Happy Trails, FL homes for sale & real estate

11 homes

Sort:

Recommended

8310 Happy Trl, Kissimmee, FL 34747
8310 Happy Trl, Kissimmee, FL 34747
8310 Happy Trl, Kissimmee, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
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 gates. If you long for country life and want to be close to everything in Central Florida then this quiet oasis is for you. Minutes to shopping, schools, and theme parks. Golfers will find several premier golf courses just minutes away. This unique home is set back from the road amongst pretty oaks with plenty of space for your new pool, gardens and if you like, farm animals. Rocking chair front porch leads the way to your elegant entrance and views to the open atrium. The fireplace living roo

$819,700

3 beds2 baths2,660 sq ft

8310 Happy Trl, Kissimmee, FL 34747

5.01 acre lot • $49 HOA • 2 garage spots

3D WALKTHROUGH

8590 Apache Trl, Kissimmee, FL 34747
8590 Apache Trl, Kissimmee, FL 34747
8590 Apache Trl, Kissimmee, FL 34747
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

$5,900,000

5 beds7 baths11,138 sq ft

8590 Apache Trl, Kissimmee, FL 34747

5 acre lot • $16 HOA • 5 garage spots

2477 Thacker, FL 34747
2477 Thacker, FL 34747
2477 Thacker, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
SAFETY PRIVACY & FLORIDA LIVING AT ITS BEST. This 6.2 acre EQUESTRIAN ESTATE is located in HAPPY TRAILS at the end of a dead end street. Gated entrance to the community provides exceptional privacy and tranquility with a glimpse of a vanishing old Florida. Newly revovated 4/2 with 1/1 in law quarters and 0/1 offiice/studio. New laminate floors throughout; kitchen cabinets w/ quartz countertops & stainless steel appliances; remodeled bathrooms w/ 16X16 ceramic tile, new cabinetry & quartz countertops. New metal roof and 2 zone HVAC. Interior freshly painted; exterior Dec 2023. Equestrian ready property includes lean to barn with room for 3 stalls & tack room or large

$1,199,000

6 beds5 baths4,004 sq ft

2477 Thacker

$49 HOA • 2 garage spots • Car-dependent

Keefer Trl, Kissimmee, FL 34747
Keefer Trl, Kissimmee, FL 34747
Keefer Trl, Kissimmee, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
LOCATION, LOCATION. .. Parcel located in the exclusive GATED community of HAPPY TRAILS. This lot will require mitigation. Natural Flowing Stream on Property and Wetlands. Each Buyer must independently verify and is solely responsible for the feasibility study, environmental due diligence, and survey to determine whether the Property is suitable for Buyer's intended use. Offering seclusion and privacy, Happy Trails is in a fantastic location, just a few miles from Walt Disney World and nearby Champions Gate. Make your appointment today!

$100,000

— beds— baths— sq ft

Keefer Trl, Kissimmee, FL 34747

5.01 acre lot • $50 HOA • Car-dependent

2370 Thacker Trl, Kissimmee, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
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 Happy Trails—a 5.98-acre haven that seamlessly blends the tranquility of rural living with unparalleled convenience. Nestled close to Disney, ChampionsGate, and an array of shopping and dining options, this parcel offers you a slice of peaceful countryside while keeping you connected to the excitement of Kissimmee and Orlando. Your future dream home awaits in this idyllic setting, offering a private oasis just minutes from major highways like Hwy 429 and I-4. ?? Nature and Convenience

$374,999

— beds— baths— sq ft

2370 Thacker Trl, Kissimmee, FL 34747

5.98 acre lot • $50 HOA • Car-dependent

Property at 0 Robin Trl, Kissimmee, FL 34747

$355,000

— beds— baths— sq ft

0 Robin Trl, Kissimmee, FL 34747

Property at 8531 Sweetwater Trl, Kissimmee, FL 34747

$900,000

— beds— baths— sq ft

8531 Sweetwater Trl, Kissimmee, FL 34747

Property at Thacker Trl, Kissimmee, FL 34747

$425,000

— beds— baths— sq ft

Thacker Trl, Kissimmee, FL 34747

Property at 8674 Sweetwater Trl, Kissimmee, FL 34747

$365,000

— beds— baths— sq ft

8674 Sweetwater Trl, Kissimmee, FL 34747

Property at Sweetwater Trl #156, Kissimmee, FL 34747

$135,000

— beds— baths— sq ft

Sweetwater Trl #156, Kissimmee, FL 34747

Property at 0 Patricia Trl, Kissimmee, FL 34747

$154,000

— beds— baths— sq ft

0 Patricia Trl, Kissimmee, FL 34747

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

Within 1 mile

3D & VIDEO TOUR

1005 Coyote Creek Way, Reunion, FL 34747
1005 Coyote Creek Way, Reunion, FL 34747
1005 Coyote Creek Way, Reunion, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
One or more photo(s) has been virtually staged. MOTIVATED SELLER! Step into a world of exceptional design and resort-style living with this meticulously crafted 9-bedroom, 9.5-bathroom luxury estate, located within the prestigious gates of Reunion Resort and Club—Central Florida’s premier active-lifestyle, gated golf community. Purpose-built to exceed the expectations of today’s discerning buyer, this stunning residence is professionally decorated and offered FULLY FURNISHED with top-tier designer appointments and state-of-the-art electronics throughout. Situated on an oversized lot and designed to accommodate up to 24 guests, the home’s expansive open-concept layout

