Kissimmee Homes with Maintenance Amenities

Kissimmee Homes with Maintenance Amenities

Welcome to Kissimmee, Florida—where sunshine meets charm and adventure awaits at every corner! Nestled just south of Orlando, Kissimmee is a vibrant city known for its stunning landscapes, family-friendly attractions, and rich cultural heritage. With its close proximity to world-renowned theme parks like Walt Disney World and Universal Studios, Kissimmee serves as the perfect gateway for those seeking a magical lifestyle.

But Kissimmee is more than just a tourist destination; it boasts a warm community atmosphere, excellent schools, and a variety of recreational activities. From the picturesque Lake Tohopekaliga, perfect for fishing and boating, to the lush parks and nature trails, residents enjoy an active outdoor lifestyle year-round. The city also features a bustling downtown area filled with charming shops, delightful restaurants, and local events that foster a strong sense of community.

For those considering a move to Kissimmee, you’ll find an array of homes that cater to diverse lifestyles, especially those with maintenance amenities. Imagine living in a beautifully designed home where landscaping, pool maintenance, and exterior upkeep are taken care of for you. These homes offer the perfect blend of comfort and convenience, allowing you to spend more time enjoying the Florida sunshine and less time worrying about chores.

Whether you’re a first-time homebuyer, a growing family, or looking for a serene retirement haven, Kissimmee’s real estate market is brimming with opportunities. Experience the magic of Kissimmee and discover your dream home in this enchanting city!

Newest Kissimmee Homes with Maintenance Amenities

7491 Gathering Drive, Kissimmee
$1,420,000
5 Beds ⋅ 5 Baths ⋅ Reunion Ph 1 Prcl 1 Unit 3 SubDv. ⋅ 34747 Zip Code
Luxury, Legacy and Lifestyle are on display at one of Reunion’s most unique floorplans and it’s yours to enjoy at 7491 Gathering Drive. *REUNION RESORT MEMBERSHP** Home went through a series of major upgrades. Nestled in the historic Homestead Community at Reunion Resort you will find this 4,664 square foot home that offers 2 OVERSIZED SUITES, a large open floor plan, along with a home office, loft and media spaces and an extremely private SCREENED in pool and spa area. The home is surrounded by mature trees and really feels like the best of Golf Course Community Living. You enter the home and are greeted by tall ceilings, a large staircase and tons of natural light. Once inside you will see that the first floor of the home wraps itself around the pool area and this sets the tone for relaxation. The home office is a new addition to the property and is the perfect way to be able to enjoy working from home but be careful, you could get caught daydreaming about jumping in the pool. Exploring deeper into the home you will see great use of space with an oversized open concept kitchen and living area. New countertops, reimagined island space and white cabinets only add to the clean lines of the home. Along with bar stool seating there is a separate dining area that is well thought out and very accommodating. Glass doors outline the back wall of the property and create an Oasis like feeling while also giving you pristine golf course views. You are located on the Watson Course, hole number 2. Once outside on the first-floor patio of the home you are then again reminded of the quietness of the property and the green space that surrounds you. There are two bedrooms on the first floor of the home that have been re-imagined spaces. At the rear of the home is where you will find one of two master suites at the property. It is accented by a large walk-in closet space and large picture windows that are framed by exterior foliage. A laundry room and a spacious 2 CAR GARAGE round out the first floor. Upstairs you are greeted by new designs that include new flooring, an additional bathroom, re-designed shower spaces and re-thought media and loft areas that help the home continue to excite. The media room has a newly installed oversized projection screen and projector. The additional three bedrooms are located on the second floor led by the second master suite that overlooks the golf course. The second master also has received special attention during the re-imagination and now boasts a spa like feel with a new shower and seating area. The large game room loft is connected to the second story balcony and does not disappoint. You can watch golf on the big screen and on the balcony at the same time! This home has it all. 7491 Gathering Drive, does have an active Reunion Resort Transferable Membership, along with tankless water heaters and 1 new AC and newer roof. If you are looking for the best of quiet Golf Course living in Reunion, you have found it. Reunion Resort has everything you want in a community including 3 signature golf courses, world class dining, waterparks, lazy river, water slides, firework viewing areas, tree lined streets, dog park, playground, golf simulator, member events, in-resort shuttle service, and event space and close to all the major attractions. Welcome Home!

