Searching on:
  1. Subdivision Like Windermere Trails
11849 Cave Run Avenue
Virtual Tour
More Like This
Details for 11849 Cave Run Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $765,000.00
  2. Price sqft: $169.77 / sqft
  3. Previous Price: $799,000
  4. Last Price Change: 10/17/25
  5. Days On Market: 65
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4506
  10. Acreage: 0.15 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2014
MLS#: O6338823
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails Phase 1c 801
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: WRA BUSINESS & REAL ESTATE
  9. mfrmls
  10. DMCA Notice
Immaculate and light filled 4 bedroom, 3.5 bath home with a huge bonus room and flex space, located in the desirable Windermere Trails community. Just one block from the elementary school and right ac
Listing Details and 62 Additional Pictures
Request more information about this listing.
8160 Iron Mountain Trail
Virtual Tour
More Like This
Details for 8160 Iron Mountain Trail, WINDERMERE, FL 34786
Single Family
  1. Price: $539,000.00
  2. Price sqft: $191.47 / sqft
  3. Previous Price: $546,000
  4. Last Price Change: 09/22/25
  5. Days On Market: 166
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2815
  10. Acreage: 0.09 acres
  11. Pool: No
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 2016
MLS#: O6309028
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: BHHS FLORIDA REALTY
  9. mfrmls
  10. DMCA Notice
Nestled in the highly desirable Windermere Trails community, this beautiful home offers an unparalleled blend of modern design, high end finishes and everyday functionality. The 3 bedrooms, 2 1/2 bath
Listing Details and 39 Additional Pictures
Request more information about this listing.
8160 Iron Mountain Trail
Virtual Tour
More Like This
Details for 8160 Iron Mountain Trail, Windermere, FL 34786
Single Family
  1. Price: $539,000.00
  2. Price sqft: $191.47 / sqft
  3. Previous Price: $546,000
  4. Last Price Change: 09/22/25
  5. Days On Market: 166
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2815
  10. Acreage: 0.09 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 2016
MLS#: O6309028
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: BHHS FLORIDA REALTY
  9. Provided through
  10. DMCA Notice
Nestled in the highly desirable Windermere Trails community, this beautiful home offers an unparalleled blend of modern design, high end finishes and everyday functionality. The 3 bedrooms, 2 1/2 bath
Listing Details and 39 Additional Pictures
Request more information about this listing.
8298 Lookout Pointe Drive
Virtual Tour
More Like This
Details for 8298 Lookout Pointe Drive, WINDERMERE, FL 34786
Rental
  1. Price: $4,950.00
  2. Price sqft: $0.87 / sqft
  3. Days On Market: 24
  4. Bedrooms: 6
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5670
  8. Acreage: 0.17 acres
  9. Pool: No
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2016
MLS#: S5136133
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails Ph 3b
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: TRANSCEND REALTY
  9. mfrmls
  10. DMCA Notice
Stunning home in the beautiful Windermere Trails Community sitting on a Special Conservation View Lot, 500ft walking distance from the Clubhouse. This fully upgraded Magnificent 6 bedroom 4 Full Ba
Listing Details and 40 Additional Pictures
Request more information about this listing.
8298 Lookout Pointe Drive
Virtual Tour
More Like This
Details for 8298 Lookout Pointe Drive, Windermere, FL 34786
Rental
  1. Price: $4,950.00
  2. Price sqft: $0.87 / sqft
  3. Days On Market: 24
  4. Bedrooms: 6
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5670
  8. Acreage: 0.17 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2016
MLS#: S5136133
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails Ph 3b
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: TRANSCEND REALTY
  9. Provided through
  10. DMCA Notice
Stunning home in the beautiful Windermere Trails Community sitting on a Special Conservation View Lot, 500ft walking distance from the Clubhouse. This fully upgraded Magnificent 6 bedroom 4 Full Ba
Listing Details and 40 Additional Pictures
Request more information about this listing.
8712 Crescendo Avenue
Virtual Tour
Green Listing
More Like This
Details for 8712 Crescendo Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $3,700.00
  2. Price sqft: $1.12 / sqft
  3. Days On Market: 16
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3311
  8. Acreage: 0.14 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2016
MLS#: S5136631
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails
  5. Elementary School: Sunset Park Elem
  6. Middle School: Bridgewater
  7. High School: West Orange
  8. Provided by: TOPSKY REALTY INC
  9. mfrmls
  10. DMCA Notice
Welcome to this energy efficient home like new with brand new vinyl plant flooring on second floor and fresh interior paint! The home features a spacious kitchen with Whirlpool SS appliances, 42" upp
Listing Details and 10 Additional Pictures
Request more information about this listing.
8712 Crescendo Avenue
Virtual Tour
Green Listing
More Like This
Details for 8712 Crescendo Avenue, Windermere, FL 34786
Rental
  1. Price: $3,700.00
  2. Price sqft: $1.12 / sqft
  3. Days On Market: 17
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3311
  8. Acreage: 0.14 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2016
MLS#: S5136631
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails
  5. Elementary School: Sunset Park Elem
  6. Middle School: Bridgewater
  7. High School: West Orange
  8. Provided by: TOPSKY REALTY INC
  9. Provided through
  10. DMCA Notice
Welcome to this energy efficient home like new with brand new vinyl plant flooring on second floor and fresh interior paint! The home features a spacious kitchen with Whirlpool SS appliances, 42" upp
Listing Details and 10 Additional Pictures
Request more information about this listing.
8620 Wellington Blue Ln
More Like This
Details for 8620 Wellington Blue Ln, WINDERMERE, FL 34786
Rental
  1. Price: $2,800.00
  2. Price sqft: $1.19 / sqft
  3. Days On Market: 99
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2357
  8. Acreage: 0.13 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2015
MLS#: O6325630
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: SOUTHERN REALTY GROUP LLC
  9. mfrmls
  10. DMCA Notice
Beautiful townhome in Windermere Trails with first floor master bedroom. Excellent location walking distance to Bay Lake Elementary, as well as shopping and dining. This well maintained unit offers
Listing Details and 21 Additional Pictures
Request more information about this listing.