Windsong Lookout Landing 43/79
Homes for Sale in Winter Park, FL

This is a small, established enclave of large homes in Winter Park's Orange County footprint, built out over roughly two decades and dominated by owner-occupants rather than turnover stock. Expect scale and stability over volume.

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.

Windsong Lookout Landing 43/79 is too small for its own price trend, so here is the market around it.

In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.

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

ZIP and county figures describe the wider market, not Windsong Lookout Landing 43/79 specifically. Momentum Research analysis of MLS records.

The housing stock spans construction from 2001 to 2019, with the median home dating to 2007. That range means you'll find both early-2000s builds and later, more current floor plans within the same community — layouts, systems, and finishes will vary meaningfully by vintage, so due diligence on age of roof, HVAC, and mechanicals should be property-specific.

With homestead occupancy at roughly 77 percent, the large majority of these homes are owner-occupied. That tends to correlate with slower turnover and homes that are lived in and maintained rather than cycled. For a buyer, it also means when something does list, it may be the only real option in its size class for a while.

In a community this small, pricing is an art of thin comps and condition adjustments — the wrong anchor can cost a seller real money or lead a buyer to overpay. We read each home on its own terms, weigh vintage and finish against the median, and tell you plainly where a property sits. When only a handful of homes trade, being early and being accurate is the whole game.

Listings in this community report association dues of about $262 per month ($3,144 a year) — the median AssociationFee across 3 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.