Please ensure Javascript is enabled for purposes of website accessibility

Enjoy the Central Florida lifestyle at The Oaks. This beautiful, gated Kissimmee community features various condominiums and single-family homes situated within three unique subdivisions: Eagle's Nest, Osprey Cove, and Shingle Creek Reserve. The elegant homes, resort-style amenities, and excellent proximity make The Oaks a desirable place to live.

The Oaks

22 Properties Found. Page 1 of 1.
Photo of Listing #S5085901
MLS® # S5085901
7 Beds, 4 Baths, 4,303 Sf
Photo of Listing #S5085566
MLS® # S5085566
4 Beds, 3 Baths, 2,808 Sf
Photo of Listing #S5084527
MLS® # S5084527
3 Beds, 3 Baths, 2,435 Sf
Photo of Listing #O6111431
MLS® # O6111431
3 Beds, 2 Baths, 1,136 Sf
Photo of Listing #T3433561
Reduced 0.9%
MLS® # T3433561
3 Beds, 4 Baths, 2,303 Sf
Photo of Listing #S5083240
MLS® # S5083240
4 Beds, 3 Baths, 3,216 Sf
Photo of Listing #S5084086
MLS® # S5084086
4 Beds, 3 Baths, 2,829 Sf
Photo of Listing #S5084422
MLS® # S5084422
4 Beds, 3 Baths, 2,720 Sf
Photo of Listing #O6100532
MLS® # O6100532
3 Beds, 2 Baths, 1,405 Sf
Photo of Listing #S5084020
MLS® # S5084020
3 Beds, 2 Baths, 2,792 Sf
Photo of Listing #O6105689
MLS® # O6105689
3 Beds, 3 Baths, 2,260 Sf
Photo of Listing #O6104273
MLS® # O6104273
4 Beds, 3 Baths, 2,005 Sf
Photo of Listing #O6104224
MLS® # O6104224
5 Beds, 4 Baths, 3,478 Sf
Photo of Listing #O6094343
MLS® # O6094343
3 Beds, 2 Baths, 1,664 Sf
Photo of Listing #S5079828
MLS® # S5079828
3 Beds, 2 Baths, 1,808 Sf
Photo of Listing #S5081655
Reduced 3.2%
MLS® # S5081655
4 Beds, 3 Baths, 2,196 Sf
Photo of Listing #S5081054
Reduced 4.1%
MLS® # S5081054
4 Beds, 4 Baths, 2,553 Sf
Photo of Listing #S5079817
MLS® # S5079817
4 Beds, 3 Baths, 2,538 Sf
Photo of Listing #O6084514
Reduced 1.2%
MLS® # O6084514
4 Beds, 3 Baths, 2,005 Sf
Photo of Listing #O6053495
MLS® # O6053495
3 Beds, 2 Baths, 1,715 Sf
Photo of Listing #O6045910
MLS® # O6045910
4 Beds, 2 Baths, 2,670 Sf
Photo of Listing #T3400469
MLS® # T3400469
4 Beds, 3 Baths, 2,604 Sf

Built in the early 2000s, this serene and picturesque community features multiple floor plans providing approximately 1,000 to 4,500 sq. ft. of living space. The 2-6 bedroom homes feature 2-4.5 baths and are nestled on well-maintained lots, with many of the homes featuring golf-course, woods, and waterfront views. Many homes feature luxury upgrades, open floor plans, master suites, and private lanais and pools. Residents also enjoy numerous onsite amenities, including a boat ramp with access to Lake Tohopekaliga, two playgrounds, grills, and athletic courts. The community also enjoys a full social calendar with special events and holiday gatherings.

Located off US-17 and the Oaks Blvd, this Central Florida subdivision is in a prime location with easy drives to local entertainment, recreation, and theme parks. Enjoy the lakes and nature trails on property or experience Kissimmee Lakefront Park for boating, hiking, and outdoor fun! Daily living is a breeze with shopping centers, restaurants, offices, and more just minutes away. This community is less than seven miles to Osceola County Public Schools and surrounded by top medical facilities, large retail stores, spas, and more.

The Oaks provides easy access to John Young Parkway, Highway 192, and the Florida Turnpike, making exploring and commuting around Orlando fun and easy. Take advantage of the excellent proximity and experience Orlando's best attractions, including Disney World, Sea World, and Universal Orlando Resort.

Contact us today to learn more about The Oaks real estate.

The Oaks Community Information

Location: US-17 & The Oaks Blvd
Surrounding Lakes: Lake Tohopekaliga
Year(s) Built: 2003-2005
# of Homesites: 1000+
HOA: Yes
Square Footage: 1,617 to 4,580
Community Amenities:  Boat Ramp, Golf, 2 Playgrounds, Tennis Courts, BBQ Grills, Nature Trails, Basketball Courts, Boat lift, Water Access to Lake Toho

Osceola County Public Schools

  • Pleasant Hill Elementary School: Pre-K-5th - Distance: 1 mile
  • Horizon Middle School: 6th-8th Distance - 2 miles
  • Liberty High School: Grades Pre-K -12th - Distance: 7 miles

Dining and Shopping

  • Pleasant Hill Commons with Publix Grocery- Distance: 1 mile
  • Shoppes of Kissimmee Shopping Center-Distance: .5 mile
  • Kissimmee Lakefront Park- Distance: 3 miles
  • Kissimmee Historic District-Distance: 4 miles
  • Loop West Shopping Center- Distance: 7 miles
  • Orlando Premium Outlet- Distance: 9 miles
  • Restaurant Row- Distance: 18 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 18 miles
  • Downtown Orlando - Distance: 28 miles

Parks and Recreation

  • Walt Disney World Resort-Distance: 14 miles
  • Shingle Creek Regional Park- Distance: 6.5 miles
  • Kissimmee Lakefront Park- Distance: 4 miles
  • Kissimmee Oaks Golf Club-Distance: .5 mile
  • Central Florida Athletic Association - Distance: .5 mile
  • Osceola YMCA Family Center - Distance: 4 miles


  • Osceola Regional Medical Center - Distance: 4 miles
  • Advent Health Kissimmee Hospital - Distance: 6 miles

*Distances are approximately measured from the The Oaks community entrance.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 7th, 2023 at 3:20pm EDT.