Neighborhood · Winter Park, Florida
Maitland Shores
Lakefront living minutes from downtown Winter Park
3
Homes for sale
$5,600,000
Median list price
$1,147
Avg price / sqft
1
Median days on market
Maitland Shores sits at the northern edge of Winter Park, a small enclave of large lots and waterfront lifestyle where homes back up to the chain of lakes near Lake Killarney. This is old-Florida shade and generous acreage within a short drive of the shops and dining that define the wider Winter Park experience, with neighbors in established pockets like Winter Park Pines and Kenilworth. Downtown Orlando is about 22 minutes out and MCO roughly 35, so you get the quiet without giving up access.
The market here is thin and top-heavy: just 3 active listings, with a median list price of $5.6M and a range from $3.5M to nearly $6.9M. That said, the three homes that actually sold in the past year traded at a median of $1,650,000 — a reminder that what closes here runs well below the aspirational list numbers currently on the board. With inventory this scarce, well-priced homes move fast, and sellers are getting about 96% of asking.
Maitland Shores is a community in Winter Park, Florida.
Quick facts
$3,500,000 – $6.9M price range
4,636 sqft median home
3 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
$3,500,000
2240 VENETIAN WAY, WINTER PARK
4 bd · 3.5 ba · 4,036 sqft
$5,600,000
2228 AZALEA PLACE, WINTER PARK
5 bd · 5.5 ba · 5,152 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
3
Sold, last 12 months
$1,650,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
63 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
≈ $31,907/mo
$5,600,000 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 quiet, established waterfront neighborhood on Winter Park's north side, with large lots and a strong public-school assignment to Dommerich Elementary, Maitland Middle, and Winter Park High. You're about 22 minutes from downtown Orlando and 35 from MCO, so it balances seclusion with real access. Nearby communities like Lake Killarney share the same lake-focused lifestyle.
Is Maitland Shores expensive?+
Yes — it's one of the higher-end pockets in the area, with a median list price of $5,600,000 and active homes ranging from $3,500,000 to $6,888,888. Average pricing works out to roughly $1,147 per square foot. Actual closings tell a more grounded story, with a median sold price of $1,650,000 over the past year.
What do homes cost in Maitland Shores?+
Currently the three active listings sit between $3.5M and nearly $6.9M, with a median list of $5.6M and a median home size around 4,636 square feet. But the homes that sold in the last 12 months closed at a median of $1,650,000, so there's a wide gap between list ambitions and realized prices. Buyers exploring the broader Winter Park market will find more consistent pricing nearby.
How is the market in Maitland Shores?+
It's extremely low-inventory: just 3 active listings and only 3 sales in the past year. When homes are priced right they move fast — median days on market is 1 — and sellers are averaging about 96% of asking. Neighboring areas like Winter Park Pines can offer more options if timing is tight.
What about HOA fees and property taxes?+
There's no reported HOA figure for the active listings here, which is common for large-lot custom-home neighborhoods. Property taxes, however, reflect the price point — the median runs about $26,300 per year. Budget for that carrying cost alongside your mortgage when comparing homes in Kenilworth and other nearby enclaves.
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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