Homes for Sale Near West Side in Kissimmee - 148 homes

Remarks: Under contract-accepting backup offers. Priced below the owner's purchase price, this home offers an incredible opportunity to gain instant value while owning a turnkey, income-producing property in one of Central Florida's most desirable resort communities. Welcome to this beautiful 2024-built townhouse in the highly desirable Summerville Resort! Offering 5 bedrooms and 5 full bathrooms, this move-in-ready home features an open-concept floor plan that's perfect for entertaining. Every bedroom has its own private bathroom, making it ideal for guests and maximizing rental potential. Built in 2024, the home includes all-new HVAC, commercial-grade tankless water heater, roof, plumbing, and electrical, along with quartz countertops, stainless steel appliances, a washer and dryer, fresh interior paint, and a spacious rear patio. Zoned for short-term rentals, this is an excellent Airbnb/income-producing opportunity just minutes from Walt Disney World, shopping, dining, and major attractions. Summerville Resort offers a pool, jacuzzi, fitness center, and clubhouse, making it the perfect vacation destination for owners and guests alike.

Listing is courtesy of: EXP REALTY LLC (407-641-2808)

Listing Agent: Jeffrey Osborn, Jr (407-221-7134)

Remarks: Welcome to 8424 Crystal Cove Loop, a stunning retreat in the heart of Kissimmee, FL, where comfort meets convenience just minutes from world-famous attractions. This beautifully maintained 3-bedroom, 2.5 bathroom home is nestled in the sought-after Emerald Island Resort community, offering an unbeatable combination of style, location, and amenities. Step inside to discover an open and airy floor plan bathed in natural light. The spacious living area flows seamlessly into a well-appointed kitchen featuring newer Whirlpool stainless steel appliances, and plenty of cabinet space—perfect for whipping up family meals or entertaining guests. Also included is an all new LVP flooring throughout, updated Rheem hot water heater, polywood balcony and a Nest Doorbell. The master suite is a true sanctuary, complete with a private en-suite bathroom and walk-in closet, while additional bedrooms provide ample space for family or visitors. The HVAC system is new in 2025, with UV light system and WIFI thermostat. Outside, you’ll find your very own slice of paradise. The lanai and view of the community pool make for the ultimate spot to unwind after a long day, whether you're soaking up the Florida sunshine or enjoying a quiet evening under the stars. The home also comes fully furnished, making it an ideal turn-key opportunity for investors or families seeking a vacation home. As part of Emerald Island Resort, you’ll have access to incredible amenities, including a clubhouse, heated community pool, fitness center, tennis courts, and playgrounds—not to mention 24-hour gated security for peace of mind. Located just a short drive from Disney, shopping, dining, and entertainment, this property truly has it all. Don’t miss your chance to own this gem in one of Central Florida’s premier communities. Schedule your private showing today and start living the Florida dream!

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Jill Kline Royka Kline (330-715-1740)

Remarks: Excellent investment opportunity in the gated resort-style community of Regal Oaks. This fully furnished 2-bedroom, 2.5-bath townhome is Airbnb-ready and has a strong history of successful short-term rental income. Ideally located near Disney, Old Town, and Fun Spot, this property consistently attracts vacationers looking for comfort, location, and resort amenities. Features include an open-concept floor plan, granite countertops, stainless steel appliances, tile flooring, private screened lanai with hot tub, and two spacious en-suite bedrooms. One of the most desirable locations in the community with peaceful courtyard and garden views. Regal Oaks offers resort-style amenities including a lakefront pool, water slides, hot tubs, tennis courts, fitness center, clubhouse, restaurant, and poolside bar. Turnkey investment with excellent income potential in one of Central Florida’s top vacation rental areas.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Mouna Hilali (267-974-9763)

