Neighborhood · Maitland, Florida
Winfield
Established Maitland living minutes from downtown Orlando
2
Homes for sale
$517,500
Median list price
$223
Avg price / sqft
92
Median days on market
Winfield sits in the heart of Maitland, a mature Orange County pocket where tree-lined streets and single-family homes give the neighborhood a settled, residential feel. You're surrounded by well-known communities like Dommerich Hills, Lake Fairview, and Greenwood Gardens, with downtown Orlando roughly 16 minutes away and Orlando International about 34. It's the kind of central location that keeps commutes short without putting you in the middle of the noise.
For buyers, the market here is thin and moves deliberately. There's currently just one active listing at $519,999, while the 12 homes sold over the past year closed at a median of $395,200 — a reminder that list prices and actual sale prices can diverge. With a median 119 days on market and sellers collecting about 97% of asking, there's room to be patient and negotiate when the right home comes up.
Winfield is a community in Maitland, Florida.
Quick facts
$515,000 – $520K price range
2,320 sqft median home
$17/mo median HOA
14 sold in 12 months
Drive times
On the market now
Homes for sale in Winfield
$515,000
2141 FALKNER ROAD, MAITLAND
4 bd · 2.5 ba · 2,295 sqft
$519,999$522,999
1776 BOBTAIL DRIVE, MAITLAND
4 bd · 3 ba · 2,344 sqft
Every active listing inside the Winfield boundary
Open full map search →The numbers that matter
The Winfield market
14
Sold, last 12 months
$406,700
Median sold price
97%
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
▼ 15.7% 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
≈ $3,163/mo
$517,500 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.
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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