Winter Garden Trails
Homes for Sale in Winter Garden, FL

Winter Garden Trails market snapshot (as of September 12, 2026): the median sale price is about $485K ($210 per sq ft over the trailing 12 months of closed sales), and a median 29 days on market for closed sales.

In ZIP 34787 (Winter Garden), 2,123 homes closed in the last 12 months at a median of $595K ($252/sq ft), down 0.9% year over year, with a median 37 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.

Stellar MLS sales records identify 20 homes in Winter Garden Trails that have changed hands since 2015, built between 2005 and 2007 (median 2006), with a median living area of about 2,460 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.

A single-phase, deed-restricted community in Winter Garden built out over a tight two-to-three year span in the mid-2000s, offering a consistent size and age profile rather than a mix of eras.

Because Winter Garden Trls 01 3 was built out entirely between 2005 and 2007, buyers aren't choosing between old and new construction here - every home shares a similar age and general construction era, with the main variables being condition, updates, and lot position. At a median 2,381 square feet, these are mid-sized homes, not the smallest or largest product in the broader Winter Garden market.

The current snapshot shows zero active listings, based on the last 3 months of closing activity used to establish these figures. That combination - no listings, a homestead share suggesting most owners are settled in as primary residences, and a median 51-day market time - points to a community where available homes are the exception, not the rule, and where a serious buyer needs to move with a plan already in place rather than expecting a deep pool to shop from.

In a community with no active listings, the work happens before a sign ever goes up - tracking off-market activity, understanding what recent closings actually looked like inside these 55 homes, and being ready to act the moment something surfaces. We treat a near-zero-inventory pocket like this one as a watch-and-wait assignment, not a browse-the-listings one.

Listings in this community report association dues of about $657 a year ($55 a month) - the median AssociationFee across 4 MLS records, normalised to a monthly figure; most are billed annually. 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, 2026-10.

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