Neighborhood · Winter Springs, Florida
Highlands
Established Winter Springs living with an easy Orlando commute
7
Homes for sale
$415,000
Median list price
—
Avg price / sqft
—
Median days on market
Highlands is a settled residential pocket of Winter Springs in Seminole County, the kind of place where mature trees and a low $35/month HOA signal a neighborhood that's been lived in and loved. It sits among familiar names like Tuscawilla, Deer Run, and North Orlando Ranches, with Highlands Elementary right in the fold and Winter Springs High School assigned to the area. Downtown Orlando is about 29 minutes out, and both the airport and Universal land near the 40-minute mark, so you get suburban calm without cutting yourself off from the city.
For buyers, this is a tight, competitive market: just 6 homes are active right now, with a median list price of $419,999 and asking prices running from $361,000 to $475,000. Homes here move at a healthy clip — a median of about 34 days on market — and over the past year sellers have collected roughly 98% of their asking price. If you find the right one, be ready to act, because inventory this thin doesn't sit long.
Highlands is a community in Winter Springs, Florida.
Quick facts
Drive times
On the market now
Homes for sale in Highlands
$425,000$450,000
758 N GRETNA COURT, WINTER SPRINGS
4 bd · 3 ba · 2,150 sqft
$361,000
830 DUNBAR TERRACE, WINTER SPRINGS
3 bd · 2.5 ba · 1,792 sqft
$475,000$479,000
629 RYAN COURT, WINTER SPRINGS
3 bd · 2 ba · 1,857 sqft
$375,000
807 BUCKIE DRIVE, WINTER SPRINGS
3 bd · 2 ba · 1,574 sqft
$424,997$438,997
872 FALKIRK DRIVE, WINTER SPRINGS
3 bd · 2 ba · 1,554 sqft
Every active listing inside the Highlands boundary
Open full map search →The numbers that matter
The Highlands market
Highlands vs Winter Springs
Median list price
Median sold price — 3-yr, 3-mo rolling
▼ 1.5% 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
≈ $2,777/mo
$415,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
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.
On the calendar
Near Highlands
Jul
16
Thu
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
16
Thu
Thursday Thinks Trivia
7:30pm
This challenging trivia night promises a wide range of engaging questions, ensuring something new and exciting for everyone - from pop culture, geography, and history, to…
Jul
16
Thu
Salsa Dance Class
8:30pm
The Salsa Cubana class offers a fun and energetic environment, focusing on body movement, musicality, and styling for both men and women. It's a judgment-free zone where…
Jul
16
Thu
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
Jul
16
Thu
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
16
Thu
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Straight answers
Highlands FAQs
Is Highlands a good place to live?+
It's an established Winter Springs neighborhood with assigned schools including Highlands Elementary and Winter Springs High, plus a location roughly 29 minutes from downtown Orlando. The low $35/month median HOA and its setting among longtime communities like Cypress Club make it a practical pick for families and commuters alike.
Is Highlands expensive?+
It sits in a comfortable mid-market range, with a median list price of $419,999 and homes running from $361,000 to $475,000. At about $235 per square foot, it's a reasonable value for Seminole County given the schools and commute.
What do homes cost in Highlands?+
Current active listings have a median list price of $419,999, while homes that sold over the past 12 months closed at a median of $382,500. The typical home is around 1,742 square feet, and you'll occasionally find a pool home in the mix.
How is the market in Highlands right now?+
It's lean and active — only 6 homes are listed, and the median time on market is about 34 days. With sellers averaging 98% of asking over the last year on 9 recorded sales, buyers should expect to move decisively when the right home appears.
What are the HOA fees and property taxes like?+
The median HOA here is just $35 a month, which is light for an established community. Median property taxes run about $3,364 a year, typical for a home in this Seminole County price range.
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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