Longleaf at Oakland

The suburban community of Longleaf is a great option when shopping for Oakland real estate. Positioned in the heart of Oakland, homes for sale in Longleaf are located only minutes from the world-class West Orange Trail and the Oakland Nature Reserve. Winter Garden is only two miles to the East, and the fast-growing city of Clermont lies only a few miles further to the West. This region of Central Florida, 19 miles west of the city of Orlando, is booming.

Longleaf at Oakland Homes for Sale

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New
1300 S Dewey Street, EUSTIS

$260,000

1300 S Dewey Street, EUSTIS

3 Beds 2 Baths 1,300 SqFt Residential MLS® # O6448218
New
2071 Dixie Belle Drive 2071m, ORLANDO

$169,900

2071 Dixie Belle Drive 2071m, ORLANDO

3 Beds 2 Baths 1,192 SqFt Residential MLS® # O6448576
New
2218 Grand Cayman Court 1335, KISSIMMEE

$197,500

2218 Grand Cayman Court 1335, KISSIMMEE

2 Beds 2 Baths 1,026 SqFt Residential MLS® # S5159189
1756 Tanglewood Drive, KISSIMMEE

$599,900

1756 Tanglewood Drive, KISSIMMEE

5 Beds 3 Baths 2,532 SqFt Residential Income MLS® # O6415364
358 Fulton Street, DAYTONA BEACH

$85,000

358 Fulton Street, DAYTONA BEACH

0 Beds 0 Baths 0 SqFt Land MLS® # FC310658
1756 Tanglewood Drive, KISSIMMEE

$599,900

1756 Tanglewood Drive, KISSIMMEE

5 Beds 3 Baths 2,532 SqFt Residential MLS® # O6414176
New
166 Catfish Street, HAINES CITY

$499,900

166 Catfish Street, HAINES CITY

3 Beds 2 Baths 1,867 SqFt Residential MLS® # L4965609
New
910 Big Tree Road 7-2, SOUTH DAYTONA

$159,999

910 Big Tree Road 7-2, SOUTH DAYTONA

3 Beds 2 Baths 1,442 SqFt Residential MLS® # O6448376
1111 Long Oak Way, SANFORD

$249,900

1111 Long Oak Way, SANFORD

3 Beds 3 Baths 1,409 SqFt Residential MLS® # O6427597
New
2307 Butterfly Palm Way 302, KISSIMMEE

$225,000

2307 Butterfly Palm Way 302, KISSIMMEE

2 Beds 2 Baths 1,022 SqFt Residential MLS® # S5158942
New
3607 S Crystal Lake Drive, ORLANDO

$389,000

3607 S Crystal Lake Drive, ORLANDO

3 Beds 2 Baths 1,118 SqFt Residential MLS® # G5118753
New Open House
6549 State Road 33, CLERMONT

$799,900

6549 State Road 33, CLERMONT

3 Beds 2 Baths 1,878 SqFt Residential
Fri, Oct 9th, 2026 @ 11am - 2pm
MLS® # S5158854
New
9932 Earlston Street, ORLANDO

$415,000

9932 Earlston Street, ORLANDO

4 Beds 2 Baths 1,578 SqFt Residential MLS® # O6448505
New
3603 Lismore Drive, LAKELAND

$389,000

3603 Lismore Drive, LAKELAND

4 Beds 2 Baths 1,636 SqFt Residential MLS® # P4940112
New
2630 High Ridge Drive, LAKELAND

$575,000

2630 High Ridge Drive, LAKELAND

3 Beds 3 Baths 3,304 SqFt Residential MLS® # O6448482
New
601 N Mcdonald Street 103, MOUNT DORA

$295,000

601 N Mcdonald Street 103, MOUNT DORA

2 Beds 2 Baths 1,209 SqFt Residential MLS® # G5118695
New
7163 Oakmoss Loop, DAVENPORT

$444,000

7163 Oakmoss Loop, DAVENPORT

5 Beds 5 Baths 2,281 SqFt Residential MLS® # O6447952
New Open House
1085 Eagles Nest Avenue, DELTONA

$299,900

1085 Eagles Nest Avenue, DELTONA

3 Beds 2 Baths 1,274 SqFt Residential MLS® # V4951550
6292 Twain Street 107, ORLANDO

$280,000

6292 Twain Street 107, ORLANDO

3 Beds 3 Baths 1,682 SqFt Residential MLS® # O6398364
Open House
14156 Alafaya Oak Bend, ORLANDO

$750,000

14156 Alafaya Oak Bend, ORLANDO

4 Beds 4 Baths 3,413 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # O6430135
New
255 Northcote Court, DELAND

$375,000

255 Northcote Court, DELAND

3 Beds 2 Baths 1,507 SqFt Residential MLS® # V4951058
46 E Princeton Street, ORLANDO

$568,300

46 E Princeton Street, ORLANDO

4 Beds 3 Baths 2,016 SqFt Residential Income MLS® # O6440485
New Open House
1580 Deland Avenue, ORANGE CITY

$329,900

1580 Deland Avenue, ORANGE CITY

3 Beds 2 Baths 1,380 SqFt Residential MLS® # V4951641
25551 Hawks Run Lane, SORRENTO

$925,000

25551 Hawks Run Lane, SORRENTO

5 Beds 5 Baths 4,343 SqFt Residential MLS® # O6346583
New
11347 Pine Ridge Road, LEESBURG

$549,000

11347 Pine Ridge Road, LEESBURG

4 Beds 3 Baths 1,727 SqFt Residential MLS® # G5118779
New
39914 Sunbeam Way, LADY LAKE

$319,999

39914 Sunbeam Way, LADY LAKE

3 Beds 2 Baths 2,034 SqFt Residential MLS® # O6447413
New
3342 Veltre Way, THE VILLAGES

$499,900

3342 Veltre Way, THE VILLAGES

4 Beds 2 Baths 2,013 SqFt Residential MLS® # G5118796
New
2014 W Colonial Drive, ORLANDO

$8,500,000

2014 W Colonial Drive, ORLANDO

0 Beds 0 Baths 62,369 SqFt Commercial Sale MLS® # O6448580
New
1028 S Terry Avenue, LAKELAND

$315,000

1028 S Terry Avenue, LAKELAND

4 Beds 2 Baths 1,705 SqFt Residential MLS® # TB8556329
1721 Freeman Drive, KISSIMMEE

$359,900

1721 Freeman Drive, KISSIMMEE

3 Beds 2 Baths 1,842 SqFt Residential MLS® # O6424008

