The Oaks

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

Sort by:
New
2321 The Oaks Boulevard, KISSIMMEE

$561,900

2321 The Oaks Boulevard, KISSIMMEE

5 Beds 4 Baths 3,592 SqFt Residential MLS® # S5156742
2119 Putter Place, KISSIMMEE

$439,000

2119 Putter Place, KISSIMMEE

4 Beds 3 Baths 3,363 SqFt Residential MLS® # O6436932
2912 Boating Boulevard, KISSIMMEE

$540,000

↓ $10,000

2912 Boating Boulevard, KISSIMMEE

4 Beds 2 Baths 1,935 SqFt Residential MLS® # TB8540714
1812 Ironwood Way, KISSIMMEE

$361,300

1812 Ironwood Way, KISSIMMEE

3 Beds 2 Baths 1,890 SqFt Residential MLS® # S5156042
1953 The Oaks Boulevard, KISSIMMEE

$375,000

1953 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,038 SqFt Residential MLS® # R4911760
2120 Bunker View Court, KISSIMMEE

$785,000

↓ $4,999

2120 Bunker View Court, KISSIMMEE

5 Beds 5 Baths 4,580 SqFt Residential MLS® # O6433662
2106 The Oaks Boulevard, KISSIMMEE

$419,995

2106 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,045 SqFt Residential MLS® # O6431874
1718 Golfview Drive, KISSIMMEE

$395,000

↓ $14,000

1718 Golfview Drive, KISSIMMEE

3 Beds 2 Baths 1,538 SqFt Residential MLS® # S5155173
1709 Golfview Drive, KISSIMMEE

$395,000

1709 Golfview Drive, KISSIMMEE

3 Beds 2 Baths 2,302 SqFt Residential MLS® # S5154295
2270 Tournament Court, KISSIMMEE

$749,900

2270 Tournament Court, KISSIMMEE

4 Beds 4 Baths 3,325 SqFt Residential MLS® # S5152857
1944 The Oaks Boulevard, KISSIMMEE

$359,900

↓ $20,000

1944 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,288 SqFt Residential MLS® # S5152726
2114 The Oaks Boulevard, KISSIMMEE

$400,000

↓ $4,000

2114 The Oaks Boulevard, KISSIMMEE

3 Beds 2 Baths 2,609 SqFt Residential MLS® # C7525948
2801 Baywood Lane, KISSIMMEE

$419,000

↓ $20,900

2801 Baywood Lane, KISSIMMEE

3 Beds 3 Baths 2,259 SqFt Residential MLS® # S5137135
1524 The Oaks Boulevard, KISSIMMEE

$539,900

↓ $10,000

1524 The Oaks Boulevard, KISSIMMEE

4 Beds 3 Baths 2,829 SqFt Residential MLS® # O6371236
2110 Bunker View Court, KISSIMMEE

$385,000

↓ $33,000

2110 Bunker View Court, KISSIMMEE

3 Beds 3 Baths 2,039 SqFt Residential MLS® # O6362653


Sold Homes in The Oaks Kissimmee

The Oaks Real Estate Market Statistics

Average Price $475K
Lowest Price $360K
Highest Price $785K
Total Listings 15
Avg. Days On Market 70
Avg. Price/SQFT $190
List to Sell Price Percentage 97 %

Property Types (active listings)

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
Number 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

Hospitals

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

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

Orlando - Windermere Home

Discover the Dream Home Today

Convenient access to unparalleled hyper-local information. From in the comfort of your house, or on the go, RealtyInOrlando.com provides the Orlando neighborhood data home buyers & seller are seeking.