Kissimmee Homes with Trees/Woods View

Kissimmee Homes with Trees/Woods View

Welcome to Kissimmee, Florida—where the charm of small-town living meets the excitement of nearby attractions! Nestled in the heart of Osceola County, Kissimmee is renowned for its stunning landscapes, vibrant culture, and proximity to world-famous theme parks, making it a perfect destination for families and adventure-seekers alike.

One of the most enchanting features of Kissimmee is its abundance of homes that offer breathtaking views of lush trees and serene wooded areas. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes not only provide a tranquil escape from the hustle and bustle of daily life but also create a picturesque backdrop for your everyday moments.

Whether you're a nature enthusiast or simply appreciate the beauty of the outdoors, Kissimmee's tree-lined neighborhoods offer a unique blend of privacy and community. Enjoy leisurely strolls through scenic parks, explore nearby nature trails, or unwind in your backyard oasis surrounded by the natural beauty that this region has to offer.

With a diverse selection of homes available, each boasting its own distinct charm and character, you’re sure to find the perfect place to call home in Kissimmee. From cozy single-family residences to spacious family homes, the options are abundant. Embrace the lifestyle you’ve always dreamed of in a community that celebrates both nature and adventure. Come discover the magic of Kissimmee—where your dream home awaits amidst the trees!

Newest Kissimmee Homes with Trees/Woods View

2452 Winchester Boulevard, Kissimmee
$420,000
4 Beds ⋅ 2 Baths ⋅ Remington Pointe Ph 4 SubDv. ⋅ 34743 Zip Code
PRIVATE POOL, NO REAR NEIGHBORS, AND BEAUTIFUL CONSERVATION VIEWS YOUR OWN FLORIDA BACKYARD RETREAT AWAITS! Welcome to this beautiful 4 bedroom, 2 bathroom home offering over 1,800 square feet of living space in the desirable Remington Pointe community of Kissimmee! One of this home's most impressive features is its PRIVATE SCREENED-IN POOL OVERLOOKING A PEACEFUL CONSERVATION AREA WITH NO REAR NEIGHBORS, providing a wonderful sense of privacy and a relaxing natural backdrop. Imagine enjoying your morning coffee, spending sunny afternoons by the pool, or entertaining family and friends while surrounded by greenery instead of neighboring backyards! Inside, you'll discover a welcoming floor plan featuring an UPDATED KITCHEN, renovated approximately four years ago, offering a refreshed space for everyday living and entertaining. Additional highlights include a ROOF APPROXIMATELY 7 YEARS OLD WITH REMAINING WARRANTY, a WATER HEATER LESS THAN ONE YEAR OLD, and an A/C system approximately 10 years old. The outdoor living space offers even more value with a NEW POOL SYSTEM INSTALLED APPROXIMATELY ONE YEAR AGO and a POOL ENCLOSURE RE-SCREENED LAST YEAR! Location is another major advantage! Conveniently situated near Osceola Parkway and the Florida Turnpike, this home offers easy access to LAKE NONA, ORLANDO INTERNATIONAL AIRPORT, THE LOOP SHOPPING CENTER, restaurants, entertainment, and everything Central Florida has to offer. Complete with a 2-car garage, valuable improvements, and an exceptional backyard setting, this home delivers the perfect combination of comfort, convenience, privacy, and Florida living. NO REAR NEIGHBORS, CONSERVATION VIEWS, AND YOUR OWN PRIVATE POOL DON'T MISS THIS OPPORTUNITY!

2452 Winchester Boulevard, Kissimmee
1894 Cassidy Knoll Drive, Kissimmee
$540,000
5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to 1894 Cassidy Knoll, an exceptional home in the highly sought-after Kindred community featuring one of the largest and most desirable floor plans ever offered in the neighborhood. No longer available from the builder, this expansive design is known for its generously sized rooms, outstanding functionality, and flexible living spaces. The enormous first-floor primary suite offers exceptional privacy and convenience, complete with a massive walk-in closet and a unique, code-compliant doorway providing direct access to the garage. This thoughtful upgrade allows homeowners to come and go without disturbing the rest of the household. The home also features another spacious bedroom with a private en-suite bathroom, ideal for guests or multigenerational living, along with a versatile flex room that could serve as a formal dining room, home office, or potential sixth bedroom. What truly separates this home from others in Kindred is the extensive investment in aftermarket upgrades. The backyard features a massive 44-by-15-foot professionally installed paver lanai, offering approximately 660 square feet of outdoor entertaining space. A newly fenced backyard and a 7-by-7-foot shed/workshop, which conveys with the property, provide even more functionality. Inside, all carpeted areas have been replaced with premium luxury vinyl plank flooring. Exterior improvements include a widened driveway designed to accommodate larger vehicles and a paver walkway connecting to the driveway. The garage is equally impressive, featuring epoxy flooring, multiple 220-volt outlets suitable for electric vehicle charging equipment, a granite-topped utility sink, and additional washer and dryer hookups. While the main laundry room is upstairs, the garage provides the flexibility for a second laundry area. Two separate garage access points and a newer whole-home water softener and filtration system add even more convenience. Kindred offers an outstanding location just minutes from Florida's Turnpike, allowing residents to bypass much of the congestion along US 192. Shopping, dining, and everyday conveniences are nearby, while Walt Disney World is approximately 25 to 30 minutes away. The community also features its own K-8 school and resort-style amenities, including a swimming pool, clubhouse, fitness center, tennis courts, and basketball courts. A future commercial section is also planned within the community. With its rarely available floor plan, oversized bedrooms, first-floor primary suite, incredible outdoor entertaining space, and extensive upgrades, 1894 Cassidy Knoll offers a combination of size, comfort, and functionality that is increasingly difficult to find in today's new construction.

1894 Cassidy Knoll Drive, Kissimmee
2512 Brookstone Drive, Kissimmee
$452,000
4 Beds ⋅ 3 Baths ⋅ Remington Prcl I SubDv. ⋅ 34744 Zip Code
Virtually Staged. MUST SEE! Discover an exceptional combination of space, flexibility, and indoor-outdoor living in this impressive 2,469-square-foot home located in the gated Remington Golf Resort community. Featuring 4 bedrooms, a flexible lower level bonus room that can be used as a fifth bedroom, 3 full bathrooms, and a 3-car garage, this home offers the generous living space and versatility today’s buyers are searching for. Even better—a NEW ROOF will be installed before closing with a full price offer! Step inside to a bright, expansive floor plan with updated flooring (2023), refreshed lighting (2023), updated bathroom spaces, abundant natural light, and generously sized rooms throughout. The flexible bonus room provides valuable additional living space and can be used as a fifth bedroom, home office, media room, playroom, or guest retreat. HVAC installed 2021, Water heater 2023, appliances - stove, microwave, dishwasher and washer/dryer 2023. The spacious primary suite opens through French doors to a private deck—an ideal setting for morning coffee, evening relaxation, or your own outdoor retreat. A separate screened patio creates even more space to relax, entertain, and enjoy Florida living throughout the year. The freshly painted exterior makes a striking first impression with Web Gray, Extra White accents, and a Loyal Blue front door. Additional highlights include Ring cameras positioned at the front, side, and rear of the home; dusk-to-dawn front exterior lighting; storage; multiple flexible living areas; a 3-car garage; a low HOA; and the added value of a new roof before closing. Conveniently located near shopping, dining, major roadways, Central Florida attractions, and area recreation, this move-in-ready home delivers the space, updates, and lifestyle features that are increasingly difficult to find. Schedule your private showing—this is a must-see opportunity! Seller is Listing Agent.

2512 Brookstone Drive, Kissimmee
3058 Cadence Sound Lane, Kissimmee
$457,000
4 Beds ⋅ 2 Baths ⋅ Seasons At Big Sky Ph 2 SubDv. ⋅ 34744 Zip Code
Welcome to 3058 Cadence Sound Ln, Kissimmee, FL 34744! This beautiful 4-bedroom, 2-bathroom home offers a comfortable and functional layout with inviting living spaces designed for everyday living and entertaining. If features an upgraded Epoxy garage Floor and a whole- house purified water System, The well-planned floor plan provides plenty of room for family, guests, a home office, or additional flex space. Conveniently located in Kissimmee with easy access to major roadways, shopping, dining, schools, and the many attractions and amenities Central Florida. Don’t miss the opportunity to make this wonderful property your next home. Schedule your private showing today. Super LOW Association fee: $80.00 MONTHTLY..

3058 Cadence Sound Lane, Kissimmee
2330 Santa Lucia Street, Kissimmee
$355,000
3 Beds ⋅ 3 Baths ⋅ Monterey Village Ph 1 Unit 1 SubDv. ⋅ 34743 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2330 Santa Lucia Street in Kissimmee, a two-story, 3-bedroom, 2.5-bath home in the Lakeside community. Offering multiple gathering areas and inviting outdoor space, the home provides a flexible layout for relaxing, entertaining, and everyday living. Inside, the home features both a living room and family room, providing separate spaces for gathering, relaxing, or entertaining. Three bedrooms offer comfortable accommodations, while 2.5 bathrooms provide added convenience for residents and guests. Outside, a screen-enclosed in-ground pool creates a private setting for enjoying the Florida weather. The surrounding pool deck and patio provide plenty of space for lounging, outdoor dining, and entertaining. Beyond the pool area, the private yard offers an open canvas for personalization, whether envisioned as a garden, play area, or additional outdoor retreat. Located in the Lakeside area of Kissimmee, the home is convenient to neighborhood schools, shopping, dining, parks, and everyday services. The location also provides easy access to East Lake Tohopekaliga, major roadways, Orlando International Airport, and other Central Florida destinations.

