Happy Trails, FL homes for sale & real estate

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ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Priced to sell ! This is by far the best deal in Happy Trails. Quite possibly priced below appraisal. Seize the opportunity to become the new owner of this modern Farm Retreat on 5 Acres located in the Gated section of Happy Trails – in Kissimmee, FL Discover the perfect blend of country living and modern comfort in this stunning 3-bedroom, 2-bath home located in the exclusive gated section of Happy Trails. Nestled on 5 private acres, this residence offers serenity, space, and sophistication just minutes from the attractions, dining, and shopping of Kissimmee. Step inside and be welcomed by a beautifully renovated interior showcasing a modern farmhouse design—bright, open spa

$749,000

3 beds2 baths2,072 sq ft

305 Hargrove Ln, Kissimmee, FL 34747

30x50 workshop • Tranquil fountain • Rv carport

3D WALKTHROUGH

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to this one-of-a-kind GOLF FRONT equestrian estate home on 5 high and dry private acres. This mediterranean property features over 6,500 of living SQFT with 3 bedrooms, 3 full bathrooms, 2 half bathrooms, extensive natural light throughout, 2 fireplaces, 2 laundry areas, a theater ready room, ample entertaining space all thoughtfully positioned between a North and South wing. The primary suite is situated in the South wing and has its own private fireplace with extensive views of the 14th fairway of Champion’s Gate award winning National Golf Course, a massive walk-in closet and custom travertine fitted bathroom with jetted tub, separate shower and dual vanities. Extra rooms i

$1,390,000

3 beds4 baths6,559 sq ft

222 Pawnee Trl, Kissimmee, FL 34747

Private acres • Natural light • Equestrian estate

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
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, with a Master suite and oversized walking closet. The kitchen features large windows with abundant natural light, facing the beauty of nature, a perfect place to enjoy your morning coffee. The living and dining room reflect a spacious open space, ideal for gathering friends and family. There is a small pond on the property, a 12x50 workshop/shed and an additional garden shed. This property has a separate private entrance thru beautiful mature landscape, your own private entrance to this heaven

$860,000

4 beds2 baths2,120 sq ft

2478 Thacker Trl, Kissimmee, FL 34747

Master suite • Large windows • 8.7 acre property

3D WALKTHROUGH

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
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 living space, where every detail has been thoughtfully curated for the discerning homeowner. As you enter through the private gate, you are greeted by a stunning family room featuring a handcrafted stone gas fireplace and soaring ceilings that create an inviting atmosphere. The elegant curving marble staircase, adorned with a magnificent Swarovski crystal chandelier, sets the tone for the opulence that awaits. This estate offers 5 spacious bedrooms, each with large walk-in closets and en-suite

$5,850,000

5 beds7 baths11,138 sq ft

8590 Apache Trl, Kissimmee, FL 34747

Exquisite woodwork • Outdoor oasis • Media room

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Ready to build! This 5-acre Happy Trails property includes a boundary survey and building plans for a stunning 4,000 sqft home. The lot is partially cleared, offering mature trees, natural beauty, and a serene country feel. Enjoy quiet living among gorgeous neighboring estates while staying close to Orlando attractions and amenities. Horses are permitted, and you’re only minutes from Disney, major highways, shopping, dining, and Champions Gate. Excellent road access makes travel to both coasts and Orlando International Airport simple and convenient. Create your dream home or the perfect vacation getaway here. Schedule your private showing today.

$299,000

— beds— baths— sq ft

8401 Amelia Trl, Kissimmee, FL 34747

Building plans • Horses permitted • 5 acre property

Property at Keefer Trl, Kissimmee, FL 34747

$80,000

— beds— baths— sq ft

Keefer Trl, Kissimmee, FL 34747

Property at Sioux Trl, Kissimmee, FL 34747

$349,900

— beds— baths— sq ft

Sioux Trl, Kissimmee, FL 34747

Property at Thacker Trl, Kissimmee, FL 34747

$375,000

— beds— baths— sq ft

Thacker Trl, Kissimmee, FL 34747

Property at 0 Robin Trl, Kissimmee, FL 34747

$355,000

— beds— baths— sq ft

0 Robin Trl, Kissimmee, FL 34747

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NEW 6 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Turnkey 3-Bedroom Home Near Disney – Fully Furnished! Located in the desirable, guard-gated Windsor Palms Resort community, this well-kept 3-bedroom, 2-bath pool home residence is just minutes from Walt Disney World and major attractions. Offered fully furnished and ready for immediate occupancy, the home is ideal as a full-time residence, vacation retreat, or income-producing property with both short-term and long-term rental options. Residents and guests enjoy access to outstanding resort amenities, including a clubhouse, community pool, fitness center, and more. A fantastic opportunity for personal use or investment in one of the area’s most popular resort communities. Additi