$2,190,000

9 beds9.5 baths6,000 sq ft

1005 Coyote Creek Way, Reunion, FL 34747

0.27 acre lot • $633 HOA • 2 garage spots

8801 Corcovado Dr, Kissimmee, FL 34747
8801 Corcovado Dr, Kissimmee, FL 34747
8801 Corcovado Dr, Kissimmee, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to this stunning 8-bedroom, 6-bathroom vacation home in the highly sought-after resort community of Windsor at Westside. Situated on a corner lot with a partial pond view, this turn-key property was built in 2019 and is fully furnished and professionally decorated to maximize short-term rental income. The home features a spacious open floor plan with a modern kitchen boasting granite countertops and stainless steel appliances. Designed with fun and comfort in mind, the home includes three themed bedrooms (Star Wars, Batman, and Little Mermaid), a Spider-Man themed loft with a TV, sofa, and pool table, and a fully converted garage game room with an Avatar theme, pool table, air hocke

$685,000

8 beds6 baths4,041 sq ft

8801 Corcovado Dr, Kissimmee, FL 34747

7,405 sq ft lot • $561 HOA • 2 garage spots

1084 Castle Pines Ct, Reunion, FL 34747
1084 Castle Pines Ct, Reunion, FL 34747
1084 Castle Pines Ct, Reunion, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Pristine 5-Bedroom, 5.5-Bath Home boasting 3,328 Sq. Ft. of refined living space and is located along Hole #6 of the Signature Jack Nicklaus Course. The home has been meticulously maintained and has served exclusively as a second home. NEVER RENTED! As you step inside, you're welcomed by a first-floor primary suite, complete with a luxurious en-suite bath featuring a garden tub, separate walk-in shower, stone countertops, and custom hardwood cabinetry. The open-concept main living area offers seamless flow and sophistication, highlighted by custom built-in shelving. The spacious island kitchen is equipped with stainless steel appliances, stone countertops, and hardwood cabinets with crown m

$1,125,000

5 beds5.5 baths3,328 sq ft

1084 Castle Pines Ct, Reunion, FL 34747

4,879 sq ft lot • $520 HOA • 2 garage spots

783 Ocean Course Ave, Davenport, FL 33896
783 Ocean Course Ave, Davenport, FL 33896
783 Ocean Course Ave, Davenport, FL 33896
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Welcome to your slice of paradise at 783 Ocean Course Ave in the highly sought-after ChampionsGate Resort! This stunning fully furnished 3-bedroom, 2-bathroom townhome is the ideal vacation retreat and a lucrative short-term rental investment—bookings already in place through the new year make it truly turn-key for the savvy buyer. Step inside this spacious 1,787 sq. ft. home and enjoy modern finishes, an open layout, and abundant natural light throughout. The garage has been thoughtfully converted into a fun-filled game room complete with a pool table, adding extra entertainment appeal for guests and family alike. Nestled in a quiet, guard-gated community, the home offers the perfect

$395,000

3 beds2 baths1,787 sq ft

783 Ocean Course Ave, Davenport, FL 33896

2,054 sq ft lot • $496 HOA • Garage

VIDEO TOUR

7802 Palmilla Ct, Reunion, FL 34747
7802 Palmilla Ct, Reunion, FL 34747
7802 Palmilla Ct, Reunion, FL 34747
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
Exemplary Executive Golf Course Home with AMAZING PANORAMIC VIEWS is available for purchase in the exclusive gated, active lifestyle golf community of Reunion Resort! This FULLY FURNISHED 9-bedroom, 12.5-bath purpose-built home, comes professionally themed and decorated to an elite standard and offers an immersive luxury experience. Positioned on a superior southwest-facing lot overlooking the 10th and 11th holes of the Nicklaus Golf Course, it delivers captivating sunsets, year-round sun, and unforgettable vistas. The outdoor living space is everyone’s dream, featuring a covered lanai, oversized pool with sun shelf and hot tub, firepit, cabana-style daybed and generous lounging areas