2330 Santa Lucia Street, Kissimmee
4419 Azure Isle Way, Kissimmee
$465,000
3 Beds ⋅ 2 Baths ⋅ North Point SubDv. ⋅ 34744 Zip Code
Virtually Staged. Pond views through the trees, a screened paver patio, and mature fruit trees make the backyard a highlight of this three-bedroom, two-bath home in gated North Point. Inside, 1,941 square feet unfold across a single-story layout with separate front gathering rooms, an open kitchen and rear living area, and a primary suite with its own patio access. Fresh interior paint and recently updated major systems complement the home's architectural detail. A paver driveway and recessed entry lead to arched openings, decorative columns, and tray ceilings that give the front rooms definition without closing them off. The family room sits beside the foyer, with a bay-style arrangement of windows overlooking the front lawn. An adjoining dining room offers space for a full dining table, while ceramic tile carries through the main living areas. The kitchen brings color and character to the center of the home with blue cabinetry, stone counters, and pendant lighting. An island with raised breakfast-bar seating provides a place to gather while meals take shape, with additional cabinetry below. Open to the kitchen, the rear living room looks out toward the backyard, with sliding doors extending the gathering space onto the screened patio. At the rear of the home, the primary suite pairs a tray ceiling and hard-surface vinyl flooring with a walk-in closet and direct access outdoors. The en suite bath offers dual sinks, stone counters, a soaking tub, a separate shower, and an enclosed toilet area. Two additional bedrooms have built-in closets and share a bathroom with a separate vanity area and walk-in shower. A dedicated interior laundry room adds cabinetry, shelving, and a utility sink near the attached two-car garage. Out back, the screened patio has paver flooring, ceiling fans, and space for dining and lounging. A curved paver sitting area extends beyond the enclosure into the fully fenced lawn, where mature mango, lemon, and olive trees add another layer to the landscape. Trees along the rear outlook frame views toward the pond, giving the outdoor spaces an appealing sense of separation. The A/C system and water heater are both less than three years old, and the roof year is reported as 2013. An epoxy-coated garage floor completes the practical updates. North Point residents enjoy a community pool, with Boggy Creek Road and SR 417 providing connections to Lake Nona and the wider Orlando area. Some images have been virtually staged.

4419 Azure Isle Way, Kissimmee
2092 Cross Prairie Parkway, Kissimmee
$399,999
3 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 4b SubDv. ⋅ 34744 Zip Code
Virtually Staged. Experience refined Florida living at 2092 Cross Prairie Parkway, Kissimmee, a beautifully designed residence offering an exceptional combination of modern style, generous space, and effortless everyday living. Located in the sought-after Tohoqua community, this impressive home welcomes you with an abundance of natural light, creating an elegant sense of openness from the moment you step inside. Every area has been thoughtfully arranged to provide both sophistication and functionality, making this a home you'll be proud to own. The main level is designed for seamless living and entertaining, with an expansive open-concept floor plan that allows the kitchen, dining, and living spaces to flow beautifully together. A dedicated formal living room adds an elevated touch for hosting guests or enjoying quieter moments, while the versatile flex room offers endless possibilities. Transform it into a sophisticated home office, private library, stylish lounge, media room, or personalized retreat—the choice is yours. Indoor-outdoor living comes naturally with the covered lanai, providing a private extension of the home's living space. Whether you're enjoying a peaceful morning coffee, hosting an intimate dinner, or unwinding beneath the Florida sky, this inviting outdoor area creates the perfect setting for enjoying the lifestyle you've envisioned. A rear-entry garage with additional storage and built-in cabinetry adds both convenience and functionality, keeping the home organized without compromising its clean, polished aesthetic. Upstairs, a thoughtfully designed bedroom layout creates a private and comfortable retreat. The spacious primary suite offers an inviting sanctuary at the end of the day, with ample room to relax and recharge. Additional bedrooms provide exceptional flexibility for family, overnight guests, or dedicated personal spaces. An conveniently located upstairs laundry area adds a level of practicality that makes everyday routines feel effortless. Beyond your front door, the Tohoqua lifestyle elevates everyday living with an impressive collection of community amenities. Enjoy resort-style relaxation at the sparkling community pool, stay active in the fitness center, gather with friends at the welcoming clubhouse, or take advantage of the playground and sports courts. Designed with connection, recreation, and wellness in mind, Tohoqua offers an exceptional community atmosphere for today's modern homeowner. The location is equally impressive, placing you within convenient reach of shopping, dining, schools, major commuter routes, and Central Florida's world-renowned attractions. Enjoy easy access to the area's entertainment and recreational destinations while coming home to the comfort and tranquility of a beautifully planned community. More than a residence, 2092 Cross Prairie Parkway is an opportunity to embrace a lifestyle defined by space, style, flexibility, and convenience. Discover a home where modern design meets elevated everyday living—and where your next chapter in Central Florida begins.

