Kissimmee Homes with Rain Gutters Exterior Features

Kissimmee Homes with Rain Gutters Exterior Features

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the magic of Florida’s theme parks with the charm of a close-knit community. Nestled just south of Orlando, Kissimmee boasts a rich tapestry of culture, recreation, and natural beauty. Known for its year-round sunshine and warm tropical climate, residents enjoy an array of outdoor activities, from exploring the scenic Lake Tohopekaliga to indulging in the excitement of nearby Walt Disney World and Universal Studios.

Kissimmee is not just a destination for tourists; it’s a thriving community where families, retirees, and young professionals find their ideal homes. The city offers a diverse selection of real estate options, including charming single-family homes, modern condos, and spacious townhouses. One standout feature that many homes in Kissimmee offer is the inclusion of rain gutters.

Rain gutters are an essential exterior feature that protects your investment by directing rainwater away from the foundation of your home. This not only helps prevent water damage but also safeguards your landscaping and enhances the overall curb appeal of your property. Homes equipped with rain gutters provide peace of mind, ensuring that your living space remains dry and well-maintained, even during Florida's summer storms.

Whether you’re drawn to the enchanting attractions or the welcoming community atmosphere, Kissimmee is a place where you can truly feel at home. Explore our listings today and discover the perfect property that meets your needs and dreams in this delightful city!

Newest Kissimmee Homes with Rain Gutters Exterior Features

$175,000
2 Beds ⋅ 1 Baths ⋅ Pine Grove SubDv. ⋅ 34744 Zip Code
Don’t miss this opportunity near the corner of Carroll Street and Sample Street in Kissimmee. Situated on approximately 0.15 acres, the property is currently zoned RS-3 (Residential) and features an existing residential home. The property’s Future Land Use designation of Medium Density/Intensity may provide potential for future redevelopment or rezoning, subject to applicable governmental approvals. Take advantage of this opportunity in a convenient Kissimmee location.

2714 Sample Street, Kissimmee
$474,000
4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code
Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee
$280,000
3 Beds ⋅ 2 Baths ⋅ Windsong SubDv. ⋅ 34744 Zip Code
Investor Opportunity! This 3-bedroom, 2-bathroom home is situated on an oversized lot with a spacious fenced yard, tucked away on a quiet cul-de-sac in a desirable location. The property offers tremendous potential for the right buyer or investor seeking a renovation project with strong upside. This property needs renovations and is being sold in its current condition. With the right improvements, this home could be transformed into an excellent investment or future residence. HOA fees, property square footage, lot size, and all other property information should be independently verified by the buyer and/or buyer's agent. Don't miss this opportunity—schedule your showing today!

2114 Wind Jammer Court, Kissimmee
$359,900
3 Beds ⋅ 3 Baths ⋅ Tohoqua Ph 1 SubDv. ⋅ 34744 Zip Code
Welcome to this move-in ready three-bedroom, 2.5-bathroom townhome located in the desirable Tohoqua neighborhood. This home features an open-concept floor plan highlighted by soaring tall ceilings in the main living area, creating a spacious and airy feel throughout. The updated kitchen comes fully equipped with sleek stainless steel appliances, making it a functional and stylish space for cooking and everyday living. Upstairs, the primary bedroom serves as a comfortable retreat, complete with a large walk-in closet and an ensuite bathroom featuring a double-sink vanity. Ideally located, this property keeps you close to everything you need within a short drive. Enjoy the convenience of having schools very nearby, while taking advantage of easy access to all the shopping, dining, and amenities that Kissimmee and St. Cloud have to offer.

1752 Fulfillment Drive, Kissimmee
$470,000
4 Beds ⋅ 2 Baths ⋅ Oaks Ph 1 B2 SubDv. ⋅ 34746 Zip Code
2111 Eagleview Ct, Kissimmee, FL 34746 The Oaks – Golf & Lake Community Welcome home to this beautifully maintained 4-bedroom, 2-bath pool home nestled on a quiet cul-de-sac in the sought-after Oaks golf community. Enjoy front-row views of the 9th tee box along with a peaceful water and nature backdrop right from your screened lanai. Inside, soaring 10'6" ceilings and 18x18 tile set the stage in the open kitchen/family room combo, while separate formal living and dining rooms add versatility for entertaining. The well-appointed kitchen features a closet pantry, breakfast bar, crown-molded cabinetry, and stainless steel appliances. The thoughtful 3-way split floor plan places all four bedrooms for maximum privacy, and the spacious primary suite offers a large walk-in closet, dual sinks, garden tub, and separate shower. Step outside to your private, heated in-ground pool with screen enclosure and child safety fence — the perfect spot to soak up the Florida sunshine. A 2-car garage with drop-down attic stairs adds extra storage. Additional highlights: NEW ROOF (2024), newer water heater, rounded corners, chair rail, decorative columns, and lighted display niche. The Oaks offers resort-style amenities including an 18-hole championship golf course winding through century-old oaks, tennis and basketball courts, a playground, and community lake access with a boat ramp and lift on Lake Toho — plus RV/boat storage available for a fee. Conveniently located near shopping, dining, top schools, medical facilities, theme parks, and the airport. Don't miss this rare opportunity to enjoy the Florida lifestyle in a premier golf and lake community! Beds: 4 | Baths: 2 | Heated SF: 2,109 | Total SF: 2,925 | Year Built: 2005 | Lot: 0.18 acres | Garage: 2-car attached | Pool: Private, heated, screened | HOA: $288/yr | CDD: $543/yr | Flood Zone: X

