Kissimmee Homes with Gated Community - Guard Community Features

3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code

Welcome to 2725 Coupe Street, a fully furnished, turnkey 3-bedroom, 3-bathroom townhome located in the highly sought-after Regal Oaks Resort, just minutes from Walt Disney World and a short walk from the shopping, dining, and entertainment of Old Town Kissimmee. Whether you're searching for a vacation home, second home, or income-producing short-term rental, this property offers an outstanding combination of location, flexibility, and resort-style living. The thoughtfully designed floor plan is ideal for owners and vacation guests alike. The first floor features a queen bedroom and full bathroom, providing convenient accommodation without the need to use stairs. Upstairs you'll find a spacious king bedroom with private ensuite, along with a second bedroom featuring two twin beds and its own ensuite bathroom. The home also includes a fully equipped kitchen, comfortable living and dining areas, in-unit washer and dryer, multiple TVs, and is being offered fully furnished and ready for its next owner. Step outside to your private screened patio and hot tub, the perfect place to relax after a day at the theme parks. As an added advantage for investors, the property is already established as a vacation rental, giving a new owner the opportunity to continue operating in one of Central Florida's most popular tourism destinations. Regal Oaks provides an impressive collection of resort amenities, including a large, heated resort-style pool, dual waterslides, jacuzzi, poolside bar, restaurant, fitness center, tennis courts, business center, clubhouse, and gated entry. Even better, the resort amenities are only a short walk from the home. Location is where this property truly shines. Old Town is within walking distance, Walt Disney World is approximately 5 miles away, and Universal Orlando is approximately 13 miles away, with countless restaurants, shopping destinations, golf courses, and Central Florida attractions nearby. With its prime location, private hot tub, flexible 3-bedroom/3-bath layout, full furnishings, established vacation-rental use, and extensive resort amenities, this home offers the complete package. Schedule your private showing today and discover why Regal Oaks continues to be a favorite among Central Florida vacation-home owners and guests.

2725 Coupe Street, Kissimmee

$355,000

4 Beds ⋅ 3 Baths ⋅ Paradise Palms Resort Ph 2 SubDv. ⋅ 34747 Zip Code

A LITTLE PIECE OF PARADISE WITH RESORT LIVING & SPRINKLED WITH DISNEY MAGIC.....Imagine waking up to TRANQUIL WATER VIEWS, enjoying your morning coffee on the screened lanai, and ending the day relaxing by your private splash pool while watching HOT AIR BALLOONS LAUNCH NEARBY. This beautifully FULLY FURNISHED 4 BEDROOM, 3 FULL BATH TOWNHOME offers something truly special: a peaceful setting with NO HOMES DIRECTLY BEHIND YOU, yet just a 3 MINUTE WALK TO THE CLUBHOUSE AND RESORT POOL. FULLY FURNISHED AND TURNKEY, this home is beautifully equipped with everything you need for a comfortable stay. The thoughtfully designed layout features TWO SPACIOUS OWNER SUITES, with one conveniently located on the first floor and another upstairs, along with TWO ADDITIONAL THEMED BEDROOMS perfect for family, friends or guests. ZONED FOR SHORT TERM RENTALS, you can enjoy your own Florida getaway while generating rental income when you're away. Paradise Palms Resort offers some of the most exceptional amenities that will leave a LASTING IMPRESSION on you and your guests. Featuring a 9,500 SQ. FT. CLUBHOUSE, spectacular LAGOON STYLE POOL WITH WATER SLIDE, GROTTO & SPA, kiddie splash area, TIKI BAR & GRILL, STATE OF THE ART FITNESS ROOM, SAUNA, 50 SEAT MOVIE THEATER, GAME ROOM, TENNIS/PICKLEBALL, BASKETBALL, SAND VOLLEYBALL, SEVERAL PLAYGROUNDS AND A WALKING TRAIL, and more! AS A BONUS, CABLE, INTERNET & TRASH ARE ALSO INCLUDED IN THE HOA ASSESSMENTS. Located approximately 5.5 MILES TO THE GATES OF WALT DISNEY WORLD, with shopping, fine and casual dining just around the corner, and Orlando's world famous attractions close by. Whether you're looking for a HOME, SECOND HOME, VACATION GETAWAY OR INVESTMENT PROPERTY, this is your opportunity to own a little piece of paradise where RESORT AMENITIES, WATERFRONT SERENITY AND DISNEY MAGIC COME TOGETHER. ****Recent improvements include NEW LVP FLOORING, NEW POOL HEATER, NEW POOL PUMP AND NEW DISHWASHER (2026), NEW WASHER & DRYER (2025), along with a TWICE YEARLY AC MAINTENANCE PLAN! (Last AC maintenance completed on 4/27/2026.) With these recent updates and thoughtful maintenance, this beautiful townhome is move in ready and waiting for you! Call today to schedule your private showing!

