Canton Ave Cottages
Homes for Sale in Winter Park, FL

A compact, deed-restricted pocket of Winter Park built out in stages from the 1920s through the 2020s, with a median home size of 1,220 square feet - cottage-scale living rather than large-format housing.

Stellar MLS sales records identify 7 homes in Canton Ave Cottages that have changed hands since 2018, built between 2016 and 2018 (median 2017), with a median living area of about 1,904 sq ft and a typical 3-bedroom, 2.5-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.

Canton Ave Cottages 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 Canton Ave Cottages specifically. Momentum Research analysis of MLS records.

• Killarney Elem · Elementary
• Maitland Middle · Middle
• Winter Park High · High

Zoned schools reflect the assignments reported on recent Canton Ave Cottages listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Canton Ave Cottages address.

The build years here run from 1923 to 2023, which is an unusually wide range for a community of only 115 homes. The median year built of 1971 sits in the middle of that span, but it masks real variation - pre-war cottages, mid-century homes, and recent construction all sit within the same deed restrictions. That mix means renovation history and permit records matter more than the tax roll year alone.

The community carries HOA-level maintenance, deed restrictions, reclaimed water irrigation, and a community mailbox - standard shared-service infrastructure for a smaller, tightly bounded neighborhood rather than a resort-style amenity package. Just under half of homes here (48%) currently carry a homestead exemption, worth noting for buyers weighing whether a purchase functions as a primary residence or a non-homestead property under Florida tax rules.

With only 1 active listing at last count, comps are thin and pricing a home here by algorithm or by pulling three nearby sales is unreliable. We track the actual condition and permit history behind each sale in this community so you're not pricing a 2023-built home off a 1923 comp, or the reverse.

Listings in this community report association dues of about $400 per month ($4,800 a year) - the median AssociationFee across 9 MLS records, normalised to a monthly figure; most are billed monthly. 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.