Highlands Glen
Homes for Sale in Winter Springs, FL

Highlands Glen is a compact, largely owner-occupied community in Winter Springs built out mostly in the 1990s, with amenities reported to include a park, playground, pool, and tennis courts.

Stellar MLS sales records identify 21 homes in Highlands Glen that have changed hands since 2008, built between 1985 and 2000 (median 1994), with a median living area of about 1,171 sq ft and a typical 3-bedroom, 2-bath layout; 90% are townhomes. 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.

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

In ZIP 32708, 150 homes are on the market and 33% are under contract — a fast-moving corner of Winter Springs.

Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).

In ZIP 32708 (WINTER SPRINGS), 668 homes closed in the last 12 months at a median of $412K ($242/sq ft), down 1.5% year over year, with a median 33 days on market. Right now 32 active and 21 pending listings put supply at about 1.9 months - a healthy market. See the live ZIP 32708 housing market and the Seminole County market.

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

At 28 total homes, Highlands Glen is not a community where you can expect a rotating supply of choices. With zero active listings as of this snapshot, there is currently no way to benchmark pricing or condition against live comparables - anyone interested should plan to watch the community over time rather than expect an immediate transaction.

The homes themselves date to a fairly tight build window, 1985 to 2000, with a median year built of 1995 and a median living area of about 1,170 square feet. That points to a community of smaller-footprint homes from a single era of development, rather than a mix of eras or a wide range of home sizes. The high homestead share, around 82%, suggests most of these homes are lived in by their owners rather than held as rentals, which tends to correlate with more consistent upkeep and a steadier resale rhythm, though that is not something we can quantify from this data alone.

In a community this small, with no active listings to study, having someone track it closely matters more than usual. We monitor Highlands Glen for the first sign of a new listing or a status change, and we can walk you through what the limited sales history and homestead pattern actually imply for value and timing, rather than guessing from a headline number.

Listings in this community report association dues of about $62 per month ($744 a year) - the median AssociationFee across 3 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, 2026-09.

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