8849 Candy Palm Road, Kissimmee

$750,000

5 Beds ⋅ 5 Baths ⋅ Bellalago Ph 4k SubDv. ⋅ 34746 Zip Code

Discover something special at 3855 Bowfin Trail—a meticulously maintained, one-owner residence on an oversized lot within Bellalago’s sought-after 24-hour guard-gated community. Offering five spacious bedrooms, five bathrooms, a private office, and a large upstairs bonus room, this home delivers the space and flexibility today’s buyers are searching for. Inside, soaring ceilings, eight-foot doors, tray ceilings, upgraded lighting, and abundant natural light create an immediate sense of elegance. The open-concept living area flows into a gourmet-inspired kitchen featuring quartz countertops, stainless-steel GE Profile appliances, an oversized island, crown molding, a spacious dinette, and a walk-in pantry. Generous closets and a large storage area beneath the staircase provide even more room to stay organized. The first-floor primary suite feels like a private retreat, with a spacious walk-in closet, dual vanities, a soaking tub, and an oversized spa-inspired shower. Upstairs are four additional bedrooms—two sharing a full bathroom and two offering private en-suite baths—along with a versatile bonus room perfect for a theater, game room, fitness studio, or second living area. Double sliding doors reveal a fully expanded covered lanai and beautifully maintained backyard—an inviting outdoor setting that must be experienced in person. Additional features include ceiling fans throughout the home and lanai, window blinds, UV lighting in every full bathroom, an under-sink water-treatment system, preparation for a whole-home water-treatment system, and concealed outlets and wiring for wall-mounted televisions. Sellers are willing to negotiate many of the furnishings. Bellalago offers community pools, fitness centers, recreational amenities, shopping, and a private boat ramp with access to Lake Tohopekaliga—all approximately 30 minutes from Walt Disney World, Universal Orlando, and Central Florida’s famous attractions. The photographs only tell part of the story. Schedule your private tour of 3855 Bowfin Trail and experience its space, thoughtful upgrades, and resort-style setting for yourself.

