Diamondhead
Homes for Sale in Windermere, FL

This is a small-footprint community by any measure - three known homes, spanning built years from 1988 to 2016 - with large-format construction the common thread rather than any shared architectural era or documented amenity package.

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.

Diamondhead 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 Diamondhead specifically. Momentum Research analysis of MLS records.

With only three homes tied to the Diamondhead name and none currently listed, this is not a community you shop by scrolling active inventory - it's one you research house by house, likely off-market or through direct outreach, when and if something comes available.

The size profile is consistent: a median of roughly 4,471 square feet puts these among larger homes for the area, and the build-year spread (1988 to 2016, median 2004) suggests the community developed in phases rather than a single build-out. The low homestead share, at one-third, is a detail worth digging into on any specific address - it can point to second-home use, investment holding, or recent ownership changes, and it's the kind of thing we'd verify before writing an offer.

In a community this thin on active inventory, the value we add isn't filtering listings - it's tracking the handful of homes that exist, understanding their ownership status, and being ready to move the moment one of the three surfaces or a comparable nearby estate does. That kind of attention only works with someone watching the record closely, not just the MLS feed.

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