Isleworth
Homes for Sale in Windermere, FL

Isleworth is an established estate enclave in Windermere, Orange County, of 108 large homes built between 1987 and 2018. A homestead share of about 62% points to a core of owner-occupants alongside a meaningful set of second or investment holdings.

Stellar MLS sales records identify 195 homes in Isleworth that have changed hands since 2005, built between 1986 and 2026 (median 1996), with a median living area of about 6,060 sq ft and a typical 5-bedroom, 5.5-bath layout; 98% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Isleworth is too small for its own price trend, so here is the market around it.

In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34786 (Windermere), 784 homes closed in the last 12 months at a median of $622K ($262/sq ft), down 1.5% year over year, with a median 38 days on market. Right now 113 active and 37 pending listings put supply at about 3.0 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Isleworth specifically. Momentum Research analysis of MLS records.

The defining feature is size and age spread. A median build year of 1996 with a range stretching to 2018 means you will find both original-era estates and later construction within the same community. At this square footage, the cost of updating — systems, kitchens, baths, roofs on the older stock — is substantial, and it shows up directly in what a given home is worth. Two otherwise comparable addresses can price very differently based purely on how much capital has gone into them recently.

The roughly 62% homestead share tells you this is primarily a lived-in community, not a pure investor block, but the remainder signals that some inventory is held as secondary property. For a buyer, that mix can mean occasional homes that have seen lighter day-to-day use; for a seller, it means your competition may not always be actively marketed, so timing and turnkey presentation carry weight.

In a thin market where two closings anchor the recent record, comps do not do the work for you — underwriting does. We price and negotiate each estate on its own lot, finish level, and renovation history rather than leaning on a neighborhood average, and we build the case a low-volume market requires whether you are the one buyer or the one seller in a given quarter.

Listings in this community report association dues of about $1,043 per month ($12,516 a year) — the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.