Neighborhood · Winter Park, Florida
Winter Park Pines
Mid-century roots, top schools, and an easy Winter Park zip code
10
Homes for sale
$664,900
Median list price
$368
Avg price / sqft
49
Median days on market
Winter Park Pines is the kind of established, tree-shaded neighborhood where mid-century ranch homes sit on generous lots and the sidewalks lead toward some of the area's best-rated public schools. It's a quieter, family-forward pocket of Winter Park that trades flash for location — you're a short hop from Downtown Winter Park and the shops and water access near Lake Killarney, with downtown Orlando about 17 minutes away and MCO roughly 30. Nearby pockets like Eastbrook round out a neighborhood that draws buyers who want the school zone without the estate price tag.
For a buyer today, the market here is steady rather than frantic. There are 13 active listings with a median list price of $614,500, homes are averaging about $343 per square foot, and they're taking a median of 50 days to sell — enough runway to make a considered offer. Over the last year 44 homes closed at a median of $530,500, with sellers netting about 98% of asking, so well-priced properties still move and there's modest room to negotiate.
Winter Park Pines is a community in Winter Park, Florida.
Quick facts
$494,900 – $798K price range
1,633 sqft median home
$4/mo median HOA
$3,555/mo median rent
45 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Pines
$649,000
518 GILBERT ROAD, WINTER PARK
3 bd · 2 ba · 1,573 sqft
$724,900
266 N RANGER BOULEVARD, WINTER PARK
4 bd · 3 ba · 1,692 sqft
$780,000
739 ROUGHBEARD ROAD, WINTER PARK
5 bd · 3 ba · 2,194 sqft
$659,900$669,900
274 N RANGER BOULEVARD, WINTER PARK
3 bd · 2 ba · 1,420 sqft
$798,000$848,900
724 MONMOUTH WAY, WINTER PARK
5 bd · 3.5 ba · 2,832 sqft
$669,900$675,000
433 GILBERT ROAD, WINTER PARK
3 bd · 2 ba · 1,800 sqft
$494,900$498,900
2715 PRINCE JOHN ROAD, WINTER PARK
3 bd · 2 ba · 1,565 sqft
$695,000
715 S RANGER BOULEVARD, WINTER PARK
4 bd · 3 ba · 2,312 sqft
$534,900$539,900
330 ELKHORN COURT, WINTER PARK
3 bd · 2 ba · 1,570 sqft
$619,500$639,000
2758 BANCHORY ROAD, WINTER PARK
3 bd · 2.5 ba · 1,539 sqft
Every active listing inside the Winter Park Pines boundary
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Browse Winter Park Pines
By feature — on the live map
Where the market lives
The numbers that matter
The Winter Park Pines market
45
Sold, last 12 months
$515,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
13 days
Median time to sell
Winter Park Pines vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 3.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Park Pines boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Park Pines is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winter Park Pines home
≈ $4,239/mo
$664,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$4/mo
Median HOA
From current listings inside the boundary
$3,555/mo
Median rent
Homes for rent inside the boundary
Population
2,446
Median age
38
Median income
$65,221
Median home value
$443,587
Beyond the listings
Living in Winter Park Pines
Entertainment
Top 14% in the U.S.Party Life
The party don't stop until the sun comes up. Loud music, crowds, and shots are a recipe for a great night out for these people.
Entertainment
Top 15% in the U.S.Late-night Leisure
Ready to turn up when the sun goes down, this population is looking for nighttime entertainment at home or out on the town.
Active
Top 17% in the U.S.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.
Lifestyles
Top 18% in the U.S.LGBTQ Culture
This population is characterized by the expression of gay pride, gender identity, and accepting alternative lifestyles.
Entertainment
Top 19% in the U.S.Live & Local Music
This population follows the music. From local bands to current acts at the local venue, you can find these people researching band tours and how to get backstage passes.
Culture
Top 21% in the U.S.Dance Devotion
Some dance for fitness, others for fun, and a few turn it into a profession. No matter how these people groove to the music, their love for dance is what bonds them.
People who close here
Our Winter Park experts
Straight answers
Winter Park Pines FAQs
Is Winter Park Pines a good place to live?+
It's a well-established, family-oriented neighborhood with mature trees, larger lots, and assignment to Winter Park High, Glenridge Middle, and Aloma Elementary. You're minutes from Downtown Winter Park and about 17 minutes from downtown Orlando, which makes it an easy fit for commuters and families alike.
Is Winter Park Pines expensive?+
It's a mid-range slice of Winter Park — the median list price is $614,500 and listings currently run from $450,000 to about $849,000. There are no active listings above $1M here, so it reads more attainable than the lakefront estate side of town.
What do homes cost in Winter Park Pines?+
Expect a median list price around $614,500 and an average of $343 per square foot on a median home size near 1,651 square feet. Over the past year, 44 homes actually closed at a median sold price of $530,500.
How is the market right now?+
Balanced and steady — 13 homes are active and the median time to sell is 50 days, giving buyers room to think. Sellers are getting about 98% of asking on average, so realistic offers close and there's a little negotiating space.
What about HOA fees and property taxes?+
HOA costs are minimal here, with a median of just $5 per month, so you're largely free of community fees. Property taxes run a median of about $5,534 per year, and typical rents in the neighborhood sit around $2,873 a month if you're weighing an investment.
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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