Neighborhood · Winter Park, Florida
Winter Park Pines
Established Winter Park living with pools and top schools
13
Homes for sale
$598,000
Median list price
$339
Avg price / sqft
47
Median days on market
Winter Park Pines sits in the heart of Orange County's most walkable and tree-lined city, an established residential pocket close to Lake Killarney and a short hop from the shops and cafes around Hannibal Square. The neighborhood draws families who want mid-century single-family homes, mature landscaping, and quick access to downtown Orlando, which sits about 17 minutes away. Nearby pockets like Kenilworth and Eastbrook round out the area's easygoing, settled character.
For buyers today, this is a competitive but reasonable slice of the broader Winter Park market. There are 14 active listings with a median list price of $588,500, and homes are moving in about 34 days. Over the past year 38 homes sold at a median of $492,500, with sellers netting roughly 97% of asking — a sign of steady, healthy demand.
Winter Park Pines is a community in Winter Park, Florida.
Quick facts
$450,000 – $825K price range
1,660 sqft median home
$5/mo median HOA
$2,395/mo median rent
39 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Pines
View all 13 →
$825,000
722 S RANGER BOULEVARD, WINTER PARK
4 bd · 3 ba · 2,164 sqft
$498,900$504,900
2715 PRINCE JOHN ROAD, WINTER PARK
3 bd · 2 ba · 1,565 sqft
$775,000
275 N RANGER BOULEVARD, WINTER PARK
4 bd · 3 ba · 1,950 sqft
$524,990$535,000
528 SAINT DUNSTAN WAY, WINTER PARK
3 bd · 2 ba · 1,656 sqft
$579,000
333 CORNWALL ROAD, WINTER PARK
4 bd · 2 ba · 1,660 sqft
$695,000
715 S RANGER BOULEVARD, WINTER PARK
4 bd · 3 ba · 2,312 sqft
$450,000
316 BECKETT COURT, WINTER PARK
4 bd · 2 ba · 1,651 sqft
$780,000$800,000
739 ROUGHBEARD ROAD, WINTER PARK
5 bd · 3 ba · 2,194 sqft
$615,000$617,500
2708 LION HEART ROAD, WINTER PARK
3 bd · 2 ba · 1,785 sqft
$544,900$554,900
330 ELKHORN COURT, WINTER PARK
3 bd · 2 ba · 1,570 sqft
$675,000$695,000
744 CORNWALL ROAD, WINTER PARK
4 bd · 2 ba · 1,968 sqft
$475,000$485,000
346 S RANGER BOULEVARD, WINTER PARK
3 bd · 2 ba · 1,592 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
39
Sold, last 12 months
$502,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
9 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
▲ 37.8% 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
≈ $3,813/mo
$598,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$5/mo
Median HOA
From current listings inside the boundary
$2,395/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 an established, family-friendly neighborhood zoned for Winter Park High, Glenridge Middle, and Aloma Elementary, with mature streets and easy access to the rest of Winter Park. Downtown Orlando is about 17 minutes away and Orlando International Airport around 30, so commuting and travel are straightforward. The mix of pool homes and settled character makes it popular with buyers who want space without leaving the city.
Is Winter Park Pines expensive?+
It sits in the mid-to-upper range for the area, with a median list price of $588,500 and active listings running from $318,985 to $825,000. There are currently no listings above $1M, so it's more attainable than Winter Park's luxury lakefront pockets. The median sold price over the past year was $492,500.
What do homes cost in Winter Park Pines?+
Homes average about $335 per square foot, with a median size around 1,658 sqft. Active listings span $318,985 to $825,000, and the median list price is $588,500. Buyers looking at pool homes will find six of the current listings include one.
How is the market in Winter Park Pines?+
It's steady and competitive. Homes are selling in a median of 34 days, sellers are getting about 97% of asking, and 38 homes closed over the past 12 months at a median of $492,500. With just 14 active listings, well-priced homes near Eastbrook and Kenilworth don't tend to sit long.
What about HOA fees and property taxes?+
HOA costs are minimal here, with a median of just $5 a month, so most owners carry little or no association overhead. The median annual property tax is $5,349. If you're renting rather than buying, the median rent runs about $2,395 a 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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