MAITLAND SHORES 1ST ADD
Homes for Sale in WINTER PARK, FL

A small, low-turnover community in Winter Park where large-format homes spanning nearly a century of construction sit on a single shared amenity — a park — rather than a resort-style package.

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.

MAITLAND SHORES 1ST ADD is a small community — 51 recorded sales on file, most recently in 2017 — too few for its own price trend. Here is the market around it.

In ZIP 32789, 243 homes are on the market and 28% are under contract — a steady corner of WINTER PARK.

Across Orange County, 5,873 homes are active and 2,054 pending (26% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not MAITLAND SHORES 1ST ADD specifically. Momentum Research analysis of MLS records.

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

Zoned schools reflect the assignments reported on recent MAITLAND SHORES 1ST ADD 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 MAITLAND SHORES 1ST ADD address.

With only 103 homes total and construction dates ranging from 1925 to 2024, Maitland Shores 1st Addition does not read like a typical single-phase subdivision. The median year built of 1991 sits roughly in the middle of that range, which means buyers here are choosing between genuinely older construction, mid-century-plus rebuilds, and newer infill — each with different maintenance and system-age considerations that a size or price comparison alone won't surface.

The median living area of 3,363 square feet is substantial for the area, suggesting this community skews toward larger-format homes rather than compact or entry-level product. Combined with a 71% homestead share, the pattern is one of longer-term ownership rather than rapid resale — which explains why active inventory is thin. A single active listing and no recorded closings in the current window mean there is no reliable trend line right now; each transaction here has to be priced against the specific home, not a community average.

In a community this thin on active listings and closings, there is no shortcut through comparable sales data — pricing a home here requires digging into the individual property's age, condition, and square footage against the broader Winter Park and Orange County market. We do that work directly rather than leaning on a stale average, and we tell clients plainly when the data does not support a confident number yet.

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