Happy Trails
Happy Trails is an equestrian community of single family homes, and townhomes in Kissimmee, Florida, with a range of options priced between $599,000 and $5,900,000. There are currently a total of 5 homes for sale in Happy Trails. The smallest Happy Trails home presently available is a three bedroom two bathroom residence that is 1,320 square feet (1,080SF Under Air living space), and the largest of the Happy Trails homes currently on the market has five beds and five baths and is a 11,138 square foot residence.
Property management fees in Osceola County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Happy Trails range from $200 to $590. This fee includes grounds maintenance, and maintaining the community roads. Please check the individual listing pages for the exact homeowners association fees for a particular Happy Trails home.
Happy Trails amenities include a horse stables.
The Happy Trails HOA rules do allow homeowners to have pets. Dogs and cats are allowed.
There are four commercial airports that serve Happy Trails - Kissimmee Gateway (ISM), which is eleven miles away; Orlando International (MCO), which is twenty one miles away; Orlando Executive (ORL), which is twenty five miles away, and Lakeland Linder International (LAL), which is 32 miles away from Happy Trails.
Happy Trails real estate activity on the Kissimmee MLS during the past year (as of September 2025) reflects four homes changing hands, with an average asking price of $892,498 and an average selling price of $880,818. This represents a healthy list-to-sell price ratio of 99% and $145 per square foot. During this period, Happy Trails homes for sale have taken an average of 64 days to sell.
In addition, there are numerous other communities in Kissimmee to choose from, or you may browse all available Kissimmee Real Estate, including some new construction opportunities. Homes for sale in Happy Trails are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Happy Trails hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.
Happy Trails Homes For Sale
MLS#MFRO6296135
8590 Apache Trl
Kissimmee, FL 34747
5
9
5
11,138 SqFt
Pool
5 Acres
176 Days
MLS#MFRO6331214
1000 S Goodman Rd
Kissimmee, FL 34747
4
4
2
4,500 SqFt
5.07 Acres
51 Days
MLS#MFRS5127367
8310 Happy Trails
Kissimmee, FL 34747
3
2
2
2,660 SqFt
5 Acres
125 Days
MLS#MFRR4902468
1190 S Goodman Rd
Champions Gate, FL 33896
3
2
1,824 SqFt
1.39 Acres
1857 Days
MLS#MFRV4944376
2323 N Goodman Rd
Kissimmee, FL 34747
5
4
1
3,899 SqFt
5.02 Acres
41 Days
5 Active Listings in Happy Trails
What schools are Happy Trails homes zoned for?
Where you live in Kissimmee determines which public schools your children may attend, which directly influences home values. Homes in Happy Trails are zoned for the following Osceola County school districts, making school zone boundaries a key factor in property desirability and market demand.Elementary
Middle
High School
Kissimmee Communities
- Creekside At Boggy Creek
- Secret Lake Resorts
- Bellalago
- Indian Ridge Oaks
- Villa Del Sol
- Bella Vida
- Cumbrian Lakes
- Encantada
- Brighton Lakes
- Crescent Lakes
- Eagle Lake
- Hammock Trails
- Lakeside
- Coopersmith
- Laguna Bay
- Pleasant Hill Heights
- Reunion
- Solivita
- Storey Lake
- The Cascades
- Venezia At Solivita
- West Lucaya
- Artisan Club
- Blossom Park Villas
- Clabria
- Cypress Shadows
- Eagle Trace
- Fells Cove
- Heritage Lakes
- Kindred
- Legacy Park
- Marbella
- North Shore
- Paradise Cay
- Pennyroyal
- Remington
- Stepping Stone
- Sweet Water Club
- Trafalgar Village
- Villas At Shadow Bay
- Windsor Hills
- Casa Bella
- Country Creek Estates
- Cypress Hammock
- Eagle Hammock
- Encore Resort At Reunion
- Hamiltons Reserve
- Lake Wilson Reserve
The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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