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  1. Subdivision Like Happy Trails
8590 Apache Trail
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Details for 8590 Apache Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $5,850,000.00
  2. Price sqft: $525.23 / sqft
  3. Previous Price: $5,900,000
  4. Last Price Change: 07/22/25
  5. Days On Market: 284
  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 ORLANDO
  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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222 Pawnee Trail
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Details for 222 Pawnee Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $1,390,000.00
  2. Price sqft: $133.45 / sqft
  3. Previous Price: $1,590,000
  4. Last Price Change: 12/29/25
  5. Days On Market: 103
  6. Bedrooms: 3
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 10416
  10. Acreage: 5.00 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2006
MLS#: O6349038
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside Elem
  6. Middle School: Horizon
  7. High School: Celebration
  8. Provided by: NESTA REAL ESTATE CONSULTANTS
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Welcome to this one of a kind GOLF FRONT equestrian estate home on 5 high and dry private acres. This mediterranean property features over 6,500 of living SQFT with 3 bedrooms, 3 full bathrooms, 2 hal
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2478 Thacker Trail
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Details for 2478 Thacker Trail, KISSIMMEE, FL 34747
Single Family
  1. Price: $860,000.00
  2. Price sqft: $338.58 / sqft
  3. Previous Price: $879,000
  4. Last Price Change: 08/25/25
  5. Days On Market: 264
  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
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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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305 Hargrove Lane
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Details for 305 Hargrove Lane, KISSIMMEE, FL 34747
Single Family
  1. Price: $749,000.00
  2. Price sqft: $361.49 / sqft
  3. Previous Price: $799,000
  4. Last Price Change: 11/28/25
  5. Days On Market: 86
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 8
  9. Bldg sqft: 2072
  10. Acreage: 5.01 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Pond
  15. Year Built: 1986
MLS#: O6353540
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. High School: Celebration
  6. Provided by: FCG REALTY
  7. mfrmls
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Priced to sell ! This is by far the best deal in Happy Trails. Quite possibly priced below appraisal. Seize the opportunity to become the new owner of this modern Farm Retreat on 5 Acres located in th
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Thacker Trail
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Details for Thacker Trail, KISSIMMEE, FL 34747
Land
  1. Price: $375,000.00
  2. Previous Price: $425,000
  3. Last Price Change: 10/31/25
  4. Days On Market: 322
  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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JUST REDUCED $50K!! 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 n
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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: 308
  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
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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: 312
  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
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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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Sioux Trail
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Details for Sioux Trail , KISSIMMEE, FL 34747
Land
  1. Price: $349,900.00
  2. Previous Price: $379,000
  3. Last Price Change: 12/28/25
  4. Days On Market: 125
  5. Acreage: 5.00 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: O6342940
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Provided by: COLDWELL BANKER REALTY
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Final price drop, Discover an Exceptional 5 Acre Lot in Happy Trails A Rare Opportunity Near Champions Gate, Reunion, and Disney. Nestled in the prestigious Happy Trails community, this expansive 5
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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: 14
  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 lot is partially cleared, offering mature trees, natural beauty, and
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Keefer Trail
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Details for Keefer Trail, KISSIMMEE, FL 34747
Land
  1. Price: $80,000.00
  2. Previous Price: $96,000
  3. Last Price Change: 11/26/25
  4. Days On Market: 285
  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
  6. mfrmls
  7. DMCA Notice
LOCATION, LOCATION...Parcel located in the exclusive GATED community of HAPPY TRAILS. This lot will require mitigation. Natural Flowing Stream on Property and Wetlands. Each Buyer must independently v
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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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Datafeed Last updated on January 13, 2026 @ 12:00 am
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