Neighborhood · Winter Springs, Florida
Highlands
Established Seminole County living with easy Orlando access
4
Homes for sale
$361,500
Median list price
$193
Avg price / sqft
92
Median days on market
Highlands sits in the heart of Winter Springs, an established Seminole County neighborhood of tree-lined streets and mature lots that feels settled rather than under construction. It's close enough to neighbors like Tuscawilla, Deer Run, and Oak Forest to share their schools and amenities while keeping its own quiet identity. Families land here for Highlands Elementary, South Seminole Middle, and Winter Springs High — and for a commute that puts downtown Orlando roughly 29 minutes away.
For a buyer today, this is a tight, low-inventory market: just 3 active listings with a median list price of $354,000, ranging from $301,000 to $400,000. Homes run about $181 per square foot on a median size of 1,878 square feet, and over the past year 12 homes sold at a median of $396,000. With sellers collecting 98% of asking and a median 56 days on market, you'll want to move deliberately but come prepared to compete.
Highlands is a community in Winter Springs, Florida.
Quick facts
$301,000 – $485K price range
1,932 sqft median home
$35/mo median HOA
14 sold in 12 months
Drive times
On the market now
Homes for sale in Highlands
$485,000
627 CLEARN COURT, WINTER SPRINGS
5 bd · 3.5 ba · 1,986 sqft
$379,000$390,000
758 N GRETNA COURT, WINTER SPRINGS
4 bd · 3 ba · 2,150 sqft
$344,000$354,000
830 DUNBAR TERRACE, WINTER SPRINGS
3 bd · 2.5 ba · 1,792 sqft
$301,000$313,700
702 GLASGOW COURT, WINTER SPRINGS
4 bd · 2.5 ba · 1,878 sqft
Every active listing inside the Highlands boundary
Open full map search →Find your fit
Browse Highlands
By feature — on the live map
Where the market lives
The numbers that matter
The Highlands market
14
Sold, last 12 months
$384,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
40 days
Median time to sell
Highlands vs Winter Springs
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 13.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Highlands boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Highlands is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Highlands home
≈ $2,498/mo
$361,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$35/mo
Median HOA
From current listings inside the boundary
Population
1,427
Median age
33
Median income
$60,173
Median home value
$270,564
Beyond the listings
Living in Highlands
Hobbies & Interests
Top 16% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Hobbies & Interests
Top 18% in the U.S.Dog Lovers
Pups are just another member of the family. Dog lovers adore their tail-wagging friends and are looking for new ways to make them happy.
Active
Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Active
Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Food & Drink
Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Beliefs
Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Straight answers
Highlands FAQs
Is Highlands a good place to live?+
It's an established Winter Springs neighborhood zoned for Highlands Elementary, South Seminole Middle, and Winter Springs High School, which is a big draw for families. You're surrounded by well-known communities like Deersong and Oak Forest, with downtown Orlando about 29 minutes away for work and weekends.
Is Highlands expensive?+
It's mid-market for the area, with a median list price of $354,000 and active listings running from $301,000 to $400,000. At roughly $181 per square foot, you're paying for settled, mature homes rather than a premium new-build tag.
What do homes cost in Highlands?+
Current active listings sit at a median of $354,000, while homes that actually sold over the past 12 months closed at a median of $396,000 across 12 sales. The typical home is about 1,878 square feet, which puts pricing near $181 per square foot.
How is the market right now?+
Inventory is very tight — just 3 active listings — and sellers are collecting 98% of asking on average. Homes take a median of 56 days to sell, so come pre-approved and ready to act when the right one lists.
What about HOA fees and property taxes?+
The median HOA here is a modest $35 per month, one of the lighter loads in the Winter Springs area. Median annual property tax runs about $3,285, so plan roughly that into your monthly carrying costs alongside the low HOA.
Keep exploring
More Winter Springs neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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