Kissimmee (Downtown East) Homes with Rain Gutters Exterior Features

Kissimmee (Downtown East) Homes with Rain Gutters Exterior Features

Welcome to Downtown East Kissimmee, a vibrant and charming neighborhood nestled in the heart of Osceola County, Florida. Known for its rich history and welcoming atmosphere, this area is a hidden gem that offers a unique blend of modern conveniences and traditional charm. Just a stone's throw away from the magical attractions of Orlando, Downtown East Kissimmee provides residents with easy access to world-class entertainment, shopping, and dining, all while maintaining a cozy, small-town feel.

One of the standout features of homes in this delightful region is the presence of rain gutters, an exterior detail that not only enhances the aesthetic appeal but also offers practical benefits. These thoughtfully designed rain gutters help to channel rainwater away from your home’s foundation, protecting your investment from potential water damage and erosion. This feature is especially valuable in Florida's tropical climate, where sudden downpours can occur.

The homes in Downtown East Kissimmee boast a variety of architectural styles, each with its own unique character. Many properties are surrounded by lush landscaping and mature trees, creating a picturesque setting that invites you to enjoy the outdoors. As you stroll through the neighborhood, you'll discover friendly neighbors, local parks, and quaint shops that contribute to the community's inviting atmosphere.

Whether you're looking for a family-friendly abode or a charming retreat, Downtown East Kissimmee offers a diverse range of housing options, all enhanced by functional features like rain gutters. Discover your dream home in this enchanting neighborhood where comfort and convenience meet!

Newest Kissimmee (Downtown East) Homes with Rain Gutters Exterior Features

1106 June Street, Kissimmee
$364,990
3 Beds ⋅ 3 Baths ⋅ S5160267 MLS ⋅ 1106 BLDG.
STUNNING, ALMOST BRAND-NEW HOME WITH NO HOA & NO CDD! Discover modern luxury, privacy, and an unbeatable location in the heart of Kissimmee! This beautiful two-story home features high ceilings, gorgeous quartz countertops, elegant finishes, and NO CARPET throughout! Enjoy a fully fenced backyard offering comfort and privacy. LOCATION, LOCATION, LOCATION! Conveniently located near Downtown Kissimmee, shopping, restaurants, schools, major hospitals, and highways. Approximately 35 minutes from Disney World and 30 minutes from Orlando International Airport, depending on traffic. THIS HOME CHECKS ALL THE BOXES! Don't miss this incredible opportunity. Schedule your private showing today!

1106 June Street, Kissimmee
1102 June Street, Kissimmee
$414,990
4 Beds ⋅ 3 Baths ⋅ S5160261 MLS ⋅ 1102 BLDG.
STUNNING, ALMOST BRAND-NEW HOME WITH NO HOA & NO CDD! Experience the perfect blend of modern luxury, privacy, and an excellent location in the heart of Kissimmee! This beautiful two-story home showcases an elegant design with high ceilings, stunning quartz countertops, beautiful finishes, and stylish flooring throughout with NO CARPET! Step outside to your fully fenced backyard, providing the privacy and outdoor space you've been looking for! LOCATION, LOCATION, LOCATION! Perfectly situated near Downtown Kissimmee, shopping centers, restaurants, schools, and major highways, with convenient access to Florida's Turnpike and US-192. Just minutes from major medical facilities, approximately 35 minutes from Walt Disney World and 30 minutes from Orlando International Airport. THIS HOME HAS EVERYTHING YOU NEED! DON'T MISS THIS INCREDIBLE OPPORTUNITY! Schedule your private showing today.

