The Cloisters
The Cloisters Homes Sold in the Past 12 Months
The Cloisters: Local Questions Answered
Where is The Cloisters in Winter Park?
The Cloisters is at 100–104 South Interlachen Avenue on Lake Osceola, part of the Winter Park Chain of Lakes. It is inside City of Winter Park limits, with Winter Park 32789 addresses.
What types of homes are in The Cloisters?
The Cloisters is a mid-rise condominium with 92 units built in 1971, according to Orange County Property Appraiser records: 71 two-bedroom, 20 three-bedroom and one four-bedroom unit. Units range from about 900 to 2,290 square feet. There are no single-family homes.
How much do condos cost in The Cloisters?
Over the past two years (MLS data, October 2026), units in The Cloisters sold 16 times for a median of about $778,000, ranging from about $520,000 to $1.2 million. For today's listings, see the top of this page.
What are the HOA fees in The Cloisters?
MLS listings show a wide range of condominium association dues, so confirm the current amount with the association. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for The Cloisters, but check the property tax bill for any special assessments. The association is Cloisters Condominium Association, Inc.
What schools serve The Cloisters?
Orange County Public Schools' 2026-27 school zones place The Cloisters in Audubon Park School (K-8) and Winter Park High School.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Does The Cloisters have boat slips on Lake Osceola?
Yes. MLS listings and a realtor page describe a dock with boat slips on Lake Osceola, and listings say the slips are assigned to residents. The association's common parcel touches the lake. The Cloisters condominium is separate from Cloister Grove, an older plat near Via Tuscany that is part of The Vias.
Can you rent condos in The Cloisters short term?
No Cloisters-specific rental rules turned up in our research. Condominium documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
