Roberts Landing

Roberts Landing, a lush neighborhood of only forty-two custom homes nestled on the shores of sparkling Lake Olivia, is the perfect place to begin searching for Windermere real estate. Located off Westover Roberts Road just west of Apopka Vineland, Roberts Landing is a rare-find, a community of unique single-family homes with three to five bedrooms and two to 3.5 baths. Each residence has a custom feel boasting up to 3,900 square feet and offering oversized lushly landscaped homesites. Individual features like a private tennis court, resort-style pool, mature fruit trees, and private lake access can be found at many homes. 

Roberts Landing 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

Sold Homes in Roberts Landing Windermere

Roberts Landing Real Estate Market Statistics

Average Price $550K
Lowest Price $550K
Highest Price $550K
Total Listings 1
Avg. Days On Market 293
Avg. Price/SQFT $0
List to Sell Price Percentage 102 %

Property Types (active listings)


Residences have attractive features like gourmet kitchens, spacious owners’ suite with walk-in closets, luxurious ensuite, and light-filled open-plan living areas. Executive modern home offices and contemporary details are found in some homes while others retain more classic traditional styles.

Located only twelve miles west of Downtown Orlando, this community is convenient to retail, eclectic dining, and daily necessities. Only a short drive away from the charm of downtown, homes for sale in Windermere are prized for their excellent location and air of being a part of something unique. Locally beloved Yellow Dog Eats draws fans with delicious food in a casual, quirky setting. Downtown Windermere, with its charming old-world feel, hosts a weekly farmers market and popular local events. Adjacent Dr. Phillips offers diverse dining options along Restaurant Row as well as popular upscale shopping venues. Walt Disney World, SeaWorld, and Universal Orlando are all easily accessible, and nearby highways I-4, 408, and the Floridas Turnpike offer a direct connection to airports and other attractions. Local Orange County Public Schools are highly rated, providing quality education for students from Pre-K through High School.

Take advantage of a rare opportunity to live in this highly desirable Central Florida location. See for yourself the magic of Roberts Landing.

Roberts Landing Community Information

Location: Westover Roberts Rd & Roberts Landing Rd
Year(s) Built: 1982 - 1991
Homesites: 42
HOA: Yes
Square Footage:  2,184 - 3,964 

Orange County Public Schools

  • Thornebrooke Elementary: Grades Pre-K - 5th - Distance: 2 miles
  • Gotha Middle School: Grades 6th - 8th Distance: 1.2 miles
  • Olympia High School: Grades 9th - 12th Distance: 2 miles

Dining and Shopping

  • Publix Supermarket at The Grove with fitness, medical offices dining, and retail - Distance: 2.5 miles
  • Publix Supermarket at Plantation Grove with UPS and dining - Distance: 2.5 miles
  • Winter Garden Village with Shopping, Dining and Services - Distance: 5.5 miles
  • Downtown Windermere with library and weekly farmers market - Distance: 4 miles
  • Walmart - Distance: 2 miles
  • Downtown Winter Garden - Distance: 7.5 miles
  • Restaurant Row - Distance: 6 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 7.5 miles
  • Orlando International Premium Outlets - Distance: 7.5 miles
  • Downtown Orlando - Distance: 12 miles

Parks and Recreation

  • Bill Fredrick Park and Pool - Distance: 3 miles
  • Gotha Park - Distance: 1.5 miles
  • Central Park - Distance: 4.5 miles
  • RD Keene Park - Distance: 6 miles
  • Roper YMCA Family Center - Distance: 4.5 miles
  • Freedom Park - Distance: 2 miles
  • Nehrling Gardens - Distance: 1.5 miles
  • SeaWorld - Distance: 11 miles
  • Universal Orlando Resort - Distance: 6.5 miles
  • Walt Disney World Resort - Distance: 12 miles

Hospitals

  • Orlando Health - Health Central Hospital: Distance: 3 miles
  • AdventHealth Winter Garden - Distance: 6.5 miles

Airports

  • Orlando International Airport - Distance: 21.5 miles

*Distances are approximately measured from the Roberts Landing community entrance.

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