Highland Village
Homes for Sale in Winter Springs, FL
All 130 homes for sale in WINTER SPRINGS, FL · median $422,445 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 4 recorded sales closed at a median of $374,500, $236 per square foot, a median 24 days on market, sellers accepting 96% of original asking (-3% versus the prior year). Homes listed or recently sold were built 1989 - 1993; 4 of 4 report an HOA (median $20/mo); none of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 46 ft). At the median price and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $5,690 ($5,090 with the full homestead exemption).
Highland Village right now
🟡 Off the recent peak. The trailing-12-month median ($374K) is down 2.7% from the prior 12 months ($385K). With about 2 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (4 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Highland Village 2 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
Highland Village market snapshot (as of September 12, 2026): the median sale price is about $374K ($236 per sq ft over the trailing 12 months of closed sales), and a median 25 days on market for closed sales. The trailing-12-month median is down 3% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
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.
Stellar MLS sales records identify 85 homes in Highland Village that have changed hands since 2004, built between 1981 and 1993 (median 1989), with a median living area of about 1,579 sq ft and a typical 3-bedroom, 2-bath layout; 99% 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.
The setting & the homes.
Aerial and on-site photos of Highland Village. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Highland VillagePhotos from Stellar MLS listings in Highland Village; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($374K) IS the median in the snapshot above, and the move from 2025 ($385K) IS the -2.7% one-year change.
Windows contain 0 to 5 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2026. Deemed reliable but not guaranteed.
HIGHLAND VILLAGE 2 Market Scorecard
HIGHLAND VILLAGE 2 is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32708 ZIP is $427,790, about 2.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · 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.
Housing distress & ownership in Highland Village 2 Winter Springs, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Highland Village on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Highland Village
- Pool · reported on 5 of 5 listings
- Park · reported on 4 of 5 listings
- Playground · reported on 4 of 5 listings
- Clubhouse · reported on 2 of 5 listings
- Tennis Court(s) · reported on 2 of 5 listings
- Deed Restrictions · reported on 2 of 5 listings
- Pickleball Court(s) · reported on 1 of 5 listings
- Recreation Facilities · reported on 1 of 5 listings
- Trail(s) · reported on 1 of 5 listings
- Fence Restrictions · reported on 1 of 5 listings
- Community Mailbox · reported on 1 of 5 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Highland Village buying strategy.
If we were buying in Highland Village 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 Highland Village.
A closer look at the Highland Village market
At a median of $236 per square foot, Highland Village prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 3% year over year. Homes that do trade take a median 25 days on market, useful leverage on any listing that has lingered.
The location and the amenities are priced into every listing in Highland Village. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $6/month · median of 6 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $6 per month - the median AssociationFee across 6 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.
Tools for a Highland Village 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 Highland Village sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Village, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highland Village home worth?
Get a no-obligation home value based on real comparable sales in Highland Village, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Highland Village?
How long do homes in Highland Village take to sell?
Who is the best real estate agent for Highland Village?
How do I find a top Winter Springs real estate agent who knows Highland Village?
Can Momentum Realty connect me with an agent for Highland Village?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (31 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.
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See how Highland Village 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
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