Neighborhood · Winter Park, Florida
Golfside Villas
Affordable Winter Park living close to everything
5
Homes for sale
$138,000
Median list price
$163
Avg price / sqft
99
Median days on market
Golfside Villas is one of the more approachable corners of Winter Park, a compact villa community that trades big lots for low-maintenance living and a genuinely central location. You're about 13 minutes from downtown Orlando and 27 from MCO, with the shops and restaurants around Lake Killarney close by and the walkable dining of Hannibal Square an easy drive away. It feeds into well-regarded assigned schools — Winter Park High, Glenridge Middle, and Brookshire Elementary — which keeps demand steady. If you want a Winter Park address without a Winter Park price tag, this is where the math works.
The market here is small and moves quickly: five homes are active right now, with a median list price of $138,000 and a median of just 14 days on market. Over the past year seven homes sold at a median of $119,000, and sellers collected about 93% of asking — so there's a little negotiating room, but not much time to deliberate. Compared to the rest of Winter Park homes for sale or established neighborhoods like Winter Park Pines, this is the entry point. Bring a pre-approval and be ready to act.
Golfside Villas is a community in Winter Park, Florida.
Quick facts
$105,000 – $138K price range
776 sqft median home
$355/mo median HOA
$1,123/mo median rent
6 sold in 12 months
Drive times
On the market now
Homes for sale in Golfside Villas
$105,000$110,000
1000 S SEMORAN BOULEVARD UNIT 302, WINTER PARK
1 bd · 1 ba · 796 sqft
$115,000$129,000
1000 S SEMORAN BOULEVARD UNIT 305, WINTER PARK
1 bd · 1 ba · 735 sqft
$138,000$148,000
1000 S SEMORAN BOULEVARD UNIT 404, WINTER PARK
1 bd · 1 ba · 776 sqft
$138,000$148,000
1000 S SEMORAN BOULEVARD UNIT 306, WINTER PARK
1 bd · 1 ba · 796 sqft
$138,000$148,000
1000 S SEMORAN BOULEVARD UNIT 408, WINTER PARK
1 bd · 1 ba · 776 sqft
Every active listing inside the Golfside Villas boundary
Open full map search →Find your fit
Browse Golfside Villas
By feature — on the live map
The numbers that matter
The Golfside Villas market
6
Sold, last 12 months
$123,000
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
80 days
Median time to sell
Golfside Villas vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 10.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Golfside Villas boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Golfside Villas is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Golfside Villas home
≈ $1,453/mo
$138,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$355/mo
Median HOA
From current listings inside the boundary
$1,123/mo
Median rent
Homes for rent inside the boundary
Population
235
Median age
43
Median income
$95,640
Median home value
$479,600
Beyond the listings
Living in Golfside Villas
Emotional
Top 9% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Appearance oriented
Top 11% in the U.S.Fitness Fashion
Workout clothes aren't just for working out anymore. This population enjoys wearing name-brand athletic apparel for fashion and functional purposes.
Relationships
Top 11% in the U.S.Dating Life
With dating comes highs, lows, and lots of questions. You can find this population talking about dating advice, breakups and how to express their feelings.
Relationships
Top 12% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Beliefs
Top 13% in the U.S.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.
Active
Top 16% in the U.S.Organized Sports
From tryouts and casual pick-up games, to varsity tournaments and intramural matches, this population includes people who participate in organized athletics. Often through schools or public recreational areas.
People who close here
Our Winter Park experts
Straight answers
Golfside Villas FAQs
Is Golfside Villas a good place to live?+
It's a solid fit if you want a central Winter Park location without a large single-family price tag. The villas are low-maintenance and close to everything — about 13 minutes to downtown Orlando — and the assigned schools include Winter Park High, Glenridge Middle, and Brookshire Elementary. For proximity to shopping and dining, spots like Lake Killarney are just minutes away.
Is Golfside Villas expensive?+
Quite the opposite for this area — it's one of the most affordable pockets of Winter Park. The median list price is $138,000 with active listings ranging from $115,000 to $138,000, well below what you'll find in neighborhoods like Kenilworth. That makes it a genuine entry point for first-time buyers and investors.
What do homes cost in Golfside Villas?+
Currently active homes are priced between $115,000 and $138,000, with a median list price of $138,000 and an average of about $166 per square foot. Over the last 12 months, seven homes sold at a median price of $119,000. Median home size is compact at around 776 square feet.
How is the market in Golfside Villas?+
It's small but brisk. Five homes are active right now and the median days on market is just 14, so listings don't linger. Sellers have been getting about 93% of asking on average, which leaves a little room to negotiate but rewards buyers who move fast.
What about HOA fees and property taxes?+
Expect an HOA around $355 per month, which typically covers the maintenance benefits of villa living. The median property tax runs about $1,937 per year. If you're weighing it as a rental, the median rent in the area is roughly $1,150 per month.
Keep exploring
More Winter Park 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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