$3,459 +2.7%$292,707 -4.1%
        2016$3,367 +0.2%$305,265 +8.6%
        2015$3,358 -2.4%$281,080 +12.8%
        2014$3,440 +2.4%$249,205 +9.6%
        2013$3,359 +0.5%$227,454 +1%
        2012$3,344 -18.5%$225,259 -1.5%
        2011$4,103 +17.6%$228,738 -4.5%
        2010$3,490 $239,539 -15.2%
        2009-- $282,554 -21.2%
        2008$3,565 -2.4%$358,365 -7.1%
        2007$3,652 -7.8%$385,675 +19.9%
        2006$3,960 0%$321,681 +28.6%
        2005$3,961 +15.2%$250,156 +12.8%
        2004$3,438 +0.2%$221,730 +0.8%
        2003$3,432 +2.8%$219,981 +5.8%
        2002$3,339 $208,000
        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.
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        Climate risks

        Neighborhood: 34787

        Getting around

        42 / 100
        Car-Dependent
        63 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Dillard Street Elem
        • Middle: Lakeview 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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