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  1. Subdivision Like Oakland Hills
15198 Oakland Avenue
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Details for 15198 Oakland Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $2,195,000.00
  2. Price sqft: $414.62 / sqft
  3. Previous Price: $2,295,000
  4. Last Price Change: 07/21/25
  5. Days On Market: 61
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5294
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2023
MLS#: O6312014
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Oakland Hills
  5. Elementary School: Tildenville Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: IAD FLORIDA LLC
  9. mfrmls
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Price reduction! Welcome to this stunning farmhouse style home nestled on a premium corner lot in one of the most sought after communities near Historic Winter Garden. Thoughtfully designed and beauti
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255 Rotonda Boulevard W A And B
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Details for 255 Rotonda Boulevard W A And B, ROTONDA WEST, FL 33947
Multi-Family
  1. Price: $620,000.00
  2. Price sqft: $193.15 / sqft
  3. Days On Market: 104
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 3210
  8. Acreage: 0.73 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1987
MLS#: D6142059
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Provided by: PARADISE EXCLUSIVE INC
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Completely modernized Income Producing Duplex (Units A & B )on acre property! Zoned to add Two MORE DUPLEXES! Survey available... Design and build a mini complex in a highly sought area on Rotonda
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42 Boundary Boulevard
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Details for 42 Boundary Boulevard, ROTONDA WEST, FL 33947
Multi-Family
  1. Price: $575,000.00
  2. Price sqft: $166.38 / sqft
  3. Days On Market: 167
  4. Bedrooms: 8
  5. Baths: 4
  6. Bldg sqft: 3456
  7. Acreage: 0.33 acres
  8. Pool: No
  9. Waterfront: Yes
  10. Wateraccess: Yes
  11. Waterfront Type: Canal - Freshwater
  12. Year Built: 1979
MLS#: D6140803
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: KW COASTAL LIVING
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Quadruple your income with this fully rented WATERFRONT QUADPLEX in Rotonda West! Attention investors, here's your chance to own a rarely available, fully occupied quadplex in the desirable, deed rest
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40 Golfview Court
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Details for 40 Golfview Court, ROTONDA WEST, FL 33947
Single Family
  1. Price: $399,000.00
  2. Price sqft: $143.53 / sqft
  3. Days On Market: 111
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 2780
  8. Acreage: 0.22 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2025
MLS#: D6141976
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Pre Construction. To be built. BRAND NEW TO BE BUILT, get in now and have the opportunity to choose colors and some changes may be accommodated! Impact windows and ready to move in! Welcome to your se
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87 Rotonda Circle
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Details for 87 Rotonda Circle, ROTONDA WEST, FL 33947
Single Family
  1. Price: $395,000.00
  2. Price sqft: $181.69 / sqft
  3. Days On Market: 222
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2174
  8. Acreage: 0.46 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater
  13. Year Built: 1972
MLS#: TB8331271
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Provided by: WILD REALTY & INV. CO., INC.
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Located in Rotonda West Oakland Hills nestled on a Bonus Double lot with almost a 1/2 Acre sits this 2 Bedroom/ 2 Bathroom Waterfront Pool Home with 160' on the canal. Other features include a metal
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209 Annapolis Lane
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Details for 209 Annapolis Lane, ROTONDA WEST, FL 33947
Single Family
  1. Price: $389,500.00
  2. Price sqft: $127.04 / sqft
  3. Previous Price: $394,500
  4. Last Price Change: 06/04/25
  5. Days On Market: 160
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3066
  10. Acreage: 0.20 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2025
MLS#: C7505907
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: ADAMS HOMES REALTY
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Under Construction. Under Construction! Discover your beachy dream home: a brand new 4 bedroom, 3 bathroom, 2 car garage rock solid gem with an amazing open layout that will captivate you! This stunni
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32 Oakland Hills Court
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Details for 32 Oakland Hills Court, ROTONDA WEST, FL 33947
Single Family
  1. Price: $386,000.00
  2. Price sqft: $186.20 / sqft
  3. Days On Market: 8
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2073
  8. Acreage: 0.44 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Pond
  13. Year Built: 2003
MLS#: C7512877
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Oakland Hills Rotonda West
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: MICHAEL SAUNDERS & COMPANY
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Welcome to this beautifully maintained Florida retreat, nestled on a rare double lot in the desirable, deed restricted golf community of Rotonda West. Built in 2003, this timeless 4 bedroom, 2 bathroo
Listing Details and 44 Additional Pictures
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32 Oakland Hills Court
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Details for 32 Oakland Hills Court, Rotonda West, FL 33947
Single Family
  1. Price: $386,000.00
  2. Price sqft: $186.20 / sqft
  3. Days On Market: 8
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2073
  8. Acreage: 0.44 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Pond
  13. Year Built: 2003
MLS#: C7512877
  1. County: CHARLOTTE
  2. City: Rotonda West
  3. Zipcode: 33947
  4. Subdivision: Oakland Hills Rotonda West
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: MICHAEL SAUNDERS & COMPANY
  9. Provided through
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Welcome to this beautifully maintained Florida retreat, nestled on a rare double lot in the desirable, deed restricted golf community of Rotonda West. Built in 2003, this timeless 4 bedroom, 2 bathroo
Listing Details and 44 Additional Pictures
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76 Caddy Road
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Details for 76 Caddy Road, ROTONDA WEST, FL 33947
Single Family
  1. Price: $369,000.00
  2. Price sqft: $92.92 / sqft
  3. Previous Price: $379,000
  4. Last Price Change: 07/16/25
  5. Days On Market: 515
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3971
  10. Acreage: 0.44 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1973
MLS#: D6135265
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: PARADISE EXCLUSIVE INC
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One or more photo(s) has been virtually staged. A recent price adjustment makes this home a must see! No flooding or hurricane damage from helene or milton move in ready home! The opportunity to put
Listing Details and 61 Additional Pictures
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18 Annapolis Lane
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Details for 18 Annapolis Lane, ROTONDA WEST, FL 33947
Single Family
  1. Price: $359,000.00
  2. Price sqft: $137.81 / sqft
  3. Previous Price: $379,000
  4. Last Price Change: 06/13/25
  5. Days On Market: 126
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2605
  10. Acreage: 0.23 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1973
MLS#: D6141695
  1. County: CHARLOTTE
  2. City: ROTONDA WEST
  3. Zipcode: 33947
  4. Subdivision: Rotonda West Oakland Hills
  5. Elementary School: Vineland
  6. Middle School: L.A. Ainger
  7. High School: Lemon Bay
  8. Provided by: COLDWELL BANKER SUNSTAR REALTY
  9. mfrmls
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Spacious pool home with fully screened in lanai area perfect for entertaining. Find luxury and comfort in this skillfully crafted and well maintained home in the community of Rotonda West. Let the rel
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