Winters Landing

Winters Landing is a well-established community located in the quaint town of Oakland, Florida. Founded in 1887, Oakland was once a major center of commerce. Today, the town nestled between Johns Lake and Lake Apopka is noted for its laid-back lifestyle and sprawling age-old oak trees.

Winters Landing Homes for Sale

Sort by:
New
1533 Tiger Lake Road, LAKE WALES

$195,000

1533 Tiger Lake Road, LAKE WALES

2 Beds 2 Baths 896 SqFt Residential MLS® # O6447957
Sold
681 Coronado Drive, KISSIMMEE

$257,900

681 Coronado Drive, KISSIMMEE

2 Beds 2 Baths 1,700 SqFt Residential MLS® # O6221432
Sold
1510 Richmond Road, LAKELAND

$259,900

1510 Richmond Road, LAKELAND

4 Beds 2 Baths 1,128 SqFt Residential MLS® # P4931029
Sold
Treasure Island Road, LEESBURG

$197,000

Treasure Island Road, LEESBURG

0 Beds 0 Baths 0 SqFt Land MLS® # G5084179
Sold
924 S Florida Avenue, LAKELAND

$1,200,000

924 S Florida Avenue, LAKELAND

0 Beds 0 Baths 4,353 SqFt Commercial Sale MLS® # P4930916
Sold
315 Lucaya Loop 315, DAVENPORT

$199,000

315 Lucaya Loop 315, DAVENPORT

3 Beds 2 Baths 1,227 SqFt Residential MLS® # O6221568
Sold
Marker Street, ALTAMONTE SPRINGS

$44,888

Marker Street, ALTAMONTE SPRINGS

0 Beds 0 Baths 0 SqFt Land MLS® # T3536172
Sold
33 N Primrose Drive, ORLANDO

$475,000

33 N Primrose Drive, ORLANDO

0 Beds 0 Baths 1,208 SqFt Commercial Sale MLS® # O6221692
Sold
1134 Harbor Hill Street, WINTER GARDEN

$540,000

1134 Harbor Hill Street, WINTER GARDEN

4 Beds 3 Baths 2,754 SqFt Residential MLS® # O6217343
Sold
1234 Tagliamento Lane, HAINES CITY

$266,875

1234 Tagliamento Lane, HAINES CITY

3 Beds 2 Baths 1,512 SqFt Residential MLS® # P4930978
Sold
251 Patterson Road D39, HAINES CITY

$64,900

251 Patterson Road D39, HAINES CITY

1 Bed 1 Bath 560 SqFt Residential MLS® # P4931085
Sold
555 Sanctuary Golf Place, APOPKA

$800,000

555 Sanctuary Golf Place, APOPKA

4 Beds 4 Baths 2,642 SqFt Residential MLS® # O6219097
Sold
201 Tranquility Cove, ALTAMONTE SPRINGS

$1,100,000

201 Tranquility Cove, ALTAMONTE SPRINGS

7 Beds 7 Baths 6,485 SqFt Residential MLS® # O6220472
Sold
1304 Salisbury Drive, WINTER HAVEN

$38,000

1304 Salisbury Drive, WINTER HAVEN

0 Beds 0 Baths 0 SqFt Land MLS® # S5107136
Sold
502 Tanaro Lane, HAINES CITY

$299,789

502 Tanaro Lane, HAINES CITY

4 Beds 2 Baths 1,820 SqFt Residential MLS® # P4931078
Sold
180 Flag Lilly Lane, UMATILLA

$429,950

180 Flag Lilly Lane, UMATILLA

5 Beds 4 Baths 3,030 SqFt Residential MLS® # S5107909
Sold
1037 Ambleside Drive, HAINES CITY

$259,990

1037 Ambleside Drive, HAINES CITY

3 Beds 2 Baths 1,409 SqFt Residential MLS® # C7494888
Sold
15516 Pendio Drive, BELLA COLLINA

$515,000

15516 Pendio Drive, BELLA COLLINA

0 Beds 0 Baths 0 SqFt Land MLS® # G5084454
Sold
31817 Sunpark Circle, LEESBURG

$309,900

31817 Sunpark Circle, LEESBURG

4 Beds 2 Baths 2,010 SqFt Residential MLS® # T3538838
Sold
1113 Oakland Circle, TAVARES

$150,000

1113 Oakland Circle, TAVARES

3 Beds 2 Baths 1,242 SqFt Residential MLS® # G5083768
Sold
4063 Bannock Avenue, TAVARES

$389,950

4063 Bannock Avenue, TAVARES

4 Beds 3 Baths 2,070 SqFt Residential MLS® # S5107877
Sold
1269 Baltic Drive, KISSIMMEE

$13,900

1269 Baltic Drive, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # T3540414
Sold
1813 Grassmere Street, HAINES CITY

