Wintermere Harbor
Homes for Sale in Winter Garden, FL

A compact enclave of 127 homes in Winter Garden, Orange County, where mature construction and generous square footage matter more than any headline number.

Stellar MLS sales records identify 59 homes in Wintermere Harbor that have changed hands since 2004, built between 1999 and 2003 (median 2001), with a median living area of about 2,852 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.

Wintermere Harbor is too small for its own price trend, so here is the market around it.

In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Winter Garden.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34787 (Winter Garden), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Wintermere Harbor specifically. Momentum Research analysis of MLS records.

With homes dating from 1986 to 2014 and a median build year around 2000, Wintermere Harbor spans roughly three decades of construction. That range matters: the oldest homes may be original inside, while others have been updated over time. Buyers should underwrite by condition, not by the median — roofs, systems, and kitchens are where value diverges in a community this age.

The median living area of about 2,690 square feet points to substantial homes rather than starter product. Combined with only 127 total homes, inventory is naturally limited. An 86% homestead share reinforces that this is a stay-put community, so the pace can feel slow. When a home does list, the well-maintained ones tend to command attention precisely because comparable options are scarce.

In a 127-home community with thin turnover, the difference between a fair price and a good one comes down to reading condition against the median and knowing which recent closings actually compare. We track this pocket closely, help buyers move quickly when the right floor plan surfaces, and help sellers position a home so its updates are priced fairly in a market where condition — not a single number — sets value.

Listings in this community report association dues of about $131 per month ($1,572 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.