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  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
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3826 Gaines Court
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Details for 3826 Gaines Court, WINTER HAVEN, FL 33884
Single Family
  1. Price: $1,859,999.00
  2. Price sqft: $251.52 / sqft
  3. Previous Price: $1,959,999
  4. Last Price Change: 12/02/25
  5. Days On Market: 257
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 7395
  10. Acreage: 1.86 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front,Lake Privileges
  15. Year Built: 1989
MLS#: P4934458
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Gaines Cove
  5. Elementary School: Pinewood Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: NEW HOME ADVANTAGE LLC
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  10. DMCA Notice
Winter Haven Chain of Lakes Executive Home on 1.86 Acres with Lake Eloise Frontage! Welcome to this elegant two story home nestled on nearly 2 acres in a serene, park like setting on Lake Eloise. From
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3824 Gaines Drive
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Details for 3824 Gaines Drive, WINTER HAVEN, FL 33884
Single Family
  1. Price: $1,549,000.00
  2. Price sqft: $177.94 / sqft
  3. Previous Price: $1,575,000
  4. Last Price Change: 12/10/25
  5. Days On Market: 70
  6. Bedrooms: 7
  7. Baths: 7
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 8705
  10. Acreage: 0.64 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front,Lake Privileges
  16. Year Built: 1980
MLS#: P4936581
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Gaines Cove
  5. Elementary School: Pinewood Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: THE STONES REAL ESTATE FIRM
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A true luxury lakefront masterpiece on the shores of Lake Eloise, one of the most beautiful lakes on the world famous Winter Haven Chain of Lakes. This architecturally stunning modern estate delivers
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157 Lake Roy Drive
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Details for 157 Lake Roy Drive, WINTER HAVEN, FL 33884
Single Family
  1. Price: $919,000.00
  2. Price sqft: $201.62 / sqft
  3. Days On Market: 38
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 4558
  8. Acreage: 0.65 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 1987
MLS#: L4957283
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Eloise Woods Lake Roy
  5. Elementary School: Chain O Lakes Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: THE STONES REAL ESTATE FIRM
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One or more photo(s) has been virtually staged. Welcome to 157 Lake Roy Drivea rare lakefront offering on the world famous Winter Haven Chain of Lakes. Perfectly positioned on Lake Roy, one of the Cha
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200 Island Way
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Details for 200 Island Way, WINTER HAVEN, FL 33884
Single Family
  1. Price: $899,900.00
  2. Price sqft: $168.17 / sqft
  3. Previous Price: $925,000
  4. Last Price Change: 12/09/25
  5. Days On Market: 169
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5351
  10. Acreage: 1.05 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1970
MLS#: P4935447
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Elementary School: Elbert Elem
  5. Middle School: Denison
  6. High School: Winter Haven Senior
  7. Provided by: LOCKHART & ASSOCIATES INC
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Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought after gated community of Orchid Springs Estates! This stunning Mediterranean style estate offers
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2683 Wyndsor Oaks Way
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Details for 2683 Wyndsor Oaks Way, WINTER HAVEN, FL 33884
Single Family
  1. Price: $825,000.00
  2. Price sqft: $180.96 / sqft
  3. Previous Price: $849,000
  4. Last Price Change: 07/25/25
  5. Days On Market: 339
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4559
  10. Acreage: 0.57 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2002
MLS#: P4933374
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Wyndsor At Lake Winterset
  5. Elementary School: Chain O Lakes Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: RE/MAX HERITAGE PROFESSIONALS
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Back on market, property passed inspections already. Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL an extraordinary residence in the highly sought after gated Wyndsor at Lake Winterset community
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220 Ruby Lake Lane
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Details for 220 Ruby Lake Lane, WINTER HAVEN, FL 33884
Single Family
  1. Price: $799,977.00
  2. Price sqft: $228.83 / sqft
  3. Previous Price: $824,900
  4. Last Price Change: 10/23/25
  5. Days On Market: 93
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3496
  10. Acreage: 0.42 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front,Lake Privileges
  15. Year Built: 2001
MLS#: P4936358
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Ruby Lake Ph 04
  5. Elementary School: Chain O Lakes Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: THE STONES REAL ESTATE FIRM
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Welcome to 220 Ruby Lake Lane, a stunning lakefront pool residence in the highly sought after gated community of Ruby Lake, where modern upgrades blend effortlessly with timeless design and waterfront
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3211 Heron Cove
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Details for 3211 Heron Cove, WINTER HAVEN, FL 33884
Single Family
  1. Price: $799,000.00
  2. Price sqft: $186.99 / sqft
  3. Previous Price: $849,000
  4. Last Price Change: 10/21/25
  5. Days On Market: 123
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4273
  10. Acreage: 0.66 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1996
MLS#: P4935890
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Heron Cay
  5. Elementary School: John Snively Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: THE STONES REAL ESTATE FIRM
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Welcome to 3211 Heron Cove, a custom gated estate in the exclusive community of Heron Cay, an intimate enclave of just 24 homes along Lake Eloise on the world famous Winter Haven Chain of Lakes. This
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238 Ruby Lake Lane
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Details for 238 Ruby Lake Lane, WINTER HAVEN, FL 33884
Single Family
  1. Price: $795,000.00
  2. Price sqft: $232.52 / sqft
  3. Days On Market: 59
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3419
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front,Lake Privileges
  13. Year Built: 2000
MLS#: P4936774
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Ruby Lake Ph 04
  5. Elementary School: Chain O Lakes Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: LOCKHART & ASSOCIATES INC
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A truly wonderful lifestyle! Nestled in the charming, gated community of Ruby Lake, this beautiful 4 bedroom, 3 bath pool home provides the perfect blend of elegance and comfort. Known for being two o
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264 Ruby Lake Lane
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Details for 264 Ruby Lake Lane, WINTER HAVEN, FL 33884
Single Family
  1. Price: $750,000.00
  2. Price sqft: $246.71 / sqft
  3. Days On Market: 69
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3040
  8. Acreage: 0.46 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1999
MLS#: P4936678
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33884
  4. Subdivision: Ruby Lake Ph 04
  5. Elementary School: Chain O Lakes Elem
  6. Middle School: Denison
  7. High School: Lake Region
  8. Provided by: KELLER WILLIAMS REALTY SMART 1
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Lakefront gem in southeast winter haven! This clean and ready to move in 4 bedroom, 2 bathroom home with office sits on the private access lake bess with slalom ski course. Connected to lake ruby, you
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329 Hamilton Shores Drive Ne
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Details for 329 Hamilton Shores Drive Ne, WINTER HAVEN, FL 33881
Single Family
  1. Price: $750,000.00
  2. Price sqft: $200.43 / sqft
  3. Previous Price: $800,000
  4. Last Price Change: 10/21/25
  5. Days On Market: 269
  6. Bedrooms: 5
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3742
  10. Acreage: 0.98 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1997
MLS#: P4934289
  1. County: POLK
  2. City: WINTER HAVEN
  3. Zipcode: 33881
  4. Subdivision: Hamilton Pointe
  5. Elementary School: Elbert Elem
  6. Middle School: Denison
  7. High School: Winter Haven Senior
  8. Provided by: COLDWELL BANKER REALTY
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This beautiful home overlooks Lake Hamilton being the largest lake on a chain of three, Lake Hamilton, Middle Lake Hamilton, and Little Lake Hamilton in Winter Haven Florida making Hamilton Pointe a s
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