$399,999

3 beds2 baths1,664 sq ft

8204 Fan Palm Way, Kissimmee, FL 34747

Fitness center • Community pool • 6,055 sq ft lot

NEW 10 HRS AGO

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to this beautiful POOL HOME retreat in the heart of one of Kissimmee’s well-established communities. With NO HOA and NO CDD, this property offers rare flexibility and freedom, whether you're looking for a primary residence, a vacation getaway, or a high-earning SHORT-TERM RENTAL, AIRBNB, or long-term rental. The interior has been thoughtfully redesigned with modern finishes, an open layout, and an emphasis on light, flow, and comfort. Updated fixtures, contemporary design touches, and fresh surfaces throughout provide a move-in-ready experience. This FIVE BEDROOM residence features an inviting living space that seamlessly connects to the kitchen and dining areas, creating an i

$439,900

5 beds3 baths1,864 sq ft

1653 Oak Hill Trl, Kissimmee, FL 34747

No cdd • Pool home • Short-term rental

NEW 11 HRS AGO3D & VIDEO TOUR

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to your DREAM VACATION HOME in the highly sought-after, Airbnb-friendly resort community of Windsor at Westside. This property comes with strong rental history and over $40,000 in updates to the home which were just done in 2024! This exceptional vacation home stands out for several reason. The prime location of this property, stunning water views, and numerous recent upgrades. Ideally situated just steps from the clubhouse, gym, pool, and restaurant, convenience is at your doorstep. Enjoy water views from the front of the home and multiple rooms inside. Unlike many other short-term rentals on the market this home was recently updated. Recent upgrades include all-new appliances,

$610,000

6 beds4.5 baths3,142 sq ft

8869 Rhodes St, Kissimmee, FL 34747

Private pool • Open concept kitchen • Hot tub

NEW 30 HRS AGO

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to 8851 Geneve Ct in Kissimmee, located within a resort-style, short-term rental friendly gated community offering flexibility for a variety of lifestyles and investment strategies. This thoughtfully positioned home provides everyday convenience with quick access to major roadways, allowing for easy travel to Orlando and surrounding areas while still maintaining a neighborhood feel. Nearby shopping, dining, schools, parks, and essential services make daily errands and commuting simple and efficient. The surrounding area continues to experience steady growth, supported by ongoing improvements to nearby commercial centers and infrastructure. This continued development enhances both li

$419,000

5 beds4.5 baths2,265 sq ft

8851 Geneve Ct, Kissimmee, FL 34747

Gated community • Nearby dining • Nearby shopping

NEW CONSTRUCTION

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
This exceptional two-story home features six bedrooms, five bathrooms and a large combination dining and family room that overlooks the covered patio. There are two stunning owner suites, a fully-equipped kitchen, a one-car garage, and an upstairs loft. Affordability and value you have come to expect from Lennar. We have a limited release of NEW homes that sit on well-maintained sites, perfect for relaxing with friends and loved ones. With “Everything’s Included”, luxury and value go hand in hand. New highly energy efficient homes feature beautiful cabinetry, quartz countertops in both kitchen and bathrooms. Have the good life at Reunion Village! This stunning new communit

$614,990

6 beds5 baths3,275 sq ft

7894 Poplin St, Kissimmee, FL 34747

Quartz countertops • Upstairs loft • Covered patio

3D WALKTHROUGH

ABOUT THIS HOME
Happy Trails, FL Homes for Sale
REUNION RESORT MEMBERHIP PROPERTY. Luxury, Lifestyle and Legacy- This is Reunion Resort and now this is your chance to own a true Reunion legacy property located at 350 Muirfield Loop. This is a custom built 12-bedroom, 12 full bath, 2 half bath, golf course view home that is located on a highly desirable double lot inside one of the most revered areas in all of Reunion, Legends Corner. Overlooking the 10th hole of the Nicklaus Golf Course, this home possesses undeniable curb appeal and comes in at 13,000 square feet of living, entertaining, and memory making space. Once inside the home you instantly find yourself wanting to discover all of its secrets. Starting with the first floor that bo

