MLS Listings for Sale in Happy Trails, FL

9 homes

Sort:

Recommended

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Modern Farm Retreat on 5 Acres in Gated Happy Trails – 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 over 2,000-square-foot 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 spaces, elegant finishes, and top-of-the-line appliances throughout with Quartz Countertops and extra large farm sink. Ton of storage with two walk in pantries. T

$799,000

3 beds2 baths2,072 sq ft

305 Hargrove Ln, Kissimmee, FL 34747

30x50 workshop • Tranquil fountain • Rv carport

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
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

$1,790,000

3 beds4 baths6,559 sq ft

222 Pawnee Trl, Kissimmee, FL 34747

Private acres • Natural light • Equestrian estate

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
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. Beautiful land, no wet areas. Agriculture zoned, horses, chickens invited! Rocking chair front porch leads the way to y

$805,000

3 beds2 baths2,660 sq ft

8310 Happy Trl, Kissimmee, FL 34747

Quiet oasis • Minutes to shopping • Five acres

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
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!

$96,000

— beds— baths— sq ft

Keefer Trl, Kissimmee, FL 34747

Gated community • 5.01 acre lot • Listed 224 days

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Final price drop, Discover an Exceptional 5-Acre Lot in Happy Trails – A Rare Opportunity Near Champions Gate, Reunion, and Disney. Nestled in the prestigious Happy Trails community, this expansive 5-acre vacant lot presents a one-of-a-kind opportunity to bring your dream estate to life. Perfectly situated in one of the highest-elevated areas of the neighborhood, this property offers both privacy and prestige—right next to world-renowned communities such as Champions Gate, Reunion, and just minutes from Disney. The seller is a civil engineer expert in mitigation and has the plan in place to build on 1/3 of an acre. please review attachments mitigation strategy included. This lot

$379,000

— beds— baths— sq ft

Sioux Trl, Kissimmee, FL 34747

5 acre lot • Architectural design • Preliminary plans

Property at Amelia Trl, Kissimmee, FL 34747

$236,000

— beds— baths— sq ft

Amelia Trl, Kissimmee, FL 34747

Property at Thacker Trl, Kissimmee, FL 34747

$375,000

— beds— baths— sq ft

Thacker Trl, Kissimmee, FL 34747

$374,999

— beds— baths— sq ft

2370 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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 11 MINS AGO

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Experience the ultimate vacation lifestyle in this beautifully furnished 5bedroom, 3bath pool home located in the highly sought after Windsor Resort, just minutes from the theme parks! This turnkey property is actively operating as a successful short-term rental, offering strong income potential for investors. Featuring an open concept layout, a modern kitchen with stainless steel appliances, and stylish finishes throughout. Enjoy the private screened-in pool and covered lanai erfect for entertaining or relaxing after a day at the parks. Resort amenities include a clubhouse, fitness center, community pool, and more, making it ideal for guests and families alike.

$585,000

5 beds3.5 baths2,255 sq ft

8016 King Palm Cir, Kissimmee, FL 34747

5,750 sq ft lot • $520 HOA • 2 garage spots

NEW 2 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Luxury Meets Comfort Minutes from Disney! - Cul-De-Sac lot! Welcome to your dream getaway at Windsor at Westside — a luxurious yet charming retreat just 10 minutes from Mickey’s doorstep. Perfectly located near Orlando’s top attractions, this modern home offers the ideal blend of relaxation, entertainment, and style. Step inside and discover a bright, open-concept living space designed for comfort and connection. The gourmet kitchen features gleaming granite countertops, stainless steel appliances, and an oversized island with seating for six — perfect for breakfast pancakes or late-night snacks. Gather your loved ones around the elegant dining table for twelve an

$650,000

8 beds6 baths4,041 sq ft

8801 Bengal Ct, Kissimmee, FL 34747

4,860 sq ft lot • $697 HOA • 2 garage spots

NEW 4 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Turnkey Luxury Vacation Home in Windsor at Westside – Fully Furnished and Airbnb-Ready! Welcome to this stunning, fully furnished luxury home in the highly sought-after gated resort community, where comfort meets investment opportunity. Professionally decorated and beautifully maintained, this income-producing property is Airbnb-ready and designed to impress both owners and guests alike. Featuring 7 spacious bedrooms (including master suites on both floors) and 5.5 bathrooms, this home comfortably accommodates up to 16 guests, ensuring strong rental performance year-round. The open-concept main floor showcases ceramic tile flooring, upgraded granite countertops, stainless steel app

$550,000

7 beds5.5 baths3,314 sq ft

1865 Nice Ct, Kissimmee, FL 34747

4,792 sq ft lot • $697 HOA • 2 garage spots

OPEN SAT, 4AM TO 7PM

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Discover lifestyle and location at its finest in this beautiful Ridge Villas home! Just minutes from Walt Disney World Resort and Central Florida’s top attractions, this property offers comfort, convenience, and community amenities. * * Home Features: * * The home features a roof just 6 years old and a water heater replaced 2 years ago! * 3 bedrooms, 2 bathrooms, spacious living areas * Updated kitchen and bathrooms with modern finishes * Master suite with soaking tub and separate shower * Covered front porch and screened lanai for outdoor living * Two-car attached garage and whole-house water treatment system * Low-maintenance fenced backyard with Astroturf