1102 June Street, Kissimmee
1098 June Street, Kissimmee
$424,990
4 Beds ⋅ 3 Baths ⋅ S5160254 MLS ⋅ 1098 BLDG.
Virtually Staged. STUNNING, ALMOST BRAND-NEW HOME WITH NO HOA & NO CDD! Discover the perfect combination of modern luxury, privacy, and an unbeatable location in the heart of Kissimmee! This gorgeous two-story home offers a elegant design with high ceilings, beautiful quartz countertops, elegant finishes, and stylish flooring throughout with NO CARPET! Step outside to your fully fenced backyard, offering the privacy and outdoor space you've been dreaming of! LOCATION, LOCATION, LOCATION! Conveniently situated near Downtown Kissimmee, shopping centers, restaurants, schools and major highways, with easy access to Florida's Turnpike and US-192. Just minutes from major medical facilities. 35 minutes from Walt Disney World and 30 minutes from Orlando International Airport. Whether you're looking for your dream home or a beautiful property in a highly convenient Central Florida location, THIS HOME CHECKS ALL THE BOXES! DON'T MISS THIS AMAZING OPPORTUNITY! Schedule your private showing today and fall in love with everything this exceptional home has to bring!

1098 June Street, Kissimmee
Kissimmee
$349,999
3 Beds ⋅ 2 Baths ⋅ S5159825 MLS
Well-maintained home conveniently located near downtown Kissimmee, restaurants, shopping, lakefront amenities, medical facilities, and more. Situated on a corner lot, the property features a one-car carport, open parking, a fenced backyard, storage shed, and an uncovered rear patio. The entrance opens into the living room, with a hallway leading to three bedrooms and a full bathroom with a tub/shower combination. The equipped kitchen offers generous counter and cabinet space, a closet pantry, a pass-through to the family room, and an eating area. The interior utility room includes access to the carport, shelving, storage space, a water heater, and washer/dryer hookups. The spacious family room features hardwood flooring, high ceilings, and access to the rear patio and backyard. This versatile space can also serve as a dining room. The bedrooms feature light oak-style laminate flooring, while neutral tile runs throughout the tiled areas of the home.

Kissimmee
21 S Palm Avenue, Kissimmee
$355,000
4 Beds ⋅ 3 Baths ⋅ O6449645 MLS
NO HOA! This versatile property features a 3-bedroom, 2-bath main home plus a separate private ADU studio on the side with its own bathroom and private entrance, offering added flexibility for guests, extended family, or a private workspace. Inside the main home, vaulted ceilings and exposed wood beams add character to the living area, while newer flooring complements the space. The kitchen features granite countertops, gray cabinetry, and a breakfast bar overlooking the living room. Outside, enjoy a spacious, fully fenced backyard with mature shade trees, a storage shed, and no immediate rear neighbors—providing plenty of room for gardening, outdoor gatherings, or simply relaxing. A covered rear patio adds a shaded spot to enjoy the outdoors with a pond view. All windows and three exterior doors were replaced approximately one year ago with impact-rated products, and the roof was replaced in 2019 and features gutters. With a private studio, valuable updates, and generous outdoor space, this property offers plenty of possibilities! Conveniently located near historic Downtown Kissimmee’s shops and restaurants and Kissimmee Lakefront Park on Lake Tohopekaliga, where you can enjoy waterfront walking paths, picnic areas, and outdoor recreation. Nearby John Young Parkway and US-192 provide convenient connections to shopping, dining, and destinations throughout Central Florida.

21 S Palm Avenue, Kissimmee
1604 Columbia Arms Circle Unit 216, Kissimmee
$226,000
3 Beds ⋅ 2 Baths ⋅ S5158735 MLS ⋅ 1604 BLDG.
Enjoy peaceful lake views from this spacious 3-bedroom, 2-bathroom condo located on the second floor of a gated community. The unit features brand-new carpet throughout all living areas, creating a fresh and inviting atmosphere. The kitchen comes fully equipped with a refrigerator, range, range hood, dishwasher, garbage disposal, washer, and dryer, offering convenience and functionality from day one. In addition, this unit is privileged with an independent storage garage, perfect for extra storage or for generating additional income for the owner through rental. The community offers exceptional amenities, including a swimming pool, fitness center, playground, pickleball courts, basketball court, and an in-ground spa—ideal for those seeking an active and balanced lifestyle. Its location is unbeatable, close to schools, shopping centers, restaurants, gyms, daycares, pharmacies, hospitals, banks, and major commercial areas. There is an administrative fee payable to the association that the new owner must pay ($750). The HOA fee includes sewer, trash, and pest control. The unit is currently occupied with a tenant. Owner is motivated.

