Recently Viewed Properties
See This Home
Save This Listing
Close

$460,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2,312 Sq. Ft.
  • Updated 5 days ago
See This Home
Save This Home
See This Home
Save This Home
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

  • Sold For: $460,000
  • Taxes: $3,426 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5150034
  • Added to Site: 98 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
  • Living Area: 2,312 Sq. Ft.
  • 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
Sold by Exp Realty Llc

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

Get Pre-Approved

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

Date
Details
Price
Change
Source
8/13/2026
Sold
$460,000
—
MLS
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
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Keller Williams Legacy Realty
Sold by Exp Realty Llc

Similar Properties near 1550 Regal Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

231 Strathmore Cir, Kissimmee, FL 34744 - Photo 1
$459,900

231 Strathmore Cir  Kissimmee, FL 34744

  • Single Family
  • Active
  • Updated 12 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,262
    Sq. Ft.
Listed by Century 21 All Homes & Propert
2305 Jessica Ln, Kissimmee, FL 34744 - Photo 1
$462,000

2305 Jessica Ln  Kissimmee, FL 34744

  • Single Family
  • Active
  • 4
    Beds
  • 2
    Total Baths
  • 1,820
    Sq. Ft.
Listed by Broker Hub Realty Group Llc
1538 Bitteroot St, Kissimmee, FL 34744 - Photo 1
$455,000

1538 Bitteroot St  Kissimmee, FL 34744

  • Single Family
  • Active
  • 4
    Beds
  • 2
    Total Baths
  • 1,846
    Sq. Ft.
Listed by Odry Vargas Realty Group
1503 Beechmont Dr, Kissimmee, FL 34744 - Photo 1
$451,990

1503 Beechmont Dr  Kissimmee, FL 34744

  • Single Family
  • Active
  • 4
    Beds
  • 2
    Total Baths
  • 1,828
    Sq. Ft.
Listed by Dr Horton Realty Of Central Florida Llc

Just Listed near 1550 Regal Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2301 Betsy Ross Ln, Saint Cloud, FL 34769 - Photo 1 Just Listed
$229,995

2301 Betsy Ross Ln  #Unit A  Saint Cloud, FL 34769

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,273
    Sq. Ft.
Listed by Sharina George (407) 750-3959
4745 Avon Ct, Saint Cloud, FL 34769 - Photo 1 Just Listed
$145,000

4745 Avon Ct  #4745  Saint Cloud, FL 34769

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 967
    Sq. Ft.
Listed by The Quiroz group (407) 647-1211
1405 Starboard Dr, Saint Cloud, FL 34771 - Photo 1 Just Listed
$200,000

1405 Starboard Dr  Saint Cloud, FL 34771

  • Mobile Home
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 935
    Sq. Ft.
Listed by St. Cloud Real Estate
5148 Natalia Dr, Saint Cloud, FL 34772 - Photo 1 Just Listed
$359,690

5148 Natalia Dr  Saint Cloud, FL 34772

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,071
    Sq. Ft.
Listed by Lennar Realty

Price Reduced near 1550 Regal Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1551 Immokalee St, Intercession City, FL 33848 - Photo 1 Price Reduced
-$4,999 (-10%)
$45,000

1551 Immokalee St  Intercession City, FL 33848

  • Lots/Land
  • Active
  • Updated 6 days ago
  • 0.14
    Acres
Listed by La Rosa Realty Orlando Llc
529 Water St, Celebration, FL 34747 - Photo 1 Price Reduced
-$20,000 (-5.57%)
$339,000
Open House

529 Water St  #529  Celebration, FL 34747

  • Condo
  • Active
  • Updated 2 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 830
    Sq. Ft.
Listed by Stanica Realty Group
3133 House Finch Rd, Saint Cloud, FL 34773 - Photo 1 Price Reduced
-$10,990 (-2.71%)
$395,000

3133 House Finch Rd  Saint Cloud, FL 34773

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,828
    Sq. Ft.
Listed by Dr Horton Realty Of Central Florida Llc
2317 Avellino Ave, Saint Cloud, FL 34771 - Photo 1 Price Reduced
-$1 (0%)
$464,999

2317 Avellino Ave  Saint Cloud, FL 34771

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,788
    Sq. Ft.
Listed by Nona Legacy Powered By La Rosa

Recent Sales near 1550 Regal Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1511 Grandview Blvd, Kissimmee, FL 34744 - Photo 1 Sold
$515,000

1511 Grandview Blvd  Kissimmee, FL 34744

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,981
    Sq. Ft.
Listed by Star Bay Realty Corp.
Sold by Nona Legacy Powered By La Rosa
1601 Regal Oak Dr, Kissimmee, FL 34744 - Photo 1 Sold
$525,000

1601 Regal Oak Dr  Kissimmee, FL 34744

  • Single Family
  • Closed
  • 5
    Beds
  • 2
    Total Baths
  • 2,242
    Sq. Ft.
1595 Shady Oak Dr, Kissimmee, FL 34744 - Photo 1 Sold
$435,000

1595 Shady Oak Dr  Kissimmee, FL 34744

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,116
    Sq. Ft.
Listed by Lpt Realty, Llc
Sold by La Rosa Realty Llc
1575 Skyline Dr, Kissimmee, FL 34744 - Photo 1 Sold
$395,000

1575 Skyline Dr  Kissimmee, FL 34744

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,716
    Sq. Ft.
Listed by Nona Legacy Powered By La Rosa
Sold by Florida Realty Results Llc

1550 Regal Oak Drive, Kissimmee, FL 34744 (MLS# S5150034) is a Single Family property that was sold at $460,000 on August 13, 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.