Neighborhood · Winter Park, Florida
The Cloisters
Lakeside living minutes from downtown Winter Park
1
Homes for sale
$1,299,000
Median list price
$749
Avg price / sqft
128
Median days on market
The Cloisters sits in one of Winter Park's most walkable pockets, close enough to Lake Killarney that water is part of daily life here. It's the kind of neighborhood where you can be downtown Orlando in under 20 minutes yet still feel tucked into an established, tree-lined stretch of Orange County. Nearby communities like Winter Park Pines and Hannibal Square round out an area built for people who want city access without city noise.
Inventory is genuinely tight — there's currently one active listing, priced at $1,299,000, so buyers should be ready to move when the right home appears. Over the last 12 months, six homes sold at a median of $807,500, with sellers collecting about 96% of asking. Homes here can take time to trade, with a median 128 days on market, which means patience and preparation both pay off.
The Cloisters is a community in Winter Park, Florida.
Quick facts
$1,299,000 – $1.3M price range
1,734 sqft median home
$1,503/mo median HOA
6 sold in 12 months
Drive times
On the market now
Homes for sale in The Cloisters
Every active listing inside the The Cloisters boundary
Open full map search →Find your fit
Browse The Cloisters
By feature — on the live map
The numbers that matter
The The Cloisters market
6
Sold, last 12 months
$807,500
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
81 days
Median time to sell
The Cloisters vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 69.2% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the The Cloisters boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools The Cloisters is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median The Cloisters home
≈ $9,337/mo
$1,299,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$1,503/mo
Median HOA
From current listings inside the boundary
Population
308
Median age
20
Median income
$82,083
Median home value
$619,000
Beyond the listings
Living in The Cloisters
Hobbies & Interests
Top 1% 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.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Lifestyles
Top 5% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Hobbies & Interests
Top 6% 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.
Relationships
Top 7% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Food & Drink
Top 7% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
People who close here
Our Winter Park experts
Straight answers
The Cloisters FAQs
Is The Cloisters a good place to live?+
It's a strong fit for buyers who want an established Winter Park address with easy access to the water near Lake Killarney. You're about 19 minutes from downtown Orlando and zoned for Winter Park High and Audubon Park School, which adds appeal for families.
Is The Cloisters expensive?+
Yes, it sits at the higher end of the Winter Park market. The current active listing is priced at $1,299,000, though homes have actually closed at a median of $807,500 over the past year, so real sale prices run below top asking figures.
What do homes cost in The Cloisters?+
Pricing runs high, with an average of about $749 per square foot and a median home size around 1,734 square feet. The single active listing is at $1,299,000, while the median sold price over the last 12 months was $807,500 across six sales.
How is the market in The Cloisters?+
It's a low-inventory, patient market — just one home is active right now, and the median time on market is 128 days. Sellers have been getting about 96% of asking, so priced-right homes still trade close to list. You can compare nearby options in Eastbrook if timing is tight.
What about HOA fees and property taxes?+
The median HOA here runs about $1,503 per month, which is on the higher side and typically reflects a more managed community setting. Median property taxes come in around $9,362 per year, so budget for both when running your numbers.
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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