Searching on:
    1. Subdivision Like Happy Trails
    2. Listing Status = Active
    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: 400
    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
    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: 29
    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
    10. DMCA Notice
    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
    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: 29
    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
    10. DMCA Notice
    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
    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: 36
    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
    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: 380
    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,
    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: 109
    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
    Details for 0 Robin Trail, KISSIMMEE, FL 34747
    Land
    1. Price: $355,000.00
    2. Days On Market: 428
    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
    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: 437
    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
    Details for Lot 48 Amelia Trail, KISSIMMEE, FL 34747
    Land
    1. Price: $275,000.00
    2. Days On Market: 32
    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
    Details for Shelley Trail, KISSIMMEE, FL 34747
    Land
    1. Price: $100,000.00
    2. Previous Price: $115,000
    3. Last Price Change: 05/05/26
    4. Days On Market: 67
    5. Acreage: 8.01 acres
    6. Pool: No
    7. Waterfront: No
    8. Year Built: Not Available
    MLS#: TB8481722
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Happy Trails
    5. Provided by: FIELDS OF PROSPER LLC
    6. mfrmls
    7. DMCA Notice
    Seller Financing Available. 8 Acres OAE5 Zoning Osceola County, FL APN# 21 25 27 3302 0001 0070 Rare opportunity to own approximately 8 acres in unincorporated Osceola County zoned OAE5, typi
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