Cloisters Condos

With its beautiful lakefront setting and excellent convenience to downtown, Cloisters Condos boasts beautiful Winter Park condominiums for sale. The 6-story community is located off 100 S. Interlachen Avenue in the heart of the cultural district. 

Cloisters Condos for Sale

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2015 Summerfield Road, WINTER PARK

$1,250,000

2015 Summerfield Road, WINTER PARK

4 Beds 4 Baths 3,024 SqFt Residential MLS® # O6418198
New
3811 Eagle Isles Circle, KISSIMMEE

$649,000

3811 Eagle Isles Circle, KISSIMMEE

5 Beds 5 Baths 3,651 SqFt Residential MLS® # S5158740
New
226 Pine Street, ORLANDO

$420,000

226 Pine Street, ORLANDO

3 Beds 2 Baths 1,603 SqFt Residential MLS® # S5159132
New
1848 Everhart Drive, ORLANDO

$525,000

1848 Everhart Drive, ORLANDO

3 Beds 2 Baths 1,683 SqFt Residential MLS® # O6448256
New
5469 Gingham Drive, KISSIMMEE

$441,940

5469 Gingham Drive, KISSIMMEE

4 Beds 3 Baths 2,753 SqFt Residential MLS® # W7890215
New
4149 S Semoran Boulevard 9, ORLANDO

$147,000

4149 S Semoran Boulevard 9, ORLANDO

2 Beds 2 Baths 1,214 SqFt Residential MLS® # G5118805
New
2229 Mango Tree Drive, EDGEWATER

$295,000

2229 Mango Tree Drive, EDGEWATER

3 Beds 2 Baths 1,038 SqFt Residential MLS® # O6448391
New
8844 Cabot Cliffs Drive, DAVENPORT

$580,000

8844 Cabot Cliffs Drive, DAVENPORT

6 Beds 6 Baths 3,339 SqFt Residential MLS® # O6448535
Open House
1233 Parker Road, LAKELAND

$475,000

1233 Parker Road, LAKELAND

4 Beds 2 Baths 2,612 SqFt Residential MLS® # L4962153
New
106 Harbor Way, AUBURNDALE

$327,000

106 Harbor Way, AUBURNDALE

3 Beds 2 Baths 1,427 SqFt Residential MLS® # P4940115
779 E Chapman Road, OVIEDO

$1,500,000

779 E Chapman Road, OVIEDO

5 Beds 5 Baths 5,219 SqFt Residential MLS® # O6426258
Sold
26029 Oakmount Drive, LEESBURG

$330,000

26029 Oakmount Drive, LEESBURG

2 Beds 2 Baths 1,869 SqFt Residential MLS® # J1006016
New
2388 Grand Central Parkway 2, ORLANDO

$205,000

2388 Grand Central Parkway 2, ORLANDO

3 Beds 2 Baths 1,457 SqFt Residential MLS® # O6447903
New
828 N Scott Avenue, LAKELAND

$255,000

828 N Scott Avenue, LAKELAND

3 Beds 2 Baths 1,261 SqFt Residential MLS® # O6448319
New Open House
381 Augustine Court, OVIEDO

$600,000

381 Augustine Court, OVIEDO

4 Beds 3 Baths 2,725 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 2pm
MLS® # O6448356

Sold Homes in Cloisters Condos Winter Park

Cloisters Condos Real Estate Market Statistics

Average Price $1.3M
Lowest Price $850K
Highest Price $1.8M
Total Listings 3
Avg. Days On Market 44
Avg. Price/SQFT $754
List to Sell Price Percentage 93 %

Property Types (active listings)

Cloisters is situated on a lovely, well-manicured street with an entrance through a canopy of two towering trees. Built in the early 1970s, Cloisters features units with approximately 900 to 1,950 square feet with 2 - 3 bedrooms and 1 - 2.5 baths. Many of the units offer abundant natural light, extra storage, and balconies or patios with gorgeous views of Lake Osceola.

Residents can enjoy on-site amenities like a heated community pool, putting green, fitness center, on-site manager, and a private lakefront park with boat docks. And there are plenty more activities within proximity, as well. Central Park, a popular spot that features fountains and a picturesque rose garden, is less than a half-mile away. Downtown Winter Park, a cultural, dining, and retail hub, is also within 1 mile and features everything from a Farmers’ Market, museum and sculpture gardens, sidewalk cafes, and unique shops.

Everyday shopping and conveniences are close by, as well. There is a Publix Grocery Store just 1 mile away at Winter Park Village and a Walmart Supercenter just 3 miles away. The community is also convenient to higher education institutions, with Rollins College and Valencia College, Winter Park Campus, under 1 mile away.

Call us today to find out more about Cloisters Condos.

Cloisters Condos Community Information

  • Location: 100 S. Interlachen Avenue
  • Number of Homesites: 91 units
  • Year Built: 1971
  • Square Footage: 901 square feet 1,950+ square feet
  • HOA: Yes
  • Community Amenities: heated community pool, putting green, fitness center, on-site manager, and a private lakefront park with boat docks

Orange County Public Schools

  • Audobon Park: Grades K-8th  Distance: 3 miles
  • Winter Park High School: Grades 9th - 12th  Distance: 3 miles

Dining and Shopping

  • Downtown Winter Park – Distance: 0.5 mile
  • Winter Park Village with Publix Grocery Store – Distance: 1 mile
  • Lakeside Shopping Center – Distance: 1 mile
  • Aloma Shopping Center – Distance: 2 miles
  • The Villages Plaza – Distance: 2.5 miles
  • Walmart Supercenter – Distance: 3 miles
  • Baldwin Park with Publix Grocery Store – Distance: 4 miles
  • Fashion Square Mall – Distance: 5 miles
  • Downtown Orlando – Distance: 6 miles

Parks and Recreation

  • Central Park – Distance: 0.5 mile
  • Shady Park – Distance: 0.5 mile
  • Martin Luther King, Jr. Park – Distance: 1 mile
  • Phelps Park – Distance: 2 miles
  • Ward Park – Distance: 2.5 miles
  • Lake Baldwin Dog Park – Distance: 3 miles
  • Minnehaha Park – Distance: 3 miles
  • Goldenrod Park – Distance: 4.5 miles
  • Amway Center – Distance: 7 miles
  • Walt Disney World Resort – Distance: 22 miles
  • Universal Studios – Distance: 15 miles
  • SeaWorld – Distance: 20 miles

Hospitals

  • Florida Hospital – Distance: 3 miles
  • AdventHealth Winter Park – Distance: 2 miles

Distances are approximately measured from the main entrance to the Cloisters Condos subdivision.

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