2111 Eagleview Court, Kissimmee
$3,199,999
11 Beds ⋅ 13 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Welcome to an exceptional luxury estate located within the prestigious Reunion Resort, where sophisticated design, expansive living spaces, and resort-style entertainment come together to create an extraordinary Central Florida retreat. Spanning three thoughtfully designed levels, this impressive 11-bedroom, 11-bath residence has been curated for both luxurious everyday living and the highly desirable vacation rental market. The main level welcomes you with beautifully appointed living and dining spaces anchored by a spacious gourmet kitchen designed for entertaining. An impressive game room offers skeeball, basketball, air hockey, arcade games and shuffleboard, while multiple gathering areas throughout the home provide plenty of space for guests to relax and entertain. Step outside to your private resort-style pool and spillover spa surrounded by generous patio space, outdoor seating and a built-in barbecue—creating the perfect setting for enjoying Florida's year-round sunshine. Entertainment continues throughout the upper levels with a dedicated movie theater featuring reclining theater seating, fitness area, playroom, billiards room, dual gaming stations and multiple screened balconies. The home's extensive bedroom configuration includes multiple king suites along with imaginative themed bunk rooms, offering exceptional flexibility for large families and vacationing groups. Located within Reunion Resort's sought-after Legends Corner neighborhood, the property combines privacy with convenient access to the world-class attractions, dining, golf and entertainment that make the Orlando area one of the world's premier vacation destinations. Whether envisioned as an impressive personal retreat, second home or luxury vacation-rental investment, this remarkable Reunion estate delivers the space, amenities and entertainment today's resort buyer is looking for—all in one unforgettable property.

550 Muirfield Loop, Kissimmee
$495,000
4 Beds ⋅ 2 Baths ⋅ Casa Bella SubDv. ⋅ 34746 Zip Code
WELCOME HOME! Beautifully upgraded 4-bedroom, 2-bath, 2,168 sq. ft. KB Home with a 2-car garage, premium conservation lot, no CDD, and HOA $194.72 per quarter. This open-concept home features porcelain tile throughout, an upgraded kitchen with a microwave vented to the exterior, quartz island, granite finishes, upgraded to stage 3 Maple wood cabinetry, water filtration, 2 newer refrigerators and standup freezer. The spacious primary suite offers privacy, while upgraded bathrooms with extended granite countertops, sound and thermal insulation, illuminated closets, ceiling fans, Wi-Fi garage opener, and custom garage shelving add comfort and convenience. Enjoy your own screened Florida oasis with an 8,000-gallon, approximately 5-foot-deep gunite pool featuring automatic cleaning, lighting, and Wi-Fi controls. The screened patio includes a ceiling fan, lighting, hurricane screening, and a remote-controlled electric awning. The beautifully landscaped yard includes new St. Augustine grass, river rock, full fencing with critter-resistant netting, permanent landscape lighting, Wi-Fi-controlled irrigation, and exterior Nest cameras. Remote-controlled hurricane screens provide additional protection. Energy-efficient features include a 10.92 kW solar system with Enphase microinverters and a stated 25-year warranty. The home also includes Massey termite protection with in-ground bait stations. This home truly has so much to offer! Please refer to the MLS attachments for a detailed list of upgrades. Manuals and warranties will be provided upon request. Don’t miss this opportunity to own an exceptionally upgraded Florida home with a private pool, conservation views, and extensive features. Schedule your private showing today!

4521 Casablanca Avenue, Kissimmee
$580,000
4 Beds ⋅ 2 Baths ⋅ Southwood Estates SubDv. ⋅ 34746 Zip Code
Private 2-Acre Custom Home in Southwood Estates — No HOA! Welcome to your own private retreat in Southwood Estates, a small, desirable development of custom-built homes with no HOA. Situated on 2 fully fenced acres, this 4-bedroom, 2-bath home offers privacy, space, and an abundance of thoughtfully designed features. A private security gate and wooded setting create a peaceful atmosphere while still providing convenient access to everyday amenities. The home is designed for both comfortable living and entertaining, featuring a spacious Florida room with a built-in wet bar and JennAir grill, perfect for gatherings year-round. Step outside to the covered, screened lanai, complete with a 4-person ThermoSpas hot tub, where you can relax and enjoy the tranquil surroundings. The primary suite offers dual walk-in closets and a separate dressing area outside the primary bathroom. Bedroom 2 features built-in shelving, while Bedroom 3 includes a built-in desk, upper and lower cabinets, and file drawers, making it ideal for a home office. A bonus room attached to Bedroom 3 provides even more flexibility for an office, hobby room, guest space, or additional living area. Storage is abundant throughout the home, with many closets, an inside utility room with sink and cabinets, and an oversized 2-car garage. The property also includes multiple outbuildings. A separate workshop features a vinyl-tiled floor, built-in vacuum system, work table, tool cabinet, drill press, and table saw. The workshop equipment is available for purchase separately or may be negotiable with a full-price contract. Two additional storage sheds—one metal and one wood—provide even more space for tools, equipment, and outdoor storage. If you’re looking for acreage, privacy, no HOA, abundant storage, and a home designed for both everyday living and entertaining, this unique Southwood Estates property is a must-see!

