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Headshot for Associate Michelle Hill
  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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  1. Subdivision Like Happy Trails
  2. Listing Status = Active
8590 Apache Trail
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Details for 8590 Apache Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $5,650,000.00
  2. Price sqft: $507.27 / sqft
  3. Previous Price: $5,750,000
  4. Last Price Change: 03/14/26
  5. Days On Market: 388
  6. Bedrooms: 5
  7. Baths: 9
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 11138
  10. Acreage: 5.00 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2009
MLS#: O6296135
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: THE AGENCY FL
  6. mfrmls
  7. DMCA Notice
Welcome to a truly unparalleled luxury estate, nestled on 5 acres of serene privacy. This custom built masterpiece, completed in 2009, boasts an impressive 11,138 square feet of meticulously designed
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8398 Happy Trail
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Details for 8398 Happy Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $2,200,000.00
  2. Price sqft: $419.45 / sqft
  3. Days On Market: 17
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5245
  8. Acreage: 5.01 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6396464
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside Elem
  6. Middle School: West Side
  7. High School: Celebration
  8. Provided by: FUTURE HOME REALTY INC
  9. mfrmls
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Custom Built 2024 Private 5 Acre Estate. High & Dry in Gated Happy Trails. Welcome to a rare opportunity to own this exceptional estate situated on 5 pristine high and dry acres, one of the highest el
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2477 Thacker Trail
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Details for 2477 Thacker Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $990,000.00
  2. Price sqft: $309.96 / sqft
  3. Days On Market: 24
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3194
  8. Acreage: 6.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6395094
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: UNITED REALTY GROUP INC.
  6. mfrmls
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Peaceful living at its finest in Happy Trails, a gated community, minutes from the Disney Resort! Renovated 4/3 main house with separate 927 sf in law quarters and office/studio with 483 sf. This pro
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2478 Thacker Trail
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Details for 2478 Thacker Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $920,000.00
  2. Price sqft: $362.21 / sqft
  3. Previous Price: $860,000
  4. Last Price Change: 03/18/26
  5. Days On Market: 368
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2540
  10. Acreage: 8.71 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2003
MLS#: O6301945
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails Sub
  5. Elementary School: Westside Elem
  6. Middle School: West Side
  7. High School: Celebration
  8. Provided by: UNITED REALTY GROUP INC
  9. mfrmls
  10. DMCA Notice
Welcome to beautiful Happy Trails. A gated community. This unique property combines rural living and modern living just minutes from Disney, This 8.7 acre property holds a 4 Bedroom, 2 bathroom home,
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8531 Sweetwater Trail
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Details for 8531 Sweetwater Trail, KISSIMMEE, FL 34747
Land
  1. Price: $500,000.00
  2. Previous Price: $550,000
  3. Last Price Change: 04/08/26
  4. Days On Market: 97
  5. Acreage: 5.01 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: S5142072
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: TOP VILLAS REALTY LLC
  6. mfrmls
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Expansive 5 Acre Opportunity on Sweet Water Trail! Discover the potential of this impressive five acre parcel on Sweet Water Trail, ideally situated in a sought after area of Kissimmee, Florida. Th
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2370 Thacker Trail
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Listing Details for 2370 Thacker Trail, KISSIMMEE, FL 34747
Land
  1. Price: $374,999.00
  2. Days On Market: 412
  3. Acreage: 5.98 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: S5122296
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: FUTURE HOME REALTY INC
  6. mfrmls
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Discover Your Dream Oasis in Happy Trails! ?? Location, location, location! Imagine waking up every day in a serene, gated community where your investment not only holds value but thrives! Welcome to
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0 Robin Trail
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Details for 0 Robin Trail, KISSIMMEE, FL 34747
Land
  1. Price: $355,000.00
  2. Days On Market: 416
  3. Acreage: 5.04 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: TB8357799
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: HOMELIFE REALTY COASTAL PROPERTIES LLC
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***Vacant Land for Sale 5.04 Acres in the serene Happy Trails Community in Kissimmee, FL*** If youve ever envisioned building your custom home in a peaceful, natural setting, this 5.04 acre parcel i
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Thacker Trail
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Details for Thacker Trail, KISSIMMEE, FL 34747
Land
  1. Price: $349,900.00
  2. Previous Price: $375,000
  3. Last Price Change: 02/16/26
  4. Days On Market: 426
  5. Acreage: 6.38 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: W7872619
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside Elem
  6. Middle School: West Side
  7. High School: Celebration
  8. Provided by: RE/MAX CHAMPIONS
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THIS IS THE OPPORTUNITY YOU HAVE BEEN WAITING FOR!! Build your new home on this magnificent 6.38 acre parcel of land that is located on a cul de sac within the gated and quaintly named Happy Trails su
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8401 Amelia Trail
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Details for 8401 Amelia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $299,000.00
  2. Days On Market: 118
  3. Acreage: 5.00 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6369754
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: CHARLES RUTENBERG REALTY ORLANDO
  6. mfrmls
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Ready to build! This 5 acre Happy Trails property includes a boundary survey and building plans for a stunning 4,000 sqft home. The property offers mature trees, natural beauty, and a serene country f
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Lot 48 Amelia Trail
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Details for Lot 48 Amelia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $275,000.00
  2. Days On Market: 20
  3. Acreage: 10.08 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: S5147245
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside K
  6. Middle School: Horizon
  7. High School: Celebration
  8. Provided by: KELLER WILLIAMS REALTY AT THE LAKES
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10 acre wooded parcel in a peaceful country setting located in the desirable Happy Trails gated community. This beautiful property offers privacy, natural surroundings and perfect opportunity for hors
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