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  1. School = Keene Crossing
  2. Listing Status = Active
13734 Lake Cawood Drive
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Details for 13734 Lake Cawood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $1,620,000.00
  2. Price sqft: $239.57 / sqft
  3. Previous Price: $1,720,000
  4. Last Price Change: 03/15/26
  5. Days On Market: 45
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6762
  10. Acreage: 0.99 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2006
MLS#: G5107723
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Cawood Estates
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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NEW PRICE SELLER MOTIVATED! Welcome to this stunning single story luxury estate located in the highly sought after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly
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13858 Caywood Pond Drive
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Details for 13858 Caywood Pond Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $959,900.00
  2. Price sqft: $226.07 / sqft
  3. Previous Price: $1,050,000
  4. Last Price Change: 03/12/26
  5. Days On Market: 25
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4246
  10. Acreage: 0.52 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 2004
MLS#: O6382987
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Summerport Ph 1
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: SPRING REALTY ONE LLC
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JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly p
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14423 Wabasso Loop
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Details for 14423 Wabasso Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $939,900.00
  2. Price sqft: $167.30 / sqft
  3. Previous Price: $954,000
  4. Last Price Change: 03/03/26
  5. Days On Market: 73
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5618
  10. Acreage: 0.15 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2023
MLS#: O6368408
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Tilden Placewinter Garden
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: PREFERRED REAL ESTATE BROKERS
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New Pricing! Welcome home to this stunning two story residence in the gated community of Tilden Place, ideally located in the heart of Winter Garden. Just minutes from Winter Garden Village with its a
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4937 Wildwood Pointe Road
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Details for 4937 Wildwood Pointe Road, WINTER GARDEN, FL 34787
Single Family
  1. Price: $879,000.00
  2. Price sqft: $245.87 / sqft
  3. Previous Price: $889,000
  4. Last Price Change: 02/28/26
  5. Days On Market: 47
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3575
  10. Acreage: 0.14 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2015
MLS#: S5142834
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Orchard Hills Ph 2
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: OLIVO REALTY GROUP, LLC
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Welcome to this spacious and beautifully maintained 5 bedroom, 4 bathroom home in the desirable Winter Garden area. Situated on a premium lot with no rear neighbors, this home backs onto a peaceful pr
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14321 Wabasso Loop
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Details for 14321 Wabasso Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $799,000.00
  2. Price sqft: $207.64 / sqft
  3. Days On Market: 10
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3848
  8. Acreage: 0.14 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2022
MLS#: S5145413
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Tilden Place
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: LPT REALTY, LLC
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Welcome to your dream home! This stunning 4 bedroom, 3. 5 bathroom residence combines modern elegance with luxurious living in a sought after gated community. Designed with high end finishes and thoug
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13609 Ancilla Boulevard
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Details for 13609 Ancilla Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $789,000.00
  2. Price sqft: $234.82 / sqft
  3. Previous Price: $799,000
  4. Last Price Change: 03/17/26
  5. Days On Market: 36
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 3360
  10. Acreage: 0.24 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2005
MLS#: O6381542
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Summerport Ph 03
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: WRA BUSINESS & REAL ESTATE
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Welcome to this stunning and spacious single family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated livin
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5018 River Gem Avenue
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Details for 5018 River Gem Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $785,000.00
  2. Price sqft: $232.11 / sqft
  3. Days On Market: 52
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3382
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2005
MLS#: TB8469061
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Summerport Ph 03
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS SOUTH TAMPA
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Welcome to 5018 River Gem Avenue, an exceptional one story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience
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14345 Wabasso Loop
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Details for 14345 Wabasso Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $740,000.00
  2. Price sqft: $196.81 / sqft
  3. Days On Market: 44
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3760
  8. Acreage: 0.16 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2022
MLS#: O6376609
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Tilden Placewinter Garden
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: COMPASS FLORIDA LLC
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Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Gardens most convenient locations. The main
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4918 Wildwood Pointe Road
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Details for 4918 Wildwood Pointe Road, WINTER GARDEN, FL 34787
Single Family
  1. Price: $710,000.00
  2. Price sqft: $189.23 / sqft
  3. Previous Price: $720,000
  4. Last Price Change: 11/03/25
  5. Days On Market: 280
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3752
  10. Acreage: 0.19 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2015
MLS#: S5129072
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Orchard Hills Ph 2
  5. Elementary School: Keene Crossing
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: AGENT TRUST REALTY CORPORATION
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Located in the highly sought after community of Orchard Hills, this stunning home offers the epitome of Central Florida living. Orchard Hills is a community that attracts buyers from all walks of life
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5531 Cypress Hill Road
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Details for 5531 Cypress Hill Road, WINTER GARDEN, FL 34787
Single Family
  1. Price: $625,000.00
  2. Price sqft: $222.90 / sqft
  3. Days On Market: 50
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2804
  8. Acreage: 0.15 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2016
MLS#: O6378167
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Elementary School: Keene Crossing
  5. Middle School: Bridgewater
  6. High School: Windermere
  7. Provided by: OLYMPUS EXECUTIVE REALTY INC
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Exquisitely upgraded 4 bedroom, 3 bath smart home in the highly sought after Orchard Hills community of Winter Garden. Situated on a premium lot with no rear neighbors, this move in ready home offers
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2026 Royal Palm Coast Realtor® Association
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Datafeed Last updated on March 22, 2026 @ 12:00 am
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