Neighborhood · Winter Park, Florida
Maitland Shores
Lakefront living minutes from Winter Park's core
4
Homes for sale
$4,550,000
Median list price
$1,001
Avg price / sqft
64
Median days on market
Maitland Shores sits on the northern edge of Winter Park, where large lots and water views define the character more than traffic or storefronts. It's a quiet, established pocket zoned to Dommerich Elementary, Maitland Middle, and Winter Park High, with easy reach to neighbors like Lake Killarney, Eastbrook, and the shops and restaurants that make up broader Winter Park homes for sale. Downtown Orlando is about 22 minutes out and MCO roughly 35, so you get seclusion without isolation.
For buyers, this is a thin, high-end market. There are only 4 active listings right now, with a median list price of $4,550,000 and a range running from $950,000 up to just under $6M — so pricing swings hard depending on lot, water frontage, and condition. Just 6 homes sold over the past year at a median of $2,112,500, and sellers are collecting about 94% of asking, which tells you there's room to negotiate if you come prepared. If you're weighing this against nearby areas like Orwin Manor or Hannibal Square, expect fewer options here but bigger footprints.
Maitland Shores is a community in Winter Park, Florida.
Quick facts
$950,000 – $6.0M price range
3,958 sqft median home
6 sold in 12 months
Drive times
On the market now
Homes for sale in Maitland Shores
$950,000
913 MOSS LANE, WINTER PARK
3 bd · 2 ba · 1,887 sqft
$5,999,990
2661 VIA TUSCANY, WINTER PARK
4 bd · 4.5 ba · 3,880 sqft
$5,600,000
2228 AZALEA PLACE, WINTER PARK
5 bd · 5.5 ba · 5,152 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
Open full map search →Find your fit
Browse Maitland Shores
By feature — on the live map
Where the market lives
The numbers that matter
The Maitland Shores market
6
Sold, last 12 months
$2,112,500
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
77 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
▲ 125.0% 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
≈ $26,400/mo
$4,550,000 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 neighborhood on the north side of Winter Park with large lots, lake access, and a location about 22 minutes from downtown Orlando. Homes are zoned to Dommerich Elementary, Maitland Middle, and Winter Park High, which draws families. You're close to the shops and dining across greater Winter Park homes for sale without sitting in the middle of them.
Is Maitland Shores expensive?+
Yes — it leans luxury. The median list price is $4,550,000 and three of the four active listings are priced above $1M, with average price per square foot around $1,001. That said, the range starts near $950,000, so there are entry points well below the top.
What do homes cost in Maitland Shores?+
Active listings range from $950,000 to just under $6M, with a median list of $4,550,000 on a typical home size near 3,958 square feet. Over the past year, 6 homes actually sold at a median of $2,112,500 — a useful reality check against the higher asking prices. Compare that with nearby Eastbrook if you want a sense of the broader Winter Park price spread.
How is the market in Maitland Shores?+
It's a low-inventory, high-value market with just 4 active listings and 6 sales in the past 12 months. Homes move at a median of 24 days, and sellers are getting about 94% of asking on average — so there's meaningful negotiating room, especially at the top of the price range.
What about HOA fees and property taxes?+
There's no consistent HOA data reported for the neighborhood, so many of these homes aren't tied to mandatory association dues. Property taxes, however, run high given the values here — the median annual property tax is about $26,602, which you'll want to build into your carrying costs.
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.
Never miss a listing
New Maitland Shores homes, in your inbox
A daily digest of new Winter Park listings — straight from the MLS. Unsubscribe anytime.