Neighborhood · Winter Park, Florida
Golfside
Small-scale Winter Park living close to everything
6
Homes for sale
$138,000
Median list price
$193
Avg price / sqft
38
Median days on market
Golfside sits in the heart of Winter Park, an Orange County community known for tree-lined streets and easy access to the culture and dining that define this part of metro Orlando. You're minutes from established neighborhoods like Lake Killarney and Winter Park Pines, with the character-rich Hannibal Square district close by. Downtown Orlando is about a 13-minute drive, and Orlando International Airport sits roughly 27 minutes out — a genuinely central location.
For buyers, Golfside is a tight, low-inventory pocket: just 6 active listings right now, with a median list price of $138,000. That price point points to attainable condo or townhome-style ownership rather than large single-family homes, which makes it worth watching if you want a Winter Park address without a Winter Park single-family budget. Because the neighborhood is small, listings move on their own timeline — it pays to compare against the broader Winter Park homes for sale market when you shop.
Golfside is a community in Winter Park, Florida.
Quick facts
$110,000 – $690K price range
786 sqft median home
$355/mo median HOA
$1,173/mo median rent
15 sold in 12 months
Drive times
On the market now
Homes for sale in Golfside
$689,900
943 FAIRWAY DRIVE, WINTER PARK
4 bd · 3 ba · 2,067 sqft
$115,000$129,000
1000 S SEMORAN BOULEVARD UNIT 305, WINTER PARK
1 bd · 1 ba · 735 sqft
$110,000$115,000
1000 S SEMORAN BOULEVARD UNIT 302, WINTER PARK
1 bd · 1 ba · 796 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 boundary
Open full map search →Find your fit
Browse Golfside
By feature — on the live map
Where the market lives
The numbers that matter
The Golfside market
15
Sold, last 12 months
$455,000
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
45 days
Median time to sell
Golfside vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 28.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Golfside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Golfside is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Golfside 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
$1,173/mo
Median rent
Homes for rent inside the boundary
Population
667
Median age
43
Median income
$95,640
Median home value
$479,600
Beyond the listings
Living in Golfside
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 FAQs
Is Golfside a good place to live?+
It's a small Winter Park community with a genuinely central location — about 13 minutes to downtown Orlando and 27 to the airport. Homes are assigned to Winter Park High, Glenridge Middle, and Brookshire Elementary, and you're close to established areas like Eastbrook. For buyers who want a Winter Park address without a large-home price tag, it's worth a serious look.
Is Golfside expensive?+
Not by Winter Park standards. The median list price is currently $138,000, which sits well below the city's single-family norms and points to condo or townhome-style ownership. It's one of the more attainable entry points into the area.
What do homes cost in Golfside?+
Right now there are 6 active listings with a median list price of $138,000. Because the neighborhood is small, the mix of available homes shifts quickly, so it helps to compare against the wider Winter Park homes for sale market when you're setting expectations.
How is the market in Golfside?+
It's a low-inventory pocket with 6 homes active and no recorded sales in the past 12 months, which reflects how tightly held and small the community is. That means fewer comparable sales to lean on, so pricing and negotiation benefit from local guidance and a look at nearby areas like Winter Park Pines.
What about HOA fees and property taxes in Golfside?+
Specific HOA and property tax figures aren't available in the current data for Golfside, and they can vary by individual community and unit type. Given the price point, expect an HOA structure typical of condo or townhome ownership — always confirm the exact monthly dues and tax history on any listing before you make an offer.
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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