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Searching on:
- Subdivision Like Happy Trails
- Listing Status = Active
Single Family
- Price: $5,650,000.00
- Price sqft: $507.27 / sqft
- Previous Price: $5,750,000
- Last Price Change: 03/13/26
- Days On Market: 391
- Bedrooms: 5
- Baths: 9
- Garage / Parking Spaces: 5
- Bldg sqft: 11138
- Acreage: 5.00 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2009
MLS#: O6296135
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: THE AGENCY FL
- DMCA Notice
Description
- 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
Single Family
- Price: $2,200,000.00
- Price sqft: $419.45 / sqft
- Days On Market: 19
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 3
- Bldg sqft: 5245
- Acreage: 5.01 acres
- Pool: No
- Waterfront: No
- Year Built: 2024
MLS#: O6396464
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside Elem
- Middle School: West Side
- High School: Celebration High
- Provided by: FUTURE HOME REALTY INC
-
- DMCA Notice
Description
- 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
Single Family
- Price: $990,000.00
- Price sqft: $309.96 / sqft
- Days On Market: 26
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3194
- Acreage: 6.20 acres
- Pool: No
- Waterfront: No
- Year Built: 2003
MLS#: O6395094
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: UNITED REALTY GROUP INC.
-
- DMCA Notice
Description
- 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
Single Family
- Price: $920,000.00
- Price sqft: $362.21 / sqft
- Previous Price: $860,000
- Last Price Change: 03/17/26
- Days On Market: 371
- Bedrooms: 4
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2540
- Acreage: 8.71 acres
- Pool: No
- Waterfront: No
- Year Built: 2003
MLS#: O6301945
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails Sub
- Elementary School: Westside Elem
- Middle School: West Side
- High School: Celebration High
- Provided by: UNITED REALTY GROUP INC
-
- DMCA Notice
Description
- 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,
Land
- Price: $500,000.00
- Previous Price: $550,000
- Last Price Change: 04/07/26
- Days On Market: 99
- Acreage: 5.01 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: S5142072
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: TOP VILLAS REALTY LLC
-
- DMCA Notice
Description
- 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
Land
- Price: $374,999.00
- Days On Market: 414
- Acreage: 5.98 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: S5122296
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: FUTURE HOME REALTY INC
-
- DMCA Notice
Description
- 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
Land
- Price: $355,000.00
- Previous Price: $385,000
- Last Price Change: 01/17/26
- Days On Market: 419
- Acreage: 5.04 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: TB8357799
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: HOMELIFE REALTY COASTAL PROPERTIES LLC
-
- DMCA Notice
Description
- ***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
Land
- Price: $349,900.00
- Previous Price: $375,000
- Last Price Change: 04/24/26
- Days On Market: 428
- Acreage: 6.38 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: W7872619
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside Elem
- Middle School: West Side
- High School: Celebration High
- Provided by: RE/MAX CHAMPIONS
-
- DMCA Notice
Description
- 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
Land
- Price: $299,000.00
- Days On Market: 120
- Acreage: 5.00 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: O6369754
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: CHARLES RUTENBERG REALTY ORLANDO
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- DMCA Notice
Description
- 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
Land
- Price: $275,000.00
- Days On Market: 22
- Acreage: 10.08 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: S5147245
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside K 8
- Middle School: Horizon Middle
- High School: Celebration High
- Provided by: KELLER WILLIAMS REALTY AT THE LAKES
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- DMCA Notice
Description
- 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
