Cloisters Condos is a 1970s neighborhood in Winter Park, in the 32789 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 900 and 1,800 square feet under air, and the median lot is about 0.03 acres.
Homes here carry an HOA, billed quarterly, typically around $1,459. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 1970s.
Construction Block and stucco. Tile roofs on 88% of homes.
Style Mediterranean, Florida, Traditional. Predominantly single story.
Size Most homes fall between about 900 and 1,800 square feet under air.
Bedrooms Two bedrooms is the most common plan, then three.
Lot The median lot is about 0.03 acres.
HOA Billed quarterly, typically around $1,459. Confirm on a specific parcel before relying on it.
Where Cloisters Condos is
Cloisters Condos, centered at 28.597275, -81.347843. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Cloisters Condos, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Driving to
Time
Miles
Downtown Orlando
21 min
6.6
Walt Disney World
36 min
26.5
Orlando International Airport
38 min
15.2
Universal Orlando
28 min
14.6
Public schools nearby
Lakemont Elementary School 9 min, 2.2 mi
Park Maitland School of Winter Park 10 min, 2.0 mi
Winter Park High School 13 min, 3.6 mi
Brookshire Elementary School 13 min, 3.0 mi
Private schools nearby
St. Margaret Mary Catholic School 5 min, 0.5 mi
Parks and recreation
Downtown Winter Park 3 min, 0.3 mi
Central Park 4 min, 0.3 mi
Winter Park 5 min, 0.5 mi
Dinky Dock Park 6 min, 0.6 mi
Groceries and errands
Greater Lifestyle Foods 5 min, 0.5 mi
The Ancient Olive Gourmet of Winter Park 6 min, 0.5 mi
Publix Super Market at Winter Park Village 8 min, 1.2 mi
Nearest is not the same as zoned. The schools above are the closest ones to Cloisters Condos by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.
Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Cloisters Condos actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 7 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.
Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.
What homes sold for in Cloisters Condos
$1,100,000Median sale price
$735Median per square foot
151 daysMedian days to contract
7Homes sold in 12 months
Sale prices ran from $535,000 to $1,735,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
7
$1,100,000
$735
151 days
A price per foot taken from the whole neighborhood should never be applied straight to one house.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Never reduced 3 sales, closed at 92.1% of asking110 days
Reduced at least once 4 sales, closed at 95.5% of the reduced price154 days
Sellers who held their number went under contract in a median 110 days. Sellers who had to reduce took 154 days and still closed at 95.5% of their already reduced price, after a typical cut of $92,500.
How buyers paid
Cash 5 sales71%
Conventional 2 sales29%
Cash was 71% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Cloisters Condos, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Cloisters Condos in Winter Park, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.