3385 Woodberry Court, Kissimmee
$539,000
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
$324,990
3 Beds ⋅ 2 Baths ⋅ Poinciana Village 2 Nbhd 1 SubDv. ⋅ 34758 Zip Code
Welcome to this beautifully updated POOL HOME featuring an open floor plan, vaulted ceilings, and a spacious layout designed for comfortable everyday living and entertaining. The kitchen offers solid-surface countertops, stainless steel appliances, ample cabinetry, and an open connection to the main living areas. The primary suite features a walk-in closet and a spacious bathroom with dual sinks, a walk-in shower, and a Jacuzzi-style garden tub. The home has been thoughtfully updated throughout, including refreshed bathrooms with attractive tile finishes, and offers a clean, well-maintained interior that is ready for its next owner. Step outside to your own private retreat with a screened-in lanai and swimming pool, offering plenty of space to relax, entertain, or enjoy Florida living year-round. The POOL was resurfaced in 2024, and the pool pump was replaced in 2023. Additional recent improvements include a NEW ROOF and WATER HEATER in 2024, new window blinds in 2026, and fresh interior and exterior paint in 2026. Located in Poinciana Village 2 with no CDD, residents enjoy access to community amenities including internet and cable, a fitness center, community pool, playgrounds, parks, and recreational facilities. Conveniently located near shopping, dining, schools, medical facilities, and major roadways. With numerous recent updates, a private pool, and generous indoor and outdoor living space, this home is ready for its next owner. Schedule your private showing today.

1025 Derbyshire Drive, Kissimmee
$725,000
6 Beds ⋅ 6 Baths ⋅ Sonoma Resort At Tapestry Ph 1 SubDv. ⋅ 34741 Zip Code
Super rare opportunity to own a professionally designed home in the exclusive guard-gated resort community of Sonoma Resort at Tapestry! Lightly and gently used as a vacation retreat, this immaculate 6-bedroom, 6-bath contemporary residence has been meticulously maintained and is offered fully furnished. The interior was specially designed by acclaimed Brazilian-born Orlando interior designer Flavia Gueiros, whose signature blend of modern design and a light-toned palette gives the home a bright, clean, and elevated aesthetic throughout. Soaring high ceilings, an open floor plan, and a seamless living/dining combination create an airy, light-filled atmosphere from the moment you step inside. Ceramic tile flooring runs throughout, and the chef's kitchen features an eating space, dry bar, and generous storage. Enjoy your own private in-ground pool and spa overlooking serene water and pond views. The screened, covered lanai extends the living space outdoors, complete with a built-in outdoor kitchen and grill—ideal for entertaining or unwinding in the Florida sunshine. Additional highlights include a two-car attached garage, upper-level laundry, masonry fencing, tile roof, and a full suite of modern appliances. Sonoma Resort at Tapestry offers 24-hour guard-gated security, a resort-style pool, clubhouse, and fitness center. Ideally positioned near Orlando's world-famous attractions, dining, and major roadways, this community also permits short-term rentals—an excellent option for investors or vacation-home buyers. Built in 2018 and move-in ready, this turnkey designer home is a true standout. Schedule your private showing today!

2667 Calistoga Avenue, Kissimmee
$409,900
4 Beds ⋅ 2 Baths ⋅ Eagle Bay Ph 2 SubDv. ⋅ 34743 Zip Code
Welcome to this beautifully maintained, one-owner home conveniently located just 17 minutes from the Lake Nona VA Medical Center and approximately 15 minutes from Orlando International Airport. This 4-bedroom, 2-bath home offers a comfortable and functional layout, a two-car garage, and no carpet throughout. The home has been meticulously cared for and features several recent improvements, including fresh interior and exterior paint completed in July 2026 and a brand-new interior A/C unit, also replaced in July 2026. Additional features include a water softener, high-efficiency water heater, solar panels, a fully fenced yard, and an extended screened-in back porch that provides a comfortable space to relax, entertain, or simply enjoy the Florida weather year-round. With thoughtful upgrades, a well-maintained interior, and a convenient Central Florida location, this home is truly move-in ready and ready for its next owner.

2587 Tanner Terrace, Kissimmee
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