7491 Gathering Drive, Kissimmee
4764 Ormond Beach Way, Kissimmee
$270,000
3 Beds ⋅ 3 Baths ⋅ Terra Verde Villas Ph 1 SubDv. ⋅ 34746 Zip Code
IMMEDIATELY AVAILABLE! Discover the low-maintenance lifestyle and versatility of this fully furnished, turnkey townhouse located in the resort community of Terra Verde. Whether you're looking for a primary residence, second home, long-term rental, short-term rental, or a combination of personalI use and rental income while you're away, this property offers multiple possibilities. The thoughtfully designed floor plan features tile flooring throughout the main living areas, with carpet on the stairs and upstairs bedrooms. The first floor offers an open-concept kitchen, dining area, and living room, creating a comfortable space for everyday living and entertaining. An interior laundry room and additional storage areas add convenience, while the oversized private, walled patio at the rear of the home provides a great outdoor space for relaxing, dining, or entertaining. Upstairs, you'll find the spacious primary suite with a private bathroom, along with two additional guest bedrooms that provide accommodations for up to six additional guests or residents. The property is being offered fully furnished and turnkey, making it an ideal option for those looking for a vacation home or investment property with minimal setup required. Terra Verde offers an impressive collection of resort-style amenities, including a resort pool, poolside tiki bar, fitness center, mini golf, arcade, movie theater, basketball and tennis courts, volleyball area, and two stocked lakes offering catch-and-release fishing. The community's 24-hour gated security provides added peace of mind. Located just minutes from Walt Disney World, Universal Orlando, shopping, dining, entertainment, and everything Central Florida has to offer, this property puts you in the heart of one of the world's most popular vacation destinations. Resort living. Flexible ownership options. Turnkey convenience. Investment potential. Whether you're looking for a place to call your own, a vacation retreat, or an income-producing property, this Terra Verde townhouse deserves a closer look.

4764 Ormond Beach Way, Kissimmee
2641 Tranquility Way, Kissimmee
$550,000
6 Beds ⋅ 5 Baths ⋅ Veranda Palms Ph 2a SubDv. ⋅ 34746 Zip Code
Fully Furnished Disney Resort Vacation Home on a Corner Lot with a Large Private Heated Pool! Located in the highly sought-after, 24-hour manned-gated community of Veranda Palms, this home offers everything you need for the perfect short-term rental or vacation retreat. From the moment you arrive, the lush landscaping and pristine curb appeal welcome you inside. This home has been meticulously maintained and lovingly cared for as a private vacation retreat, and it shows! It features all-new luxury resort-style furnishings that elevate the space to feel both comfortable and elegant. The pool deck was resurfaced in 2021 and painted in 2026. The home boasts a brand-new AC. The chef of the family will love the brand-new stainless steel appliances, granite countertops, and natural gas stove, powered by underground natural gas—an uncommon and valuable feature! The open floor plan is perfect for entertaining, with the kitchen overlooking the family room and out to the sparkling private pool, which offers the perfect backdrop for those breathtaking Florida sunrises. With two master suites (one on each level), it’s designed to accommodate everyone comfortably. Upstairs, you’ll find a bright and spacious loft, perfect as a second living space or entertainment area. The home offers five additional bedrooms, each custom-designed and themed to delight guests of all ages, from Disney’s Frozen and Mickey Mouse to more elegant designs. Located just 10 minutes from Walt Disney World, Veranda Palms offers exclusive access to incredible amenities, including a modern clubhouse, resort-style pool with a dual-slide mini waterpark, splash pad, a zero-entry pool, a large Jacuzzi, a covered picnic area, and a state-of-the-art fitness center. It’s surrounded by world-class golf courses, award-winning restaurants, and is just 15 minutes from SeaWorld, 20 minutes from Universal Studios, and close to all the fun in Orlando. Whether you’re looking for a vacation home or an investment property, this is an ideal opportunity in a fantastic location!

2641 Tranquility Way, Kissimmee
9055 Treasure Trove Lane Unit 204, Kissimmee
$249,000
3 Beds ⋅ 2 Baths ⋅ Caribe Cove Condo Ph 4 SubDv. ⋅ 34747 Zip Code
Enjoy the best of Central Florida living just a short drive from Walt Disney World® Resort! Welcome to Caribe Cove, This spacious 3-bedroom, 2-bathroom condo offers a flexible opportunity for those looking for a Florida getaway, primary residence, or short-term rental property. The open-concept layout provides plenty of space to relax and entertain, with a well-appointed kitchen overlooking the dining and living areas. The desirable split-bedroom floor plan offers added privacy, while generously sized bedrooms and bathrooms provide comfortable accommodations. One of the highlights of this unit is its beautiful lagoon view. Step outside to the screened balcony and enjoy the peaceful scenery—an inviting setting for morning coffee or simply relaxing after a day enjoying Central Florida. Caribe Cove offers resort-style living with convenient access to Highway 192, theme parks, shopping, dining, entertainment, and the many attractions of the Kissimmee/Orlando area. The community currently allows short-term rentals, offering additional flexibility for owners. Buyers should independently verify current rental restrictions, requirements, and applicable regulations.

9055 Treasure Trove Lane Unit 204, Kissimmee
4978 Pall Mall Street W, Kissimmee
$379,900
4 Beds ⋅ 3 Baths ⋅ Trafalgar Village Ph 2 SubDv. ⋅ 34758 Zip Code
WELCOME HOME TO THIS BEAUTIFULLY MAINTAINED 4-BEDROOM, 3-BATHROOM HOME IN A GATED, GUARD-SECURED COMMUNITY, WHERE COMFORT, RESORT-STYLE LIVING, AND INVESTMENT POTENTIAL COME TOGETHER! This spacious home features an OPEN FLOOR PLAN designed for entertaining, relaxing, and enjoying time with family and friends. The impressive primary suite is truly a retreat, featuring double-door entry, generous space, a beautiful an-suite bathroom, and a walk-in closet. The upgrades make this home even more appealing: ROOF (2026), A/C (2022), TANKLESS WATER HEATER (2020), POOL EQUIPMENT (2021), TILE FLOORING (2021), APPLIANCES (2022), and AUTOMATIC SPRINKLER SYSTEM (2024). A WHOLE-HOUSE WATER SOFTENER provides added comfort, while the security cameras will remain with the property. The WASHER AND DRYER ARE ALSO INCLUDED. Step outside and enjoy your PRIVATE HEATED POOL AND SPA, perfect for Florida living year-round. The outdoor area also features a GAS BBQ, making it ideal for entertaining or simply enjoying a relaxing evening at home. The attached one-car garage and spacious driveway provide parking for up to three vehicles. Located in a desirable guard-gated community offering an impressive array of amenities, including a THEATER, GYM, LARGE COMMUNITY POOL, TRAILS, BOULEVARD, BASKETBALL COURTS, AND MORE. Whether you're looking for a full-time residence, a vacation home, or an investment property, this home offers exceptional flexibility with opportunities for BOTH SHORT-TERM AND LONG-TERM RENTALS, subject to community rules and applicable regulations. Enjoy the home during your holidays and generate rental income when you're away! This is the kind of property you need to EXPERIENCE IN PERSON to truly appreciate. Schedule your private showing today and come see everything this exceptional Florida home has to offer!

