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 charm of small-town living with the excitement of nearby attractions. Nestled just south of Orlando, Kissimmee is renowned for its stunning landscapes, rich cultural heritage, and proximity to world-famous theme parks like Walt Disney World and Universal Studios. Whether you're drawn to the area's lush natural beauty, bustling downtown, or the warm, welcoming community, Kissimmee offers something for everyone.

As you explore the diverse neighborhoods of Kissimmee, you'll discover a wide range of homes designed to meet your lifestyle needs. One standout feature of many properties in this area is the inclusion of rain gutters. These essential exterior features not only enhance the aesthetic appeal of your home but also serve a practical purpose. Rain gutters effectively channel rainwater away from your property, protecting your foundation and landscaping from water damage. This thoughtful addition ensures that your home remains in pristine condition, even during Florida's rainy season.

Kissimmee's real estate market boasts a variety of homes with rain gutters, catering to families, retirees, and everyone in between. From charming single-family residences to modern townhomes, these properties are designed with both functionality and style in mind. With the added benefit of rain gutters, you can enjoy peace of mind knowing that your investment is protected.

Discover your perfect home in Kissimmee, where the sun shines bright, and the possibilities are endless. Embrace a lifestyle filled with adventure, community, and the comfort of a well-maintained home.

Newest Kissimmee Homes with Rain Gutters Exterior Features

$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. One or more photo(s) was virtually staged. Welcome to this Spanish-Mediterranean single-family home located in the gated community of Villa Sol in Kissimmee! Offering 4 bedrooms, 3 full bathrooms, a 2-car garage, and 2,351 sq. ft. of heated living space, this single-story residence combines flexible living with pond views. A key feature of the home is the attached in-law suite with its own private exterior back entrance, bedroom, and full bathroom. Inside, an open floor plan is filled with natural light, featuring polished porcelain tile flooring, vaulted ceilings, and architectural archways. The kitchen includes granite countertops, a multi-level breakfast bar, light grey cabinetry, stainless steel appliances, and pendant lighting. The primary bedroom suite offers luxury vinyl plank flooring, vaulted ceilings, a walk-in closet, and sliding glass door access to the pool deck. The en-suite bath features a dual-sink granite vanity, light grey cabinetry, a corner jetted soaking tub, and a separate glass-enclosed shower. Step outside to your private rear screen enclosure featuring an in-ground pool and integrated spa overlooking serene water views on an oversized lot. Villa Sol community amenities include a gated entry, clubhouse, fully equipped fitness center, resort-style community pool, tennis courts, basketball court, and playground, with cable TV and high-speed internet included in the low HOA fee. Perfectly positioned in Kissimmee, this home offers quick access to SR-417, US-192, and Boggy Creek Road, putting Lake Nona, Medical City, and Orlando International Airport (MCO) just a short drive away. Zoned for East Lake Elementary, Neptune Middle, and Tohopekaliga High School, you are also minutes from local shopping centers, dining, Lake Tohopekaliga parks, golf courses, and Central Florida's major theme parks and attractions. Schedule your private tour today!

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
$385,000
3 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr F SubDv. ⋅ 34744 Zip Code
Beautiful 3 Bedroom/2 Bathroom Home with a Private Pool. This home includes newer floors, newer plumbing (i.e. hot and cold water lines replaced to new), newer roof (2018), a screened pool, stainless steel appliances, updated AC May 2021, newer ceiling fans, and a 2 car garage. It is located in a golf course community which features a gated entry, community pool, walkways, tennis courts, shopping marts, an elementary school, a charter school, clubhouse, playgrounds, fitness center, basketball courts and much more. Close to shopping, dining and entertainment. Pet friendly. This property won't last! Call today!

209 Westmoreland Circle, Kissimmee
$2,250,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34744 Zip Code
Nearly 6 acres of private waterfront on beautiful East Lake Tohopekaliga (East Lake Toho)—an exceptionally rare opportunity to own one of Central Florida's most unique waterfront properties. Offering direct lake access, majestic oak trees, and an existing residence, this remarkable property is the perfect setting to build your dream waterfront estate, create a private family compound, or secure a one-of-a-kind investment. The existing home provides immediate use while you design your future vision. With no HOA, you'll enjoy the freedom to create the lifestyle you've always imagined, with room for boats, RVs, detached garages, workshops, expansive outdoor living, and more. Whether your vision is a custom waterfront estate, a multi-generational family compound, or exploring future development or rezoning opportunities, this remarkable property offers exceptional flexibility, subject to zoning, county approvals, and buyer due diligence. Enjoy world-class boating and fishing, breathtaking sunsets, abundant wildlife, and the peaceful privacy that only waterfront acreage can provide—all while being just minutes from Lake Nona, Medical City, Orlando International Airport, SR-417, Florida's Turnpike, shopping, dining, and entertainment. Large waterfront parcels of this size in such a prime location rarely come to market. Whether you're looking to build your forever home, create a legacy property for generations to enjoy, or invest in one of Central Florida's most desirable waterfront locations, this is an opportunity that is becoming increasingly difficult to find. Nearly 6 private waterfront acres. No HOA. Endless possibilities. A place to build not just a home—but a legacy.

