Cortland Park
Homes for Sale in Winter Park, FL

Cortland Park is a small, established pocket of 85 homes in Winter Park where the housing stock spans more than a century of construction, from early-1900s originals to recent rebuilds, with a median home dating to 1951.

Stellar MLS sales records identify 22 homes in Cortland Park that have changed hands since 2004, built between 1925 and 2012 (median 1948), with a median living area of about 3,118 sq ft and a typical 4-bedroom, 3-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.

Cortland Park 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 Cortland Park specifically. Momentum Research analysis of MLS records.

The living space profile skews larger than a typical infill neighborhood - a median of 2,394 square feet - which suggests many of the homes here have been expanded or rebuilt at some point rather than left untouched at their original 1900s-era footprint. Combined with the wide year-built spread, this is a community where two homes on the same block can represent very different generations of construction, finish level, and system age, even if the lot sizes and street pattern look similar.

The homestead share of just over 70% is worth sitting with: it points to a neighborhood where most owners have filed for the exemption tied to a primary residence, which typically correlates with longer hold periods and less speculative turnover. That, paired with zero active listings and only one closing in the current window, means Cortland Park does not behave like a fast-moving subdivision - inventory is thin by nature, not by a temporary market shift, and no community amenities are listed in current MLS data, so whatever draws a buyer here is the home and the location itself, not a shared clubhouse or pool.

With no active listings to compare against, pricing a home in Cortland Park correctly means pulling from off-MLS context and recent comparable closings rather than trusting what is currently showing online - that is where a broker who tracks this pocket closely earns their keep, on both the buy and sell side.

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