Neighborhood · Winter Park, Florida
Winter Woods
Attainable living minutes from Winter Park's core
6
Homes for sale
$97,250
Median list price
$150
Avg price / sqft
11
Median days on market
Winter Woods sits inside one of Central Florida's most walkable, tree-lined communities, close to neighborhoods like Lake Killarney and Winter Park Pines that give this pocket of Winter Park its steady, established feel. You're about 19 minutes from Downtown Orlando and roughly a half hour to both Universal and MCO, so the daily commute stays short without sacrificing the quiet residential streets buyers come here for.
The market reality is refreshingly grounded: with a median list price of $97,250 and an average of $150 per square foot, this is some of the most attainable footing you'll find near Hannibal Square and Eastbrook. Homes here move fast — a median of 11 days on market — but sellers are landing about 92% of asking, which leaves real room for a prepared buyer to negotiate.
Winter Woods is a community in Winter Park, Florida.
Quick facts
$80,000 – $549K price range
1,053 sqft median home
$880/mo median HOA
$1,200/mo median rent
21 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Woods
$85,000
252 SCOTTSDALE SQ UNIT 252, WINTER PARK
2 bd · 1.5 ba · 1,085 sqft
$549,000
1956 JAPONICA ROAD, WINTER PARK
3 bd · 2 ba · 1,923 sqft
$80,000
263 SCOTTSDALE SQUARE UNIT 263, WINTER PARK
2 bd · 2 ba · 1,020 sqft
$80,000
303 SCOTTSDALE SQUARE UNIT 303, WINTER PARK
2 bd · 2 ba · 1,020 sqft
$499,000$519,999
2217 SUSSEX ROAD, WINTER PARK
4 bd · 2 ba · 2,092 sqft
$109,500$109,900
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
21
Sold, last 12 months
$85,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
10 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
▲ 39.1% 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
≈ $1,728/mo
$97,250 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
$1,200/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 well-located, established community near the heart of Winter Park, with Downtown Orlando about 19 minutes away and Universal Orlando roughly 31 minutes out. Assigned schools include English Estates Elementary, Tuskawilla Middle and Lake Howell High. The steady residential feel and short commutes make it a practical choice for buyers who want proximity without premium pricing.
Is Winter Woods expensive?+
Not by Winter Park standards — the median list price is $97,250 and the average is $150 per square foot, well below what you'd pay closer to Lake Killarney. Active listings currently range from $80,000 up to $549,000, so there's a spread depending on size and condition. For the area, this is about as attainable as it gets.
What do homes cost in Winter Woods?+
Current active listings show a median list price of $97,250 with a range of $80,000 to $549,000, and the median home is around 1,053 square feet. Over the last 12 months, 21 homes sold at a median price of $85,000. If you're renting first, the median rent here runs about $1,200 a month.
How is the market in Winter Woods right now?+
It's brisk — homes are selling in a median of 11 days with just 6 active listings on the market. Sellers are averaging 92% of their asking price, so while demand is real, there's still negotiating room for a buyer who comes in prepared. The 21 sales over the past year point to consistent, healthy turnover.
What about HOA fees and property taxes?+
The median HOA here is $880 per month, which typically reflects condo or townhome-style ownership with shared maintenance, so factor that into your monthly budget. Median property taxes are comparatively light at $1,514 per year. Always confirm exactly what the HOA covers 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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