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$480,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2,312 Sq. Ft.
  • Updated 2 days ago
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Welcome to this beautifully maintained 4 bedroom, 2 bathroom pool home located in the established community of Regal Oak Shores in Kissimmee, Florida. Situated on a spacious oversized lot surrounded by mature oak trees, this property offers privacy, tranquility, and the charm that is hard to find in newer developments. The home features a resurfaced saltwater pool completed in 2026 with warranty, solar panels installed in 2018 that will be fully paid off at closing allowing the new homeowners to enjoy extremely low to nearly zero electric bills, a hybrid water heater, two interior brick fireplaces, an updated kitchen perfect for entertaining, and abundant natural light throughout. Major upgrades include a roof replaced in 2016, AC system updated in 2018, water heater replaced in 2019, drain field replaced in 2018, Hardie board siding installed in 2019, brick sealed in 2021, new pool pump installed in 2022, saltwater system added in 2025, garage door opener and springs replaced in 2024, soffit replacement, and tile flooring throughout the home, providing peace of mind for years to come. Ideally located near the Florida Turnpike, shopping, restaurants, hospitals, Orlando International Airport, and Central Florida's world famous theme parks, this home offers the perfect combination of comfort, convenience, and long term value.

Full Property Details for 1550 Regal Oak Dr

General

  • Price: $480,000
  • Taxes: $3,426 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5150034
  • Updated: 5/16/2026
  • Added to Site: 4 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 3
  • Interior Features: Ceiling Fan(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room, Stone, Wood Burning
  • Appliances: Dishwasher, Range
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Lighting, Salt Water

Exterior

  • Exterior Features: Sidewalk

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34744 - Kissimmee
  • County: Osceola
  • Development Name: 34744 - Kissimmee
  • Subdivision: REGAL OAK SHORES UNIT 4
  • Driving 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
  • Direction Faces: South

Community

  • Community Name: 34744 - Kissimmee

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Private, Public

Structural Information

  • Exterior Const.: Cement Siding, Stone
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,312
  • Sq. Ft. Source: Public Records
  • Year Built: 1983

Lot Features

  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 14,898
  • Lot Size: 14898
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $3,426
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: REGAL OAK SHORES UN 4 PB 2 PG 208 LOT 20
  • Flood Zone Info: X
  • APN: 22629479100010200
  • Property ID: 22629479100010200
  • Block/Lot/Section: 1

Listed by Keller Williams Legacy Realty

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Listing agent

— 1550 Regal Oak Dr —

  • Keller Williams Legacy Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1550 Regal Oak Dr

School District:Osceola County School District
NameGradesDistance
Partin Settlement Elementary School
2434 Remington Boulevard, Kissimmee, FL 34744
PK-53.7 mi
Neptune Middle School
2727 Neptune Road, Kissimmee, FL 34744
6-82.9 mi
Osceola High School
420 South Thacker Avenue, Kissimmee, FL 34741
9-123.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1550 Regal Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/15/2026
Listed
$480,000
84.62%
MLS
5/17/2017
Sold
$260,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1550 Regal Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,426
5%
$236,701
3%
2024
$3,250
2%
$230,031
3%
2023
$3,180
5%
$223,332
6%
2021
$3,021
-1%
$210,513
-3%
2022
$3,046
1%
$216,828
4%
2021
$3,021
7%
$207,607
4%
2018
$2,823
-3%
$199,157
-2%
2019
$2,925
-15%
$202,940
-2%
2017
$3,423
13%
$207,500
23%
2016
$3,042
5%
$169,100
8%
2015
$2,908
57%
$156,900
20%
2014
$1,848
1%
$130,992
1%
2013
$1,821
—
$129,057
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams Legacy Realty

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1550 Regal Oak Drive, Kissimmee, FL 34744 (MLS# S5150034) is a Single Family property with 4 bedrooms and 2 full bathrooms. 1550 Regal Oak Drive is currently listed for $480,000 and was received on May 15, 2026. Want to learn more about 1550 Regal Oak Drive? Do you have questions about finding other Single Family real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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