Remarks: Welcome to Calabria at Westside, where resort-style living meets everyday comfort just minutes from Central Florida's world-famous attractions. Situated on a nicely sized corner lot in this beautifully maintained community, this Mediterranean-inspired pool home offers 6 bedrooms, 3 full bathrooms, 1 half bath, and a spacious upstairs family room, creating the perfect blend of flexibility, comfort, and style. From the moment you arrive, you'll appreciate the curb appeal and welcoming feel of the neighborhood. Step inside to a spacious entryway accented by porcelain tile, with a formal dining room just off the foyer that could also serve beautifully as a home office or flex space. The heart of the home features an open-concept kitchen, living room, and dinette, designed for gathering and entertaining while enjoying views of the sparkling screened-in pool. The first floor also includes a convenient half bath, garage access, and a generously sized primary suite with sliding glass doors overlooking the pool, a walk-in closet, and a spacious ensuite bath. Upstairs, you'll find a huge family room/bonus space that offers endless possibilities for a second living area, game room, or media space. The thoughtfully designed split-bedroom layout places 2 bedrooms and a full bath on one side, with 3 additional bedrooms and another full bath on the other. The largest upstairs bedroom is located at the front of the home and is currently being used as an impressive office space. Step outside to enjoy your screened-in lanai and private pool, perfect for relaxing after a day at the parks or entertaining family and friends. As an added bonus, the reasonable HOA includes lawn care, cable, and internet, making ownership even more convenient. And if you'd like to meet your neighbors, simply step outside for a stroll through this active, well-kept community where you'll often see residents enjoying their daily walks with their four-legged family members. This is your opportunity to own a spacious, well-appointed Central Florida retreat in a sought-after location close to shopping, dining, and area attractions.

Listing is courtesy of: RE/MAX HERITAGE (863-424-2309)

Listing Agent: Gene May Sandobal (321-559-9448)

Remarks: Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophistication, and excellent investment potential. With 6 bedrooms, 4 full bathrooms, and 1 powder room, the house features a modern open-concept layout, providing spacious, integrated, and well-lit environments. Upon entering, a charming veranda with a garden welcomes you and creates a cozy atmosphere. Inside, you'll find a spacious living room with ceiling fans, integrated with the dining room and kitchen, forming an ideal environment for both everyday life and entertaining guests. Sliding glass doors lead to the outdoor area, where the private pool and covered veranda are located—the perfect space for leisure and relaxation. The kitchen is fully equipped with appliances, wooden cabinets, and a breakfast bar, combining practicality and elegance. The master suite is located on the first floor, offering privacy, a large bathroom, and a walk-in closet. On the second floor are the other five bedrooms—all with closets and carpeting—as well as a spacious loft that can be used as a TV room, game room, or additional living space. The condominium offers a complete resort-style structure, with a clubhouse, swimming pool, gym, volleyball courts, playground, game room, and security, providing leisure and convenience for the whole family. The location is privileged: just 15 minutes from Walt Disney World, close to golf courses, outlets, restaurants, supermarkets, and with easy access to the region's main highways. It is also about 30 minutes from Orlando International Airport, facilitating travel for domestic and international trips. Whether for living or investing in vacation rentals, this is a unique opportunity in one of Florida's most desirable areas.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Rosania Taylor (407-580-6137)

Remarks: Discover the perfect blend of comfort, convenience, and investment potential in this beautifully maintained 2-bedroom, 2-bathroom condo located in the highly desirable Oakwater Community of Kissimmee. This spacious residence features an open-concept floor plan with abundant natural light, a well-appointed kitchen, and a comfortable living and dining area designed for both everyday living and entertaining. The generous primary suite offers a private retreat with an en-suite bathroom, while the second bedroom and bath provide flexibility for guests, family, or rental opportunities. Enjoy relaxing on your private screened lanai and take advantage of the resort-style amenities Oakwater is known for, including a community pool, fitness center, clubhouse, playground, tennis courts, and more. Ideally situated just minutes from Walt Disney World®, world-class attractions, shopping, dining, and major highways, this property is perfect as a primary residence, vacation home, or short-term rental investment. Experience the best of Central Florida living in one of Kissimmee's most sought-after resort communities. Schedule your private showing today and see why Oakwater continues to be a favorite destination for residents and visitors alike!

