1550 REGAL OAK DRIVE
Kissimmee, FL, 34744 $ 460,000
Bedrooms4 Baths2.0 Sq 2,312 Monthly Estimate*
$ 2,904
for $460,000 with 4 bedrooms and 2 full baths. This 2,312 square foot home was built in 1983 on a lot size of 0.34.
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.
See more
FeaturesGeneralSewer Septic Tank
Heating Central
Cooling Central Air
Utilities Private Public
Roof Shingle
Appliances Dishwasher Range
Zoning ORS1
Garage Spaces 2
Pool Features In Ground Lighting Salt Water
Construction Materials Cement Siding Stone
Year Built 1983
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Osceola
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name REGAL OAK SHORES UNIT 4
Facing Direction South
Garage Y/N true
Total Rooms 3
Full Baths 2
Status Pending
Directions From the intersection of Neptune Rd and Kings Hwy go south on Kings Hwy. Turn right on Regal Oak Dr house will be on your left
City KISSIMMEE
Senior Community Y/N false
MLS Area 34744 - Kissimmee
Lot Size Units Square Feet
Lot Size Square Feet 14898
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Land Lease Y/N false
Tax Annual Amount 3426
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/S5150034
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active Under Contract
Occupancy Type Owner
Tax Lot 20
Legal Description REGAL OAK SHORES UN 4 PB 2 PG 208 LOT 20
Minimum Lease 6 Months
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
In Law Suite YN false
See more
InteriorInterior Amenities Ceiling Fan(s)
Flooring Ceramic Tile
Furnished Y/N Unfurnished
Fireplace Features Living Room Stone Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 2
See more
ExteriorExterior Amenities Sidewalk
Water Source Public
Lot Size Area 14898
Foundation Details Slab
Building Area Total 2795
Lot Size Acres 0.34
Road Surface Type Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
See more
* Excluded FeaturesList ByKeller Williams Legacy RealtyBroker
santacruzgroup@kw.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $2,904
- Monthly Property Taxes
- $286
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Kissimmee, FL
Average List Price $509,848
Percent of Sale Price 11%
About Kissimmee, FL 69,545 Population
45% Since 2002
$ 38,806 Median Income
36.6 Median Age
32% Households with Children
Trends Information provided by ATTOM Data Solutions.
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/29/2026 | $460,000 | -2.13% | Price Down |
| 6/9/2026 | $470,000 | -2.08% | Price Down |
| 5/15/2026 | $480,000 | | Listed Price |