2794 Holiday Woods Drive, Kissimmee
$565,000
4 Beds ⋅ 3 Baths ⋅ Georgetown At Celebration Condo SubDv. ⋅ 34747 Zip Code
Welcome to Georgetown at Celebration, where style, comfort, and convenience come together in one exceptional home. This beautifully updated three-story townhome features a rear-entry two-car garage, four spacious bedrooms—including a first-floor bedroom perfect for guests, a home office, or multigenerational living—and 2.5 bathrooms. The thoughtfully designed floor plan offers an open kitchen, dining, and family room combination, along with a separate living room that provides additional space to relax or entertain. As a desirable end unit, you'll also enjoy an impressive 24-foot covered porch, the perfect spot to unwind and enjoy the fresh Florida air. Inside, you'll find numerous updates including luxury vinyl plank flooring, tile in select areas, granite countertops, fresh interior paint, and a true move-in-ready condition. Georgetown residents enjoy outstanding amenities including a clubhouse, resort-style swimming pool, tennis and pickleball courts, a fitness center, and a playground. Located in the heart of Celebration (celebration.fl.us/amenities/), you'll be just moments from charming restaurants, boutique shopping, year-round entertainment, scenic walking trails, and world-famous attractions—allowing you to enjoy the unique experience of living in a destination. Best of all, the homeowners association maintains the exterior of the property, providing a low-maintenance lifestyle so you can spend more time enjoying everything Celebration has to offer. This is truly a home that must be seen to be fully appreciated.

236 Celebration Boulevard Unit 236, Celebration
$425,000
4 Beds ⋅ 2 Baths ⋅ Mallard Creek SubDv. ⋅ 34743 Zip Code
Welcome home to this beautifully remodeled 4 bedroom, 2 bathroom split floor plan, offering both privacy and an open, inviting flow between the main living areas. Solid block construction, a newer roof (2022), Interior Paint (2026), Exterior Paint (2026), Updated Kitchen (2026), completely remodeled bathrooms (2026) and a 6-year-old HVAC system giving you peace of mind for years to come. Step inside to find luxury vinyl plank flooring throughout, complemented by fresh interior and exterior Sherwin Williams paint. The completely reimagined kitchen is a showstopper, featuring soft-close cabinetry, a hidden pull out trash can bin, a built-in spice rack, solid stone countertops, and a stylish island topped with butcher block for a warm, modern touch. Both bathrooms have been fully remodeled with contemporary fixtures and eye catching Venetian plaster accent walls, adding a designer feel throughout the home. Updated light fixtures shine throughout the home. Nothing in this home was left untouched, even the 2-car garage received some love and has been freshly painted for a clean, finished look including upgraded smart home accessories. Outside, unwind on the screened rear porch, the perfect spot for morning coffee or evening relaxation giving you outdoor living space to enjoy year round. Ideally located just minutes from major roadways, shopping, dining, top rated schools, and Orlando International Airport, this home offers the perfect blend of comfort, style, and convenience. Don't miss this move in ready gem, schedule your showing today!

2104 Mallard Creek Circle, Kissimmee
$469,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code
GORGEOUS 'ONCE UPON A LIME' 3 Bed 3 Bath COTTAGE with Additional Bonus Room at Margaritaville Resort Orlando! This AMAZING Two-Floor Home features an Open Concept Living and Dining Room with Ceiling Fan, a Kitchen with QUARTZ Countertops, Stainless Steel Appliances, Side By-Side Washer and Dryer and Abundant Natural Light. Each of the Three Bedrooms and Living Room has Ceiling Fans, One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Gorgeous Landscaping, Palm Trees and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares Package with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8061 Lost Shaker Lane, Kissimmee
$585,000
4 Beds ⋅ 3 Baths ⋅ Ashley Cove Unit 1 SubDv. ⋅ 34744 Zip Code
Nestled on an oversized corner lot in the gated community of Ashley Cove, this spacious 4-bedroom, 3-bathroom pool home with an upstairs bonus room offers generous living space, beautiful water views, and a layout designed for both everyday comfort and entertaining. A double-door entry opens to a bright interior with tall ceilings, crown molding, and multiple living and dining areas. Large sliding glass doors connect the main living space to the screened pool area while bringing in natural light and showcasing the pond views beyond. The kitchen features abundant cabinetry, solid-surface countertops, stainless steel appliances, built-in ovens, a center prep island, breakfast bar seating, a pantry, and a breakfast nook overlooking the pool. The primary suite is privately positioned and includes wood flooring, tray ceilings, direct access to the lanai, and an en-suite bathroom with dual vanities, a soaking tub, a separate walk-in shower, and a walk-in closet. Three additional bedrooms and two full bathrooms provide plenty of space for family and guests. Upstairs, the spacious bonus room offers flexible use as a media room, game room, home office, fitness area, or guest space. Outside, the expansive screened lanai surrounds the pool and spa with plenty of brick-paver decking for outdoor seating, dining, and entertaining. The corner lot and pond views create a peaceful backdrop with added space around the home. Additional features include an indoor laundry room, generous storage, mature landscaping, and a driveway that leads to the garage along the side of the property. Conveniently located near shopping, dining, major roadways, Lake Tohopekaliga, Downtown Kissimmee, Orlando International Airport, and Central Florida attractions, this home offers an impressive combination of space, privacy, and waterfront scenery.

1605 Marina Lake Drive, Kissimmee
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