HIGHLANDS GLEN in WINTER SPRINGS

HIGHLANDS GLEN
Homes for Sale in WINTER SPRINGS, FL

Community in WINTER SPRINGS · Seminole County · ZIP 32708
28 homesBuilt 1985–2000
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Built fromLive Stellar MLS data20 years of closingsFL DOR public recordsUpdated twice daily
Live · HIGHLANDS GLEN Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Ownership and context
82%
Owner-occupied · HIGHLANDS GLEN
23 of 28 parcels homesteaded (FL DOR 2025)
18%
Non-owner-occupied · HIGHLANDS GLEN
incl. 14% trust or LLC-held · 0% out-of-state
0%
Cash buyers · HIGHLANDS GLEN
0 of 3 sales, 12 mo ending June 2023
28
Homes in the community
28 residential parcels (FL DOR 2025)
Track record · 20 years of records
Est. 1985
Community established
homes built 1985-2000, median 1995 (FL DOR 2025)
0
Failed listings · 2021
peaked at 2 in 2007
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Highlands Glen is a small, established pocket of Winter Springs with only 28 homes total, and right now there is zero active inventory on the market. That is the single most important fact for anyone watching this community: there is nothing to compare against and nothing to buy until something turns over.

With homes built between 1985 and 2000 (median year built 1995) and a median living area around 1,170 square feet, this reads as a community of modest-footprint, established homes rather than new construction. Roughly 82% of homes carry a homestead exemption, which points to a base of owner-occupied properties rather than a transient rental pool. For a buyer, that combination means patience is part of the strategy here; for a seller, it means a listing in this community is not competing against a stack of similar options.

The 60-Second Overview

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.

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.

Best for

  • A buyer who wants a smaller, easy-to-maintain home in an established Winter Springs setting and can be patient for the right listing.
  • A buyer drawn to a community with shared park, playground, pool, and tennis court amenities over a larger private lot.
  • A buyer comfortable purchasing in a community with limited comparable sales history, relying on close market tracking instead.

Probably not for

  • A buyer who needs to move quickly and cannot wait out a community with zero current listings.
  • A buyer who wants a larger living area than the community's median footprint of roughly 1,170 square feet.
  • A buyer who wants a wide range of build years or architectural styles to choose from.

The market around HIGHLANDS GLEN

HIGHLANDS GLEN is a small community — 9 recorded sales on file, most recently in 2021 — too few for its own price trend. Here is the market around it.

In ZIP 32708, 185 homes are on the market and 36% are under contract — a fast-moving corner of WINTER SPRINGS.

Across Seminole County, 1,574 homes are active and 662 pending (30% under contract).

The housing mix here is 82% townhouse, 9% villa, 6% single family residence.

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

Housing distress & ownership in HIGHLANDS GLEN, WINTER SPRINGS

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 16 listings
Distress share trend — 0.0% now (2026-08-12 → 2026-08-24)

Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period August 2026 through August 2026. Deemed reliable but not guaranteed.

Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.

If we were buying in HIGHLANDS GLEN today, this is the order of operations we would run for our clients.

1

Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in HIGHLANDS GLEN.

Best Buy
Buyers who want a small, established Winter Springs community and are willing to wait for the right listing to surface.
Biggest Risk
Zero active inventory means there is currently nothing to purchase and no live comps to gauge pricing.
Sweet Spot
A buyer targeting a compact, single-era home (built 1985-2000) around 1,170 square feet in a quiet, established setting.
Avoid If
You need to buy on a fixed timeline or want a wide selection of home sizes and styles to choose from.

A small, quiet footprint with nothing currently for sale

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.

The location and the amenities are priced into every listing in HIGHLANDS GLEN. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

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.

HIGHLANDS GLEN in 15 seconds.

Best forBuyers who want a small, established Winter Springs community and are willing to wait for the right listing to surface.
Biggest advantageA tight, largely owner-occupied pool of just 28 homes with shared amenities including a pool and tennis courts.
Biggest riskZero active inventory means there is currently nothing to purchase and no live comps to gauge pricing.
Sweet spotA buyer targeting a compact, single-era home (built 1985-2000) around 1,170 square feet in a quiet, established setting.
Avoid ifYou need to buy on a fixed timeline or want a wide selection of home sizes and styles to choose from.

HOA, CDD & Fees

In short
  • Mandatory HOA. Confirm current dues
  • Any club/amenity membership is billed separately

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

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed HIGHLANDS GLEN sales matched to your home.

What is your HIGHLANDS GLEN home worth?

Get a no-obligation home value based on real comparable sales in HIGHLANDS GLEN, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in HIGHLANDS GLEN on the map →

Real comps, not an automated estimate.

HIGHLANDS GLEN Market Scorecard

Thin data

HIGHLANDS GLEN is currently a thin data market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
n/a
Median sold
n/a
Per sqft
n/a
Days on mkt
0/1/0
Active/Pend/Sold

Go deeper: true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

How many homes are in HIGHLANDS GLEN?
The Florida DOR 2025 assessment roll shows 28 homes in HIGHLANDS GLEN (public records).
What share of HIGHLANDS GLEN is owner-occupied?
82% of HIGHLANDS GLEN parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in HIGHLANDS GLEN built?
Homes in HIGHLANDS GLEN were built between 1985 and 2000, with a median year built of 1995 (FL DOR 2025 roll).
Do cash buyers compete in HIGHLANDS GLEN?
Cash buyers took 0% of HIGHLANDS GLEN sales in the 12 months ending June 2023 (0 of 3 closings, Stellar MLS).
Who is the best real estate agent for HIGHLANDS GLEN?
The best agent for HIGHLANDS GLEN is one who actively works WINTER SPRINGS and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for HIGHLANDS GLEN.
How do I find a top WINTER SPRINGS real estate agent who knows HIGHLANDS GLEN?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows HIGHLANDS GLEN and the wider WINTER SPRINGS area.
Can Momentum Realty connect me with an agent for HIGHLANDS GLEN?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your HIGHLANDS GLEN purchase or sale - no call center and no pressure.
A buyer who wants a smaller, easy-to-maintain home in an established Winter Springs setting and can be patient for the right listing.Excellent fit
A buyer drawn to a community with shared park, playground, pool, and tennis court amenities over a larger private lot.Excellent fit
A buyer comfortable purchasing in a community with limited comparable sales history, relying on close market tracking instead.Excellent fit
A buyer who needs to move quickly and cannot wait out a community with zero current listings.Probably not
A buyer who wants a larger living area than the community's median footprint of roughly 1,170 square feet.Probably not
A buyer who wants a wide range of build years or architectural styles to choose from.Probably not

Nearby Communities

Explore more neighborhoods near HIGHLANDS GLEN with Momentum Realty’s local guides.

Highland Village 1 Winter Springs0.2 mi awayNorth Orlando 1St Add Winter Springs0.2 mi awayNorth Orlando Winter Springs0.4 mi awayHighland Village 2 Winter Springs0.4 mi awayHarbor Winds Winter Springs0.5 mi awayGreenspointe Winter Springs0.5 mi awayBaytree Village Winter Springs0.5 mi awayNorth Orlando 2Nd Add Winter Springs0.5 mi away

Browse all Florida neighborhood guides →

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: August 2, 2026)
Housing stock & ownershipFlorida DOR 2025 assessment roll (community parcel extract)
Under-contract sharesStellar MLS records, as of 2026-08-01
Historical depthClosed-sale records back to 2006 (10 transactions analyzed)

Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.

Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.

Own a home here?

You just read the data. Now see what your home is worth.

The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.

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