The Cloisters Winter Park

The Cloisters is a condominium building in Winter Park, Florida, with a range of options priced between $564,900 and $1,200,000. There are currently a total of 4 condos for sale in The Cloisters. The smallest Cloisters condo presently available is a two bedroom one bathroom residence that is 901 square feet, and the largest of the The Cloisters condos currently on the market has two beds and two baths and is a 1,290 square foot (1,267SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between units in the building. The current Condo fees for The Cloisters range from $2,535 to $3,205. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and real estate taxes for common areas. Also included is property insurance, water, trash removal, sewer, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular The Cloisters condo.

Building amenities include a clubhouse, swimming pool, a state-of-the-art fitness center, sauna, and laundry facilities.

The Cloisters HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve The Cloisters - Orlando Executive (ORL), which is four miles away; Orlando International (MCO), which is twelve miles away; Orlando Sanford International (SFB), which is fourteen miles away, and Kissimmee Gateway (ISM), which is twenty two miles away from the The Cloisters condominium location.

The Cloisters real estate activity on the Winter Park MLS during the past year (as of September 2025) reflects nine condos changing hands, with an average asking price of $758,656 and an average selling price of $723,778. This represents a healthy list-to-sell price ratio of 95% and $565 per square foot. During this period, The Cloisters condos for sale have taken an average of 35 days to sell.

In addition, there are numerous other condo buildings in Winter Park to choose from, or you may browse all available Condos for sale in Winter Park. Condos for sale in The Cloisters are selling quickly. Set up a new listing alert, and we will notify you immediately when a new condo in The Cloisters hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

The Cloisters Condos For Sale

$1,200,000

MLS#MFRO6330566

100 S Interlachen Ave #404
Winter Park, FL 32789

2

2

1,290 Sq Ft

15 Days

Under Contract

$799,000

$880,000

MLS#MFRO6323374

100 S Interlachen Ave #204d
Winter Park, FL 32789

2

2

1,227 Sq Ft

0.03 Acres

65 Days

Under Contract

$775,000

MLS#MFRO6337352

100 S Interlachen Ave #203d
Winter Park, FL 32789

2

2

1,267 Sq Ft

0.03 Acres

15 Days

$564,900

MLS#MFRO6303353

100 S Interlachen Ave #410f
Winter Park, FL 32789

2

1

901 Sq Ft

Water Front

0.02 Acres

127 Days

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4 Active Listings in The Cloisters