Homes zoned for
Maitland Middle
Tree-lined streets and a coveted school assignment
140
Homes for sale
$950,000
Median list price
$508
Avg price / sqft
38
Median days on market
The Maitland Middle attendance zone sits in the leafy, established part of the Winter Park area, where mature oaks, brick streets, and a mix of mid-century ranches and newer custom builds set the tone. Families are drawn here as much for the walkable neighborhoods as for the schools — feeding into standouts like Winter Park High and nearby options such as Glenridge Middle keeps demand steady year after year. It's a quieter, residential counterpoint to the tourist corridor, with Universal Orlando about 36 minutes away when you want the theme-park day.
For buyers, this is a competitive but navigable market. There are 134 active listings right now with a median list price of $924,500, and homes are moving at a median of 37 days with sellers collecting about 97% of asking. If your budget lands under the median, you'll be shopping against a lot of buyers, so it pays to browse Winter Park homes for sale and watch the live map closely to move fast on the right listing.
Maitland Middle is an attendance zone in Winter Park, Florida.
Quick facts
$179,900 – $7.0M price range
2,316 sqft median home
$419/mo median HOA
$2,738/mo median rent
472 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 140 →
$6,995,000
901 GOLFVIEW TERRACE, WINTER PARK
5 bd · 5.5 ba · 5,479 sqft
$4,400,000
702 VIA BELLA, WINTER PARK
4 bd · 5.5 ba · 3,720 sqft
$3,695,999
1742 TEMPLE DRIVE, WINTER PARK
4 bd · 5 ba · 3,658 sqft
$440,000
27 N CALHOUN AVENUE, MAITLAND
4 bd · 2 ba · 1,809 sqft
$5,500,000
1166 PALMER AVENUE, WINTER PARK
5 bd · 6 ba · 5,181 sqft
$5,195,900
825 PALMER AVENUE, WINTER PARK
5 bd · 6 ba · 5,122 sqft
$3,950,000
540 N PENNSYLVANIA AVENUE, WINTER PARK
4 bd · 2 ba · 1,652 sqft
$2,725,000
1773 WALNUT AVENUE, WINTER PARK
5 bd · 4.5 ba · 3,784 sqft
$1,800,000
1130 MECHANIC STREET, MAITLAND
4 bd · 4.5 ba · 3,567 sqft
$1,579,000
2417 CHANTILLY AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,718 sqft
$1,319,950
952 MOSS LANE, WINTER PARK
4 bd · 3.5 ba · 3,474 sqft
$1,300,000
504 W SWOOPE AVENUE, WINTER PARK
3 bd · 2.5 ba · 2,563 sqft
Every active listing inside the Maitland Middle attendance boundary
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Browse the zone
By feature — on the live map
Where the market lives
The numbers that matter
The Maitland Middle market
472
Sold, last 12 months
$650,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
25 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
▲ 9.9% 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
≈ $6,179/mo
$950,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$419/mo
Median HOA
From current listings inside the boundary
$2,738/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 the more sought-after residential pockets in the Winter Park area, prized for its tree-lined streets and school assignments feeding schools like Winter Park High. With 471 homes sold in the last 12 months, it's an active, family-oriented community rather than a quiet backwater. Universal Orlando is roughly 36 minutes out when you want it, but daily life here is residential and calm.
Is it expensive to buy here?+
Yes, this is a higher-priced part of the market — the median list price is $924,500 and average pricing runs about $497 per square foot. That said, the range is wide, from $184,900 up to $6,900,000, so there's more variety than the median suggests. Sixty of the 134 active listings are priced above $1M, which tells you where the weight of the inventory sits.
What do homes cost in this zone?+
The median sold price over the past year was $665,000, noticeably below the $924,500 median list price, which reflects how much high-end inventory is currently on the market. A typical home runs about 2,242 square feet at roughly $497 per square foot. Where you land depends heavily on whether you want a pool, water frontage, or new construction.
How is the market right now?+
It's competitive but reasonable. Homes are selling in a median of 37 days, and sellers are collecting about 97% of their asking price on average — a sign of steady, healthy demand. With 134 active listings against 471 sales in the past year, there's enough turnover to keep options open if you're ready to act; the live map is the fastest way to track what's new.
What about HOA fees and property taxes?+
The median HOA fee runs about $410 per month, though only a small share of listings are gated, so many homes carry lower or no association dues. Median property tax comes in around $6,435 per year. If you're weighing a rental instead, the median rent in the zone is about $2,675 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.
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