1604 Columbia Arms Circle Unit 216, Kissimmee
3471 Dovetail Avenue, Kissimmee
$740,000
6 Beds ⋅ 4 Baths ⋅ O6431892 MLS
Welcome to 3471 Dovetail Avenue, where modern Florida living meets comfort, style, and convenience in the heart of Kissimmee. Nestled within a sought-after community, this beautifully maintained home offers spacious living, thoughtful design, and the perfect setting for creating lasting memories. Step inside to an inviting open-concept floor plan filled with natural light, seamlessly connecting the living, dining, and kitchen spaces—ideal for everyday living and entertaining alike. The well-appointed kitchen serves as the heart of the home, providing ample workspace, generous cabinetry, and a welcoming atmosphere for family gatherings and special occasions. The private owner’s retreat offers a peaceful escape, while the additional bedrooms provide flexibility for family, guests, or a home office. Every space has been designed with comfort and functionality in mind, making this home as practical as it is inviting. Step outside to your own backyard oasis, offering room to relax, entertain, or simply enjoy Florida’s year-round sunshine. Whether you’re hosting weekend barbecues, watching the kids play, or enjoying a quiet evening outdoors, this outdoor space is ready to fit your lifestyle. Perfectly positioned just minutes from shopping, dining, schools, major highways, and Orlando’s world-famous attractions, this home offers the ideal balance of neighborhood tranquility and everyday convenience. You’ll enjoy easy access to Lake Nona, Orlando International Airport, Disney, and everything Central Florida has to offer. 3471 Dovetail Avenue isn’t just a house—it’s a place to grow, gather, and truly feel at home. Schedule your private showing today and discover why this exceptional Kissimmee property is the perfect place to begin your next chapter.

3471 Dovetail Avenue, Kissimmee
3227 Chesswood Avenue, Kissimmee
$219,000
3 Beds ⋅ 2 Baths ⋅ O6441475 MLS ⋅ 3227 BLDG.
WELCOME HOME! LOW HOA! Seller offering $10,000 to Buyer for closing costs or renovations. This beautifully positioned 3-bedroom, 2-full-bath end-unit townhome in Chelsea Square is READY NOW and offers an excellent opportunity for a first-time home buyer, buyer looking for an affordable starter home, or investor seeking an income-producing rental property. Located toward the back of the community, this home offers a desirable open floor plan with the secondary bedrooms toward the front and the spacious primary suite privately situated in the rear. Tile flooring flows throughout the main living areas, laundry room, and bathrooms, while the primary bedroom and one secondary bedroom feature carpet. Bedroom 3 offers upgraded flooring. The kitchen is equipped with stainless steel appliances and granite countertops, making it both functional and inviting. Step outside to the screened-in back porch and private backyard, creating a comfortable space to enjoy your morning coffee, entertain guests, or unwind after a long day. Ample open parking is available for residents and guests. Chelsea Square also features a community pool for residents to enjoy. Conveniently located near shopping, restaurants, everyday conveniences, and major roadways, this home offers easy access to the surrounding area. Whether you're looking to stop renting and start building equity, purchase your first home, or add a rental property to your investment portfolio, this Chelsea Square townhome is an opportunity worth exploring.

3227 Chesswood Avenue, Kissimmee
2931 Rio Grande Trail Unit 2981, Kissimmee
$180,000
2 Beds ⋅ 2 Baths ⋅ G5117642 MLS ⋅ 8 BLDG.
Virtually Staged. INVESTOR OPPORTUNITY! This 2-bedroom, 2-bath condo is located in Villas at Shadow Bay, an established community in the heart of Kissimmee. Vacant and ready for its next owner or tenant, the property offers excellent long-term rental potential with no existing lease to assume. Conveniently located near The Loop, Valencia College, major roadways, shopping, dining, and Central Florida attractions. Property is being sold As-Is. Buyers and their agents are encouraged to independently verify room measurements, HOA fees, leasing and pet restrictions, association approval requirements, and any other information deemed important. Schedule all showings through ShowingTime. All offers must include a pre-approval letter or proof of funds.

