Windsong Knowles Place
Homes for Sale in Winter Park, FL

A small deed-restricted enclave of larger-format homes built in the 2008-2017 window, Windsong Knowles Place sits within Winter Park in Orange County and carries amenities typical of a planned community - pool, clubhouse, tennis, and shared green space.

Stellar MLS sales records identify 25 homes in Windsong Knowles Place that have changed hands since 2011, built between 2009 and 2015 (median 2013), with a median living area of about 3,482 sq ft and a typical 4-bedroom, 4-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 Knowles Place 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 Knowles Place specifically. Momentum Research analysis of MLS records.

The story here is scale and consistency. Forty-one homes is a small enough footprint that this community rarely produces more than a listing or two at a time, and the build window - 2008 through 2017 with a 2013 median - means most of the housing stock shares a similar generation of construction, finishes, and systems rather than spanning decades of styles and ages.

Living space runs large, with a median of roughly 3,647 square feet, which points to a community built around bigger-footprint homes rather than starter product. Combined with deed restrictions and a homestead share near 88%, this reads as a community of owners who bought to stay, not to flip - which is consistent with the near-total absence of active inventory at the time of this snapshot.

A community with zero active listings and only 41 homes total is not one you can shop by browsing the portals - you need someone tracking it closely enough to know when something is about to move. We watch communities like this for early signals, off-market conversations, and the timing that lets a buyer or seller act before a listing goes wide.

Listings in this community report association dues of about $265 per month ($3,180 a year) - the median AssociationFee across 6 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.