Longleaf at Oakland Real Estate Market Statistics

Average Price $434K
Lowest Price $340K
Highest Price $515K
Total Listings 4
Avg. Days On Market 19
Avg. Price/SQFT $250
List to Sell Price Percentage 98 %

Property Types (active listings)

Homes for sale in Oakland are popular with buyers looking for an opportunity to establish themselves in this highly desirable location. Winter Garden Village at Fowler's Grove contains a selection of shopping and dining venues, and further everyday conveniences can be found along W. Colonial Drive. Nearby access to area highways 429, 408, and Floridas Turnpike take residents to such destinations like Disney, Universal, and SeaWorld. Downtown Orlando's cultural offerings, eclectic dining opportunities, and varied entertainment venues are a short drive away. Orange County Schools are highly rated catering to students from pre-K through High School.

Longleaf at Oakland is a community of 185 residences with both townhomes and free-standing single-family homes. Developed and built by Pulte Homes, Longleaf offers ten unique floor plans available, each having customizable exterior options. Townhomes have between two and four bedrooms and between two and four bathrooms. Single-family homes are designed with either front or rear garage and contain between three and six bedrooms and two to four and a half baths. All of these beautiful homes are designed to maximize natural light and are pre-wired for Smart Home technology. Attractive features include open-plan living spaces, walk-in showers, and upscale master suites as well as upgraded options like a second full owners suite guest suite or bonus room. Neighborhood amenities include a refreshing community pool with adjacent cabana, tot lot, and numerous green spaces, including a pond and mature shady trees.

The town of Oakland has a long history first settled in the 1800s. After a booming start with success in local agricultural industries, a citrus freeze and later fire effectively pushed the pause button, and for many years Oakland remained a sleepy little village. Recent growth in the area has increased demand for available real estate, but city planning favors development in step with the rural history and laid-back feel of the town. Residents can savor the opportunity to live in this hidden gem while enjoying all the advantages of Winter Garden, known for its historic downtown district rich with local boutique shops and restaurants, an exceptional farmers market, and even a local brewery. This family-friendly city hosts multiple annual events and is a recognized cultural hub.

The community of Longleaf at Oakland offers a chance to live in a modern residential neighborhood in a great Central Florida location. Schedule your opportunity today to the checkout Longleaf first hand!

Longleaf at Oakland Community Information

Location: Bobcat Chase Blvd & Sansparilla Rd
Year(s) Built: 2019-2020
Homesites: 185
HOA: Yes
Square Footage: 1,497 - 3,053
Community Amenities: Community Pool, Cabana, Tot Lot, Walking Paths, Parklands, Community Pond, Direct West Orange Trail Access

Orange County Public Schools

  • Tildenville Elementary: Grades Pre-K - 5th Distance: 2.5 miles
  • Lakeview Middle School: Grades 6th - 8th Distance: 3 miles
  • West Orange High School: Grades 9th - 12th Distance: 5 miles

Dining and Shopping

  • Plaza Collina with Costco, Dining, Shopping - Distance: 2 miles
  • Publix Supermarket at East Towne Center - Distance: 3 miles
  • West Point Commons with grocery and dining - Distance: 3 miles
  • Downtown Winter Garden - Distance: 3.5 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 5.5 miles
  • Clermont Landing with retail, dining and movie theater - Distance: 7.5 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 18 miles
  • Restaurant Row - Distance: 18.5 miles
  • Downtown Orlando - Distance: 19.5 miles

Parks and Recreation

  • Oakland Nature Preserve - Distance: .5 miles
  • West Orange Soccer Complex - Distance: 5.5 miles
  • West Orange Trail Kilarney Station with bike rental - Distance: 1.5 miles
  • Roper YMCA Family Center - Distance: 5 miles
  • West Orange Recreation Center - Distance 5 miles
  • Tucker Ranch Recreation and Nature Complex - Distance 2.5 miles
  • Southwest Aquatics - Distance: 5.5 miles
  • National Training Center - Distance: 5.5 miles

Hospitals

  • AdventHealth Winter Garden - Distance: 5.5 miles
  • Orlando Health - South Lake Hospital: Distance - 5.5 miles

*Distances are approximately measured from the Longleaf at Oakland community entrance

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