$5,749,900

12 beds13 baths12,962 sq ft

350 Muirfield Loop, Reunion, FL 34747

Golf course view • In home theatre • Double lot

Property at 2543 Holtrock St, Kissimmee, FL 34747, 6 beds, 4 baths

$619,000

6 beds4 baths2,812 sq ft

2543 Holtrock St, Kissimmee, FL 34747

Property at 2604 Luiseno Way, Kissimmee, FL 34747, 5 beds, 4 baths

$439,000

5 beds4 baths2,136 sq ft

2604 Luiseno Way, Kissimmee, FL 34747

Property at 1001 Lester Ridge Ct, Kissimmee, FL 34747, 5 beds, 2 baths

$434,990

5 beds2 baths1,999 sq ft

1001 Lester Ridge Ct, Kissimmee, FL 34747

Property at 7916 Hanson Bay Pl, Kissimmee, FL 34747, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,470 sq ft

7916 Hanson Bay Pl, Kissimmee, FL 34747

Property at 1208 Payne Stewart Dr, Davenport, FL 33896, 3 beds, 2.5 baths

$349,000

3 beds2.5 baths1,912 sq ft

1208 Payne Stewart Dr, Davenport, FL 33896

Property at 7924 Draw St, Reunion, FL 34747, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,704 sq ft

7924 Draw St, Reunion, FL 34747

Property at 507 Ocean Course Ave #507, Davenport, FL 33896, 2 beds, 2 baths

$320,000

2 beds2 baths1,388 sq ft

507 Ocean Course Ave #507, Davenport, FL 33896

Property at 1220 Payne Stewart Dr, Davenport, FL 33896, 3 beds, 2.5 baths

$310,000

3 beds2.5 baths2,114 sq ft

1220 Payne Stewart Dr, Davenport, FL 33896

Property at 8891 Geneve Ct, Kissimmee, FL 34747, 5 beds, 4.5 baths

$450,000

5 beds4.5 baths2,263 sq ft

8891 Geneve Ct, Kissimmee, FL 34747

Property at 8833 Bethpage Ln, Davenport, FL 33896, 4 beds, 2.5 baths

$485,000

4 beds2.5 baths2,334 sq ft

8833 Bethpage Ln, Davenport, FL 33896

Property at 2382 Silver Palm Dr E, Kissimmee, FL 34747, 3 beds, 3 baths

$339,000

3 beds3 baths1,440 sq ft

2382 Silver Palm Dr E, Kissimmee, FL 34747

Property at 8029 Twin Eagles Loop, Reunion, FL 34747

$595,000

— beds— baths— sq ft

8029 Twin Eagles Loop, Reunion, FL 34747

Property at 8031 Twin Eagles Loop, Reunion, FL 34747

$595,000

— beds— baths— sq ft

8031 Twin Eagles Loop, Reunion, FL 34747

Property at 8033 Twin Eagles Loop, Reunion, FL 34747

$595,000

— beds— baths— sq ft

8033 Twin Eagles Loop, Reunion, FL 34747

Based on information submitted to the MLS GRID as of Sat Jan 03 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Happy Trails, FL

Cities

Neighborhoods

Highlands Reserve homes for sale
$275,000
Paradise Palms homes for sale
$392,448
Caribe Cove homes for sale
$220,000
Margaritaville Resort Orlando homes for sale
$445,000
Citrus Ridge homes for sale
$450,000
Four Corners homes for sale
$455,000
Windsor Hills homes for sale
$620,000
Reunion homes for sale
$424,990
Championsgate homes for sale
$450,500
Emerald Island homes for sale
$485,000

Happy Trails, FL real estate trends

$705K

Sale price

$324

Sale $/sq ft

Under list price

Days on market

108

Down payment

—

Total homes sold

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