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Paul Donovan (407-785-7070)

Remarks: This beautifully located property is part of the highly desirable Margaritaville Resort Orlando, delivering a true resort-style lifestyle just minutes from Walt Disney World, shopping, dining, and entertainment. Enjoy a vibrant community surrounded by tropical landscaping, multiple pools, fitness amenities, and on-site restaurants, all designed for relaxed Florida living. Short-term rentals are permitted, making this an excellent option for personal use or income-producing potential. Convenient access to major highways provides easy travel to Orlando International Airport and Central Florida attractions. Experience island-inspired living where every day feels like a vacation. This property is being sold fully furnished.

Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)

Listing Agent: Yuliana Naim (818-434-9717)

Remarks: This beautifully maintained townhome offers a 4-bedroom, 4-full-bath, 1-half-bath luxury townhome, a large Laundry Room, ideally located in one of Central Florida’s most desirable communities with gated access. Level up to the featuring soaring high ceilings and a spacious open-concept layout, this home offers a bright and airy atmosphere perfect for both comfortable living and entertaining. Elegant design, modern finishes, and thoughtful details make this residence a standout, combining style, functionality, and excellent investment potential. At the heart of the home, the designer-caliber kitchen has been beautifully updated with modern finishes, offering both style and functionality for everyday living or hosting guests. A tankless water heater enhances efficiency and provides continuous comfort. Step outside to your private balcony, where you can unwind while enjoying breathtaking views toward Disney's Animal Kingdom, delivering a truly magical and one-of-a-kind experience. If you're seeking a Vacation Home in an elegant Resort Retreat this property is completely turnkey and ready to impress! Ideal for Disney Park enthusiast. Property features: 4 Bedrooms, 4 Full Bathrooms, a Half Bath, soaring ceilings & open-concept design, Updated, high-end designer kitchen, Energy-efficient tankless water heater, Private balcony from Primary Bedroom with a view to Animal Kingdom's backyard. This property is ideal for Airbnb, investment, or second vacation home. Ideally located just minutes from Walt Disney World, Margaritaville Resort Orlando, and an incredible selection of shopping, dining, and entertainment, this home offers the perfect blend of luxury living and exceptional income potential. Enjoy breathtaking views from the upstairs balcony — you can practically see Animal Kingdom and watch the fireworks light up the sky! It is truly a sight to behold and a rare opportunity to own a piece of the magic in one of Central Florida’s most desirable locations.

Listing is courtesy of: RE/MAX SELECT GROUP (321-939-3004)

Listing Agent: Anna Bipat (718-216-0965)

Remarks: Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just minutes from Walt Disney World. This spacious 6-bedroom, 4-bathroom pool home offers 2,812 sq ft of thoughtfully designed living space, perfect for large groups looking for comfort, privacy, and resort-style amenities. The open-concept main floor features a generous living and dining area, a fully equipped kitchen, a first-floor bedroom with full bath — ideal for guests who prefer single-level living — a dedicated laundry room, and a game room for added entertainment. Step outside to your private screened pool with heated spa, surrounded by a covered patio and deck — the perfect setting for relaxing afternoons under the Florida sun. Windsor Hills Resort amenities include a clubhouse, resort-style community pool, waterpark, fitness center, game room, tennis courts, and 24-hour gated security — everything your guests need without ever leaving the community. Whether you're looking for a turn-key investment property with strong short-term rental potential or a private family retreat steps from the magic of Orlando, 7765 Tosteth Street is ready to deliver. Offered fully furnished and ready to generate income from day one.

