About Roberts Landing Neighborhood
Roberts Landing sits on the east shore of Lake Olivia in northeast Windermere, with its main entrance on Westover Roberts Road just west of Apopka-Vineland Road. The 42 single-family homes here were built between 1982 and 1991, giving the streets a mature, well-shaded character distinct from the new construction that defines much of the surrounding area.
Homes range from roughly 2,184 to 3,964 square feet with three to five bedrooms and two to 3.5 baths. Lots are unusually large for Windermere — typically a full acre or close to it — and many are sloped, with homes set higher than the street. Floor plans are mixed: some are traditional 1980s-era custom builds, while others have been substantially renovated with open layouts, modernized kitchens, and updated finishes. Private pools are common, several homes have private tennis courts, and a handful of properties have direct frontage on Lake Olivia with private docks.
Lake Olivia itself anchors the neighborhood's character. The lake provides views and recreational access for waterfront homes, and the older tree canopy combined with winding streets gives Roberts Landing a settled, residential feel that's harder to find in newer Windermere subdivisions.
📊 Quick Facts
🏡 What Makes Roberts Landing Distinctive
- Acre-sized lots: Most parcels are around an acre — significantly larger than typical Windermere subdivisions.
- Lake Olivia access: A subset of homes have direct lake frontage; the remainder benefit from the lake's presence and views.
- Custom-build character: Homes were built individually rather than to a single production template, so floor plans and elevations vary house to house.
- No mandatory HOA, no CDD: One of the few Windermere neighborhoods without required association fees or community development district assessments.
- Low turnover: Listings come up infrequently — buyers often have to wait for the right home.
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Roberts Landing Location & Connections
Roberts Landing is in northeast Windermere, with its main entrance on Westover Roberts Road just west of Apopka-Vineland Road. The neighborhood is approximately 3 miles from downtown Windermere and within easy reach of the Florida Turnpike, SR 429, and I-4 — providing direct connections throughout the Orlando metro area.
🏘️ Adjacent Neighborhoods & Areas
- Lake Olivia — the lake forms the western boundary of Roberts Landing; select homes have direct frontage
- Westover Roberts Road (main arterial providing access to Apopka-Vineland Road)
- Westover Club — directly across Westover Roberts Road
- Westover Reserve — guard-gated community across Westover Roberts Road
- Lake Olivia Reserve — small lakefront community on Lake Olivia
🚗 Detailed Commute Times
- Downtown Orlando: ~22 minutes (16 miles) via SR 408
- UCF Campus: ~30 minutes (22 miles) via SR 408
- Walt Disney World: ~18 minutes (13 miles) via Western Way
- Universal Orlando: ~20 minutes (14 miles) via Florida Turnpike
- SeaWorld Orlando: ~20 minutes (14 miles) via SR 429 / I-4
- Lake Nona Medical City: ~35 minutes (26 miles) via SR 528
- Cocoa Beach: ~75 minutes (65 miles) via SR 528
- Downtown Windermere: ~10 minutes (3 miles)
- Winter Garden Village: ~12 minutes (5.5 miles)
✈️ Airport Access
- Orlando International Airport (MCO): ~25 minutes (20 miles)
- Orlando Sanford International Airport (SFB): ~45 minutes (32 miles)
- Orlando Executive Airport: ~25 minutes (17 miles)
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Roberts Landing Amenities & Lifestyle
Roberts Landing is a quiet, low-density residential neighborhood without internal amenities — no community pool, clubhouse, or shared facilities. The appeal here is the privacy of acre-sized lots, lake views, and a settled, mature feel. Residents draw on the broader Windermere area for shopping, dining, recreation, and entertainment.
Apopka-Vineland Road, just outside the neighborhood, provides quick access to grocery, retail, and dining clusters at Winter Garden Village and Plantation Grove, while downtown Windermere is about 3 miles away for local shops and the weekly farmers market.
🏊 Neighborhood Amenities
Roberts Landing has no shared community amenities. Each home stands on its own oversized lot, and amenity-style features are private to individual properties:
- Private swimming pools (common across the neighborhood)
- Private tennis courts (on select properties)
- Private docks and direct lake access (on Lake Olivia frontage homes)
- Mature tree canopy and well-shaded streets
- Winding internal streets with low traffic volume
🛍️ Shopping & Services
Roberts Landing residents have quick access to Winter Garden Village (about 5.5 miles) for major retail and a Publix at Plantation Grove (about 2.5 miles) for groceries. Downtown Windermere offers smaller boutiques and a weekly farmers market.
