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1999 Grand Oak Drive

KISSIMMEE, FL 34744

4 beds
4 baths
1,760 sqft
1,960 sqft lot
$176 per sqft
2007 build
– on site

**PRICE IMPROVEMENT** Welcome home to this spacious 4-bedroom, 3.5-bath property that offers the rare luxury of TWO PRIMARY SUITES—one conveniently located on the main floor and another upstairs, ideal for multigenerational living or added privacy. Enjoy a beautifully designed kitchen featuring a large granite island, ample cabinet space, and a seamless flow into the bright, open-concept living area. Sliding glass doors fill the space with natural light and lead to a screened-in patio—the perfect place to enjoy your morning coffee or evening relaxation. Recent updates include NEW flooring, fresh interior paint, and a new AC unit (2021). Built with solid poured concrete construction from top to bottom, this home offers durability and peace of mind. Situated in a gated community with an abundance of amenities, you’ll have access to two pools, a splash pad, clubhouse, fitness center, playground, and more!! Conveniently located just minutes from the FL Turnpike, SR-417, Silver Spurs Arena, Valencia College, shopping, dining, and close to Central Florida's best attractions. Whether you're looking for a primary residence, long-term investment, or short-term rental opportunity, this versatile property is zoned for it all. Don’t miss your chance—schedule your private showing today!

Listing courtesy of STELLAR_MLS / KELLER WILLIAMS ELITE PARTNERS III REALTY

Last checked: Checking… • Last updated Apr 22, 2025 •

MLS# S5124339 —

The Building

Year Built:

2007
New Construction:

false
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Common Walls:

End Unit
Roof:

Metal
Foundation Details:

Slab
Window Features:

Blinds
Patio And Porch Features:

Rear Porch
Building Area Total:

1768
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Ceiling Fan(s)
Flooring:

Ceramic Tile
Fireplace:

false

Room Dimensions

Living Area:

1760
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From FL Turnpike, take exit 244 onto US-192 toward Kissimmee, turn right onto E Irlo Bronson Memorial Hwy, turn left onto Heritage Key Blvd, continue to follow Heritage Key Blvd, the home will be on your right (this is an end unit).
Latitude:

28.287436
Longitude:

-81.361447
Coordinates:

-81.361447, 28.287436

The Property

Parcel Number:

252529253500010460
Property Type:

Residential
Property Subtype:

Townhouse
Lot Features:

Sidewalk
Lot Size Acres:

0.05
Lot Size Area:

1960
Lot Size SqFt:

1960
Lot Size Dimensions:

30 x 65
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

PD
Direction Faces:

South
View:

false
Exterior Features:

Rain Gutters
Water Source:

Public
Road Surface Type:

Asphalt
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

46
Tax Block:

1
Tax Legal Description:

HERITAGE KEY VILLAS PHASE ONE AND TWO PB 18 PG 121-126 LOT 46
Tax Book Number:

18-121
Tax Annual Amount:

$3,576.13

Beds

Bedrooms Total:

4

Baths

Total Baths:

3.5
Total Baths:

4
Full Baths:

3
Half Baths:

1

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/S5124339
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

BB/HS Internet Available
Sewer:

Public Sewer

Appliances

Appliances:

Dishwasher
Laundry Features:

Laundry Room

The Community

Subdivision Name:

HERITAGE KEY VILLAS PH 1 & 2
Senior Community:

false
Community Features:

Clubhouse
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Pets Allowed:

Breed Restrictions
Pet Restrictions:

Please contact HOA regarding pet restrictions.
# of Pets:

2
Max Pet Weight:

100
Association Amenities:

Clubhouse
Association:

true
Association Fee:

249
Association Fee Frequency:

Monthly
Association Fee Includes:

Community Pool
Association Fee Requirement:

Required
Monthly HOA Amount:

249
Ownership:

Fee Simple
Association Approval Required:

true

Parking

Garage:

false
Carport:

false
Parking Features:

Assigned

Monthly cost estimate

Asking price

$309,900

Expense	Monthly cost
Mortgage	$1,659
Taxes	$298
Insurance	$85
HOA fees	$249
Utilities	$145 See report
Total	$2,436/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
4/19/25 Apr 19, 2025	Price Changed	STELLAR_MLS	$309,900	-3.2%
4/9/25 Apr 9, 2025	Listed / Active	STELLAR_MLS	$320,000	-1.8% (-0.1% / YR)
5/1/10 May 1, 2010	Sold	STELLAR_MLS

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This townhouse located in Heritage Key, FL 34744 is currently for sale for $309,900. 1999 Grand Oak Drive is a 1,760 square foot townhouse with 4 beds and 4 baths that has been on Estately for 15 days. 1999 Grand Oak Drive is in the Heritage Key neighborhood of KISSIMMEE and has a WalkScore® of 25, making it car-dependent. This townhouse is in the attendance area of Denn John Middle School, Osceola High School, and Mill Creek Elementary School.

Listing Courtesy of: STELLAR_MLS and KELLER WILLIAMS ELITE PARTNERS III REALTY.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.