The Highlands
Homes for Sale in Winter Springs, FL
All 146 homes for sale in Winter Springs, FL · median $399,450 · 119 homes for sale in 32708 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 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, 501 homes closed in the last 12 months at a median of $430,000, 26 median days on market, with 116 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,530 ($5,930 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.
Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside The Highlands 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 Sec Two Tr D 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.
County records show 3 qualified sales in The Highlands across 2024–2025 (1 in 2024, 2 in 2025), median $425,000 — 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.
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, 151 homes are on the market and 30% are under contract — a steady corner of Winter Springs.
Across Seminole County, 1,676 homes are active and 570 pending (25% under contract).
In ZIP 32708 (Winter Springs), 391 homes closed in the last 12 months at a median of $396K ($241/sq ft), down 1.1% year over year, with a median 26 days on market. Right now 19 active and 12 pending listings. 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 by the numbers
From county property records and closed MLS sales for the The Highlands 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.
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 →
| Location | Winter Springs, Seminole County, FL · ZIP 32708 |
|---|---|
| Homes in the community | 26 (FL DOR 2025 assessment roll) |
| Years built | 1979–1980 (median 1979.0) |
| Typical living area | 1,652 sq ft (median) |
| Owner-occupied (homestead) share | 69% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2016 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “The Highlands key facts,” movewithmomentum.com/neighborhoods/the-highlands-sec-two-tr-d-rep, data as of September 20, 2026.
Housing distress & ownership in The Highlands Sec Two Tr D Rep, Winter Springs
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
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 November 2026 through November 2026. Deemed reliable but not guaranteed.
More Winter Springs home searches
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- Winter Springs home values: what is my house worth?
- ZIP 32708 housing scorecard
Winter Springs guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Seminole County)
- Homestead exemption (Seminole County)
- Home insurance cost
- New construction (Seminole County)
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Macgregor Road (2 homes on record)
Email me new listings in The Highlands
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about The Highlands
Have a question about the homes, fees, rules or commute here? A Momentum agent who works The Highlands will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
How many homes are in The Highlands?
What share of The Highlands is owner-occupied?
When were the homes in The Highlands built?
Who is the best real estate agent for The Highlands?
How do I find a top Winter Springs real estate agent who knows The Highlands?
Can Momentum Realty connect me with an agent for The Highlands?
Where is The Highlands, and what county is it in?
Should you buy in The Highlands?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32708)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. A Momentum agent can price yours against live local comps.
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See how The Highlands Sec Two Tr D Rep fits the bigger picture — live prices, inventory, and Momentum Scores: