Kissimmee Homes with Trail(s) Amenities

3 Beds ⋅ 2 Baths ⋅ Maple Chase At Cypress Woods SubDv. ⋅ 34758 Zip Code

Rare find in this neighborhood. Nestled in the sought-after Maple Chase community within Cypress Woods Poinciana, this stunning 3-bedroom, 2-bathroom home offers 1,876 sq ft on a generous lot — complete with a tranquil water view and no immediate rear neighbors, giving you rare privacy and open space in your backyard. Inside, two living and dining room combinations offer ultimate flexibility — perfect for formal entertaining, a family gathering space, a playroom, or a home office. The spacious layout adapts effortlessly to your lifestyle, with vinyl flooring, and no carpets. The extra-large bedrooms set this home apart, offering ample space for king-sized furniture and room to truly unwind. Minutes from dining, shopping, major highways, and Walt Disney World — this home blends suburban tranquility with Central Florida convenience. Schedule your showing today!

4442 Maple Chase Trail, Kissimmee

$654,900

7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 4 SubDv. ⋅ 34747 Zip Code

Turnkey short-term rental home, minutes to Disney! Discover a rare opportunity to own this stunning 7 bedroom, 6 bathroom pool home in the sought after Emerald Island Resort. Boasting the largest layout in the community at 3,667 sq. ft., this home is perfectly suited as a vacation getaway, income-generating investment, or forever family home. Enjoy unparalleled waterfront views framed by lush wooded backdrops, creating a serene and private retreat. The expansive screened lanai, which spans the length of the house, features a partially covered area ideal for year round entertaining. Relax by the sparkling South facing private pool and spa and take in the ultimate Florida lifestyle. Step inside to find a well designed floor plan with ample living space, ideal for families or hosting guests. The stylish kitchen is a chef’s dream with abundant cabinet and countertop space, a breakfast bar, and a breakfast nook overlooking the huge living room and pool, your new favorite spot for morning coffee or casual dining. The main floor also features two bedrooms, a formal dining room and the charming “Harry Potter” closet for extra fun and storage. The upper level is thoughtfully divided by two staircases. One leads to a loft sitting area and three themed bedrooms and the other leads to two additional themed bedrooms, all designed for comfort, as five of the bedrooms feature en-suite bathrooms, while the remaining two share a convenient Jack and Jill bath. The 3 car garage has been transformed into an entertainment haven with air conditioning, complete with a mini movie theatre (seating for 8) and a game room with a pool table. Updates include: A brand new roof (11/24), a new pool heater (04/24), newer exterior paint (01/22) and a newer A/C and heat pump (11/20), replumbed A/C lines (2024) and spa actuators replaced (2024). As part of this premier gated community, you’ll enjoy access to an impressive clubhouse with a resort-style pool, Tiki bar, fitness center, sauna, and sundry shop. Other amenities include tennis and pickleball courts, volleyball, basketball, bike rentals, and 11 acres of natural walking trails. The prime location is conveniently located near Orlando’s major attractions, including theme parks, outlet shopping, restaurants, Promenade at Sunset Walk, and Island H2O Live! water park. This home comes fully furnished and equipped with a strong rental history, ready to generate income as a short term rental or provide your family with a wonderful retreat. Schedule your tour today and experience the ultimate Florida lifestyle in this stunning property.

8557 La Isla Drive, Kissimmee

$4,495,000

4 Beds ⋅ 4 Baths ⋅ Celebration Village Unit 2 SubDv. ⋅ 34747 Zip Code

Welcome to Crescentwood, a truly rare offering in the Main Village of Celebration, a fully reimagined estate set across two homesites, creating a scale and presence seldom found within the community. Thoughtfully renovated with high-end materials and custom finishes throughout, the residence blends timeless architecture with modern luxury in a way that is both refined and highly livable. As you enter, the foyer welcomes you with substantial millwork, curated lighting, and a level of craftsmanship that immediately defines the residence. Formal and casual living spaces are elegantly proportioned, featuring beautiful tile flooring, layered ceiling details with integrated lighting, custom built-ins, French doors and oversized windows that fill the interiors with natural light. A beautiful sitting room framed by eight windows creates an inviting space bathed in natural light throughout the day. At the center of the home, the completely redesigned chef’s kitchen showcases custom Poggenpohl cabinetry, premium integrated appliances, dramatic illuminated stone surfaces, extensive preparation space, and a seamless connection to the adjacent living and dining areas, creating an ideal setting for both entertaining and everyday living. The owner’s suite serves as a luxurious private retreat with a spa-inspired bath finished in striking marble, custom fixtures, and refined architectural detailing. The suite is further enhanced by two walk-in closets, offering exceptional organization and boutique-style functionality. Each secondary bedroom are designed as private ensuite retreats complete with walk-in closets and beautifully updated bathrooms featuring elevated finishes and distinctive design details. The third-story movie room offers a true cinematic experience tucked away as a private entertainment space. Adding to the property’s versatility is a fully upgraded one-bedroom apartment featuring a private entrance, luxurious bath with a freestanding tub and separate shower, eat in space, living room and full-size washer and dryer offering ideal flexibility for guests, extended family or private office space. The main residence includes a two-car garage, while automotive enthusiasts and collectors will especially appreciate the separate temperature controlled oversized three-car garage. Designed with high ceiling height to accommodate vehicle lifts, the space has the potential to house up to six vehicles—an extraordinarily rare amenity within Celebration. The outdoor living experience is equally impressive, featuring a swimming pool and spa surrounded by elegant limestone pavers, summer kitchen, covered entertaining areas, and lush landscaping. A substantial stucco masonry wall encloses the grounds, creating an ultra-private backyard and pool setting rarely found within Celebration’s Main Village. Extensive landscape lighting beautifully illuminates the property and architectural details in the evening, enhancing the estate’s ambiance and presence after sunset. Multiple outdoor gathering spaces further elevate the estate-like atmosphere, creating the feel of a private luxury resort. Crescentwood represents a one-of-one opportunity within Celebration, offering the rarity of a double homesite, a fully renovated luxury residence and a level of finish and scale that is nearly impossible to replicate within the Main Village.

706 Golfpark Drive, Celebration

$444,000

5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code

Stunning Corner Lot Home with Exceptional Value! Don’t miss this incredible opportunity to own this spacious 5-bedroom, 3.5-bathroom home, priced below appraised value and offering up to $15,000 toward the buyer’s closing costs or rate buy-down. Designed with both comfort and functionality in mind, this beautiful home features a first-floor primary suite, providing privacy and convenience. The main level also includes a versatile flex room/den, perfect for a home office, playroom, study, or guest space. Upstairs, you’ll find a generous loft, ideal as a second living area, media room, game room, or entertainment space giving everyone room to relax and enjoy. Situated on a desirable corner lot, the property boasts a huge, fully fenced backyard with durable vinyl fencing, offering plenty of space for outdoor entertaining, pets, family gatherings, or even a future pool. With its spacious layout, premium corner location, oversized backyard, and outstanding buyer incentives, this home is an exceptional value that you won’t want to miss. Schedule your private showing today!

1876 Cassidy Knoll Drive, Kissimmee

$415,279

3 Beds ⋅ 2 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code

Under Construction. What's Special: Larger Lot | Covered Patio | Lake View | Spacious Kitchen. New Construction – October Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Thomas at 5772 Meads Bay Pond Road in Westview! A welcoming porch leads into an inviting foyer, where a private study offers the perfect space for working from home or pursuing hobbies. Beyond the foyer and rotunda, the heart of the home unfolds with a spacious great room, casual dining area, kitchen, and formal dining room thoughtfully connected for both everyday living and entertaining. Enjoy seamless indoor-outdoor living with a covered lanai overlooking the backyard. Tucked away for added privacy, the primary bedroom serves as a relaxing retreat and features two walk-in closets, an oval soaking tub, dual sink vanity, and walk-in shower. Two secondary bedrooms are situated off the rotunda and share a full bathroom, creating a comfortable space for family and guests. Welcome to Westview! Here, you can wake up to fresh morning air and the natural sounds of the outdoors in a thoughtfully planned community. You are surrounded by protected wetlands, forested uplands, ponds, open space, and miles of trails that invite you to explore right outside your door. Westview is ideally located near Poinciana Parkway in Kissimmee, Florida, placing you close to Lake Toho, Kissimmee Lakefront Park, Old Town, Walt Disney World, and more. This is a neighborhood where nature, convenience, and everyday adventure come together. Additional Highlights Include: a soaking tub with a separate shower in the primary bathroom, and a door into the primary bathroom. Photos are for representative purposes only. MLS#O6431007

