Neighborhood · Maitland, Florida
Winfield
Everyday ease minutes from downtown Orlando
2
Homes for sale
$464,950
Median list price
$246
Avg price / sqft
55
Median days on market
Winfield sits in the leafy heart of Maitland, a pocket of Orange County where established streets and mature trees set the tone. Neighboring communities like Dommerich Hills and Lake Sybelia Cove share that same settled, unhurried character, and the location is genuinely central — downtown Orlando is about 16 minutes away, Universal roughly 25, and MCO around 34. It's the kind of place that trades flash for practicality, with quiet blocks and quick access to everything.
For buyers today, the market here is tight and moves at a measured pace. There are just 2 active listings, with a median list price of $464,950 and homes averaging $246 per square foot; over the past year, 10 homes sold at a median of $412,500. Sellers are getting about 96% of asking, and homes are taking a median of 54.5 days to sell — so there's room to negotiate, but well-priced homes still trade. If inventory feels thin, it's worth watching the broader Maitland homes for sale too.
Winfield is a community in Maitland, Florida.
Quick facts
$409,900 – $520K price range
1,928 sqft median home
$17/mo median HOA
10 sold in 12 months
Drive times
On the market now
Homes for sale in Winfield
$519,999$522,999
1776 BOBTAIL DRIVE, MAITLAND
4 bd · 3 ba · 2,344 sqft
$409,900$424,900
2150 TORTOISE SHELL DRIVE, MAITLAND
4 bd · 2 ba · 1,512 sqft
Every active listing inside the Winfield boundary
Open full map search →Find your fit
Browse Winfield
Where the market lives
The numbers that matter
The Winfield market
10
Sold, last 12 months
$412,500
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
10 days
Median time to sell
Winfield vs Maitland
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 12.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winfield boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winfield is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winfield home
≈ $3,007/mo
$464,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$17/mo
Median HOA
From current listings inside the boundary
Population
1,116
Median age
35
Median income
$84,530
Median home value
$342,189
Beyond the listings
Living in Winfield
Relationships
Top 2% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Attitudes
Top 3% in the U.S.Home & Leisure
There's no place like home. This activity is highest when people are feeling relaxed, like sharing a meal with friends or enjoying their morning coffee in their own home.
Entertainment
Top 3% in the U.S.Competitive Nature
These folks have their head in the game. Whether it's creating a card game tournament with friends or cheering on the home team, these people want to win.
Attitudes
Top 4% 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.
Emotional
Top 4% 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 5% 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.
On the calendar
Near Winfield
Jul
12
Sun
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
12
Sun
Orlando Farmers Market
10:00am
The Eola Sunday Market is celebrated as one of the finest in Central Florida. Attendees can enjoy an array of fresh fruits and vegetables, homemade bread, local cuisine,…
Jul
12
Sun
Vibe, Sip, and Make Jewelry
Wanda Taylor, a seasoned craftswoman, invites the community to a workshop where she'll share her expertise in creating a wide range of handcrafted items. Attendees will h…
Jul
12
Sun
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
12
Sun
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
12
Sun
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…
Keep exploring
More Maitland 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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