Refine Search
Skip to Main Content
  1. Home
  2. Search Listings
  3. Search Results
Searching on:
  1. Subdivision Like Happy Trails
  2. Listing Status = Active
8590 Apache Trail
Virtual Tour
More Like This
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: 376
  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
Listing Details and 99 Additional Pictures
Request more information about this listing.
8398 Happy Trail
Virtual Tour
Green Listing
More Like This
Active
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: 4
  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
Listing Details and 59 Additional Pictures
Request more information about this listing.
200 Goodman Road
Virtual Tour
New Construction
Green Listing
More Like This
Active
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: 4
  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
Listing Details and 63 Additional Pictures
Request more information about this listing.
2477 Thacker Trail
Virtual Tour
More Like This
Active
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: 11
  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
Listing Details and 51 Additional Pictures
Request more information about this listing.
2478 Thacker Trail
Virtual Tour
More Like This
Active
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: 355
  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,
Listing Details and 49 Additional Pictures
Request more information about this listing.
8531 Sweetwater Trail
Reduced
More Like This
Active
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: 84
  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
Listing Details and 2 Additional Pictures
Request more information about this listing.
2370 Thacker Trail
More Like This
Active
Listing Details for 2370 Thacker Trail, KISSIMMEE, FL 34747
Land
  1. Price: $374,999.00
  2. Days On Market: 399
  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
Listing Details
Request more information about this listing.
0 Robin Trail
More Like This
Active
Details for 0 Robin Trail, KISSIMMEE, FL 34747
Land
  1. Price: $355,000.00
  2. Days On Market: 403
  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
Listing Details and 2 Additional Pictures
Request more information about this listing.
8401 Amelia Trail
Virtual Tour
More Like This
Active
Details for 8401 Amelia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $299,000.00
  2. Days On Market: 105
  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 property is partially cleared, offering mature trees, natural beauty
Listing Details and 8 Additional Pictures
Request more information about this listing.
Lot 48 Amelia Trail
More Like This
Active
Details for Lot 48 Amelia Trail, KISSIMMEE, FL 34747
Land
  1. Price: $275,000.00
  2. Days On Market: 7
  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
Listing Details and 2 Additional Pictures
Request more information about this listing.
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 April 14, 2026 @ 12:00 am
©2006-2026 brokerIDXsites.com - https://brokerIDXsites.com
We believe in accessibility for all
Your Privacy Is Important
XML Sitemap
Manage Your Account