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$479,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,116 Sq. Ft.
  • Updated 3 days ago

Next open house:

Open House: 4:00 PM - 7:00 PM

Friday 1/30 4:00 PM - 7:00 PM

1595 Shady Oak Drive,Kissimmee, FL 34744

1595 Shady Oak DriveKissimmeeFL34744

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  • Open House: 10:00 AM - 1:00 PM

    Saturday 1/31 10:00 AM - 1:00 PM

    1595 Shady Oak Drive,Kissimmee, FL 34744
    1595 Shady Oak DriveKissimmeeFL34744
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Welcome to Harbor Oaks! This is not your cookie-cutter, already dated new build. Come make this classic vintage country cottage your new home. In a highly sought-after part of Kissimmee, Harbor Oaks is the perfect neighborhood for long, quiet walks, bike riding down the shaded streets, or a quick ride downtown. 1595 Shady Oak Dr. features 2 stories, 4 bedrooms, 3 full bathrooms, a huge fireplace, an open kitchen with a giant island, air conditioned garage, and an amazing backyard. The flooring upstairs and downstairs is brand new, along with freshly painted walls, cabinets, bedrooms, and bathrooms. There is a great shed in the back yard, all appliances are included, and the roof is only 3 years old! The home has 2 brand new (2025) renovated bathrooms as well. Don't buy a house where you can touch your neighbors out your window, or where everything is grey and white. This cozy cottage will be your oasis under a roof, no matter if you are in your golden years, have an overflowing family, or just starting out! We hope you love it here!

Full Property Details for 1595 Shady Oak Dr

General

  • Price: $479,000
  • Taxes: $4,757 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8467744
  • Updated: 1/27/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 11
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Skylight(s), Solid Surface Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Garage

Additional Information

  • Security/Safety: Security System, Security System Owned

Exterior

  • Exterior Features: Sliding Doors, Storage
  • Deck/Patio: Covered, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway, Driveway, Garage Door Opener

Location

  • Area: 34744 - Kissimmee
  • County: Osceola
  • Development Name: 34744 - Kissimmee
  • Subdivision: REGAL OAK SHORES UNIT 6
  • Driving Directions: Turn onto Shady Oak Drive, pull in the roundabout driveway on either side.
  • Direction Faces: South

Community

  • Community Name: 34744 - Kissimmee

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Street Lights, Underground Utilities, Water Connected

Structural Information

  • Exterior Const.: Vinyl Siding, Wood Frame
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: Two
  • Square Feet: 2,116
  • Sq. Ft. Source: Public Records
  • Year Built: 1981

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 0.35
  • Lot Size (Sq. Ft.): 15,115
  • Lot Size: 15115
  • Lot Dimensions: 100 x 149
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $4,757.42
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: REGAL OAK SHORES UNIT 6 PB 2 PG 251 LOT 14
  • Flood Zone Info: X
  • APN: 22629479400010140
  • Property ID: 22629479400010140
  • Block/Lot/Section: 1

Listed by Flat Fee Mls Realty

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— 1595 Shady Oak Dr —

  • Flat Fee Mls Realty

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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

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Schools serving 1595 Shady Oak Dr

School District:Osceola County School District
NameGradesDistance
Partin Settlement Elementary School
2434 Remington Boulevard, Kissimmee, FL 34744
PK-53.5 mi
Neptune Middle School
2727 Neptune Road, Kissimmee, FL 34744
6-82.8 mi
Osceola High School
420 South Thacker Avenue, Kissimmee, FL 34741
9-123.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1595 Shady Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/27/2026
Listed
$479,000
18.27%
MLS
8/13/2024
Sold
$405,000
—
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 1595 Shady Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,757
143%
$332,800
135%
2024
$1,959
3%
$141,547
3%
2023
$1,910
3%
$137,425
6%
2021
$1,849
-1%
$129,537
-3%
2022
$1,873
1%
$133,423
4%
2021
$1,849
11%
$127,749
4%
2018
$1,670
1%
$122,549
2%
2017
$1,661
-6%
$120,029
-4%
2019
$1,764
8%
$124,877
6%
2016
$1,634
-1%
$117,561
1%
2015
$1,648
3%
$116,744
1%
2014
$1,605
2%
$115,818
1%
2013
$1,579
—
$114,107
—
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 Flat Fee Mls Realty

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1595 Shady Oak Drive, Kissimmee, FL 34744 (MLS# TB8467744) is a Single Family property with 4 bedrooms and 3 full bathrooms. 1595 Shady Oak Drive is currently listed for $479,000 and was received on January 27, 2026. Want to learn more about 1595 Shady 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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