Skip main navigation
Accepting backups
  • Price cut: $10K (6/29)
    $460,000

    1550 REGAL OAK DRIVE, KISSIMMEE, FL 34744

    4beds
    2,312sqft
    : 
    $2,938/mo
    Get pre-qualified
    Single Family Residence
    Built in 1983
    0.34 Acres Lot
    $453,800 Zestimate®
    $199/sqft
    $-- HOA

    What's special

    Private poolResurfaced saltwater poolMature oak treesSoffit replacementSealed brick exteriorOversized homesitesOversized lot
    Under contract-accepting backup offers. Welcome to one of the best opportunities in Regal Oak Shores, one of Kissimmee's most established communities, where oversized homesites, mature oak trees, and timeless charm create a setting that is increasingly difficult to find. This beautifully maintained 4 bedroom, 2 bathroom pool home sits on a spacious .34 acre lot and offers over 2,300 square feet of comfortable living space filled with natural light. Designed for both everyday living and entertaining, the home features an updated kitchen, two stunning wood burning brick fireplaces, ceramic tile throughout, and a resurfaced saltwater pool completed in 2026 with warranty. The seller is paying off the solar panel system at closing, allowing the new owner to enjoy exceptionally low to nearly zero electric bills while benefiting from additional major upgrades including a 2016 roof, 2018 HVAC system, 2019 hybrid water heater, 2018 drain field replacement, 2019 Hardie Board siding, sealed brick exterior, new pool pump, saltwater system, updated garage door opener and springs, and soffit replacement, providing years of peace of mind. Ideally located just minutes from the Florida Turnpike, Orlando International Airport, Lake Nona Medical City, shopping, restaurants, hospitals, and Central Florida's world famous attractions including Disney and Universal, this home combines location, value, energy efficiency, and lifestyle in one exceptional package. Homes in Regal Oak Shores with this level of upgrades, a private pool, oversized lot, and no HOA rarely become available, making this a unique opportunity you do not want to miss.
    90 days
    |
    90
    |
    1
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Maria Santacruz 407-552-8213,

    KELLER WILLIAMS LEGACY REALTY 407-855-2222

    Source: Stellar MLS,MLS#: S5150034MLS LogoOriginating MLS: Osceola

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 204 Square Feet
      • Dimensions: 12x17
      Kitchen
      • Level: First
      • Area: 204 Square Feet
      • Dimensions: 17x12
      Living room
      • Level: First
      • Area: 210 Square Feet
      • Dimensions: 14x15
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Range
      • Laundry: Laundry Room
      Features
      • Ceiling Fan(s)
      • Flooring: Ceramic Tile
      • Has fireplace: Yes
      • Fireplace features: Living Room, Stone, Wood Burning
      Interior area
      • Total structure area: 2,795
      • Total interior livable area: 2,312 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Exterior features: Sidewalk
      • Has private pool: Yes
      • Pool features: In Ground, Lighting, Salt Water
      Lot
      • Size: 0.34 Acres
      Details
      • Parcel number: 022629479100010200
      • Zoning: ORS1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Cement Siding, Stone
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1983

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Private, Public

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: REGAL OAK SHORES UNIT 4
      HOA
      • Has HOA: No
      Location
      • Region: Kissimmee

      Financial & listing details

      • Price per square foot: $199/sqft
      • Tax assessed value: $392,900
      • Annual tax amount: $3,426
      • Date on market: 5/15/2026
      • Cumulative days on market: 55 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Road surface type: Asphalt

        Estimated market value

        $453,800

        $431,000 - $476,000

        $3,281/mo

        Price history

        DateEventPrice
        8/11/2026Listed for sale$460,000$199/sqft
        Source: Stellar MLS #S5150034 Report a problem
        7/8/2026Contingent$460,000$199/sqft
        Source: Stellar MLS #S5150034 Report a problem
        7/7/2026Pending sale$460,000$199/sqft
        Source: Stellar MLS #S5150034 Report a problem
        6/29/2026Price change$460,000-2.1%$199/sqft
        Source: Stellar MLS #S5150034 Report a problem
        6/9/2026Price change$470,000-2.1%$203/sqft
        Source: Stellar MLS #S5150034 Report a problem
        5/15/2026Listed for sale$480,000+84.6%$208/sqft
        Source: Stellar MLS #S5150034 Report a problem
        5/19/2017Sold$260,000-3.1%$112/sqft
        Source: Public Record Report a problem
        9/10/2016Listed for sale$268,300+7.8%$116/sqft
        Source: LATITUDE 28 REAL ESTATE BROKER #S4835990 Report a problem
        4/28/2016Listing removed$249,000$108/sqft
        Source: LATITUDE 28 REAL ESTATE BROKER #S4820644 Report a problem
        3/8/2016Listed for sale$249,000+60.6%$108/sqft
        Source: LATITUDE 28 REAL ESTATE BROKER #S4820644 Report a problem
        4/13/2015Sold$155,000-18%$67/sqft
        Source: Public Record Report a problem
        4/7/2015Pending sale$189,080-14.2%$82/sqft
        Source: CARRINGTON REAL ESTATE SERVICE #S4807089 Report a problem
        11/14/2014Listed for sale$220,480$95/sqft
        Source: Carrington Real Estate Service #S4807089 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,426 +5.4%$392,900 +3.5%
        2024$3,250 +2.2%$379,500 +6%
        2023$3,180 +4.4%$358,100 +20.4%
        2022$3,046 +0.8%$297,500 +16.7%
        2021$3,021 +1.7%$255,000 +5.8%
        2020$2,970 +1.5%$241,000 +5.2%
        2019$2,925 $229,100 +15%
        2018$2,925 +3.6%$199,157 -4%
        2017$2,823 -17.5%$207,500 +22.7%
        2016$3,423 +12.5%$169,100 +7.8%
        2015$3,042 +64.6%$156,900 +19.8%
        2014$1,848 $130,992 +1.5%
        2013-- $129,057 +1.7%
        2012-- $126,900 -4.9%
        2011-- $133,500 -5%
        2010-- $140,500 -17%
        2009-- $169,300 -30.5%
        2008-- $243,600 -3%
        2007-- $251,200 +15.1%
        2006-- $218,200 +28.4%
        2005-- $169,900 +17.6%
        2004-- $144,500
        2003-- $144,500 +8.2%
        2002$1,771 +2%$133,522 +1.6%
        2001$1,736 +1.5%$131,419 +3%
        2000$1,710 $127,591
        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 34744

        Getting around

        1 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        32 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes