Isleworth West
Homes for Sale in Windermere, FL

A gated, guard-staffed enclave of 22 estate homes built mostly between 2001 and 2020, Isleworth West Windermere sits inside the broader Isleworth golf community footprint with deed-restricted governance and golf cart access built into daily life.

Stellar MLS sales records identify 8 homes in Isleworth West that have changed hands since 2011, built between 2002 and 2007 (median 2004), with a median living area of about 6,443 sq ft and a typical 5-bedroom, 6-bath layout; 100% 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 West 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 West specifically. Momentum Research analysis of MLS records.

• Windermere Elem · Elementary
• Bridgewater Middle · Middle
• Windermere High School · High

Zoned schools reflect the assignments reported on recent Isleworth West listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Isleworth West address.

Twenty-two homes is a small enough count that this is closer to a private cul-de-sac than a typical subdivision. The median build year of 2004 puts most of the housing stock into its third decade, which means the driving variable in any valuation conversation is less about location and more about what has been done to the home since it was built - kitchens, roofs, mechanical systems, pool equipment, all the things that separate a lightly refreshed estate from one still carrying original 2004 finishes.

Roughly six in ten homes here carry a homestead exemption, which tells you a meaningful share of this community functions as a primary residence rather than a purely seasonal or investment holding. Combined with zero active listings at this snapshot, it points to a market where turnover is infrequent and where a home coming up for sale is a genuine event rather than routine inventory replenishment.

In a 22-home community with no active listings to benchmark against, pricing and positioning cannot be pulled from a live comp sheet - it has to be built from closed history, condition assessment, and a working knowledge of what has changed inside these homes since they were built. That is the kind of groundwork we do before a listing goes live or an offer goes in, not after.

Listings in this community report association dues of about $1,224 per month ($14,688 a year) - the median AssociationFee across 9 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.