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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: $5,750,000.00
  2. Price sqft: $516.25 / sqft
  3. Previous Price: $5,850,000
  4. Last Price Change: 02/06/26
  5. Days On Market: 330
  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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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: 310
  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: $550,000.00
  2. Previous Price: $600,000
  3. Last Price Change: 02/19/26
  4. Days On Market: 38
  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: 353
  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
  7. DMCA Notice
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: 358
  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: 170
  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
  6. mfrmls
  7. DMCA Notice
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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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: 367
  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: 59
  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
  7. DMCA Notice
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: $79,000.00
  2. Previous Price: $80,000
  3. Last Price Change: 02/03/26
  4. Days On Market: 331
  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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8425 Patricia Trail
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Details for 8425 Patricia Trail, KISSIMMEE, FL 34747
Rental
  1. Price: $1,850.00
  2. Price sqft: $1.01 / sqft
  3. Previous Price: $1,900
  4. Last Price Change: 02/07/26
  5. Days On Market: 126
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1826
  9. Acreage: 5.00 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1981
MLS#: S5137213
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Happy Trails
  5. Elementary School: Westside K
  6. Middle School: Celebration K
  7. High School: Celebration
  8. Provided by: PROPERTY SHOP UNLIMITED INC
  9. mfrmls
  10. DMCA Notice
Moving special!! Looking for a quiet country living but with access to major roads? Here is your new Country Style 2 Story unique home with 3 bedrooms and 1 baths on 5 Acres of Land in Happy Trails.
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Tropic Shores Realty - Crystal River
Equal Housing Opportunity
Listing Data ©2026 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
Listing Data ©2026 REALTOR® Association of Citrus County
Listing Data ©2026 Royal Palm Coast Realtor® Association
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on February 27, 2026 @ 12:00 am
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