Windsong Lookout Landing
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.

Stellar MLS sales records identify 27 homes in Windsong Lookout Landing that have changed hands since 2004, built between 2001 and 2016 (median 2006), with a median living area of about 4,630 sq ft and a typical 5-bedroom, 4.5-bath layout; 96% 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.

Windsong Lookout Landing 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).

In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 32789 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Windsong Lookout Landing 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 22 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, 2026-10.

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