Neighborhood · Winter Springs, Florida
Highland Village
Compact, affordable living in the heart of Seminole County
1
Homes for sale
$329,900
Median list price
$280
Avg price / sqft
44
Median days on market
Highland Village is a small residential pocket of Winter Springs where modestly sized homes, low fees, and quick access to central Seminole County make everyday life easy. It sits among established neighborhoods like Tuscawilla, Deer Run, and the adjacent Highlands, and feeds well-regarded local schools including Highlands Elementary and Winter Springs High.
This is a tight, fast-moving market with just one active listing at $329,900, so buyers should be ready to act when something comes up. Over the past year only four homes sold, at a median of $364,500, and sellers pulled in about 97% of asking — a sign of steady demand for the neighborhood's smaller footprints. If you're comparing options, nearby Cypress Club is worth a look alongside Highland Village.
Highland Village is a community in Winter Springs, Florida.
Quick facts
$329,900 – $330K price range
1,178 sqft median home
$42/mo median HOA
4 sold in 12 months
Drive times
On the market now
Homes for sale in Highland Village
Every active listing inside the Highland Village boundary
Open full map search →The numbers that matter
The Highland Village market
4
Sold, last 12 months
$364,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
25 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
▼ 16.5% 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
≈ $2,298/mo
$329,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$42/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 quiet, established neighborhood within Winter Springs, surrounded by well-known communities like Tuscawilla and Deer Run. Homes are compact and the HOA is light at about $42 a month, which suits buyers who want an easy-to-maintain place in central Seminole County. Assigned schools include Highlands Elementary and Winter Springs High School.
Is Highland Village expensive?+
It's one of the more attainable corners of Winter Springs. The single active listing is priced at $329,900, and homes that sold over the past year had a median price of $364,500 — reasonable for the area given the smaller home sizes.
What do homes cost in Highland Village?+
Current pricing sits around $329,900 for the lone active listing, working out to roughly $280 per square foot on a median home of about 1,178 square feet. Recent sales closed higher, at a median of $364,500, so expect real values in the low-to-mid $300s depending on size and condition.
How is the market in Highland Village?+
It's small and moves at a measured pace — only four homes sold in the past 12 months, with a median of 44 days on market. Sellers averaged about 97% of their asking price, so well-priced homes hold their value here. With just one active listing, inventory is tight, so serious buyers should be ready to move quickly.
What about HOA fees and property taxes?+
HOA dues are modest at roughly $42 a month, which keeps monthly costs down compared to many Winter Springs communities. Property taxes run about $3,693 a year at the neighborhood's median, in line with Seminole County norms for homes in this 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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