$294,990

1813 Grassmere Street, HAINES CITY

4 Beds 3 Baths 1,941 SqFt Residential MLS® # C7494891
Sold
7220 Grace Road, ORLANDO

$1,090,000

7220 Grace Road, ORLANDO

4 Beds 3 Baths 2,904 SqFt Residential MLS® # O6218736
Sold
8612 La Isla Drive, KISSIMMEE

$460,000

8612 La Isla Drive, KISSIMMEE

5 Beds 4 Baths 2,317 SqFt Residential MLS® # S5107186
Sold
521 Mount Olympus Boulevard, NEW SMYRNA BEACH

$230,000

521 Mount Olympus Boulevard, NEW SMYRNA BEACH

3 Beds 3 Baths 1,452 SqFt Residential MLS® # NS1081897
Sold
2850 Ocean Shore Boulevard 15c, ORMOND BEACH

$230,000

2850 Ocean Shore Boulevard 15c, ORMOND BEACH

2 Beds 2 Baths 1,184 SqFt Residential MLS® # FC301910
Sold
1253 Tagliamento Lane, HAINES CITY

$269,000

1253 Tagliamento Lane, HAINES CITY

3 Beds 2 Baths 1,512 SqFt Residential MLS® # P4930981
Sold
1265 Tagliamento Lane, HAINES CITY

$274,875

1265 Tagliamento Lane, HAINES CITY

3 Beds 2 Baths 1,512 SqFt Residential MLS® # P4930980
Sold
Starry Street, ORLANDO

$189,900

Starry Street, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6217077

Sold Homes in Winters Landing Oakland

Winters Landing Real Estate Market Statistics

Average Price $0
Lowest Price $0
Highest Price $0
Total Listings 0
Avg. Price/SQFT $0
List to Sell Price Percentage 98 %

Property Types (active listings)

Homes in Winters Landing feature 3-5 bedrooms, 3-4 baths, 2-3 car garages, and bonus rooms. Built between 2005 and 2006, sought after amenities such as open floor plans with large gourmet kitchens, wood and tile flooring, crown molding, master bedrooms with large walk-in closets, and master bath suites featuring garden tubs and separate showers add to the appeal of Johns Landing. With between 2,400 and 4,000 square feet, desirable floor plans boast plenty of space for entertaining family and friends. Stunning architectural style homes and a desirable location make Winters Landing the perfect place to call home.

Part of Winters Landing’s appeal is the charming town in which it is located. Strolling through Oakland elicits a sense of nostalgia thanks in part to remnants of the one-time bustling city such as the brick Colonial Revival Style Town Hall built in 1911 and the Town Center Circle Fountain. Bikers will rejoice with direct access to the West Orange Trail, a 22-mile haven for riders. Oakland lies near another enchanting town, downtown Winter Garden. Less than 3 miles away, the famous Plant Street Market is a gathering place for locals and visitors alike. The community market is home to over 20 vendors, including a craft brewery, butcher, coal-fired pizza cafe and many more artisans. Weekends draw a crowd for the Downtown Winter Garden Farmer’s Market. In addition to the small-town vibe, modern-day conveniences such as movie theaters, big-name stores, and restaurants are located less than 5 miles away in Winter Garden Village.

There is even plenty of excitement for outdoor enthusiasts. The nearby 128-acre Oakland Nature Preserve is a great way to explore the “real” Florida or take part in the environmental education and ecotourism activities available for all ages. With close access to Central Florida’s major highways such as Florida’s Turnpike and SR 429 commuting to Downtown Orlando and the many theme parks is simple. Winters Landing is truly a hidden gem!

Winters Landing Community Information

  • Location: Located off Oakland Avenue (438) and Winters Landing Drive, north of SR 50 (Colonial Drive) and west of SR 429
  • Number of Homesites: 58
  • Year Built: 2005-2007
  • Square Footage: 2,420-4,050
  • HOA: Yes
  • Community Amenities: Direct Access to West Orange Trail

Orange County Area Schools

  • Tildenville Elementary School (Grades K-5)- Distance: 2 miles
  • Lakeview Middle (Grades 6-8) -Distance: 3 miles
  • West Orange High School (Grades 9-12) -Distance: 5 miles

Dining and Shopping

  • Plaza Collina with Costco, Dining, Shopping - Distance: 3 miles
  • Winter Garden Village (Bank, Retail, Restaurants) - Distance: 5 miles
  • Oakland Town Hall - Distance: 1 mile
  • Plant Street/Downtown Winter Garden - Distance: 2 miles
  • Grocery Store (Publix at West Point Commons) - Distance: 2 miles
  • Restaurant Row - Distance: 19 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 17 Miles
  • Downtown Orlando - Distance: 20 miles

Parks and Recreation

  • Speer Park - Distance: 0.4 miles
  • Walt Disney World Resort - Distance: 23 miles
  • Universal Orlando Resort - Distance: 18 miles
  • Jake Voss Pier (Lake Apopka) - Distance: 8 miles
  • Oakland Nature Preserve - Distance: 1 mile
  • Sanctuary Ridge Golf Club - Distance: 6 miles

Hospitals

  • Advent Health Winter Garden - Distance: 5 miles 
  • Orlando Health South Lake - Distance: 7 miles

*Distances are approximately measured from Winters Landing 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.