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$460,000 -$10,000 (-2.13%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2,312 Sq. Ft.
  • Updated 5 days ago
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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.

Full Property Details for 1550 Regal Oak Dr

General

  • Price: $460,000
  • Taxes: $3,426 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5150034
  • Updated: 6/29/2026
  • Added to Site: 50 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: Septic Tank
  • 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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— 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
6/29/2026
Price Reduced
$460,000
-2.13%
MLS
6/09/2026
Price Reduced
$470,000
-2.08%
MLS
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
2024
$3,250
—
$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.

Estimate the Cost for 1550 Regal Oak Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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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 $460,000 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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