5772 Meads Bay Pond Road, Kissimmee

$481,849

4 Beds ⋅ 4 Baths ⋅ Westview SubDv. ⋅ 34758 Zip Code

Under Construction. What's Special: No Rear Neighbors | Water View | Loft. New Construction - October Completion! Welcome to the Bermuda at 5766 Meads Bay Pond Road in Westview! This inviting two-story home blends comfort and functionality with a bright open-concept design. The spacious great room flows into the casual dining area and well-appointed kitchen featuring a large island and walk-in pantry. The first-floor primary suite offers a relaxing retreat with a spacious bathroom and walk-in closet, while a flex room near the foyer is perfect for a home office or hobby room. Upstairs, a versatile loft is accompanied by three secondary bedrooms and two full bathrooms. Enjoy outdoor living on the covered lanai, ideal for relaxing or entertaining. Welcome to Westview, a thoughtfully planned community surrounded by wetlands, ponds, open space, and miles of trails. Conveniently located near Poinciana Parkway, residents enjoy easy access to Lake Toho, Kissimmee Lakefront Park, Old Town, Walt Disney World, and more. Additional Highlights include: GE refrigerator, gourmet kitchen, and flush mount lighting package at great room. Photos are for representative purposes only. MLS#O6430976

5766 Meads Bay Pond Road, Kissimmee

$451,990

4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code

Under Construction. Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find bedroom two and a full bathroom. As you move upstairs you are greeted with a nice sized living space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet and an en suite bathroom with a double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1503 Beechmont Drive, Kissimmee

$469,990

5 Beds ⋅ 3 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code

Under Construction. Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find bedroom two and a full bathroom. As you move upstairs you are greeted with a nice sized living space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet and an en suite bathroom with a double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1876 Howard Mesa Drive, Kissimmee

$460,990

5 Beds ⋅ 3 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code

Kindred presents the Robie. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find bedroom two and a full bathroom. As you move upstairs you are greeted with a nice sized living space to utilize for work or play. Bedroom one is located just off the loft space and includes a spacious walk-in closet and an en suite bathroom with a double vanity. Three additional bedrooms share a second upstairs bathroom and linen closet. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Kindred, the Robie includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1864 Howard Mesa Drive, Kissimmee

$360,000

3 Beds ⋅ 2 Baths ⋅ Remington Prcl G Ph 2 SubDv. ⋅ 34744 Zip Code

Golf-course investment opportunity in Remington. This well-positioned three-bedroom, two-bath single-family home offers approximately 1,816 square feet of living area, a new roof installed in 2026, direct golf-course views and a covered rear lanai. The property is currently leased at $1,925 per month through February 28, 2027 and is being offered subject to the existing lease. Remington community amenities include golf, recreation facilities, pool, tennis courts and walking trails, subject to HOA confirmation. Conveniently located near Florida’s Turnpike, shopping, schools and dining. Seller will consider up to $5,000 toward buyer closing costs with an acceptable offer, subject to contract terms and lender approval. Property is being sold as-is with the buyer’s right to inspect.

