Homes zoned for
Maitland Middle
Tree-lined streets, lakefront living, and top-rated schools
135
Homes for sale
$899,000
Median list price
$486
Avg price / sqft
48
Median days on market
The Maitland Middle attendance zone sits in the leafy, lake-dotted stretch of northern Winter Park, where oak canopies, walkable neighborhoods, and easy access to the wider Winter Park homes for sale market define daily life. It's a place where families weigh school options like Winter Park High and Lake Howell High School as carefully as square footage, and where 20 waterfront listings and 67 homes with pools speak to how people actually spend their weekends here.
For buyers, this is a competitive but rational market. With 135 active listings and a median list price of $899,000, sellers are getting 97% of asking on average and homes are moving in about 47 days — brisk, but not frantic. Explore the live map to see how the range runs, from starter-priced condos near $175,000 to estate properties well past a million.
Maitland Middle is an attendance zone in Winter Park, Florida.
Quick facts
$174,900 – $13M price range
2,474 sqft median home
$394/mo median HOA
$2,290/mo median rent
470 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 135 →
$6,888,888
2661 VIA TUSCANY, WINTER PARK
4 bd · 4.5 ba · 4,636 sqft
$2,569,999
1754 TAYLOR AVENUE, WINTER PARK
5 bd · 4.5 ba · 3,670 sqft
$1,995,000
922 N PENNSYLVANIA AVENUE, WINTER PARK
4 bd · 4 ba · 3,440 sqft
$1,800,000
1130 MECHANIC STREET, MAITLAND
4 bd · 4.5 ba · 3,567 sqft
$1,800,000
281 BREWER AVENUE, WINTER PARK
5 bd · 4.5 ba · 4,029 sqft
$789,000
2080 GOLDWATER COURT, MAITLAND
4 bd · 2 ba · 2,280 sqft
$500,000
8873 ASPEN AVENUE, ORLANDO
3 bd · 2 ba · 1,940 sqft
$455,000
8422 MARGARITA DRIVE, ORLANDO
3 bd · 2 ba · 1,845 sqft
$420,000
9359 TOBY LANE, ORLANDO
3 bd · 2 ba · 1,443 sqft
$420,000
1140 S ORLANDO AVENUE UNIT K15, MAITLAND
2 bd · 1.5 ba · 816 sqft
$325,000
545 CLARK STREET, MAITLAND
3 bd · 2.5 ba · 1,950 sqft
$299,000
812 PARK LAKE CIRCLE UNIT 7, MAITLAND
3 bd · 2.5 ba · 1,565 sqft
Every active listing inside the Maitland Middle attendance boundary
Open full map search →Find your fit
Browse the zone
By feature — on the live map
Where the market lives
The numbers that matter
The Maitland Middle market
470
Sold, last 12 months
$647,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
30 days
Median time to sell
Maitland Middle vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 2.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Maitland Middle boundary. Rolling medians smooth single-month swings in small communities.
What it really costs
Owning here
Owning the median Maitland Middle home
≈ $5,905/mo
$899,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$394/mo
Median HOA
From current listings inside the boundary
$2,290/mo
Median rent
Homes for rent inside the boundary
Population
36,575
Median age
42
Median income
$123,814
Median home value
$621,743
Beyond the listings
Living in Maitland Middle
Hobbies & Interests
Top 12% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Food & Drink
Top 15% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Relationships
Top 16% 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.
Lifestyles
Top 16% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Entertainment
Top 19% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Appearance oriented
Top 19% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
People who close here
Our Winter Park experts
Straight answers
Maitland Middle FAQs
Is the Maitland Middle zone a good place to live?+
It's one of northern Winter Park's most family-oriented pockets, with lake access, tree-lined streets, and feeders into schools like Glenridge Middle. The 67 pool homes and 20 waterfront listings on the market show how much of life here happens outdoors, and Universal Orlando is about 36 minutes away when you want a bigger day out.
Is it expensive to buy here?+
It sits at the higher end of the Orlando metro, with a median list price of $899,000 and an average of $486 per square foot. That said, the range is wide — active listings start around $174,900 and climb to $12,500,000 — so there's room for both first-time buyers and luxury shoppers.
What do homes actually cost?+
Over the last 12 months, 469 homes sold at a median price of $647,000, notably below the current $899,000 list median, which tells you the mix of what's listed skews higher than what's closing. The median home runs about 2,474 square feet, and 63 active listings are priced above $1M for buyers targeting the top tier.
How is the market right now?+
It's active but measured — 135 homes are listed and the median time on market is about 47.5 days. Sellers are averaging 97% of their asking price, so well-priced homes move steadily while ambitious pricing tends to sit; browse the live map to gauge current momentum.
What should I expect for HOA fees and property taxes?+
The median HOA runs about $394 per month, though only 6 of the active listings are in gated communities, so many homes carry lower or no association dues. Median property tax is roughly $6,764 per year, and if you're weighing renting first, the median rent sits around $2,290 per month.
Keep exploring
Other Winter Park school zones
Homes matched to the official attendance boundary — school zoning changes; always verify with the district. 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.
Never miss a listing
New Maitland Middle homes, in your inbox
A daily digest of new Winter Park listings — straight from the MLS. Unsubscribe anytime.