4978 Pall Mall Street W, Kissimmee
225 Celebration Place Unit 427, Kissimmee
$214,887
2 Beds ⋅ 2 Baths ⋅ Melia Hotel SubDv. ⋅ 34747 Zip Code
*****NEW UPDATED, MODERN FURNITURE PACKAGE***** This stunning, fully furnished 2-bedroom, 2-bathroom condo is situated in the highly sought-after Melia Orlando Suite Hotel in Celebration. As a condominium hotel, it provides exceptional accommodations, amenities, and services for both guests and owners. Located just minutes away from major theme parks such as Disney, Universal Studios, and Sea World, this property offers an ideal location. The Melia provides private transportation to the theme parks, and guests can also request a complimentary day pass to the Celebration Health gym and spa, which is conveniently located across the street. The condo features a spacious, modern floor plan, complete with two private balconies that spectacular views of Celebration and the surrounding areas. Inside, the condo includes a comfortable living room and a kitchen equipped with elegant stainless steel appliances, designed for both style and functionality. The primary bedroom is inviting and includes a bathroom with both a tub and a separate glass shower stall. The Melia offers an impressive array of amenities, including a community resort pool with a 360-degree vanishing edge, a poolside restaurant and bar, a gift shop, and executive conference rooms. Additional features include a checking desk for convenience, a dog walking park, a beach volleyball court, mini soccer/ football pitch and a picnic area. The hotel is renowned for its excellent customer service and maintenance standards. The quarterly HOA/COA fees cover all utilities and recreational facilities. Owned and operated by The Melia Group, a renowned European hotelier, this property is well-maintained and conveniently located near Celebration, Water Tower Place shopping, and local dining options. It offers easy access to theme parks, Orlando International Airport, and both East and West coast beaches. This unit is perfect for personal use or for foreign nationals seeking a vacation retreat. Additionally, the hotel manages the property effectively during non-use periods, providing a hassle-free investment. This condo is a must-see for those looking to combine personal enjoyment with the benefits of hotel management.

225 Celebration Place Unit 427, Kissimmee
2721 Downing Drive, Kissimmee
$220,000
3 Beds ⋅ 2 Baths ⋅ Broadmoor SubDv. ⋅ 34758 Zip Code
WELCOME TO 2721 DOWNING DR — a versatile Kissimmee home offering comfortable living, practical updates, and strong Central Florida value! This 3-bedroom, 2-bath home features a spacious and functional layout with TWO LIVING AREAS, giving buyers flexibility for a formal living room, family room, home office, hobby space, guest area, or additional entertaining space. Step inside to a bright interior with comfortable gathering areas designed for everyday living and an easy Florida lifestyle. The kitchen is conveniently positioned near the main living spaces and includes a REVERSE OSMOSIS WATER FILTRATION SYSTEM located under the sink. The home also offers added peace of mind with an HVAC system updated in March 2026. The HOA includes INTERNET, CABLE, LAWN CARE, and ACCESS TO COMMUNITY AMENITIES, adding everyday value and convenience. The property is also close by the COMMUNITY POOL and amenities, making it a strong option for buyers looking to relax, simplify, and enjoy Central Florida living. With its practical floor plan, usable living space, and convenient Kissimmee location near shopping, dining, schools, major roads, medical services, and Central Florida attractions, this property is a great option for a PRIMARY RESIDENCE, DOWNSIZING OPPORTUNITY, or LONG-TERM INVESTMENT. Whether you are looking for your next Florida home, a low-maintenance lifestyle, or an investment opportunity in the growing Central Florida market, 2721 Downing Dr deserves a closer look. SCHEDULE YOUR PRIVATE SHOWING TODAY and discover the possibilities of calling 2721 Downing Dr home!

