$450,000
1595 Shady Oak Drive
Kissimmee, FL 34744
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
**** BRING THE BOAT! - Seller to pay $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) were replaced. The Shed in the backyard is included **** 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.
Local Insight
At $213/sqft for a 1981 home in Regal Oak Shores, you're positioned in Kissimmee's sweet spot for theme park workers and first-time buyers—the price is solid for the size and location, though you'll want a thorough inspection given the age and confirm the foundation/roof condition before committing. The no-HOA setup and X flood zone are genuine pluses, but the 0.34-acre lot is modest, so this is really a value play on square footage and location rather than land or newer construction.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history100 days on market
- Status: ActiveFeb 26, 2026
- Listed$457,000Feb 26, 2026
- Price reduced$450,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 100
- Cumulative DOM
- 121
- Subdivision
- Regal Oak Shores Unit 6
- County
- Osceola
- Year built
- 1981
- Living area
- 2,116 sq ft
- Price/sq ft
- $213
- Building area
- 2,934 sq ft (Public Records)
- Lot size
- 14,810 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12097C0069G)
- Garage
- 2 spaces
- Annual taxes
- $4,757 (2025)
- Parcel #
- 02-26-29-4794-0001-0140
- Zoning
- ORS1
- MLS #
- S5144261
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Carpet, Laminate
- Appliances
- Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Washer
- Interior features
- Ceiling Fans(s), Chair Rail, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Electric Dryer Hookup, In Garage, Washer Hookup
- Stories / Levels
- Two
- Direction faces
- South
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener, Off Street, RV Access/Parking
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- 1-7 Days
- Listing terms
- Cash, Conventional, FHA
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer to check with Osceola County for any leasing instructions & license requirements
Exterior & Construction
- Exterior features
- Lighting, Private Mailbox, Rain Gutters, Sliding Doors
- Construction materials
- Vinyl Siding, Frame
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Water Connected
Community
- Pets allowed
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 19x19 |
| Primary Bedroom | First | 20x14 |
| Dining Room | First | 12x11 |
| Kitchen | First | 14.1x11 |
| Bedroom 2 | First | 14x12 |
| Bedroom 3 | Second | 17x15 |
| Bedroom 4 | Second | 22x13 |
Listing Details
- Listing date
- 2026-02-21
- On market date
- 2026-02-26
- Original list price
- $457,000
- Occupant type
- Vacant
- MLS area
- 34744 - Kissimmee
- Listing AOR
- Orlando Regional
- Status changed
- 2026-02-26
- Tax legal description
- REGAL OAK SHORES UNIT 6 PB 2 PG 251 LOT 14
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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
Property sale history
Public records1595 SHADY OAK DR, KISSIMMEE 34744
- Aug 2024$405,000
2,444 sq ft · Built 1981 · 0.3470 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 6, 2026 at 10:56 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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