Neighborhood · Winter Springs, Florida
Highland Village
Approachable Winter Springs living with a low-key price tag
2
Homes for sale
$339,950
Median list price
$257
Avg price / sqft
23
Median days on market
Highland Village sits in the leafy, established stretch of Winter Springs that Seminole County families have quietly favored for years. It's the kind of neighborhood where homes run right-sized rather than oversized, kids feed into Highlands Elementary and Winter Springs High, and neighboring communities like Tuscawilla, Deer Run and Sunrise Estates round out the area with parks, golf and trails. Orlando's job centers and Universal Orlando (about 39 minutes away) stay within easy reach without the traffic sitting on your doorstep.
For buyers today, this is a tight, fast-moving pocket. There are just 2 active listings with a median list price of $339,950, and homes here have been going under contract in around 22 days at 98% of asking. If a place that fits comes up in your range, expect to move quickly and come in with a serious offer.
Highland Village is a community in Winter Springs, Florida.
Quick facts
$329,900 – $350K price range
1,340 sqft median home
$44/mo median HOA
5 sold in 12 months
Drive times
On the market now
Homes for sale in Highland Village
$350,000
321 KIRKCALDY DRIVE, WINTER SPRINGS
2 bd · 2 ba · 1,502 sqft
$329,900$339,900
335 KIRKCALDY DRIVE, WINTER SPRINGS
3 bd · 2 ba · 1,178 sqft
Every active listing inside the Highland Village boundary
Open full map search →The numbers that matter
The Highland Village market
5
Sold, last 12 months
$350,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
30 days
Median time to sell
Highland Village vs Winter Springs
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 10.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Highland Village boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Highland Village is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Highland Village home
≈ $2,296/mo
$339,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$44/mo
Median HOA
From current listings inside the boundary
Population
1,449
Median age
35
Median income
$62,902
Median home value
$247,221
Beyond the listings
Living in Highland Village
Food & Drink
Top 10% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Relationships
Top 11% in the U.S.Love & Romance
Love is in the air when this population is present. Includes people expressing their feelings for significant others in special ways. Common activities include anniversaries and date nights.
Appearance oriented
Top 11% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Relationships
Top 11% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Appearance oriented
Top 22% in the U.S.Men's Style
This population is all about finding the latest in men's style - from fashion to grooming. Captures guys looking to stay on trend and significant others assisting with shopping.
Entertainment
Top 22% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Straight answers
Highland Village FAQs
Is Highland Village a good place to live?+
It's a solid pick for buyers who want an established Winter Springs address without a supersized home or budget. Assigned schools include Highlands Elementary, South Seminole Middle and Winter Springs High, and you're surrounded by well-regarded communities like Deer Run. The scale is neighborhood-quiet with easy access to the wider area.
Is it expensive to buy here?+
Not by Central Florida standards. The median list price is $339,950, with active homes ranging from $329,900 to $350,000, which keeps it accessible relative to pricier Winter Springs enclaves like Tuscawilla.
What do homes cost in Highland Village?+
Expect a median list price around $339,950 and an average of about $257 per square foot on a median home size near 1,340 sqft. Over the last 12 months, the median sold price landed at $350,000, so list and sold prices track closely here.
How is the market right now?+
Fast and thin. There are only 2 active listings, homes are moving in a median of about 22 days, and sellers are averaging 98% of asking, with 5 homes sold over the past year. Be ready to act when the right listing hits.
What about HOA fees and property taxes?+
Carrying costs are modest, with a median HOA of just $44 per month. The median annual property tax runs about $3,014, in line with what you'd expect for this price point in Seminole County.
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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