Neighborhood · Winter Park, Florida
Oakcrest
Practical Winter Park living close to everything
3
Homes for sale
$325,000
Median list price
$253
Avg price / sqft
47
Median days on market
Oakcrest is a quiet residential pocket of Winter Park in Orange County, the kind of place where modest single-family homes sit within easy reach of the area's more storied corners. You're close to Lake Killarney, the shops and dining around Hannibal Square, and established neighborhoods like Eastbrook and Winter Park Pines. Downtown Orlando is about 19 minutes away and Orlando International Airport roughly 28, so commuting and travel stay simple.
For buyers, Oakcrest is one of the more attainable ways into the Winter Park area. With just 3 active listings and a median list price of $325,000, inventory is tight but priced well below the region's luxury tiers. Homes are moving in about 17 days, so when the right one lands, you'll want to be ready to act.
Oakcrest is a community in Winter Park, Florida.
Quick facts
$285,000 – $415K price range
1,509 sqft median home
2 sold in 12 months
Drive times
On the market now
Homes for sale in Oakcrest
$285,000
7348 GRAND AVENUE, WINTER PARK
3 bd · 2 ba · 1,509 sqft
$415,000$425,000
7384 GRAND AVENUE, WINTER PARK
3 bd · 2 ba · 1,162 sqft
$325,000
7393 GRAND AVENUE, WINTER PARK
3 bd · 2 ba · 1,518 sqft
Every active listing inside the Oakcrest boundary
Open full map search →Find your fit
Browse Oakcrest
Where the market lives
The numbers that matter
The Oakcrest market
2
Sold, last 12 months
$332,500
Median sold price
90%
Sale-to-list ratio
What sellers actually get vs asking
16 days
Median time to sell
Oakcrest vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 9.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Oakcrest boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Oakcrest is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Oakcrest home
≈ $2,286/mo
$325,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
465
Median age
36
Median income
$101,974
Median home value
$330,300
Beyond the listings
Living in Oakcrest
Attitudes
Top 1% in the U.S.Volunteering & Giving
Expressing a desire to give back and do good for the community, this behavior emphasizes charity. Common activities include volunteering, fundraisers, and donations.
Food & Drink
Top 1% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Relationships
Top 1% in the U.S.My Crew
Family, and friends who are like family - that's what this population is all about. These people love celebrating and nurturing their closest relationships.
Beliefs
Top 1% in the U.S.Spiritual Practices
Making it to church on Sunday, this population is drawn together by their devotion to, primarily Christian, religion. Common activities include worship services and bible studies.
Active
Top 1% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
Relationships
Top 1% in the U.S.Family Time
Family time is always a good time for these folks. Whether it's a family vacation or making ice cream sundaes at home, this population loves spending time with the people closest to them.
People who close here
Our Winter Park experts
Straight answers
Oakcrest FAQs
Is Oakcrest a good place to live?+
Oakcrest works well for buyers who want a Winter Park address without the premium price tag, with quiet streets and easy access to nearby Lake Killarney and Hannibal Square. Downtown Orlando is about 19 minutes away and the airport roughly 28, which keeps daily life convenient. Assigned schools include Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High.
Is Oakcrest expensive?+
Compared to much of Winter Park, Oakcrest is relatively attainable, with a median list price of $325,000 and active listings ranging from $285,000 to $425,000. At roughly $256 per square foot, it's a practical way into the area rather than a luxury buy.
What do homes cost in Oakcrest?+
Current listings sit between $285,000 and $425,000 with a median list price of $325,000, and the typical home is around 1,509 square feet. Over the past 12 months the one recorded sale closed at $360,000, so pricing depends heavily on condition and exact location.
How is the market in Oakcrest?+
It's a tight, quick market: only 3 homes are active right now and they're going under contract in a median of about 17 days. Sellers are getting roughly 92% of asking on average, so there's modest room to negotiate but not much time to hesitate.
What about HOA fees and property taxes?+
Oakcrest homes generally don't carry an HOA, which keeps monthly costs simpler than in many planned communities. The median annual property tax runs about $4,367, and your exact bill will depend on assessed value and any homestead exemption.
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.
Never miss a listing
New Oakcrest homes, in your inbox
A daily digest of new Winter Park listings — straight from the MLS. Unsubscribe anytime.