2721 Downing Drive, Kissimmee
1001 Via Santae Lane Unit 203, Celebration
$449,000
3 Beds ⋅ 2 Baths ⋅ Siena At Celebration Condo C SubDv. ⋅ 34747 Zip Code
Virtually Staged. Discover a stylish and spacious 3-bedroom, 2-bath condominium in Siena at Celebration, offering approximately 1,622 square feet of comfortable living space, an attached one-car garage, and a thoughtfully designed layout. From the moment you enter, the home offers a polished blend of function and contemporary style. The first level provides convenient access to the garage and laundry area, while the main living level opens to a bright, spacious floor plan with plenty of room for relaxing, dining, and entertaining. The kitchen makes an immediate impression with 42-inch soft-close cabinetry, glass display accents, a built-in wine rack, quartz countertops, and stainless-steel appliances. Coordinating cabinetry and countertops continue into both bathrooms, creating a cohesive and refined look throughout the home. Additional details include modern ceiling fans and fixtures, a sleek metal stair railing, raised ceilings in the kitchen and primary bathroom, and finishes that give the home a fresh, updated feel. The primary bathroom offers a relaxing retreat with a generous shower, built-in bench, and rainfall-style shower fixture. Beyond the home, Siena at Celebration offers access to community amenities including a pool, fitness center, playground, tennis courts, and recreational areas. Celebration is known for its distinctive setting, parks, trails, dining, shopping, community events, and convenient access to Central Florida destinations. Located near Walt Disney World Resort, major attractions, shopping, dining, and area roadways, this property offers the space, features, and location buyers are looking for. If you have been waiting for an opportunity to own in Celebration, this 3-bedroom Siena condo deserves a closer look. Schedule your private showing and experience the layout, finishes, community amenities, and location for yourself.

1001 Via Santae Lane Unit 203, Celebration
7656 Whisper Way Unit 102, Reunion
$279,000
3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square P3 Condo SubDv. ⋅ 34747 Zip Code
Virtually Staged. SHORT-TERM RENTALS ALLOWED! FULLY FURNISHED, INCOME-PRODUCING PROPERTY IN REUNION RESORT! Excellent opportunity for investors, second-home buyers, or anyone seeking a turnkey vacation property in one of Central Florida’s premier resort communities. SPECIAL FINANCING INCENTIVE: Qualified buyers may be eligible for a lender credit equal to 1% of the loan amount, which may be applied toward allowable closing costs or an interest-rate buy-down, subject to lender program requirements, buyer qualification, loan terms, and lender approval. Beautifully furnished 3-bedroom, ground-floor residence at The Villas at Reunion Resort featuring desirable south-facing exposure and a spacious covered balcony overlooking peaceful conservation views. The open-concept layout connects the kitchen, dining, and living areas, while the kitchen offers granite countertops, stainless steel appliances, generous cabinetry, and ample prep space. Offered fully furnished and professionally decorated, this property is ready for immediate enjoyment as a vacation retreat, second home, or potential income-producing rental. Located just a short walk from Reunion’s Water Park, owners and guests can enjoy three championship golf courses designed by Arnold Palmer, Tom Watson, and Jack Nicklaus, a water park with lazy river and slide, resort-style pools, tennis and pickleball courts, fitness centers, mini golf, spa services, playgrounds, and on-site dining. Reunion Resort also offers 24-hour guard-gated access and is conveniently located minutes from Walt Disney World, shopping, dining, Orlando attractions, and Orlando International Airport. The HOA includes water, sewer, trash, cable, internet, exterior maintenance, common-area electricity, and elevator service. Fully furnished. Short-term rentals allowed. Resort amenities. Income-producing potential. Preferred-lender credit available. Schedule your private showing today!

