Neighborhood · Winter Park, Florida
Winter Woods
Compact Winter Park living close to everything downtown
7
Homes for sale
$109,500
Median list price
$159
Avg price / sqft
3
Median days on market
Winter Woods sits in the well-established heart of Winter Park, an Orange County community known for tree-lined streets and easy access to the rest of Orlando. It's a place where a compact, low-maintenance home makes sense — median sizes run around 1,085 square feet — and where you're a short drive from neighbors like Lake Killarney, Winter Park Pines, and the walkable energy of Hannibal Square. Downtown Orlando is roughly 19 minutes away, with MCO and Universal both around half an hour out.
For buyers, this is one of the more attainable corners of the broader Winter Park market, with a median list price of $109,500 and homes moving fast — the median listing goes under contract in about 3 days. There are only 7 active listings right now, so options are limited and well-priced homes don't linger. Over the past year 23 homes sold at a median of $85,000, with sellers collecting about 92% of asking, which tells you buyers still have room to negotiate here.
Winter Woods is a community in Winter Park, Florida.
Quick facts
$80,000 – $549K price range
1,085 sqft median home
$880/mo median HOA
$1,200/mo median rent
23 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Woods
$375,000
2189 SUSSEX ROAD, WINTER PARK
4 bd · 2.5 ba · 1,776 sqft
$80,000
303 SCOTTSDALE SQUARE UNIT 303, WINTER PARK
2 bd · 2 ba · 1,020 sqft
$80,000
263 SCOTTSDALE SQUARE UNIT 263, WINTER PARK
2 bd · 2 ba · 1,020 sqft
$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
$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
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Browse Winter Woods
By feature — on the live map
Where the market lives
The numbers that matter
The Winter Woods market
23
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
≈ $1,803/mo
$109,500 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.
On the calendar
Near Winter Woods
Jul
14
Tue
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
14
Tue
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
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…
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
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
16
Thu
Thursday Thinks Trivia
7:30pm
This challenging trivia night promises a wide range of engaging questions, ensuring something new and exciting for everyone - from pop culture, geography, and history, to…
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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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