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
2181 The Oaks Boulevard, KISSIMMEE

$415,000

2181 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,017 SqFt Residential MLS® # O6347058
1953 The Oaks Boulevard, KISSIMMEE

$389,900

1953 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,038 SqFt Residential MLS® # R4909469
2172 The Oaks Boulevard, KISSIMMEE

$399,000

2172 The Oaks Boulevard, KISSIMMEE

4 Beds 2 Baths 2,151 SqFt Residential MLS® # S5134772
2200 The Oaks Boulevard, KISSIMMEE

$460,000

2200 The Oaks Boulevard, KISSIMMEE

4 Beds 4 Baths 2,720 SqFt Residential MLS® # O6336847
2601 Roughside Circle, KISSIMMEE

$475,000

↓ $20,000

2601 Roughside Circle, KISSIMMEE

4 Beds 3 Baths 2,605 SqFt Residential MLS® # G5100687
2622 Roughside Circle, KISSIMMEE

$499,000

↓ $11,000

2622 Roughside Circle, KISSIMMEE

4 Beds 3 Baths 2,671 SqFt Residential MLS® # O6332997
2510 Trapside Court, KISSIMMEE

$457,500

↓ $7,500

2510 Trapside Court, KISSIMMEE

4 Beds 2 Baths 1,938 SqFt Residential MLS® # O6317494
2141 The Oaks Boulevard, KISSIMMEE

$340,000

↓ $20,000

2141 The Oaks Boulevard, KISSIMMEE

3 Beds 2 Baths 1,839 SqFt Residential MLS® # S5131600
1714 Golfview Drive, KISSIMMEE

$439,900

1714 Golfview Drive, KISSIMMEE

4 Beds 3 Baths 2,540 SqFt Residential MLS® # O6284822
1976 The Oaks Boulevard, KISSIMMEE

$584,900

↓ $10,000

1976 The Oaks Boulevard, KISSIMMEE

5 Beds 4 Baths 3,566 SqFt Residential MLS® # S5126074
2108 Drive Way, KISSIMMEE

$510,000

2108 Drive Way, KISSIMMEE

4 Beds 3 Baths 2,589 SqFt Residential MLS® # O6254515
Pending
2260 The Oaks Boulevard, KISSIMMEE

$480,000

↓ $19,000

2260 The Oaks Boulevard, KISSIMMEE

5 Beds 4 Baths 3,546 SqFt Residential MLS® # O6283348
2460 The Oaks Boulevard, KISSIMMEE

$605,000

↓ $10,000

2460 The Oaks Boulevard, KISSIMMEE

5 Beds 4 Baths 3,416 SqFt Residential MLS® # O6323394
2298 The Oaks Boulevard, KISSIMMEE

$499,000

↓ $26,000

2298 The Oaks Boulevard, KISSIMMEE

5 Beds 4 Baths 3,592 SqFt Residential MLS® # O6325623
2530 The Oaks Boulevard, KISSIMMEE

$530,000

↓ $10,000

2530 The Oaks Boulevard, KISSIMMEE

4 Beds 3 Baths 3,061 SqFt Residential MLS® # O6319826
2081 The Oaks Boulevard, KISSIMMEE

$450,000

↓ $25,000

2081 The Oaks Boulevard, KISSIMMEE

4 Beds 4 Baths 3,486 SqFt Residential MLS® # O6294273
1718 Golfview Drive, KISSIMMEE

$429,000

↓ $6,000

1718 Golfview Drive, KISSIMMEE

3 Beds 2 Baths 1,538 SqFt Residential MLS® # S5122148

The Oaks Real Estate Market Statistics

Average Price $468K
Lowest Price $340K
Highest Price $605K
Total Listings 17
Avg. Days On Market 109
Avg. Price/SQFT $183
List to Sell Price Percentage 96 %

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.