Sterling Pointe
Homes for Sale in Winter Garden, FL

Sterling Pointe is a compact early-2000s neighborhood in Winter Garden's Orange County footprint, built out over just a few years, so buyers are looking at a consistent vintage rather than a mix of eras.

Stellar MLS sales records identify 38 homes in Sterling Pointe that have changed hands since 2004, built between 2001 and 2003 (median 2002), with a median living area of about 1,599 sq ft and a typical 3-bedroom, 2-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.

County records show 3 qualified sales in Sterling Pointe across 2024–2025 (2 in 2024, 1 in 2025), median $415,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

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.

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

In ZIP 34787, 932 homes are on the market and 29% are under contract — a steady corner of Winter Garden.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

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.

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

Because everything here went up between 2001 and 2003, the bones are broadly similar across the community and the median living area sits near 1,628 square feet. That consistency makes valuation more legible than in a mixed-age subdivision, but it also means the spread between the tired and the renovated is where the real money moves. Roofs, HVAC, and kitchens from the original build are now well into replacement territory, so the presence or absence of those updates is the single biggest swing factor.

The high homestead share points to a community held by long-term owners rather than churned by investors. That supports stability in how homes are maintained, but it also throttles the number of listings in any given stretch. Buyers should treat a well-updated listing as a comparatively rare event and be prepared to act; sellers of an updated home are competing against a short bench.

In a small, low-turnover community like Sterling Pointe, the difference between pricing off a tired comp and pricing off an updated one is decisive, and there are not many trades to lean on. We track condition, not just square footage, and we know which updates the market actually pays for here versus which ones are just nice to have.

Listings in this community report association dues of about $63 per month ($756 a year) — the median AssociationFee across 32 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, 2026-10.

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