Listing is courtesy of: FLORIDA 360 REALTY LLC (954-325-2625)

Listing Agent: Cristobal Murature Reggiardo (407-433-1933)

Remarks: Location, location, location! FULLY FURNISHED and Vacation Rental allowed. Amazing investment opportunity at West Lucaya Resort. Fully furnished three-bedroom, two-bathroom townhome approved for short-term rental. Resort has a beautiful community pool with plenty of lounge chairs to relax, game room, fitness center. Property is located minutes away from Disney and ready to generate income or host your next Disney Family Trip! Lots of restaurants, supermarkets, golf courses and shoppings nearby. Seller motivated / Short term rental allowed!

Listing is courtesy of: EASY REALTY SERVICES INC (321-318-1005)

Listing Agent: Gabriela Martins-Pierami (321-318-1005)

Remarks: Turnkey, fully furnished vacation retreat or exceptional multi-generational home in a gated resort community just 5 minutes from Disney! This beautifully maintained property is loaded with upgrades and includes all furniture, a fully stocked kitchen, fully stocked bathrooms, new grill, new smoker, Ring doorbell, alarm system, and Nest smart thermostats. Recent improvements include a new roof (2022), pool resurfacing (2023), new carpet throughout (2023), refrigerator (2023), spa heater (2024), pool heater (2025), water heater, complete interior and exterior painting with sealed stucco (2026), freshly sealed pool decking, and new heavy-duty lanai furniture designed for coastal durability. A climate-controlled bonus room in the garage offers flexible space for an optional 8th bedroom, movie room, game room, office, or fitness area, plus additional storage. Situated on the only double backyard lot in the community, this home offers nearly twice the pool deck space, elevated views overlooking a peaceful greenbelt, and exceptional privacy. Zoned for nightly rentals or ideal as a full-time residence, this property offers incredible versatility. Enjoy world-class resort amenities including a community pool, two restaurants, mini golf, volleyball, billiards, playgrounds, and more. Whether enjoying a staycation or spending the day at Disney, this home truly offers the best of Florida living.

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Kalani Ah-Mau (407-267-1712)

Remarks: Discover this exceptional, fully furnished 8-bedroom, 7-bathroom luxury home located in the highly sought-after Encore Resort at Reunion—a premier vacation home community just minutes from Walt Disney World. This spacious residence features an open-concept living, dining, and kitchen area with granite countertops and solid wood cabinetry throughout, creating an inviting space for large gatherings. The thoughtfully designed layout includes two bedrooms on the first floor, one with an en-suite bath, while the second level offers an additional living area and six more bedrooms, including two primary suites, two bedrooms connected by a Jack & Jill bath, and the remainder with private en-suites. Entertainment is at the forefront with a fully converted game room in the garage featuring table tennis, shuffleboard, mini basketball, a card table, and a TV. Step outside to your private oasis complete with a heated pool and spa, covered patio dining area, grill, and lounge seating—perfect for enjoying the Florida sunshine. As part of Encore Resort, guests and owners enjoy access to a 10-acre private water park with thrilling slides, a lazy river, and splash zones, along with on-site dining, fitness facilities, sports courts, arcade, and daily activities, making this property a true resort-style experience. Whether you're seeking a turnkey investment or a luxurious vacation retreat, this home delivers the ideal blend of comfort, entertainment, and location.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Frank Baloun (407-488-4969)

Remarks: Welcome to 7721 Fairfax Dr, Kissimmee, a stunning fully furnished 8-bedroom, 6.5-bath luxury home located in the gated Encore Resort at Reunion, just minutes from Disney and Orlando’s top attractions. Designed for both relaxation and entertainment, this turnkey residence features an open floor plan with a gourmet kitchen, spacious living areas, a themed game and movie room, and beautifully decorated bedrooms throughout. Step outside to enjoy your private heated pool and spa, extended lanai, and a custom-built outdoor mini golf putting area, perfect for family fun and guest entertainment. As part of Encore Resort, owners and guests enjoy access to world-class amenities including a water park, clubhouse, restaurant, fitness center, and concierge services. Whether for personal enjoyment or as a high-income short-term rental, this home offers the perfect blend of lifestyle and investment, all future bookings are included in the sale, making it a truly turnkey opportunity.

