Windsong Lakeside
Homes for Sale in Winter Park, FL

Windsong Lakeside is a 264-home community in Winter Park, Orange County, built out over a full century of construction rather than a single development phase, with a median home running large at 3,505 square feet.

Stellar MLS sales records identify 41 homes in Windsong Lakeside that have changed hands since 2005, built between 2001 and 2015 (median 2005), with a median living area of about 4,646 sq ft and a typical 5-bedroom, 5-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.

Windsong Lakeside 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), 394 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.4% year over year, with a median 40 days on market. Right now 88 active and 21 pending listings put supply at about 4.9 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 Lakeside specifically. Momentum Research analysis of MLS records.

The defining fact about this community is its build spread: homes date as far back as 1924 and as recently as 2024, with the median landing in 2002. That is an unusually wide range for a single named community, and it means buyers should not treat 'Windsong Lakeside' as shorthand for a consistent architectural style or construction era. Each listing needs to be evaluated on its own merits — systems age, prior renovation, and lot configuration will vary more here than in a community built out in one continuous phase.

Living space runs large, with a median of 3,505 square feet, and no community amenities are currently identified from active MLS listings. That combination suggests the value proposition here is the home and its footprint rather than a shared amenity package — no clubhouse, pool, or recreation facility is showing up in the data buyers are seeing. Anyone shopping this community should confirm amenity status directly rather than assume it based on comparable Winter Park communities.

A community with a century-wide build range and no confirmed amenity package requires more individualized due diligence, not less — pulling the right comparables and reading each home's condition on its own terms. We work Orange County inventory closely enough to help buyers and sellers price against the right slice of Windsong Lakeside rather than the community average.

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.