Neighborhood · Winter Park, Florida
Winter Woods
A quiet East Winter Park pocket close to everything
6
Homes for sale
$507,000
Median list price
$208
Avg price / sqft
24
Median days on market
Winter Woods sits in the eastern reach of Winter Park, a pocket of established streets where mature trees and single-family lots set the tone. You're a short hop from the lakeside stretch around Lake Killarney and the walkable energy of Hannibal Square, with downtown Orlando about 19 minutes away and MCO roughly 31. It's the kind of place that trades flash for convenience — easy commutes, familiar neighbors, and solid everyday living.
The market here is small and moves at a measured pace. With just 5 active listings and a median list price of $485,000, buyers have room to be deliberate — homes are taking about 36 days to find a contract, and sellers are landing around 93% of asking. If you're comparing options, the nearby communities of Eastbrook and Winter Park Pines round out the East Winter Park picture.
Winter Woods is a community in Winter Park, Florida.
Quick facts
$100,000 – $575K price range
1,969 sqft median home
$880/mo median HOA
$1,600/mo median rent
14 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Woods
$560,000
2067 POINCIANA ROAD, WINTER PARK
4 bd · 2 ba · 2,352 sqft
$575,000
2228 KING CHARLES COURT, WINTER PARK
4 bd · 3 ba · 2,551 sqft
$100,000
173 SCOTTSDALE SQUARE UNIT 173, WINTER PARK
1 bd · 1 ba · 785 sqft
$529,000$539,000
2211 KING RICHARDS COURT, WINTER PARK
4 bd · 2 ba · 1,845 sqft
$485,000$499,000
2217 SUSSEX ROAD, WINTER PARK
4 bd · 2 ba · 2,092 sqft
$109,400$109,500
311 SCOTTSDALE SQUARE UNIT 311, WINTER PARK
1 bd · 1 ba · 785 sqft
Every active listing inside the Winter Woods boundary
Open full map search →Find your fit
Browse Winter Woods
By feature — on the live map
Where the market lives
The numbers that matter
The Winter Woods market
14
Sold, last 12 months
$87,500
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
11 days
Median time to sell
Winter Woods vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 11.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Woods boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Woods is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winter Woods home
≈ $4,069/mo
$507,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$880/mo
Median HOA
From current listings inside the boundary
$1,600/mo
Median rent
Homes for rent inside the boundary
Population
1,050
Median age
49
Median income
$113,044
Median home value
$327,669
Beyond the listings
Living in Winter Woods
Active
Top 2% 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 3% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
Beliefs
Top 7% 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.
Emotional
Top 7% in the U.S.Memory Lane
Intentionally preserving memories of lost loved ones, joyful times, or reflecting on painful experiences in the past.
Beliefs
Top 9% in the U.S.Mindfulness & Spirituality
Seeking peace and well-being through meditation, gratitude and spirituality.
Attitudes
Top 9% in the U.S.Past Reflections
This population enjoys thinking about past historical events, including family genealogy, landmarks, and political affairs.
People who close here
Our Winter Park experts
Straight answers
Winter Woods FAQs
Is Winter Woods a good place to live?+
It's a settled, residential pocket of East Winter Park that favors convenience — downtown Orlando is about 19 minutes away and MCO roughly 31. Assigned schools include English Estates Elementary, Tuskawilla Middle, and Lake Howell High. The nearby Lake Killarney area adds lake access and dining within a short drive.
Is Winter Woods expensive?+
It's mid-range for the Winter Park area, with a median list price of $485,000 and homes averaging about $205 per square foot. Active prices currently run from $100,000 up to $560,000, so there's a real spread depending on size and condition.
What do homes cost in Winter Woods?+
Current active listings carry a median list price of $485,000, with a median home size around 1,845 square feet. Over the last 12 months, 14 homes sold, and sellers averaged about 93% of their asking price — so there's typically a little negotiating room.
How is the market in Winter Woods right now?+
It's a small, steady market with just 5 active listings and a median of 36 days on market. That measured pace gives buyers time to evaluate, though limited inventory means the right home can move quickly. You can compare active options across Winter Park to get a fuller read.
What about HOA fees and property taxes?+
The median HOA here runs about $880 a month, and median property tax lands around $4,898 a year. Factor both into your monthly budget, and confirm exactly what the HOA covers for any specific home before you write an offer.
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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