1595 Shady Oak Drive, FL
Stellar MLS

$450,000

1595 Shady Oak Drive

Kissimmee, FL 34744

Active
4
Beds
3
Baths
2,116
Sq Ft
0.34
Acres
1981
Built
Fireplace$213/sqft
Single Family Residence

Property type

1981

Year built

14,810 sqft

Lot size

$213

Price / sq ft

No HOA

HOA dues

100

Days on market

2

Garage spaces

X

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

Principal & interest$2,275
Property taxes$396
Home insurance (est.)$206

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

  1. Status: Active
    Feb 26, 2026
  2. Listed$457,000
    Feb 26, 2026
  3. 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

RoomLevelDimensions
Living RoomFirst19x19
Primary BedroomFirst20x14
Dining RoomFirst12x11
KitchenFirst14.1x11
Bedroom 2First14x12
Bedroom 3Second17x15
Bedroom 4Second22x13

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 riskFEMA Zone XPanel 12097C0069G

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 records

1595 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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MLS GRID

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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA