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  1. Subdivision Like Happy Trails
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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: 398
  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: 27
  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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200 Goodman Road
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Details for 200 Goodman Road, KISSIMMEE, FL 34747
Single Family
  1. Price: $1,795,000.00
  2. Price sqft: $322.96 / sqft
  3. Days On Market: 27
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5558
  8. Acreage: 5.00 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6396029
  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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One or more photo(s) has been virtually staged. Brand new custom built estate offering 4,179 sq ft of living space (5,558 sq ft under roof) on 5 private acresnever lived in! Ideally located in the sou
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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: 34
  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
  7. DMCA Notice
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: 378
  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: 107
  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
  7. DMCA Notice
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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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: 426
  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
  6. mfrmls
  7. DMCA Notice
***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: 435
  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
  9. mfrmls
  10. DMCA Notice
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: 128
  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: 30
  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
  9. mfrmls
  10. DMCA Notice
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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