3855 Bowfin Trail, Kissimmee

$475,000

2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code

Beautifully renovated 2 bedroom and 2 bathroom condo offering the look, feel, and finishes of new construction! ACTIVE TRANSFERABLE PLATINUM REUNION MEMBERSHIP AVAILABLE to the next owner. As you enter you immediately notice the EXPANSIVE open concept living and dining areas. This unit has been outfitted with luxury vinyl planking and HIGH END fixtures throughout. The NEW kitchen includes hardwood cabinets with crown moulding, quartz countertops and stainless appliances. The primary bath has had TWO spacious closets added with built-ins, dual vanity sinks, custom cabinets, and a walk-in shower. The guest bedroom has two closets within the room for added storage and the guest bathroom also has had a closet added with built-ins, dual vanity sinks, custom cabinets and walk-in shower. A reconfigured laundry room with NEW washer and dryer and a NEW wash sink for your convenience. The large windows and sliding doors provide an abundance of natural light throughout the day! As you step outside onto the patio you find fantastic panoramic views of the resort that include the driving range and the signature Tom Watson course. In addition you will enjoy watching the nightly FIREWORKS from the Disney Theme parks! This is a fantastic opportunity to utilize this condo for a primary residence, second home or vacation rental. You will appreciate the welcoming smiles of the doormen as you arrive home. There is also valet parking & front desk concierge as well as Starbucks coffee & gift shop available for your convenience. The Reunion Grande also houses many of the resorts dining options where you can enjoy fresh Sushi at the Lobby Bar, an amazing Steak at 7593 Chophouse or dinner with a view at Eleven the Rooftop restaurant. The Reunion Grande is also located adjacent to the Clubhouse with dining options and the golf pro shop for the Watson and Palmer Signature Courses. The Cove is walking distance which includes a large infinity pool, two jacuzzi tubs, bocce ball, outdoor bar & grille and fitness center. Reunion Resort is a one of a kind 2300 acre Resort and Golf community that has many amenities including a waterpark complete with water slides, lazy river, zero entry pools & food and beverage service, 3 award-winning golf courses designed by the legends of golf (Palmer, Watson & Nicklaus), 11 pools throughout the community, mini putt putt golf, world class tennis courts, pickleball courts, playgrounds, dog parks, golf cart & bike rentals and several on-site restaurants to include fine dining. Reunion Resort is located just 6 miles to Disney and the parks, and a short drive to the Orlando International Airport.

7593 Gathering Drive Unit 707, Reunion

$350,000

3 Beds ⋅ 2 Baths ⋅ Ventura At Windsor Hills Condo Ph 3 SubDv. ⋅ 34747 Zip Code

A polished, themed getaway just minutes from Disney World, this well-maintained 3-bedroom, 2-bath condo in Ventura at Windsor Hills combines TURN-KEY CONVENIENCE with the AMENITIES of a proven RESORT-STYLE ~ SHORT TERM RENTAL community! A BRAND NEW A/C (2026) adds peace of mind and the HOA maintains the building exteriors. Inside, this is the largest 3-bedroom floor plan, offered FULLY FURNISHED with stylish décor and sleeping accommodations for up to eight. The Disney-inspired theming is tasteful and understated, with fun details woven into a modern, sophisticated design that appeals to vacation guests and owners alike. The UPDATED KITCHEN features quartz countertops, refinished cabinetry and an open layout connecting via a passthrough to the living and dining areas. Step outside to the SCREENED BALCONY for additional space to relax and enjoy the Florida weather. Whether you are searching for a short-term rental INVESTMENT or home away from home near Disney, this property is ready to enjoy! Windsor Hills delivers an impressive lineup of amenities, including a recently upgraded RESORT POOL & WATER PARK, tennis, pickleball, basketball, sand volleyball, putting green, ping pong, cornhole, arcade, game room, fitness center, workspace, restaurant and market. Convenient access to SR-429, I-4 and W Irlo Bronson Memorial Highway puts shopping, dining, resort destinations, theme parks and Central Florida attractions within easy reach. Furnished, themed and positioned in one of Kissimmee's sought-after vacation rental communities – this one checks all the boxes for a Central Florida investment or personal getaway. Call today to schedule a tour!

2778 Almaton Loop Unit 204, Kissimmee

$250,000

4 Beds ⋅ 3 Baths ⋅ Venetian Bay Villages Condo Phase 3 SubDv. ⋅ 34741 Zip Code

EXCELLENT INVESTMENT OPPORTUNITY OR FLORIDA VACATION HOME! Welcome to 2260 San Vital Dr #108, a spacious 4-bedroom, 3-bathroom residence located in the desirable guard-gated resort community of Venetian Bay Villages in Kissimmee. This property offers an excellent combination of comfort, convenience, and investment potential, with short-term rentals permitted. “Beautifully updated property featuring three completely renovated bathrooms with new flooring. The entire second floor has also been upgraded with new flooring, replacing all previous carpeting. The home features a desirable dual-primary-suite floor plan, with one primary en-suite conveniently located on the first floor and a second private primary suite upstairs. The main level offers an open living and dining area with high ceilings and abundant natural light, along with a functional kitchen and breakfast bar. Two additional bedrooms share a full bathroom, providing plenty of space for family and guests. Property is offered unfurnished. Venetian Bay Villages offers an impressive selection of resort-style amenities, including 24/7 guard-gated security, four community swimming pools, a clubhouse, fitness center, movie theater, game room/arcade, business center, tennis and basketball courts, volleyball, playgrounds, picnic areas, and walking trails. Ideally located near Central Florida's world-famous attractions, shopping, dining, and major roadways, this property provides convenient access to Disney, Universal Orlando, SeaWorld, and everything the Orlando/Kissimmee area provides. With short-term rentals permitted, including Airbnb/VRBO, this property is an excellent option for investors, a vacation home, or a primary residence. Schedule your private showing today and discover all that Venetian Bay Villages provides!