Listing is courtesy of: GENSTONE REALTY (407-237-0905)

Listing Agent: Hafid Boujidi (407-729-3894)

Remarks: Welcome to 1173 Lakeshore Breeze Place, located in the Soleil community by Mattamy Homes. This well-appointed 4-bedroom, 2.5-bath home offers approximately 2,209 square feet of thoughtfully designed living space with an open-concept floor plan that seamlessly connects the kitchen, dining, and living areas. The kitchen features stainless steel appliances, a large island, ample cabinetry, and a walk-in pantry. The spacious primary suite includes a walk-in closet and a private bath with dual vanities. Additional features include a two-car garage, flex room, fenced yard, and no rear neighbors! Residents enjoy access to a community pool and playground, while the location offers convenient access to shopping, dining, major highways, and the Walt Disney World Resort area. Schedule your private showing today!

Listing is courtesy of: 4 RIVERS REALTY LLC (407-967-9616)

Listing Agent: Talles Batista Menezes (321-200-9620)

Remarks: PRICE REDUCTION: $5,000 SELLER HIGHLY MOTIVATED. Now offered $40,000 below original listing price. Fantastic townhome for sale offering comfort and convenience. This home is a standout choice for those seeking quality and value. Located in a sought after neighborhood only 15 minutes from the magic of Disney. You'll love the convenience of nearby highways and having the best local dining and shopping just around the corner. You’re minutes from everything while enjoying the quiet of a residential enclave This beautiful townhome has a new AC unit (2024), ensuring energy efficiency and comfort for years to come. An ideal option for a primary residence or an investment property, the interior features an intuitive layout that maximizes every square inch. Community Perks: Enjoy a well-maintained, quiet neighborhood with a sparkling community pool. Act fast to secure this unbeatable combination of price and position.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Colin Farrell (407-506-7233)

Remarks: Fully Furnished 3-Bed End Unit in the highly sought after Windsor Palms Resort! Resort-style living at its best and just minutes from Disney World and Margaritaville. This fully furnished, turnkey home features charming decor throughout and is zoned for short-term rental, perfect as a vacation home or investment property, and also ideal for long-term or residential living. The open-concept floor plan seamlessly connects the kitchen and living area, filled with natural light and overlooking the private pool area. A downstairs bedroom with a full bath provides great flexibility for multi-generational living or guests. Upstairs, enjoy the spacious two bedrooms, each with ensuite bathrooms, plus a laundry area with washer and dryer. Updates include fresh interior paint (2021), new exterior paint (2025), new pool heater (2025), and new mattresses (2023). Relax by your private plunge pool or take advantage of resort amenities—clubhouse, pool, movie theater, fitness center, basketball courts and tennis courts - all within a secure, gated community. Don’t miss your chance to own a piece of paradise just minutes from Central Florida’s top attractions! Schedule a showing today!

Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)

Listing Agent: Virginia Bibby (407-749-8148)

Remarks: Discover this fantastic 3-bedroom, 3-bathroom townhouse nestled within the secure, gated Windsor Palms Resort community. This home offers the perfect blend of comfort and convenience, with an open floorplan and tile flooring throughout the main living areas. Enjoy the ease of a firstfloor bedroom with an ensuite bathroom, providing flexibility and privacy. Step out onto your private screened patio and take in the serene wooded conservation views. Upstairs, you'll find two additional spacious bedrooms, both with their own attached bathrooms. Bedrooms are comfortably carpeted. Windsor Palms is more than just a community; it's a lifestyle! Residents and guests have access to an impressive array of resort-style amenities, including a sparkling pool, splash pad, playground, tennis and basketball courts, beach volleyball, an arcade, fitness center, a convenient sundries shop and more. Located with easy access to all of Orlando's world-class theme parks, shopping, dining, and more, this townhouse is ready for you! Don't miss out – be sure to check out the video tour!

