Neighborhood · Winter Park, Florida
Eastbrook
Winter Park value without the Winter Park price tag
9
Homes for sale
$399,000
Median list price
$268
Avg price / sqft
16
Median days on market
Eastbrook sits on the eastern edge of Winter Park in Orange County, an established residential pocket of tree-lined streets and single-family homes that feed into Winter Park homes for sale shoppers who want space without leaving the area. It's a genuinely convenient spot — downtown Orlando is about 22 minutes out, Orlando International is roughly 32, and you're close enough to established neighbors like Winter Park Pines and Lake Killarney to borrow their character while paying less for it. Families lean on Eastbrook Elementary right in the neighborhood, with Tuskawilla Middle and Lake Howell High rounding out the assignments.
For buyers, this is one of Winter Park's more accessible entry points. There are 8 active listings with a median list price of $399,450, ranging from $324,000 up to $500,000, and homes are moving at a median of 42.5 days — steady, not frantic. Over the last year 37 homes sold at a median of $370,000, with sellers collecting about 98% of asking, so there's room to negotiate but not to lowball. Compared to pricier addresses like Kenilworth and Hannibal Square, Eastbrook is where the math still works.
Eastbrook is a community in Winter Park, Florida.
Quick facts
$324,000 – $500K price range
1,607 sqft median home
$2,295/mo median rent
37 sold in 12 months
Drive times
On the market now
Homes for sale in Eastbrook
$375,000
885 CARNATION DRIVE, WINTER PARK
4 bd · 2 ba · 1,240 sqft
$399,000
1605 PURITAN AVENUE, WINTER PARK
3 bd · 2 ba · 1,285 sqft
$390,000
2512 EASTBROOK BOULEVARD, WINTER PARK
4 bd · 2 ba · 1,607 sqft
$399,000$410,000
1092 EASTBROOK BOULEVARD, WINTER PARK
3 bd · 2 ba · 1,122 sqft
$500,000
2054 EASTBROOK BOULEVARD, WINTER PARK
4 bd · 3 ba · 2,031 sqft
$324,000$339,000
1760 PERUVIAN LANE, WINTER PARK
3 bd · 2 ba · 1,160 sqft
$414,900$419,900
3463 ARNEL DRIVE, WINTER PARK
3 bd · 2 ba · 1,770 sqft
$440,000$445,000
2052 LEANNE COURT, WINTER PARK
4 bd · 2 ba · 2,264 sqft
$399,900$408,000
1849 VIBURNUM LANE, WINTER PARK
4 bd · 2 ba · 1,627 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
37
Sold, last 12 months
$370,000
Median sold price
98%
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
▲ 2.7% 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
≈ $2,660/mo
$399,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,295/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.
On the calendar
Near Eastbrook
Jul
13
Mon
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
13
Mon
Bite30
Bite30 in Orlando, FL, USA, is a culinary celebration that spotlights the creativity and talent of Central Florida’s top chefs and restaurants. For a set price, diners ca…
Jul
13
Mon
Emily Giffin
6:00 PM
Celebrate the release of 'LOVE YOU MORE' with its author, Emily Giffin, in a lively conversation with Madeline Martin. Attendees will need to purchase a copy of the book…
Jul
14
Tue
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
14
Tue
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
14
Tue
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
People who close here
Our Winter Park experts
Straight answers
Eastbrook FAQs
Is Eastbrook a good place to live?+
It's a settled residential neighborhood on the east side of Winter Park with its own Winter Park homes for sale appeal and Eastbrook Elementary right in the community. The location is practical — about 22 minutes to downtown Orlando and 32 to the airport — which suits families and commuters alike.
Is Eastbrook expensive?+
Not by Winter Park standards. The median list price is $399,450 and active homes run from $324,000 to $500,000, which is noticeably gentler than pricier pockets like Lake Killarney. There are no active listings above $1M here.
What do homes cost in Eastbrook?+
The median list price is $399,450 and homes average about $264 per square foot, with a median size of 1,617 square feet. Over the past 12 months, 37 homes sold at a median of $370,000, so recent sales are landing a bit below current asking prices.
How is the Eastbrook housing market right now?+
It's balanced and steady. There are 8 active listings, homes take a median of 42.5 days to sell, and sellers are getting about 98% of asking on average — a market where serious buyers have negotiating room without the pressure of a bidding war, unlike some of the tighter inventory near Winter Park Pines.
What about HOA fees and property taxes in Eastbrook?+
Property taxes run a median of about $3,908 per year. There's no significant HOA data reported for the neighborhood, so most homes here aren't carrying the monthly dues you'd find in gated communities. If you're renting instead, the median rent is around $2,295 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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