$2,790,000

9 beds12.5 baths7,000 sq ft

7802 Palmilla Ct, Reunion, FL 34747

8,451 sq ft lot • $589 HOA • 2 garage spots

OPEN SAT, 11AM TO 2PM

8961 Cabot Cliffs Dr, Davenport, FL 33896
8961 Cabot Cliffs Dr, Davenport, FL 33896
8961 Cabot Cliffs Dr, Davenport, FL 33896
ABOUT THIS HOME
Happy Trails, FL Homes for Sale
PRIVATE POOL WITH CONSERVATION VIEW – FULLY FURNISHED VACATION HOME IN CHAMPIONS GATE – Seller offering $2000 credit at closing-can be used towards buyer's closing costs or interest rate buydown. A great opportunity to save! Beautifully furnished 4-bedroom, 3-bathroom townhome, private pool located in the highly sought-after Champions Gate Resort, just minutes from Orlando’s world-famous attractions. This spacious home features an open floor plan ideal for entertaining, with a modern kitchen overlooking a covered patio and private pool – perfect for relaxing after a day of adventure. The layout includes one bedroom on the main floor, two additional bedrooms upsta

$419,000

4 beds3 baths1,914 sq ft

8961 Cabot Cliffs Dr, Davenport, FL 33896

2,614 sq ft lot • $633 HOA • Pool

Property at 2305 Butterfly Palm Way #304, Kissimmee, FL 34747, 2 beds, 2 baths

$199,900

2 beds2 baths1,022 sq ft

2305 Butterfly Palm Way #304, Kissimmee, FL 34747

Property at 1890 Flora Pass Pl, Kissimmee, FL 34747, 2 beds, 2 baths

$325,000

2 beds2 baths1,557 sq ft

1890 Flora Pass Pl, Kissimmee, FL 34747

Property at 796 Desert Mountain Ct, Reunion, FL 34747, 5 beds, 5.5 baths

$955,000

5 beds5.5 baths3,326 sq ft

796 Desert Mountain Ct, Reunion, FL 34747

Property at 8974 Cabot Cliffs Dr, Davenport, FL 33896, 5 beds, 5 baths

$570,000

5 beds5 baths3,081 sq ft

8974 Cabot Cliffs Dr, Davenport, FL 33896

Property at 8113 Sun Palm Dr, Kissimmee, FL 34747, 6 beds, 3.5 baths

$499,900

6 beds3.5 baths2,368 sq ft

8113 Sun Palm Dr, Kissimmee, FL 34747

Property at 2307 Silver Palm Dr #304, Kissimmee, FL 34747, 3 beds, 2 baths

$230,000

3 beds2 baths1,402 sq ft

2307 Silver Palm Dr #304, Kissimmee, FL 34747

Property at 8928 Coconut Breeze Dr, Kissimmee, FL 34747, 9 beds, 6.5 baths

$819,000

9 beds6.5 baths4,363 sq ft

8928 Coconut Breeze Dr, Kissimmee, FL 34747

Property at 456 Ocean Course Ave, Davenport, FL 33896, 4 beds, 3 baths

$499,990

4 beds3 baths1,914 sq ft

456 Ocean Course Ave, Davenport, FL 33896

Property at 877 Ocean Course Ave, Davenport, FL 33896, 3 beds, 2 baths

$360,000

3 beds2 baths1,787 sq ft

877 Ocean Course Ave, Davenport, FL 33896

Property at 8833 Cruden Bay Ct, Davenport, FL 33896, 8 beds, 5 baths

$850,000

8 beds5 baths3,915 sq ft

8833 Cruden Bay Ct, Davenport, FL 33896

Property at 2233 Antilles Club Dr, Kissimmee, FL 34747, 3 beds, 2 baths

$549,000

3 beds2 baths2,042 sq ft

2233 Antilles Club Dr, Kissimmee, FL 34747

Property at 2108 Antilles Club Dr, Kissimmee, FL 34747, 2 beds, 2 baths

$385,000

2 beds2 baths1,437 sq ft

2108 Antilles Club Dr, Kissimmee, FL 34747

Property at 8833 Corcovado Dr, Kissimmee, FL 34747, 9 beds, 6 baths

$699,900

9 beds6 baths4,391 sq ft

8833 Corcovado Dr, Kissimmee, FL 34747

Property at 16-25-27-0000-0074-0000 Sweetwater Trl, Kissimmee, FL 34747

$12,000

— beds— baths— sq ft

16-25-27-0000-0074-0000 Sweetwater Trl, Kissimmee, FL 34747

Based on information submitted to the MLS GRID as of Mon Jun 09 2025. 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
$290,000
Margaritaville Resort Orlando homes for sale
$459,000
Citrus Ridge homes for sale
$459,000
West Haven homes for sale
$427,000
Four Corners homes for sale
$439,500
Windsor Hills homes for sale
$629,900
Indian Ridge homes for sale
$399,999
Reunion homes for sale
$449,900
Championsgate homes for sale
$459,500
Emerald Island homes for sale
$491,000

Happy Trails, FL real estate trends

$318K

Sale price

$119

Sale $/sq ft

Over list price

17.9%

Days on market

Down payment

—

Total homes sold

See more Happy Trails, FL market insights

More to explore in Happy Trails, FL

How to buy a house in Happy Trails, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Become a Lender Partner

Subsidiaries

Rent.

ApartmentGuide

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.