2931 Rio Grande Trail Unit 2981, Kissimmee
2510 Amati Drive, Kissimmee
$483,000
3 Beds ⋅ 3 Baths ⋅ O6437788 MLS
Welcome home to this spacious 3-bedroom, 2.5-bath, two-story home offering a functional layout with plenty of room to spread out. The main floor features a beautiful kitchen with a walk-in pantry, generous cabinet and counter space, and an open flow into the living area perfect for everyday living and entertaining. A separate flex room provides additional space for a dining room, home office, or whatever best fits your needs. A convenient half bath and attached 2-car garage complete the first floor. Upstairs, retreat to the large primary suite featuring an ensuite bath with dual sinks, shower, and spacious walk-in closet. Two additional bedrooms, a full bath, and a versatile loft provide plenty of space for family, guests, or a second living area. The upstairs laundry room adds extra convenience right where you need it. Step outside to a covered back porch, perfect for relaxing and enjoying the outdoors. The fully fenced backyard provides plenty of space for pets, play, or entertaining. With a spacious floor plan, flexible living areas, and plenty of storage throughout, this home offers a comfortable and functional layout for everyday living.

2510 Amati Drive, Kissimmee
524 & 526 Sumner Street, Kissimmee
$425,000
4 Beds ⋅ 2 Baths ⋅ O6436231 MLS
Virtually Staged. OPPORTUNITY KNOCKS in the heart of Kissimmee! This FULL DUPLEX offers two separate 2-bedroom, 1-bath residences and the flexibility to GENERATE INCOME from both units or live in one while renting the other. Recent updates to BOTH sides include NEW A/C SYSTEMS (2026) and UPDATED APPLIANCES (2026), insulation and air duct replacement (2025), new front doors (2024), and the ROOF IS (2019). UNIT 526 also features FRESH INTERIOR PAINT (2026) and an UPDATED BATHROOM (2024). Set on a spacious CORNER LOT with NO HOA, each residence offers its own FRONT PORCH, SCREENED LANAI and comfortable interior finished with tile and laminate wood flooring throughout - no carpet! UNIT 524 adds a private, fenced paver patio/backyard for additional outdoor living space. With two complete homes in one property, the setup creates plenty of possibilities for an INVESTOR, MULTI-GENERATIONAL LIVING or an OWNER-OCCUPANT looking to OFFSET EXPENSES with rental income. Unit 524 is currently tenant occupied, while Unit 526 is vacant and ready for its next chapter. Location adds even more appeal – enjoy walkability to Downtown Kissimmee and Kissimmee Lakefront Park, where community events, recreation and waterfront activities are close to home. Shopping, dining, medical services, parks and several area lakes are nearby, with convenient access to S John Young Parkway and US-192 for travel throughout Central Florida and the Disney area attractions. Whether you are expanding your rental portfolio or looking for a smart live-and-rent opportunity, this Kissimmee duplex delivers versatility, income potential and no added HOA. Call today for more information and schedule a tour!

524 & 526 Sumner Street, Kissimmee
2524 Rapollo Drive, Kissimmee
$409,999
3 Beds ⋅ 2 Baths ⋅ S5155969 MLS
Welcome to this updated single-story open floor plan in Tapestry, a 24-hour guard-gated Kissimmee community. Offering 3 bedrooms, 2 baths, a flexible office/bonus room, 1,706 sq. ft. and an attached 2-car garage, the bright open layout is designed for everyday living and entertaining. The kitchen features quartz countertops, a tile backsplash, stainless steel appliances, abundant cabinetry, pendant and recessed lighting, and a center island with storage and bar seating. Tile flooring runs through the main living areas, complemented by fresh paint in many rooms, with brand-new carpet scheduled for installation on September 2. Major recent improvements include a large, fully paid-off solar system with no loan or lease for the buyer to assume, new gutters, and an updated garage door with warranty documentation. A covered lanai overlooks the fully fenced backyard, creating a private space to relax or entertain. Tapestry amenities include a zero-entry resort-style pool, cabanas, splash pad, clubhouse, fitness center, playgrounds, sports fields, dog park, BBQ pavilions, fire-pit gathering areas, and walking and biking trails. Conveniently located near The Loop, shopping, dining, major highways, area attractions and Orlando International Airport.

2524 Rapollo Drive, Kissimmee
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