2092 Cross Prairie Parkway, Kissimmee
3119 Fairfield Drive, Kissimmee
$429,900
4 Beds ⋅ 3 Baths ⋅ Strafford Park Ph 1 SubDv. ⋅ 34743 Zip Code
POOL HOME WITH 4 BED AND 3 BATH, ABUTS TO WOODS AND POND, NEWLY RENOVATED, SOLID COUNTER TOP. KITCHEN CABINET, NEW BATHROOOMS. THIS HOUSE IS IN CLOSE PROXIMITY TO AIRPORT, THEME PARKS, THE LOOPS, GROCERY SHOPPING AND ACCESS TO MAJOR HIGHWAYS.

3119 Fairfield Drive, Kissimmee
2557 Ames Haven Road, Kissimmee
$995,900
3 Beds ⋅ 2 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34744 Zip Code
FISH LAKE - 175 ft.+/- LAKEFRONT ACREAGE | RENOVATION OPPORTUNITY | DEVELOPMENT POTENTIAL | MULTI GENERATIONAL SPACE RARE OPPORTUNITY to own approximately 4.8 ACRES +/-with 175 +/-feet of TRUE LAKEFRONT on FISH LAKE in Kissimmee. Tucked behind a gated entrance and accessed by a beautiful, long driveway lined with mature natural oak trees, this property offers a level of privacy and tranquility that is increasingly difficult to find. The original 1952 three-bedroom, two-bath home has been lovingly held by the same owner since it was built and offers a unique opportunity for someone ready to bring their vision to life. While the home will likely require a full remodel, there are beautiful original details worth preserving, including wood flooring, cedar ceilings, and a lake-facing sunroom where you can take in the peaceful water views. The property also offers an impressive amount of existing utility and workspace, including a detached metal garage with three bays and a lean-to, a two-car attached carport, plus an additional enclosed bay/workshop attached to the carport. The property is serviced by two wells and two septic tanks. For those looking to create a private family compound or multigenerational retreat, the expansive acreage provides room to explore additional structures, subject to applicable zoning and permitting requirements. For investors and developers, the property carries a Future Land Use designation of LOW DENSITY RESIDENTIAL, with public water and sewer located very close to the property, creating an opportunity worth investigating with the appropriate governmental authorities. Whether your vision is to restore the existing home into a one-of-a-kind lakefront residence, create a private multigenerational property, or explore the property's development potential, 2557 Ames Haven Road offers acreage, lake frontage, privacy, and possibilities rarely found together in Kissimmee.

2557 Ames Haven Road, Kissimmee
1516 Sunset Pointe Place, Kissimmee
$1,775,000
5 Beds ⋅ 7 Baths ⋅ Sunset Pointe SubDv. ⋅ 34744 Zip Code
Welcome to 1516 Sunset Pointe Place, an extraordinary luxury estate nestled within the exclusive gated Sunset Pointe community. Perfectly positioned on a beautifully landscaped half-acre corner lot overlooking a tranquil pond, this exceptional residence offers 4,966 square feet of elegant living space, 5 spacious bedrooms, each with its own private en-suite bathroom, 2 half bathrooms, a media/bonus room, and an oversized 3-car garage. Designed for both sophisticated entertaining and everyday comfort, the home showcases soaring ceilings, designer chandeliers, rich wood, tile, and carpet flooring, three HVAC systems, and a spectacular chef's kitchen featuring premium appliances, custom cabinetry, an oversized island, luxury finishes, and a convenient pot filler above the cooktop. The owner's retreat offers a spa-inspired bath with a Jacuzzi tub, oversized walk-in shower, his-and-her walk-in closets, and an elegant mirror gallery. Outdoors, enjoy a screen-enclosed resort-style pool, summer kitchen, mature tropical landscaping, and peaceful pond views that create your own private oasis. Beyond the home, residents enjoy one of Central Florida's premier luxury lifestyles. Located just minutes from Lake Tohopekaliga (Lake Toho), Brownie Wise Park, and the award-winning St. Cloud Lakefront, you'll enjoy world-class boating, bass fishing, kayaking, waterfront parks, beaches, marinas, nature trails, dining, and year-round community events. The property is also ideally situated near NeoCity, Central Florida's internationally recognized 500-acre technology and innovation district, featuring semiconductor manufacturing, artificial intelligence, robotics, advanced research facilities, the future AdventHealth Medical Campus, the exciting NeoCity City Center, and NeoCity Academy, a National Blue Ribbon STEM school preparing students for tomorrow's high-tech careers. Conveniently located near Florida's Turnpike, US-192, US-441, Osceola Parkway, SR-417, Lake Nona Medical City, Orlando International Airport, Walt Disney World, premier shopping, fine dining, healthcare, and top-rated schools, this remarkable estate offers an exceptional blend of luxury, privacy, recreation, and long-term investment potential in one of Central Florida's fastest-growing and most desirable communities.