7656 Whisper Way Unit 102, Reunion
4733 Vero Beach Place, Kissimmee
$275,000
3 Beds ⋅ 3 Baths ⋅ Terra Verde Villas Ph 2 SubDv. ⋅ 34746 Zip Code
Fully Furnished | Income Producing | 7.2 miles to Walt Disney World | Close to Community Pool & Amenities | Zoned for Short-Term Rental | Welcome to your Turnkey Florida Getaway in Terra Verde Resort! Offered fully furnished and featuring a private screened patio with hot tub, this 3-bedroom, 2.5-bath townhome combines resort-style living with the flexibility of a vacation home, second home or short-term rental investment. Step inside to a bright, open floor plan designed for easy vacation living and entertaining. The kitchen flows into the dining and living areas, creating a comfortable gathering space for family and guests. Sliding doors extend the living area outdoors to the screened patio and private hot tub—the perfect place to relax after a day at the theme parks or enjoy a quiet Florida evening. Upstairs, three bedrooms provide plenty of space for owners and guests, while the turnkey furnishings make it easy to begin enjoying the property right away. Located within the guard gated Terra Verde Resort, owners and guests enjoy an impressive collection of amenities, including a resort-style, zero entry pool, spa, fitness center, playground, Tiki bar, tennis, movie theater, miniature golf, beach volley ball, basketball court, a fishing lake and beautifully maintained common areas. This home is zoned for short-term rental and currently operates as an active, income producing Airbnb, offering revenue potential to help offset the cost of vacation-home ownership with future bookings already in place. Conveniently located in Kissimmee close to Walt Disney World, Sea World and Universal Studios Orlando, shopping, restaurants, outlet malls, golf and Central Florida attractions, this property offers the location vacationers want with convenient access to the airport and beautiful Beaches just a short distance to either coast. Whether you’re searching for your own Florida escape, a furnished vacation rental investment, or a property that can serve as both, 4733 Vero Beach Place offers an opportunity to own in an established resort community in the heart of Orlando’s Vacation Destination!

4733 Vero Beach Place, Kissimmee
2611 Gala Road N Unit 105, Kissimmee
$205,000
3 Beds ⋅ 2 Baths ⋅ Villas At Seven Dwarfs Lane Condo SubDv. ⋅ 34746 Zip Code
LOCATION LOCATION LOCATION!! Top Orlando attractions! Stay close to Disney, Universal Parks, Outlets, I-Drive. Welcome to this high demand SEVEN DWARFS CONDO 24-7 GUARD GATED COMMUNITY offers RESORT STYLE amenities, included: tennis and basketball courts, beach-tennis, large community pool and spa, playground, club house, game room, fitness center, Tiki Bar, picnic areas, paddle-boats, scenic walking areas, car wash, and lots of spaces to relaxing. This beautiful and well maintained townhouse included a living and dining combo area, fully equipped kitchen, washer and dryer combo, 3 spacious bedrooms (PRIMARY BEDROOM DOWNSTAIRS) and 2 full bath. Community is zoned for SHORT-TERM vacation rentals, LONG-TERM rentals, or even as your PRIMARY residence. STRESS FREE: HOA FEE COVERS master building insurance, exterior painting and maintenance, cable, internet, pest control, roof, and common areas. Hurry and schedule your showing, will not last long at this price. Can provide closing cost credits with full offer.

2611 Gala Road N Unit 105, Kissimmee
3202 Sustainable Way, Kissimmee
$335,000
3 Beds ⋅ 3 Baths ⋅ Hub At Westside Reserve SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained corner unit, built in 2024 and located in the desirable The HUB at Westside Reserve community. This nearly new home features a modern and functional layout, with the added convenience of an in-unit washer and dryer. The corner location provides additional privacy, abundant natural light, and a greater sense of space. Residents can enjoy access to a variety of community amenities, creating a comfortable and enjoyable lifestyle in a well-located Central Florida community. The property is conveniently situated approximately 10 minutes by car from Disney parks, with easy access to major attractions, shopping, dining, entertainment, and other popular destinations throughout the area. Built in 2024, this home combines newer construction, modern finishes, and a convenient location near some of Central Florida’s most sought-after attractions. Whether you're looking for a primary residence, second home, or investment property, this corner unit is a great opportunity to enjoy the convenience and lifestyle of the Kissimmee area.

3202 Sustainable Way, Kissimmee
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