Homes for Sale Near Kissimmee Middle in Kissimmee - 307 homes

Remarks: *Tenant in Place Through May 2027* Located in a short-term rental approved community, offering true flexibility as a primary residence, vacation home, or income-generating investment property. Fully furnished 5-bedroom, 4.5-bathroom turnkey home with private screened pool in the resort-style, guard-gated community of Veranda Palms. Thoughtfully designed open floor plan offers versatility for personal use, vacation getaways, or income-producing short-term rental investment. Featuring dual primary suites, one on each level, this layout delivers exceptional flexibility and privacy for owners and guests alike. The kitchen showcases generous cabinetry and a breakfast bar, flowing effortlessly into the dining and living areas to create an inviting space for everyday living and entertaining. The main living area is bright and spacious, while the upstairs loft adds bonus square footage perfect for a game room, media space, or home office. No carpet throughout the home — easy-care flooring runs across every room, ideal for low-maintenance living and high-turnover rental use. All furnishings convey, making this property completely move-in or rental-ready from day one. Step outside to your private screened pool, ideal for year-round enjoyment of Florida's sunshine. The outdoor space provides the perfect setting to unwind or entertain after a day at the area's many attractions. Residents and guests enjoy access to Veranda Palms' resort-style amenities, including a clubhouse, fitness center, and community pool, all within a 24-hour guard-gated entrance. Conveniently positioned near major highways, shopping, dining, and Central Florida's world-famous theme parks and attractions.

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

Listing Agent: Jessica Souza Meuli (305-527-9574)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom townhome located in the desirable Compass Bay community, just minutes from Walt Disney World, shopping, dining, and major highways. Built in 2018, this spacious residence offers a functional open floor plan with a modern kitchen featuring cabinetry, granite countertops, and stainless steel appliances, seamlessly connecting to the living and dining areas, perfect for entertaining or everyday living. The property features a private patio area, ideal for relaxing after a long day, and generous bedroom sizes, including a comfortable primary suite. Compass Bay is a sought-after community that allows both short-term and long-term rentals, making this home an excellent opportunity for investors, vacation home buyers, or primary residents. PS: The property is being offered fully furnished Residents enjoy access to community amenities including a pool, playground, and well-maintained common areas. With low HOA fees and a prime location in the heart of Kissimmee’s tourism corridor, this property offers both convenience and flexibility. Don’t miss this opportunity to own in a highly desirable short-term rental–friendly community. Schedule your private showing today.

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

Listing Agent: Ana Gazzara (321-682-9775)

Remarks: Welcome home to this well-maintained single-family residence offering a bright and functional layout. The interior features spacious living and dining areas with tile flooring throughout the main living spaces and an open flow ideal for everyday living and entertaining. Comfortable bedrooms offer carpeting and ceiling fans, while the master bedroom has sliding doors leading to your rear screened-in lanai. Additional features include a two-car garage and a clean, neutral interior ready for its next owner. Easy to show!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: GATED KISSIMMEE CONDO WITH 2 BEDROOMS, 2 BATHROOMS, SCREENED-IN PORCH, UPDATED FINISHES, STAINLESS STEEL APPLIANCES, AND A PRIME LOCATION NEAR THE LOOP, THEME PARKS, AND ORLANDO INTERNATIONAL AIRPORT. Welcome home to comfort, convenience, and low-maintenance Florida living inside the TERRA CONDO community. This 970-SQ-FT CONDOMINIUM offers a practical split-bedroom layout with a SPACIOUS PRIMARY BEDROOM, DUAL CLOSETS, and an easy everyday flow that works well for a primary residence, seasonal home, or investment-style hold, subject to community rules. From the moment you enter, the STYLISH TILE FLOORING gives the home a clean, modern feel throughout the main living areas. The CHARMING KITCHEN features BEAUTIFUL COUNTERTOPS, STAINLESS STEEL APPLIANCES, and enough workspace to make daily meals simple and comfortable. The living area opens to a SCREENED-IN PORCH, giving you a private place to enjoy morning coffee, quiet evenings, or extra fresh-air living space without sacrificing convenience. Additional highlights include a TANKLESS WATER HEATER, LOW HOA FEES, and a location approximately 15 minutes from THE LOOP, about 25 minutes from WORLD-FAMOUS THEME PARKS, and about 30 minutes from ORLANDO INTERNATIONAL AIRPORT. IF YOU ARE LOOKING FOR A MOVE-IN-READY 2 BEDROOM, 2 BATH CONDO IN A GATED KISSIMMEE COMMUNITY WITH UPDATED FINISHES, EASY ACCESS, AND STRONG CENTRAL FLORIDA CONVENIENCE, 1030 PLANTATION DR APT C7 DESERVES TO BE SEEN.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Charles Watson (818-321-6494)

Remarks: Discover this well maintained 3 bedroom, 2 bathroom home offering 1,380 sq ft of comfortable living space. The home features a functional layout with inviting living and dining areas that flow into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to a screened-in patio with a pool—perfect for relaxing or hosting year-round. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: Raul Pino (305-662-1502)

