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Property Description
**** $5000 credit to Buyer's closing costs with a Full Price Offer. No HOA! **** Such a Cute Charming Country-style home with 4 Bedrooms, 3 Full Bathrooms, a large yard and oversized circular driveway offering plenty of room for up to 7 vehicles and all of your Recreational Toys! - Boat, Jet skis, trailers and RV **** From the moment you enter the Home, you're greeted by soaring Vaulted Ceilings with Exposed Wood Beams, a wooden Staircase & Catwalk Railing, and a traditional Brick Wood-Burning Fireplace that creates a warm, welcoming feel to YOUR NEW HOME! Waterproof laminate wood flooring flows seamlessly throughout the entire first floor, continues up the staircase, and into the Second Primary Bedroom, creating a cohesive and stylish look. **** The Open Floorplan is designed for both everyday living and entertaining. The Kitchen is truly the Heart of the Home featuring the 98"x50" Butcher-block Island, Granite Countertops, Stainless Steel Appliances and large windows overlooking the Lanai & Backyard. Dark blue Ship-lap lines the walls in the Dining Area surrounding the Sliding glass doors that lead to the expansive screened lanai measuring 11'7" x 29'7". Outside of the lanai is the oversized back yard, blending indoor and outdoor living beautifully, allowing you to enjoy the oversized backyard complete with a storage shed and plenty of room for a cookout, gardening, kickball or game of catch. **** The Primary Suite is a stylish retreat featuring decorative wall trim, ceiling fan and a sliding Barn Door that leads to the beautifully designed ensuite bathroom with unique tile flooring, a dual-sink vanity, Walk-in Closet and a grand tiled walk-in shower enhanced by a skylight for natural light. **** Adding to this home's charm, the Living Room has a delightful, little window alcove, perfect for enjoying your morning coffee or curling up with a good book in the middle of the afternoon. Marble windowsills adorn the other windows in the home. You will also find on the first floor a second Bedroom and renovated Hall bathroom with a walk-in tiled shower and a door providing convenient access to the lanai. Upstairs, a second Primary Bedroom features a vaulted ceiling with Wood Beams as well as its own modernized Ensuite Bathroom complete with decorative beadboard, a stylish Vanity, and a Skylight-an ideal private space for In laws or Guests. **** The air-conditioned Garage (with its own split A/C) adds versatility for a Workshop, Gym, or climate-controlled Storage. To add to your peace of mind, the Roof(approx. 2021), A/C(2017) and the Septic drainfield(2020) were replaced. **** The Fish Camp is less than a mile and Kissimmee's Lakefront Marina and Boat Ramp on Lake Toho, is just 5 miles down the road. For those that love to play Tourist - it is short drive to Disney, Universal's Epic Universe, Sea World, the Orlando Area Attractions and the East Coast Beaches.
Full Property Details
Full Property Details for 1595 Shady Oak Dr
General
- Price: $457,000
- Taxes: $4,757 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: S5144261
- Updated: 2/26/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 1-7 Days
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Chair Rail, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Living Room, Wood Burning
- Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Laminate
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Washer Hookup
Additional Information
- Security/Safety: Security System, Smoke Detector(s)
Exterior
- Exterior Features: Lighting, Private Mailbox, Rain Gutters, Sliding Doors
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Off Street, RV Parking
Location
- Area: 34744 - Kissimmee
- County: Osceola
- Development Name: 34744 - Kissimmee
- Subdivision: REGAL OAK SHORES UNIT 6
- Driving Directions: from OSCeola Realtors office - Partin Settlement road south, turn right onto Neptune Rd, turn left onto Kings Hwy, right onto Pine Island, left Harbor Blvd, Right onto Shady Oak Dr, home on the right
- Direction Faces: South
Community
- Community Name: 34744 - Kissimmee
- Pet Restrictions: Buyer to check with Osceola county for any restrictions
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, Phone Available, Water Connected
Structural Information
- Exterior Const.: Vinyl Siding, Wood Frame
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 2,116
- Sq. Ft. Source: Public Records
- Year Built: 1981
Lot Features
- Lot Size (Acres): 0.34
- Lot Size (Sq. Ft.): 14,810
- Lot Size: 14810
- Street/Road Desc.: Paved
Financial Considerations
- Tax Amount: $4,757
- 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 Lpt Realty, Llc
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Schools
Schools serving 1595 Shady Oak Dr
School District:Osceola County School District
| Name | Grades | Distance |
|---|---|---|
Partin Settlement Elementary School 2434 Remington Boulevard, Kissimmee, FL 34744 | PK-5 | 3.5 mi |
Neptune Middle School 2727 Neptune Road, Kissimmee, FL 34744 | 6-8 | 2.8 mi |
Osceola High School 420 South Thacker Avenue, Kissimmee, FL 34741 | 9-12 | 3.8 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
Date
Details
Price
Change
Source
2/26/2026
Listed
$457,000
12.84%
MLS
8/13/2024
Sold
$405,000
—
Public Record
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
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
—
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
Estimate the Cost for 1595 Shady Oak Dr
1595 Shady Oak Drive, Kissimmee, FL 34744 (MLS# S5144261) is a Single Family property with 4 bedrooms and 3 full bathrooms. 1595 Shady Oak Drive is currently listed for $457,000 and was received on February 26, 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.

