Neighborhood · Winter Park, Florida
Eastbrook
Practical Winter Park living close to it all
14
Homes for sale
$404,500
Median list price
$269
Avg price / sqft
74
Median days on market
Eastbrook is one of Winter Park's more approachable pockets, an established residential enclave in Orange County where mid-sized homes and mature streets sit within easy reach of the city's landmarks. You're about 22 minutes from downtown Orlando and 32 from MCO, with nearby communities like Lake Killarney, Winter Park Pines, and the shops and cafes around Hannibal Square filling out day-to-day life. It's the kind of place buyers land when they want the Winter Park address without the Park Avenue price tag.
The market here moves quickly and rewards ready buyers. With just 9 active listings and a median list price of $399,000, inventory is tight and homes are going fast — a median of 11 days on market, and sellers collecting about 99% of asking. If you're weighing options across Winter Park homes for sale, Eastbrook lands squarely in the attainable middle, so come prepared to act.
Eastbrook is a community in Winter Park, Florida.
Quick facts
$334,000 – $520K price range
1,617 sqft median home
$2,500/mo median rent
33 sold in 12 months
Drive times
On the market now
Homes for sale in Eastbrook
View all 14 →
$479,900
2020 LEANNE COURT, WINTER PARK
4 bd · 3 ba · 2,088 sqft
$379,900$395,000
3416 ARBUTUS LANE, WINTER PARK
4 bd · 3 ba · 1,421 sqft
$520,000
1905 BONANZA CT, WINTER PARK
4 bd · 2 ba · 1,774 sqft
$427,000
1386 CLEMATIS LANE, WINTER PARK
4 bd · 3 ba · 1,714 sqft
$440,000$450,000
2301 CONIFER AVENUE, WINTER PARK
4 bd · 2 ba · 2,189 sqft
$419,000
1842 PURITAN AVENUE, WINTER PARK
4 bd · 2 ba · 1,836 sqft
$425,000
1886 CLEMATIS LANE, WINTER PARK
3 bd · 2 ba · 1,238 sqft
$334,000$339,000
3562 BOUGAINVILLEA DRIVE, WINTER PARK
3 bd · 2 ba · 1,149 sqft
$368,000$375,000
885 CARNATION DRIVE, WINTER PARK
4 bd · 2 ba · 1,240 sqft
$379,000$389,000
1605 PURITAN AVENUE, WINTER PARK
3 bd · 2 ba · 1,285 sqft
$500,000
2054 EASTBROOK BOULEVARD, WINTER PARK
4 bd · 3 ba · 2,031 sqft
$390,000
2512 EASTBROOK BOULEVARD, WINTER PARK
4 bd · 2 ba · 1,607 sqft
Every active listing inside the Eastbrook boundary
Open full map search →Find your fit
Browse Eastbrook
By feature — on the live map
Where the market lives
The numbers that matter
The Eastbrook market
33
Sold, last 12 months
$376,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
30 days
Median time to sell
Eastbrook vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 5.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Eastbrook boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Eastbrook is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Eastbrook home
≈ $2,698/mo
$404,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,500/mo
Median rent
Homes for rent inside the boundary
Population
2,053
Median age
38
Median income
$73,271
Median home value
$301,613
Beyond the listings
Living in Eastbrook
Appearance oriented
Top 8% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Beliefs
Top 9% 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.
Emotional
Top 10% 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.
Entertainment
Top 11% 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 14% in the U.S.Live Experiences
When it comes to entertainment, this population is looking for the ultimate experience. Whether it's a charity fundraiser or a concert, elements such as lights, sounds, and merchandise are critical for a good time.
Culture
Top 15% 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
Eastbrook FAQs
Is Eastbrook a good place to live?+
It's a solid, established Winter Park neighborhood with quick access to downtown Orlando (about 22 minutes) and MCO (about 32). You're close to nearby communities like Kenilworth and the dining around Hannibal Square, which gives you Winter Park convenience at a more grounded pace. Assigned schools include Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High.
Is Eastbrook expensive?+
Compared with much of Winter Park, no. The median list price is $399,000 and the range runs $339,000 to $500,000, with the median home sold over the past year at $369,000. That puts it in the attainable tier for a Winter Park address.
What do homes cost in Eastbrook?+
Expect a median list price around $399,000, or roughly $293 per square foot for a median home size near 1,263 square feet. Over the last 12 months, 34 homes sold at a median of $369,000. There's currently one waterfront listing and three homes with pools among the active inventory.
How is the market in Eastbrook right now?+
It's fast and competitive. With only 9 active listings and a median of 11 days on market, homes don't linger, and sellers are averaging 99% of their asking price. Buyers who want to compete with Winter Park homes for sale in this range should be pre-approved and ready to move.
What about HOA fees and property taxes?+
There's no typical HOA figure reported for Eastbrook, so many homes here carry little to no HOA obligation. The median property tax runs about $4,330 per year. For those considering renting instead, the median rent is around $2,050 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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