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- Subdivision Like Happy Trails
Single Family
- Price: $5,850,000.00
- Price sqft: $525.23 / sqft
- Previous Price: $5,900,000
- Last Price Change: 07/22/25
- Days On Market: 142
- 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 ORLANDO
- 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
Single Family
- Price: $879,000.00
- Price sqft: $346.06 / sqft
- Previous Price: $899,000
- Last Price Change: 05/26/25
- Days On Market: 122
- 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
- Provided by: UNITED REALTY GROUP INC
- 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,
Single Family
- Price: $815,000.00
- Price sqft: $306.39 / sqft
- Previous Price: $819,700
- Last Price Change: 07/25/25
- Days On Market: 91
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2660
- Acreage: 5.00 acres
- Pool: No
- Waterfront: No
- Year Built: 1988
MLS#: S5127367
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside Elem
- High School: Celebration
- Provided by: HAPPY DAYS REALTY LLC
- DMCA Notice
Discover your own piece of paradise in Central Florida! This charming home on five acres is located in the gated area of the Happy Trails community. This special lot is completely fenced and has three
Single Family
- Price: $650,000.00
- Price sqft: $166.71 / sqft
- Days On Market: 7
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 1
- Bldg sqft: 3899
- Acreage: 5.02 acres
- Pool: No
- Waterfront: No
- Year Built: 1997
MLS#: V4944376
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside K 8
- High School: Celebration High
- Provided by: REAGAN REALTY, LLC
- DMCA Notice
Nestled in the desirable Happy Trails neighborhood, just outside Disneys Animal Kingdom and world class resorts, this 5 bedroom, 4 bath residence offers 5 acres of privacy and endless potential. High
Single Family
- Price: $650,000.00
- Price sqft: $166.71 / sqft
- Days On Market: 7
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 1
- Bldg sqft: 3899
- Acreage: 5.02 acres
- Pool: No
- Waterfront: No
- Year Built: 1997
MLS#: V4944376
- County: OSCEOLA
- City: Kissimmee
- Zipcode: 34747
- Subdivision: Happy Trails Unit 3 Unrec
- Elementary School: Westside K
- High School: Celebration
- Provided by: REAGAN REALTY, LLC
- Provided through
- DMCA Notice
Nestled in the desirable Happy Trails neighborhood, just outside Disneys Animal Kingdom and world class resorts, this 5 bedroom, 4 bath residence offers 5 acres of privacy and endless potential. High
Land
- Price: $600,000.00
- Previous Price: $900,000
- Last Price Change: 06/28/25
- Days On Market: 170
- Acreage: 5.01 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: O6287188
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Provided by: PV LUXURY GROUP PA
- DMCA Notice
5 Acres of Prime Vacant Land in Kissimmee, FL Perfect for Your Dream Project!
Discover the potential of this expansive 5 acre lot located in the heart of Kissimmee, FL. With plenty of room to buil
Land
- Price: $425,000.00
- Days On Market: 179
- 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
- Provided by: RE/MAX CHAMPIONS
- 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
Land
- Price: $374,999.00
- Days On Market: 165
- 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
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
- Days On Market: 170
- 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
***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: $253,500.00
- Days On Market: 66
- Acreage: 6.38 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: O6319328
- County: OSCEOLA
- City: KISSIMMEE
- Zipcode: 34747
- Subdivision: Happy Trails
- Elementary School: Westside K
- Middle School: Horizon
- High School: Celebration
- Provided by: KELLER WILLIAMS ELITE PARTNERS III REALTY
- DMCA Notice
6.38 Acres in Happy Trails Minutes from Disney, Unlimited Potential
Tucked away in the peaceful, gated community of Happy Trails, this 6.38 acre lot offers the perfect blend of privacy, space, and c

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