$320,000

3 beds2 baths1,262 sq ft

7811 Myrtle Oak Ln, Kissimmee, FL 34747

5,445 sq ft lot • $5 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Don’t miss this amazing opportunity to buy this impressive 9-bedroom, 6-bathroom pool home, it is situated in the vacation community of Windsor at Westside, a popular choice for Disney area vacationers. That's fully furnished and turnkey ready, offering the perfect blend of luxury and convenience. This expansive home, ideal for short-term rentals, presents a fantastic investment opportunity. The property boasts a spacious, fully equipped kitchen for culinary enthusiasts, and a game room for entertainment. Enjoy the breathtaking lake view from the expansive pool deck, creating a serene and picturesque setting. With strategic proximity to Walt Disney World and major attractions, this re

$665,000

9 beds6 baths4,391 sq ft

1606 Lima Ave Ct, Kissimmee, FL 34747

6,098 sq ft lot • $552 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Happy Trails, FL
Welcome to a 9-Bedroom vacation short-term rental pool home is located just 15 minutes from Disney and is the perfect destination for a magical getaway in the community Windsor Westside. The home features a private pool and jacuzzi, game room, bedrooms with themes and lighting. Enjoy all the thrills of a theme park vacation in the comfort and convenience of your own private paradise. Take a dip in the sparkling pool, relax in the cabanas, or enjoy a game of volleyball or basketball take a ride down the lazy river. The clubhouse has a hot tub, fitness room, and a mini golf course. With such a variety of amenities, this property is the perfect place to live and play!

$649,000

9 beds6 baths4,391 sq ft

1634 Lima Ave, Kissimmee, FL 34747

6,534 sq ft lot • $552 HOA • 2 garage spots

Property at 2533 Oneida Loop, Kissimmee, FL 34747, 4 beds, 3 baths

$429,900

4 beds3 baths1,760 sq ft

2533 Oneida Loop, Kissimmee, FL 34747

Property at 2355 Silver Palm Dr, Kissimmee, FL 34747, 3 beds, 3 baths

$300,000

3 beds3 baths1,440 sq ft

2355 Silver Palm Dr, Kissimmee, FL 34747

Property at 436 Ocean Course Ave, Davenport, FL 33896, 4 beds, 3 baths

$449,800

4 beds3 baths1,914 sq ft

436 Ocean Course Ave, Davenport, FL 33896

Property at 8012 Spring Creek Dr, Kissimmee, FL 34747, 4 beds, 3 baths

$430,000

4 beds3 baths1,760 sq ft

8012 Spring Creek Dr, Kissimmee, FL 34747

Property at 1929 Nice Ct, Kissimmee, FL 34747, 5 beds, 4 baths

$478,000

5 beds4 baths2,492 sq ft

1929 Nice Ct, Kissimmee, FL 34747

Property at 7861 Palmilla Ct, Reunion, FL 34747, 9 beds, 10 baths

$1,494,900

9 beds10 baths4,792 sq ft

7861 Palmilla Ct, Reunion, FL 34747

Property at 2214 Wyndham Palms Way, Kissimmee, FL 34747, 6 beds, 4 baths

$699,900

6 beds4 baths2,713 sq ft

2214 Wyndham Palms Way, Kissimmee, FL 34747

Property at 1901 Nice Ct, Kissimmee, FL 34747, 5 beds, 4 baths

$495,000

5 beds4 baths2,492 sq ft

1901 Nice Ct, Kissimmee, FL 34747

Property at 2160 Antilles Club Dr, Kissimmee, FL 34747, 2 beds, 2 baths

$379,990

2 beds2 baths1,778 sq ft

2160 Antilles Club Dr, Kissimmee, FL 34747

Property at 2223 Wyndham Palms Way, Kissimmee, FL 34747, 4 beds, 3 baths

$419,000

4 beds3 baths1,834 sq ft

2223 Wyndham Palms Way, Kissimmee, FL 34747

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

$496,000

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

$349,000

3 beds3 baths1,440 sq ft

2382 Silver Palm Dr E, Kissimmee, FL 34747

Property at 1188 Castle Pines Ct, Reunion, FL 34747

$499,000

— beds— baths— sq ft

1188 Castle Pines Ct, Reunion, FL 34747

Property at 861 Desert Mountain Ct, Reunion, FL 34747

$199,900

— beds— baths— sq ft

861 Desert Mountain Ct, Reunion, FL 34747

Based on information submitted to the MLS GRID as of Wed Nov 12 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.

MLS Listings for Sale in Happy Trails

There are currently 9 mls listings for sale in Happy Trails at a median listing price of $805K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Happy Trails stay on the market for 68 days. Popular neighborhoods include Margaritaville Resort Orlando, Windsor Hills, Reunion, Championsgate, and Emerald Island. This map is refreshed with the newest listings in Happy Trails every 15 minutes.

In the past month, 1 home has been sold in Happy Trails. Happy Trails is a not walkable neighborhood in Four Corners with a Walk Score of 0. Happy Trails is home to approximately 202 people. Find your dream home in Happy Trails using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Happy Trails are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Happy Trails. If you're looking to sell your home in the Happy Trails area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Happy Trails with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Happy Trails, FL

Cities

Nearby Neighborhoods

Nearby Neighborhoods with MLS Listings

Nearby Cities with MLS Listings

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

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: 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, 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

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

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.