Neighborhood · Winter Park, Florida
The Cloisters
Quiet Winter Park living with easy Orlando access
1
Homes for sale
$850,000
Median list price
$519
Avg price / sqft
5
Median days on market
The Cloisters is a small residential enclave in Winter Park, a city known for its tree-lined streets, lakes, and walkable village feel. It sits within easy reach of neighborhoods like Lake Killarney and Winter Park Pines, and the location puts downtown Orlando about 19 minutes away, with Orlando International Airport around 38 minutes out. Families here are typically zoned for Winter Park High and Audubon Park School, which anchors the area's appeal for buyers with kids.
Market-wise, The Cloisters is tight and rarely available — there are no active listings right now. Over the past 12 months just 7 homes sold, at a median sold price of $840,000, so this is a spot where you'll need patience and a ready plan. Sellers here have been getting about 95% of asking on average, which tells you buyers still have some room to negotiate when something does come up.
The Cloisters is a community in Winter Park, Florida.
Quick facts
$850,000 – $850K price range
1,639 sqft median home
$1,503/mo median HOA
5 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
5
Sold, last 12 months
$1,100,000
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
151 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
≈ $7,078/mo
$850,000 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 an established, quiet residential neighborhood in Winter Park with quick access to downtown Orlando, about 19 minutes away. Homes are typically zoned for Winter Park High and Audubon Park School, which appeals to families. If you value a settled address near Winter Park amenities, it delivers.
Is The Cloisters expensive?+
Yes, it sits at the higher end of the Winter Park market — the median sold price over the last 12 months was $840,000. It's comparable to nearby established neighborhoods like Eastbrook. Availability is limited, which tends to support prices.
What do homes cost in The Cloisters?+
There are no active listings at the moment, so recent sales are the best guide. Over the past year, 7 homes closed at a median sold price of $840,000, giving you a solid sense of the price point.
How is the market in The Cloisters?+
It's a low-inventory, low-turnover market — zero homes are listed right now and only 7 sold in the last 12 months. Sellers averaged about 95% of asking price, so there's modest negotiating room, but you'll need to be ready to move when a home hits the market.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available for the current listings since nothing is active right now. Your agent can pull exact figures from the most recent sales, and comparable Winter Park neighborhoods like Winter Park Pines can offer a useful reference point in the meantime.
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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