2260 San Vital Drives Unit 108, Kissimmee

$449,900

4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake 5 SubDv. ⋅ 34746 Zip Code

Welcome to this exceptional investment opportunity in Cove at Storey Lake, one of Kissimmee’s most desirable resort-style communities. This beautifully maintained 4-bedroom, 3-bath townhome offers the perfect combination of comfort, location, and rental potential. Featuring an open-concept layout, modern kitchen with stainless steel appliances, spacious bedrooms, and a private screened-in patio with a splash pool, this home is designed to provide an unforgettable experience for guests and families. The thoughtfully designed floor plan includes two king suites, a full-size bedroom, and a themed bunk room, comfortably accommodating large groups and vacation guests. Cove at Storey Lake offers incredible resort amenities including multiple clubhouses, resort-style pools, lazy river, water slides, splash pad, fitness center, mini golf, playgrounds, sports courts, and more. The gated community provides the ideal vacation lifestyle while allowing short-term rentals, making this property a fantastic option for investors or those looking for a second home. Located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld, shopping, dining, and major attractions, this property places guests right in the heart of Central Florida’s world-famous vacation destination. Enjoy easy access to The Loop, Orlando International Airport, and all that Kissimmee and Orlando have to offer. Whether you are looking for a high-performing vacation rental, a second home, or a long-term investment, this property delivers an outstanding opportunity in a prime location.

2461 Reading Trail, Kissimmee

$469,900

4 Beds ⋅ 3 Baths ⋅ Reunion Village Ph 4 & 5 SubDv. ⋅ 34747 Zip Code

Built in 2024, this two-story home offers four bedrooms, two full bathrooms, one half bathroom, 1,811 square feet of heated living space, and a two-car attached garage. The open-concept main level features luxury vinyl flooring, high ceilings, ceiling fans, stone countertops, a kitchen island, pantry, dining area, and comfortable living space. The kitchen includes a refrigerator, range, microwave, dishwasher, disposal, and ice maker. Upstairs, the primary suite features a walk-in closet, while the additional bedrooms and bonus space provide flexibility for guests, a home office, or recreation. Enjoy covered front and rear porches and resort-style community amenities, including gated access, a clubhouse, fitness center, community pool, tennis courts, cable TV, and internet. The property is currently operated as a short-term rental. Buyers should independently verify current HOA rental restrictions, licensing requirements, future reservation transferability, amenity access, HOA fees, and CDD information. Schedule your private showing today.

7853 Somersworth Drive, Kissimmee

$833,000

Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code

*** TRIPLE LOT*** LOTS 69, 70, & 71. This is a unique opportunity to own the last remaining huge triple lot on Muirfield Loop, situated at Legends Corner in Reunion Resort. These combined give a spectacular 176 feet frontage so you can build a huge & magnificent home or investment property, with a spacious driveway. The rear of the lots back on to conservation providing peace & privacy. These lots are being sold contingent on all lots being purchased together. They have Reunion membership. Reunion provides the very best in golf with three championship golf courses, tennis, a fabulous water park, & restaurants, just 6 miles from Disney, making this community extra special on many levels. Please call me today for more information.