119 Southampton Drive, Kissimmee

$374,900

2 Beds ⋅ 2 Baths ⋅ Solivita Ph 07a SubDv. ⋅ 34759 Zip Code

Step into this beautiful BOCA RATON model with its SERENE CONSERVATION VIEWS, watch the wild life in your backyard from the privacy of your own Lanai. This home offers WORRY FREE living as a NEW ROOF was installed in 2025, NEW HVAC installed in 2022 & NEW HOT WATER HEATER in 2017. This original OWNER has meticulously maintained & loved this home with its 8 FOOT DOORS & SLIDERS, CUSTOM window treatments, 5 1/4 INCH baseboards & interior drywall with its ROUNDED corners. The KITCHEN has rich wood UPPER CABINETS & LOWER cabinets offer convenient PULL-OUT DRAWERS. Enjoy your morning coffee in the BREAKFAST NOOK with lovely BAY WINDOWS, kitchen affords spacious PANTRY closet, STONE COUNTERS, kitchen ISLAND and extended BAR/COUNTER that opens onto the GREAT ROOM with accent pendant lighting. This 2 BEDROOM, 2 BATHROOM with versatile DEN home offers a wonderful sough after OPEN FLOOR PLAN. The rear SCREENDED (26.4 x 10.0) LANAI is accessed via Sliding glass door where you can appreciate nature, while entertaining family & friends. The PRIMARY BEDROOM is quite spacious & can access the Lanai as well. The ENSUITE BATHROOM affords a large WALK-IN CLOSET, RAISED VANITY with DUAL SINKS, private WATER CLOSET & WALK-IN SHOWER. BEDROOM 2 is conveniently located next to the HALL BATHROOM for convenience. The DEN is located off the foyer area and has DOUBLE DOORS for privacy. The LAUNDRY room features Washer/Dryer, separate UTILITY SINK & UPPER CABINETS for ADDITIONAL STORAGE. The garage has a scuttle with a easy to access PULL-DOWN ATTIC LADDER designed for safety. This homes exterior is well landscaped, has a sprinkler system (maintained by the HOA), front & rear GUTTERS & DOWNSPOUTS, brick paved driveway & walkway to the FRONT COVERED ENTRY. SOLIVITA is a PREMIER 55+ COMMUNITY with resort style living for ACTIVE ADULTS. Two Golf courses, 14 Pools, Dog Park, Kids Playground, Pickleball, Tennis, Softball diamond & OVER 200 clubs for all your social interaction with friends. The HOA maintains the LANDSCAPING & IRRIGATION systems for the common areas as well as individual homesites, FIBER Optic Internet & TV service. MANNED 24hour SECURITY GUARD located at all gates & AUTOMATED GATE ACCESS for residents via license plate reader & POLK County Sheriff provide private mobile patrol detail. Hospital, Banks, Pharmacy, Restaurants, Sprouts Grocery store & other shopping is located just outside the MAIN SOLIVITA GATE in the Poinciana Lakes Plaza. Schedule a showing & start living the "SOLIVITA LIFE" today.

280 Indian Wells Avenue, Kissimmee

$415,000

3 Beds ⋅ 3 Baths ⋅ Creekside At Boggy Creek Ph 1 SubDv. ⋅ 34744 Zip Code

Virtually Staged. Why wait to build when you can move right into this 2019 BUILT home in the GATED COMMUNITY of Creekside at Boggy Creek! Offering the perfect blend of space, style and energy efficiency, this 3-bedroom, 2.5-bath home features ***PAID-OFF SOLAR PANELS***, saving you money while adding long-term value. Just minutes from Lake Nona, this home also boasts a private FENCED BACKYARD, attractive landscaping, a paver driveway and fantastic curb appeal. Inside, TILE FLOORING flows throughout the main level where an OPEN CONCEPT living, dining and kitchen layout is filled with natural light, creating an inviting space for everyday living and effortless entertaining. The chef-inspired kitchen showcases granite countertops, STAINLESS STEEL APPLIANCES, pendant lighting, a large center ISLAND with seating and a spacious pantry. Sliding glass doors extend the living space to a COVERED LANAI overlooking the privacy-fenced backyard – perfect for relaxing, pets or weekend gatherings. Upstairs, a generous BONUS/LOFT offers flexible space for a media room, home office or playroom. All three bedrooms are thoughtfully located on the second floor, including your PRIMARY SUITE with twin windows that fill the room with natural light, a WALK-IN CLOSET and a dedicated en-suite bath. Two additional bedrooms share a full bath, and the conveniently located second-floor laundry room makes everyday chores a breeze. Wood laminate flooring enhances the primary bedroom and one secondary bedroom. Residents of Creekside at Boggy Creek enjoy a gated entrance, COMMUNITY POOL and playground just four homes away, plus an unbeatable location with quick access to Boggy Creek Road, Narcoossee Road, SR 417, shopping, dining, parks, lakes and all the conveniences of the thriving Lake Nona area. Zoned for “A-RATED” Narcoossee Middle School, this home delivers the lifestyle, location and features you have been searching for. Call today to schedule a tour ~ WELCOME HOME!

4366 Silver Creek Street, Kissimmee

Kissimmee Homes with Trail(s) Amenities

Newest Kissimmee Homes with Trail(s) Amenities