For comprehensive shopping information: View our Windermere Shopping Guide →
🍽️ Restaurants
Local favorite Yellow Dog Eats in nearby Gotha is a Windermere staple. The Grove on Conroy-Windermere Road and downtown Windermere offer additional casual and sit-down options, while Restaurant Row in Dr. Phillips is roughly 15 minutes away.
For comprehensive restaurant information: View our Windermere Restaurants Guide →
🎭 Arts & Culture
Downtown Windermere hosts community events at the historic 1890 Windermere Schoolhouse and Town Square. Larger arts venues including the Dr. Phillips Center for the Performing Arts in downtown Orlando are within a 25-minute drive.
For comprehensive arts & culture information: View our Windermere Arts & Culture Guide →
🏃 Health & Wellness
Orlando Health Dr. P. Phillips Hospital, AdventHealth Winter Garden, and AdventHealth Apopka are all within 15-20 minutes. Specialist care is available at Lake Nona Medical City approximately 35 minutes away.
For comprehensive health & wellness information: View our Windermere Hospitals Guide →
🌳 Parks & Recreation
Lake Olivia provides on-water recreation for homes with frontage. Nearby public parks include R.D. Keene Park on Lake Butler and Fernwood Park in downtown Windermere. The West Orange Trail is accessible via Winter Garden for cycling and walking.
For comprehensive parks & recreation information: View our Windermere Parks & Recreation Guide →
⚽ Sports & Athletics
Several private clubs in the area offer golf and tennis, including the Orange County National Golf Center. Homes within Roberts Landing with private tennis courts add an unusual amenity option not found in most newer Windermere subdivisions.
For comprehensive sports & athletics information: View our Windermere Sports & Athletics Guide →
🎉 Fun Things to Do
Roberts Landing's central Windermere location puts residents close to Walt Disney World, Disney Springs, Universal Orlando, and SeaWorld, all within a 20-minute drive. Downtown Windermere's farmers market and seasonal community events provide a more local alternative.
For comprehensive events & activities information: View our Windermere Events & Things To Do Guide →
🎓 Schools
Roberts Landing is served by Orange County Public Schools:
- Elementary: Thornebrooke Elementary
- Middle: Gotha Middle School
- High: Olympia High School
Note: School assignments are subject to change. Always verify current zoning with Orange County Public Schools before making a purchase decision.
For comprehensive school information: View our Windermere Schools Guide →
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How Roberts Landing Compares
Roberts Landing's value proposition is unusual in Windermere: acre-sized lots with no mandatory HOA, no CDD, and a mature 1980s-era custom-build character. The trade-off versus newer communities is older home stock that often benefits from renovation. The table below frames Roberts Landing against two common alternatives — newer guard-gated luxury and other established northeast Windermere neighborhoods.
| Feature | Roberts Landing | Westover Reserve | Newer Guard-Gated (e.g., Reserve at Belmere) |
|---|---|---|---|
| Typical Lot Size | ~1 acre | ~0.3-0.5 acre | ~0.2-0.4 acre |
| Year Built | 1982-1991 | Late 1990s-2000s | 2000s-present |
| Mandatory HOA | No (optional) | Yes | Yes |
| CDD Fee | No | No | Varies |
| Gated Entry | No | Yes (guard-gated) | Yes |
| Lake Frontage | Select homes (Lake Olivia) | Limited | Varies by community |
| Community Amenities | None (private property amenities only) | Yes (resort-style) | Yes (resort-style) |
💡 Value Proposition: Buyers who want acreage, established trees, and the freedom of no mandatory HOA fees typically choose Roberts Landing over newer gated alternatives. Buyers who prioritize resort amenities, gated security, and newer construction usually look elsewhere — both are valid choices, just different ones.
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Roberts Landing HOA & CDD Information
Roberts Landing has an optional HOA rather than a mandatory one — an unusual structure for Windermere. The neighborhood has no CDD (Community Development District) assessment, which is common for communities developed in the 1980s. There are no shared neighborhood amenities, so HOA scope tends to be narrow.
Because participation is voluntary and dues structures can change, current details should be confirmed before purchase. Read more about HOA and CDD basics on our reference pages: What's an HOA? and What's a CDD?
💰 HOA Fees & Management Contact
HOA fees and management company information often change. Please contact us and we will be happy to provide you with current information on the optional HOA, dues structure, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.
📋 What HOA Participation Typically Includes
Because Roberts Landing has no shared amenities and an optional HOA structure, participation typically focuses on neighborhood-wide concerns rather than facility maintenance:
- Entrance signage and shared common areas (if applicable)
- Architectural review (if active)
- Neighborhood communication and coordination
- Voluntary dues that may fund neighborhood improvements
For a complete and current list of what the HOA covers, please contact us.
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David Myers
