Homes zoned for
Maitland Middle
Tree-lined streets and a school zone families chase
137
Homes for sale
$989,500
Median list price
$501
Avg price / sqft
45
Median days on market
The Maitland Middle attendance zone sits in the leafy northern reaches of Winter Park, where oak-canopied streets, lakefront lots, and a mix of established homes give the area a settled, family-first character. It's the kind of place where a swimming pool is more common than not — 67 of the current listings have one — and where the pull of good schools shapes who moves in and who stays. Buyers weighing this zone often compare it against neighboring Winter Park High and Glenridge Middle boundaries, and it holds its own. You're still close to the wider slate of Winter Park homes for sale while keeping that quieter, residential feel.
The market reality here is upper-tier: 130 active listings carry a median list price of $1,017,000, and 65 of them are asking $1M or more. That said, entry points exist — active prices start at $174,900 — so the zone isn't out of reach for every budget. Homes are moving at a measured pace, with a median 48 days on market, and you can track what's live right now on the live map.
Maitland Middle is an attendance zone in Winter Park, Florida.
Quick facts
$174,900 – $13M price range
2,474 sqft median home
$384/mo median HOA
$2,200/mo median rent
467 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 137 →
$6,888,888
2661 VIA TUSCANY, WINTER PARK
4 bd · 4.5 ba · 4,636 sqft
$3,500,000
2240 VENETIAN WAY, WINTER PARK
4 bd · 3.5 ba · 4,036 sqft
$2,569,999
1754 TAYLOR AVENUE, WINTER PARK
5 bd · 4.5 ba · 3,670 sqft
$2,549,000
1823 SUNSET DRIVE, WINTER PARK
5 bd · 4.5 ba · 3,479 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
$599,000
1132 CHARMING STREET, MAITLAND
4 bd · 3.5 ba · 2,474 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
1140 S ORLANDO AVENUE UNIT K15, MAITLAND
2 bd · 1.5 ba · 816 sqft
$420,000
9359 TOBY LANE, ORLANDO
3 bd · 2 ba · 1,443 sqft
$325,000
545 CLARK STREET, MAITLAND
3 bd · 2.5 ba · 1,950 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
467
Sold, last 12 months
$650,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
31 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
≈ $6,408/mo
$989,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$384/mo
Median HOA
From current listings inside the boundary
$2,200/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 a strong fit for families drawn to Winter Park's canopied residential streets and lake access, with 23 waterfront and 67 pool homes among current listings. The school zone itself is a major draw, and it sits near other sought-after boundaries like Winter Park High. Universal Orlando is roughly a 36-minute drive when you want the theme parks.
Is it expensive to buy here?+
Yes, this is an upper-tier market — the median list price is $1,017,000, and 65 of the 130 active listings are priced at $1M or more. That said, the range is wide, from $174,900 up to $12,500,000, so there's room for different budgets.
What do homes actually cost?+
Over the past 12 months, 468 homes sold at a median price of $655,000, which sits well below the current $1,017,000 median list price and reflects a range of home types and sizes. Average price runs about $514 per square foot, with a median home size around 2,594 square feet. The gap between sold and list prices means value depends heavily on the specific home and segment.
How is the market right now?+
It's steady rather than frenzied — homes take a median 48 days to sell, and sellers are getting 97% of their asking price on average. With 130 active listings including 22 new-construction options, buyers have real choice without the pressure of a runaway market.
What about HOA fees and property taxes?+
The median HOA runs about $375 per month, though only 5 active listings are in gated communities, so many homes carry lower or no HOA dues. Median property tax is $7,227 per year, and if you're weighing renting first, the median rent in the area is around $2,200 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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