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  1. Subdivision Like Happy Trails
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8398 Happy Trail
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Details for 8398 Happy Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $2,495,000.00
  2. Price sqft: $475.69 / sqft
  3. Previous Price: $2,200,000
  4. Last Price Change: 10/05/26
  5. Days On Market: 214
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5245
  10. Acreage: 5.01 acres
  11. Pool: No
  12. Waterfront: No
  13. 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 High
  8. Provided by: FUTURE HOME REALTY INC
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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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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: $362.20 / sqft
  3. Previous Price: $860,000
  4. Last Price Change: 03/17/26
  5. Days On Market: 565
  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 High
  8. Provided by: UNITED REALTY GROUP INC
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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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8365 Choctaw Trail
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Details for 8365 Choctaw Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $775,000.00
  2. Price sqft: $362.83 / sqft
  3. Days On Market: 4
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 2136
  7. Acreage: 5.47 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 2016
MLS#: O6454947
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside K 8
  6. Middle School: West Side
  7. High School: Celebration High
  8. Provided by: HOMEVEST REALTY
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Discover the beauty of peaceful country living at 8365 Choctaw Trail! Situated on over 5 acres of private, picturesque land, this property offers the perfect combination of privacy, space, and the fre
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0 Robin Trail
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Details for 0 Robin Trail, KISSIMMEE, FL 34747
Land
  1. Price: $385,000.00
  2. Previous Price: $355,000
  3. Last Price Change: 07/15/26
  4. Days On Market: 613
  5. Acreage: 5.04 acres
  6. Pool: No
  7. Waterfront: No
  8. 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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0 Arapaho Trail
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Details for 0 Arapaho Trail, KISSIMMEE, FL 34747
Land
  1. Price: $349,000.00
  2. Days On Market: 26
  3. Acreage: 5.00 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: S5159257
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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FIVE ACRES OF SPACE, PRIVACY AND POSSIBILITY IN HAPPY TRAILS! Discover a peaceful natural setting on Arapaho Trail in this established equestrian community. Mature trees, a marsh/pond area toward the
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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: 217
  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 8
  6. Middle School: Horizon Middle
  7. High School: Celebration High
  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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8401 Amelia Trail
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Details for 8401 Amelia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $270,000.00
  2. Previous Price: $299,000
  3. Last Price Change: 11/03/26
  4. Days On Market: 112
  5. Acreage: 5.00 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: O6426570
  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 High
  8. Provided by: FCG REALTY
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Rare 5 Acre Custom Estate Lot on Amelia Trail Happy Trails Community Discover the Perfect Canvas for Your Dream Estate Tucked away in the highly sought after, gated enclave of Happy Trails, this
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0 Thacker Trail
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Listing Details for 0 Thacker Trail, KISSIMMEE, FL 34747
Land
  1. Price: $260,000.00
  2. Days On Market: 137
  3. Acreage: 6.05 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6420033
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: FLORIDA SCANDI REALTY LLC
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Discover the perfect opportunity to own a spacious piece of land in Kissimmee! This beautiful 6.05 acre vacant parcel located on Thacker Trail offers endless possibilities for those seeking privacy, s
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0 Patricia Trail
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Details for 0 Patricia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $165,000.00
  2. Days On Market: 153
  3. Acreage: 7.06 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: S5151533
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside K 8
  6. Middle School: Horizon Middle
  7. High School: Celebration High
  8. Provided by: KELLER WILLIAMS REALTY AT THE LAKES
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Are you looking for a challenge? This lot is an unusual lot deep in the woods and surrounded by woods. Triangle in shape. Plenty big for your home or toys at 7 acres. In a great location that is close
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Keefer Trail
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Details for Keefer Trail, KISSIMMEE, FL 34747
Land
  1. Price: $79,000.00
  2. Previous Price: $80,000
  3. Last Price Change: 10/23/26
  4. Days On Market: 586
  5. Acreage: 5.01 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: S5123655
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: EMPIRE NETWORK REALTY
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LOCATION, LOCATION...Parcel located in the exclusive GATED community of HAPPY TRAILS. Offering seclusion and privacy, Happy Trails is in a fantastic location, just a few miles from Walt Disney World a
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