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: John Callahan (407-716-3541)

Remarks: PRICE IMPROVEMENT!!! Stunning 9-Bedroom Vacation Home in Solara Resort – Fully Upgraded & Turnkey Welcome to this exceptional 9-bedroom, 6.5-bathroom vacation retreat located in the highly desired Solara Resort, just minutes from Walt Disney World®, Universal Studios, SeaWorld, I-Drive, Disney Springs, and Central Florida’s renowned beaches. Offering 4,363 square feet of thoughtfully designed living space and more than $170,000 in upgrades, this home presents an outstanding opportunity for investors or families seeking a luxury vacation residence. Designed to comfortably accommodate large groups, the property can host up to 30 guests, including 16 adolescents and 14 adults. There are seven private king bedrooms, each designed with its own distinct style, along with four full-over-full custom bunk rooms ideal for children and teens. Notable features include a hand-painted, custom-designed treehouse and cabin-themed bedroom with built-in bunk beds, as well as an additional Toy Story–themed bedroom with custom built-ins and professionally painted artwork. The main floor offers an expansive open-concept layout with multiple living and gathering areas and includes a master ensuite for added convenience. This home is offered fully furnished and is ready for immediate use or rental, with all furniture, décor, linens, towels, kitchenware, pool equipment, and baby equipment included. Entertainment options are extensive. The air-conditioned garage has been transformed into a glow-in-the-dark arcade, and the home provides multiple common areas ideal for hosting and relaxation. The outdoor living space features a covered patio, heated pool, and hot tub, creating a private oasis for guests of all ages. Residents and guests also enjoy access to the exceptional amenities offered by Solara Resort. These include a heated grand pool, the FlowRider® surf simulator (available for an additional fee), an on-site bar and grill, coffee bar, sundries store, fitness center, sand volleyball court, full-sized soccer and basketball courts, indoor and outdoor lounges, workstations, a tween and teen hangout center, playground, pool bar, poolside cabanas, and a game room featuring a multi-sport virtual simulator for golf, soccer, football, basketball, and more. Guests with a reservation at the home receive complimentary entry to these amenities during their stay. With its prime location, extensive upgrades, themed living spaces, and access to premium resort amenities, this Solara Resort property offers a rare opportunity for those seeking a turnkey vacation home or high-performing short-term rental investment.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Hector Leon (407-227-4568)

Remarks: Beautifully updated 3-bedroom, 2-bath condo located in the desirable Windsor Palms community. This property was completely remodeled in 2024, featuring new flooring, updated kitchen with new cabinets and appliances, and renovated bathrooms with modern finishes throughout. The unit is offered fully furnished, making it ideal as a primary residence, vacation home, or investment property. Windsor Palms is a gated resort-style community with amenities including a pool, clubhouse, fitness center, and more. Conveniently located just minutes from Disney, Universal, SeaWorld, Old Town, and a wide variety of dining, shopping, and entertainment options.

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Tarek Al Hafi (214-549-0868)

Remarks: Virtually Staged. Beautiful 3 bedrooms (all in suite with walk in closets) + loft Townhome in the desirable community The Hub at Westside. Modern and functional layout, with wood looking vinyl plank flooring and $20k in finish upgrades from the builder, including vinyl flooring in the whole house (no carpets), cabinets, wall panels, pendants and more. Kitchen with full appliances, beautiful quartz counter tops and modern hardware throughout the house. Also, the house has NO neighbors behind, giving extra privacy to the owner and guests. This home is available for short-term rent, long-term rent and/or residency. Gated community with a gym, clubhouse and a pool, and perfectly situated near the Disney parks, restaurants and shopping.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Carolina Fortes Ribeiro (407-956-7674)