Neighborhood · Winter Park, Florida
Maitland Shores
Lakeside living on the Winter Park–Maitland line
4
Homes for sale
$6,244,444
Median list price
$1,232
Avg price / sqft
20
Median days on market
Maitland Shores sits at the northern edge of Winter Park, a small pocket of lakefront and pool homes where you're minutes from the tree-lined streets that define this part of Orange County. It's a quiet, established address with easy reach to nearby communities like Lake Killarney and Winter Park Pines, and the dining and shops around Hannibal Square. Downtown Orlando is about 22 minutes away and Orlando International Airport roughly 35, so you're close to the action without living in it.
The market here is thin and high-end: just 4 active listings right now, with a median list price of $6,244,444 and homes ranging from $3.5M to nearly $6.9M. That said, actual sales tell a more grounded story — 5 homes closed over the past year at a median of $1,650,000, with sellers netting about 95% of asking. When the right home comes up it moves fast, with a median of just 9 days on market, so a serious buyer should be ready to act.
Maitland Shores is a community in Winter Park, Florida.
Quick facts
$3,500,000 – $6.9M price range
4,636 sqft median home
5 sold in 12 months
Drive times
On the market now
Homes for sale in Maitland Shores
$6,888,888
2661 VIA TUSCANY, WINTER PARK
4 bd · 4.5 ba · 4,636 sqft
$5,600,000
2228 AZALEA PLACE, WINTER PARK
5 bd · 5.5 ba · 5,152 sqft
$6,888,888
2661 Via Tuscany, Winter Park FL 32789, 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
Every active listing inside the Maitland Shores boundary
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Browse Maitland Shores
By feature — on the live map
The numbers that matter
The Maitland Shores market
5
Sold, last 12 months
$1,650,000
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
91 days
Median time to sell
Maitland Shores vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 144.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Maitland Shores boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Maitland Shores is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Maitland Shores home
≈ $34,362/mo
$6,244,444 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
273
Median age
42
Median income
$120,719
Median home value
$530,080
Beyond the listings
Living in Maitland Shores
Hobbies & Interests
Top 6% 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.
Hobbies & Interests
Top 10% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Appearance oriented
Top 14% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Beliefs
Top 14% in the U.S.Politically Engaged
Politically aware, this population is interested in civic issues on both the local and national level. They often discuss candidates for office, taxes, and political ideologies.
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.
Beliefs
Top 19% in the U.S.Conservation
Good stewards of the earth, this population advocates for a cleaner environment and responsible use of resources. They often encourage others to recycle and use clean energy.
People who close here
Our Winter Park experts
Straight answers
Maitland Shores FAQs
Is Maitland Shores a good place to live?+
It's a good fit if you want an established, lakeside Winter Park address with strong school zoning — Dommerich Elementary, Maitland Middle, and Winter Park High. You're about 22 minutes from downtown Orlando and close to neighboring pockets like Eastbrook, so you get quiet residential streets without giving up access to the metro.
Is Maitland Shores expensive?+
Yes — it's one of the higher-end pockets in the area, with current listings ranging from $3,500,000 to nearly $6,888,888 and a median list price of $6,244,444. Actual sales run lower, with a median sold price of $1,650,000 over the past year, so there's a real gap between what's listed today and what has historically closed.
What do homes cost in Maitland Shores?+
The four active listings average about $1,232 per square foot on a median home size of 4,636 square feet, and every one is priced above $1M. Over the last 12 months, five homes sold at a median of $1,650,000, which gives a better sense of realistic pricing than the current high-end inventory.
How is the market in Maitland Shores?+
It's a small, fast-moving market — only 4 homes are active right now and the median time on market is just 9 days. Sellers are getting about 95% of their asking price on average, so competitive offers matter when a home you want comes up.
What about HOA fees and property taxes?+
There's no reported HOA data for the neighborhood's current listings, which is common for these established lakeside properties. Property taxes run higher given the price point — the median is about $15,013 per year — so factor that into your monthly budget.
Keep exploring
More Winter Park 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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