570 Muirfield Loop, Reunion

$833,000

Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code

*** TRIPLE LOT*** LOTS 69, 70, & 71. This is a unique opportunity to own the last remaining huge triple lot on Muirfield Loop, situated at Legends Corner in Reunion Resort. These combined give a spectacular 176 feet frontage so you can build a huge & magnificent home or investment property, with a spacious driveway. The rear of the lots back on to conservation providing peace & privacy. These lots are being sold contingent on all lots being purchased together. They have Reunion membership. Reunion provides the very best in golf with three championship golf courses, tennis, a fabulous water park, & restaurants, just 6 miles from Disney, making this community extra special on many levels. Please call me today for more information.

564 Muirfield Loop, Reunion

$833,000

Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code

*** TRIPLE LOT*** LOTS 69, 70, & 71. This is a unique opportunity to own the last remaining huge triple lot on Muirfield Loop, situated at Legends Corner in Reunion Resort. These combined give a spectacular 176 feet frontage so you can build a huge & magnificent home or investment property, with a spacious driveway. The rear of the lots back on to conservation providing peace & privacy. These lots are being sold contingent on all lots being purchased together. They have Reunion membership. Reunion provides the very best in golf with three championship golf courses, tennis, a fabulous water park, & restaurants, just 6 miles from Disney, making this community extra special on many levels. Please call me today for more information.

574 Muirfield Loop, Reunion

$2,095,000

7 Beds ⋅ 10 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code

Active Club Membership! Located in Legend’s Corner at Reunion Resort, 445 Muirfield Loop is a fully furnished and turnkey 7-bedroom, 7-full-bathroom, 3-half-bathroom home offering approximately 6,400 square feet of heated living space, plus an additional 500 sq ft under air in the converted garage arcade. The home features a south-facing pool area overlooking the 14th hole of the Jack Nicklaus Tradition golf course and is designed with multiple indoor and outdoor living and entertainment spaces. A two-story foyer with glass railing opens to an expansive living and dining area with direct views toward the pool and golf course. The kitchen features white cabinetry, a gas cooktop, double wall ovens, built-in refrigerator and freezer, microwave, ice maker, and two dishwashers. The converted garage serves as a large arcade, while the second floor includes a dedicated theater with projector and 12 leather recliners, along with a separate game room featuring a billiards table, wet bar, additional arcade games, and seating area. The game room opens to a large second-floor balcony overlooking the pool and golf course. Each of the seven bedrooms has its own private bathroom. The first-floor primary suite includes sliding doors with direct access to the pool area, while two additional bedrooms are also located on the first floor. Upstairs, a second primary suite opens directly to the balcony. Harry Potter- and Snow White-themed bedrooms are connected by a dedicated playroom, and a seventh bedroom completes the second floor. The home also includes a first-floor laundry room, an additional upstairs laundry closet, and powder rooms on both levels. Outside, the south-facing heated pool and spa are surrounded by ample deck space. A large covered outdoor living and dining area with summer kitchen provides space for entertaining while taking advantage of the golf course setting. A pool bath is accessible directly from the exterior for added convenience. Spanning 2,300 acres just 7 miles south of Walt Disney World, Reunion Resort is the only destination in the world featuring 3 signature golf courses designed by Jack Nicklaus, Arnold Palmer and Tom Watson. Reunion is also home to the Leadbetter Golf Academy. Onsite dining options include Eleven, 7593 Chophouse, Traditions, Grande Lobby Sushi Bar, the Clubhouse, the Cove, and Drifters at the waterpark. The water park features a lazy river, slides, outdoor games, and an aquatic playground. The gift shop in the Grande offers sundries and Starbucks coffee. Complimentary shuttles to the Disney transportation and ticket center leave from the Grande daily. Additional amenities include Camp Reunion, the tennis and pickle ball center, bocce ball, mini golf, foot golf, fitness center, playgrounds, dog park, various community pools including a roof top pool on the 11th floor of the Grande, and more. Zoning for short term rentals allows homeowners to rent their property by the night providing a great opportunity for investors. Reunion also works great as a primary residence or a private vacation retreat. The resort offers three separate 24 hour guard gated entries and one owner/resident only entry.

445 Muirfield Loop, Reunion

Kissimmee Homes with Gated Community - Guard Community Features

Newest Kissimmee Homes with Gated Community - Guard Community Features