1516 Sunset Pointe Place, Kissimmee
3133 Riachuelo Lane, Kissimmee
$499,900
4 Beds ⋅ 3 Baths ⋅ Villa Sol Ph 1 Village 5 SubDv. ⋅ 34744 Zip Code
Virtually Staged. SPANISH-MEDITERRANEAN WATERVIEW OASIS WITH PRIVATE IN-LAW SUITE Located in the gated community of Villa Sol, this 4 Bed / 3 Bath single-story residence (2,351 sq ft heated) features a private pool, spa, and direct pond views—plus a dedicated, attached in-law suite with its own exterior entry. PROPERTY HIGHLIGHTS: In-Law / Guest Suite: Private exterior back entrance, separate bedroom, and full bath. Outdoor Living: Screen-enclosed heated pool and integrated spa set on an oversized lot with peaceful water views. Chef’s Kitchen: Granite countertops, multi-level breakfast bar, stainless steel appliances, and pendant lighting. Primary Suite: Vaulted ceilings, luxury vinyl plank flooring, walk-in closet, direct pool access, and en-suite with a jetted soaking tub and dual-sink vanity. Interior Design: Open layout, vaulted ceilings, polished porcelain tile, and architectural archways. LOCATION & COMMUNITY VALUE: Low HOA ($160/mo): Includes high-speed fiber internet, cable TV, and ground maintenance. Resort Amenities: Gated entry, clubhouse, fitness center, resort pool, tennis & basketball courts, and playground. Prime Location: Fast access to SR-417, US-192, Lake Nona Medical City, and MCO Airport. Zoned for top local schools.

3133 Riachuelo Lane, Kissimmee
1860 Saha Court, Kissimmee
$653,400
4 Beds ⋅ 3 Baths ⋅ Regal Oak Shores Unit 3 SubDv. ⋅ 34744 Zip Code
WELL-MAINTAINED HOME IN WELL-ESTABLISHED REGAL OAK SHORES...BEAUTIFUL TREES & GARDENS THROUGHOUT THIS DESIRABLE COMMUNITY; HOME FEATURES A LARGE LIVING PLAN WITH FORMAL LIVING & DINING ROOMS, FAMILY ROOM WITH WOOD-BURNING FIREPLACE OFF THE EQUIPPED KITCHEN, GLASS DOORWAYS TO THE SIZEABLE SCREEN ENCLOSED PATIO & POOL AREA, LARGE PAVED CIRCULAR DRIVEWAY & 3-CAR GARAGE FOR MULTIPLE VEHICLES - CARS, TRUCKS, BOATS, RVS & OTHER 'TOYS' WILL HAVE PLENTY OF SPACE, NEUTRAL CERAMIC TILE & CARPETS THROUGH THE HOME FOR EASE WITH DESIGN, SPLIT BEDROOMS OFFER PRIVACY ON BOTH SIDES OF THE HOME, STUDY/DEN/GAME ROOM IS SPACIUS AND HAS DIRECT ACCESS TO THE POOL AREA FOR GREAT ENTERTAINING OPTIONS, LOT IS JUST OVER 3/4 OF AN ACRE AND OFFERS PLENTY OF PLAY SPACE..THIS HOME IS A GEM WITH A GREAT LOCATION OFF KINGS HWY - CLOSE TO AREA SHOPPING, MAJOR ROADWAYS, MEDICAL, LAKEFRONT AMENITIES, RESTAURANTS & MORE.

1860 Saha Court, Kissimmee
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