The 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 7 closed sales in The Highlands Sec Two Tr D Rep in Winter Springs, FL since 2016, the most recent in May 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, tightly built pocket in Winter Springs — 26 homes, all constructed in a narrow 1979-1980 window. That kind of consistency means buyers are largely comparing floor plans and condition, not eras of construction, and the value story tilts heavily toward how well a given home has been maintained or updated since it was built.
With homestead exemptions filed on roughly 69% of homes here, a majority of owners are treating these as long-held primary residences rather than rotating rental or investment stock. That posture tends to keep turnover modest and inventory thin, so buyers should expect to move decisively when something in good condition comes up rather than waiting for a wide field of comparable choices.
Nearby homes for sale
No active listings inside The Highlands Sec Two Tr D 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
The Highlands Rep is a compact, single-era enclave in Seminole County where nearly every home dates to the same two-year construction window, giving the section a consistent architectural footprint rather than a mix of eras.
Stellar MLS sales records identify 19 homes in The Highlands that have changed hands since 2004, built between 1977 and 1989 (median 1979), with a median living area of about 1,829 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.
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 The Highlands is best for.
Best for
- Buyers seeking a modestly sized single-family home in Seminole County without amenity fees
- Buyers comfortable evaluating condition and updates on an older housing stock rather than new construction
- Long-term buyers who value a stable, low-turnover section over a fast-flipping market
Probably not for
- Buyers who want on-site community amenities like a pool, clubhouse, or recreation facilities
- Buyers wanting a wide selection of active listings to choose from at any given time
- Buyers seeking newer construction with fewer age-related maintenance considerations
The market around The Highlands
The 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 The Highlands specifically. Momentum Research analysis of MLS records.
The Highlands Rep by the numbers
From county property records and closed MLS sales for the The Highlands Rep subdivision: 6 homes on record; built 1979–1980; typical size about 1,830 heated sq ft; 3 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2017 | 2 | $179,350 |
| 2023 | 1 | $399,900 |
| 2024 | 1 | $425,000 |
| 2025 | 2 | $423,800 |
Newest recorded sale: $432,600 on 2025-05-07.
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 The Highlands buying strategy.
If we were buying in The 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 The Highlands.
One era, one footprint
With a median living area around 1,650 square feet and a build window confined to 1979-1980, homes in this section share similar scale and structural bones. Differences between listings here come down almost entirely to interior updates, systems age, and how a given owner has maintained the property over four-plus decades, not to differences in original layout or lot-era construction standards.
No community amenities are identified from current MLS listings, which points to this being a straightforward residential section rather than an amenity-driven community. Buyers are paying for the home and its location within Winter Springs, not for a clubhouse, pool, or shared recreation infrastructure.
The location and the amenities are priced into every listing in The Highlands. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a section this small, generic comps do not tell you much — with only 26 homes total, a handful of recent updates or deferred-maintenance issues can swing value more than square footage. We track individual listing history and condition detail in this specific section so buyers and sellers are pricing off what is actually comparable, not off a broader Winter Springs average that does not reflect a single-era, no-amenity pocket like this one.
The 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 The 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 The Highlands sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in The 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 The Highlands home worth?
Get a no-obligation home value based on real comparable sales in The 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 The 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 2016 (7 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 The Highlands Rep fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about The Highlands
Where is The Highlands?
The Highlands is a community in Winter Springs, Seminole County, Florida, ZIP 32708.
How many homes are in The Highlands?
County property records list 6 homes in The Highlands, built between 1979 and 1980; the typical home is about 1,830 heated square feet.
What do homes in The Highlands sell for?
The Highlands has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (2 sales, median $423,800). For context, ZIP 32708 has 150 homes on the market with 33% under contract.
Are there homes for sale in The Highlands right now?
No active listings inside The 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 The Highlands have an HOA or CDD?
No HOA is on record for The 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 The Highlands with Momentum Realty’s local guides.