Highlands
Homes for Sale in Winter Springs, FL
All 126 homes for sale in Winter Springs, FL · median $422,445 · 62 homes for sale in 32708 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 5 closed sales in Highlands Sec 6 1St Rep in Winter Springs, FL since 2017, the most recent in July 2025. Across Winter Springs as a whole, 253 homes closed in the last 12 months at a median of $446,000, 33 median days on market, with 32 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,770 ($6,170 with the full homestead exemption).
This is a small, established pocket of Winter Springs — 32 homes total, all built in a tight window between 1980 and 1985. That kind of construction consistency means the homes share a similar footprint and era of systems, which simplifies comparison but also means most of the housing stock is now over four decades old. Condition and updates, not floor plan variety, are what separate one listing from the next here.
With a median living area around 1,134 square feet, these are compact homes by current standards, which keeps the buyer pool focused on smaller households or investors rather than move-up buyers seeking larger square footage. A homestead share near 59% tells us a majority of owners are treating these as primary residences rather than rentals or second homes, which tends to support steadier upkeep and a more stable resale environment over time.
Nearby homes for sale
No active listings inside Highlands Sec 6 1St Rep right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Highlands Sec 6 1st Rep is a compact, early-1980s subdivision in Winter Springs with no identified community amenities — the value proposition here is the home and location itself, not a clubhouse or shared recreation.
Stellar MLS sales records identify 193 homes in Highlands that have changed hands since 2004, built between 1972 and 2003 (median 1978), with a median living area of about 1,607 sq ft and a typical 3-bedroom, 2-bath layout; 87% 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.
Who Highlands is best for.
Best for
- A buyer seeking a smaller, lower-maintenance home footprint under 1,200 square feet.
- An owner-occupant comfortable with an older home and planning for gradual updates.
- An investor evaluating a small, established rental or resale opportunity in Seminole County.
Probably not for
- A buyer who wants a pool, clubhouse, or other on-site shared amenities.
- A buyer prioritizing larger living space or newer construction systems.
- A buyer unwilling to budget for updates typical of homes built in the early 1980s.
The market around Highlands
Highlands 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 specifically. Momentum Research analysis of MLS records.
Highlands Rep by the numbers
From county property records and closed MLS sales for the Highlands Rep subdivision: 8 homes on record; built 1980–1982; typical size about 1,134 heated sq ft; 3 bedrooms is the median. Housing mix: townhome 62%, single-family 37%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2017 | 1 | $126,500 |
| 2018 | 1 | $182,000 |
| 2021 | 1 | $222,000 |
| 2023 | 1 | $275,000 |
| 2024 | 1 | $291,000 |
| 2025 | 2 | $326,000 |
Newest recorded sale: $337,000 on 2025-07-31.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
The Highlands buying strategy.
If we were buying in Highlands today, this is the order of operations we would run for our clients.
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.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
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.
A Small, Aging Footprint
With only 32 homes and every one of them built in a five-year span, this community reads more like a single construction phase than a sprawling subdivision. That narrow build window is useful for buyers: it means roofs, electrical, and plumbing across the neighborhood are generally facing similar age-related decisions, so a pre-purchase inspection matters more here than in a newer or more staggered community.
There is no identified community amenity package tied to this section — no pool, clubhouse, or shared recreation noted in current MLS data. That keeps HOA-type costs and obligations, if any, minimal, but it also means the appeal is squarely about the individual home, its lot, and its proximity to the rest of Winter Springs rather than any shared community draw.
The location and the amenities are priced into every listing in Highlands. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, older subdivision like this, the differences between homes come down to what has been updated and what hasn't — details that don't always show up clearly in a listing. We walk buyers through condition-by-condition comparisons across the 32 homes here, and we help sellers position a dated or updated home accurately so it doesn't get lumped in with the rest of the block.
Highlands in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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.
Tools for a Highlands buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Highlands sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highlands, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highlands home worth?
Get a no-obligation home value based on real comparable sales in Highlands, 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 all homes for sale in Winter Springs →
Should you buy in Highlands?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2017 (5 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 local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Highlands Rep fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Highlands
Where is Highlands?
Highlands is a community in Winter Springs, Seminole County, Florida, ZIP 32708.
How many homes are in Highlands?
County property records list 8 homes in Highlands, built between 1980 and 1982; the typical home is about 1,134 heated square feet.
What do homes in Highlands sell for?
Highlands has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (2 sales, median $326,000). For context, ZIP 32708 has 150 homes on the market with 33% under contract.
Are there homes for sale in Highlands right now?
No active listings inside Highlands at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Highlands have an HOA or CDD?
No HOA is on record for Highlands in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Highlands with Momentum Realty’s local guides.