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Lake Olivia, Windermere: Five Enclaves, Five Price Levels
Lake Olivia, Windermere, is ringed by five small enclaves, Roberts Landing, Weatherstone on Lake Olivia, Woods of Windermere, Worthington Park and Lake Olivia Reserve, with 79 homes in all, assessed from a $574,770 median in Roberts Landing to more than $2 million for the newest lakefront builds.
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Buying or Selling on Lake Olivia
Lake Olivia homes for sale range from mid-1980s homes on acre lots to houses built since 2020 on the shore. Most are in the Census-designated place of Gotha, though all use Windermere addresses. Tuscany Ridge and Westover Reserve are each under half a mile from Roberts Landing.
The Five Enclaves
- Roberts Landing: 41 homes built mostly 1984 to 1988 on acre lots, median $574,770; the 9 on the lake are assessed at nearly twice the rest.
- Weatherstone on Lake Olivia: 13 homes built 1999 to 2007 on median 2.54-acre lots, median $1,859,890.
- Woods of Windermere: 12 homes built 2012 to 2014 on lots of about 0.64 acres, median $1,174,400, none on the lake.
- Worthington Park: 10 homes on English Pine Court, eight built 2002 to 2005, median $1,570,110, none on the lake.
- Lake Olivia Reserve: 3 lakefront homes built 2020 to 2025, the highest-valued around the lake.
Choosing an Enclave Before a House
Each enclave is small and uniform inside, and very different from the next. A Roberts Landing buyer is choosing an acre and a 1980s house at a low value for Windermere; a Weatherstone buyer, two and a half acres and a larger 2000s house; a Lake Olivia Reserve buyer, new construction on the lake. Our agents help you decide which trade-off fits first, then compare homes only with sales from the same enclave and side of the water, and confirm frontage, dock permits and the survey for any lot on the lake.
Older and Newer Homes
Thirty-seven of the 79 homes date from before 1990, all in Roberts Landing. For those, we help plan inspections and weigh renovating against rebuilding with the county's permitting steps and the septic setup in view.
Lake Olivia's Tax Districts and Flood Zones
The enclaves sit in two unincorporated districts, at 16.0858 and 16.1366 mills for 2025. Before exemptions, a new owner's property tax runs roughly $9,000 to $24,000 a year for the middle half of these homes, mirroring the range in values. All 21 lakefront lots touch a FEMA special flood hazard area, plus 4 inland ones. School assignment for any of these addresses is in Find My School.
For Lake Olivia Owners Thinking of Selling
County records show 13 homes across the five enclaves with a most recent recorded sale from 2022 through 2026, a thin record for any one enclave. We price from your own enclave's sales first and widen carefully, explaining each adjustment.
See the Windermere lakefront guide and the Windermere neighborhood comparison.
The Own Luxury Homes® Perspective
On Lake Olivia, the enclave sets the price range before the house does.
The five Lake Olivia enclaves span from a $535,300 median for Roberts Landing's off-lake homes to more than $2 million for Lake Olivia Reserve's new builds on the 2026 tax roll, around one 88-acre lake.
Around Lake Olivia, picking the enclave is picking the price range. Decide what you want, an acre at a low value, estate land or new construction, then compare homes only within that enclave.
Lake Olivia Questions
Is Lake Olivia part of the Butler Chain?
No. It isn't among the 13 chain lakes the Orange County Water Atlas lists.
Is Roberts Landing, Windermere, on Lake Olivia?
Partly: 9 of its 41 homes touch the lake, and the rest sit on acre lots off the water.
Is Worthington Park, Windermere, on the lake?
No. Its 10 homes, like Woods of Windermere's, are off the water; Weatherstone, Lake Olivia Reserve and homes on the old Gotha town plat front the lake.
Are Lake Olivia homes in Gotha or Windermere?
They use Windermere addresses; most fall within the Census-designated place of Gotha, and none is inside the Town of Windermere.
How many Lake Olivia homes have recently sold?
Thirteen across the five enclaves show a most recent recorded sale from 2022 through 2026.
A Private, More Intentional Beginning
Tell us about your decision
Tell us what you are buying or selling, where, the approximate price range, your timing, and what matters most.
Speak with a local real estate professional.
Discuss your goals, the property, the market, and the questions that will help you decide how to proceed.
Choose your next step.
Take the time you need. There is no obligation to move forward.
Sources:
Orange County GIS, parcel data (2026 tax roll); Orange County GIS, recorded subdivision plats; Orange County GIS, hydrology (lakes); Orange County Water Atlas, Butler Chain of Lakes; Orange County Property Appraiser, 2025 final millage rates; Orange County GIS, FEMA flood zones; Orange County Public Schools, Find My School. Checked October 2026.
Figures: homes with a Windermere site address outside the Horizon West planning boundary, from Orange County parcel data; values are county just values on the 2026 tax roll, not sale prices; medians. Tax estimates multiply each home's 2026 county just value by the 2025 final millage for its tax district, before exemptions and non-ad valorem assessments, and are rounded. Flood counts are homes with at least 1% of the lot in a FEMA special flood hazard area (zones A, AE or AH) on the county's FEMA layer.
Reviewed by Ryan Brown, Licensed Real Estate Broker and CEO, Own Luxury Homes®