Remarks: Under contract-accepting backup offers. Fully furnished and with a private pool — this 3-bedroom, 2.5-bath townhome in Encantada Resort, Kissimmee, FL is a turnkey opportunity ready to rent from day one. Located at 8553 Bay Lilly Loop, the property offers approximately 1,295 sq ft across a practical two-level layout designed for buyers seeking a vacation home, short-term rental opportunity, second residence, or low-maintenance resort-style property in one of Kissimmee's most searched vacation corridors. The main level connects the living, dining, and kitchen areas for an easy guest-friendly flow, with a convenient half bath downstairs. Upstairs, the bedrooms are positioned away from the main living spaces, including a primary suite with ensuite bath. The rear outdoor area includes a screened patio and private splash pool — additional space for relaxing after time at nearby attractions. Encantada Resort amenities are reported to include a clubhouse, community pools, spas, fitness center, playground, game room, cyber café, walking areas, and resort-style gathering spaces. The location provides direct access to US-192, SR-429, I-4, and Osceola Parkway, with Margaritaville Resort Orlando, Sunset Walk, Island H2O Water Park, golf, grocery stores, restaurants, and Central Florida attractions minutes away. This property is especially appealing for buyers searching for a furnished Kissimmee vacation rental near Disney, an Orlando-area investment property, a Central Florida townhome with resort amenities, or a short-term rental option near shopping, dining, water parks, golf, and major road access. The two-level floor plan, furnished setup, private pool, and proximity to major tourism anchors support strong search visibility for buyers comparing homes near Disney, townhomes in Encantada Resort, and properties along the US-192 corridor. Schedule your private showing today and explore the furnished resort-style location, rental potential, and Central Florida access this Kissimmee townhome offers.

Listing is courtesy of: DREAM FINDERS REALTY GROUP CORP (407-873-8379)

Listing Agent: Angela Rodriguez (407-873-8379)

Remarks: Townhome available and ready to move in, featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage, located in the gated community of Flora Ridge, conveniently near the Loop. The welcoming entry opens to a well-appointed kitchen with breakfast bar, seamlessly flowing into the open-concept living room and dining area—perfect for everyday living and entertaining. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a built-in workstation ideal for remote work or study. Enjoy close proximity to Shopping, Schools, Dining, and more. Schedule your private showing today!

Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)

Listing Agent: Rich Canelon (407-341-4035)

Remarks: Under contract-accepting backup offers. Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: INVESTORS OPPORTUNITY !!!! TENANT OCCUPIED. Fully remodeled, this inviting single-family home at 709 S Dillingham Ave in Kissimmee is designed for comfort and flexibility. The thoughtfully updated interior offers modern finishes throughout, creating a fresh and welcoming feel from the moment you arrive. Ideal for multi-generational living, the home includes a private mother-in-law suite with 2 bedrooms and 1 bathroom, perfect for extended family or guests while still maintaining privacy or for a great rental income. Centrally located near downtown Kissimmee, shopping, dining, schools, and major roadways. Enjoy peace of mind with a beautifully updated home ready for its next chapter. A wonderful opportunity to settle into a space where everyone feels at home. Buyer to verify all measurements and information.

Listing is courtesy of: GPS PROPERTY GROUP INC. (407-439-2527)

Listing Agent: Abel Jimenez (407-452-4119)

Remarks: Experience stylish and comfortable living in this beautifully designed townhome located within the sought-after Tapestry community. Perfectly positioned at 2504 Fassona Drive, this residence offers convenient access to Central Florida’s major highways, shopping, dining, and top attractions. Featuring 3 spacious bedrooms, 2.5 bathrooms, a downstairs primary suite, and a screened lanai, this home blends functionality with modern elegance. Interior highlights include quartz countertops, expansive windows that fill the home with natural light, and sleek railing details that create an open and inviting atmosphere. Move-in ready and thoughtfully designed, residents also enjoy resort-style amenities including a fitness center, 24-hour security, and a guarded gated entrance.

Listing is courtesy of: THE AGENT, INC (407-278-7090)

Listing Agent: Maria Godoy (407-906-0112)

Remarks: Opportunity is knocking with this stunning property nestled within the highly sought-after Stonefield community in Hunter’s Creek. This is a rare chance to own a spacious, updated townhome with an ASSUMABLE FHA LOAN at an incredible 3.375 interest rate, a true game changer in today’s market! But wait that’s not all! This 2-bedroom, 2-bath home with a 1-car garage features three additional flex rooms, offering incredible versatility for your lifestyle. Whether you need a private home office, formal dining room, cozy den, or guest suite, this floor plan easily adapts to your needs. Enjoy the perks of modern living and energy efficiency with a paid off solar energy system providing substantial savings, plus a newer 2021 energy-efficient A/C unit. Inside, you’ll find tile and laminate flooring throughout, appliances and an interior laundry room with washer & dryer included along with built-in cabinetry for convenient storage. The primary suite offers abundant natural light, a spacious walk-in closet, private ensuite bathroom featuring double vanities and an oversized walk-in linen closet. Upstairs, you’ll discover two large bonus rooms perfect for an office, studio, guest quarters or extra storage that many homes lack. The second bedroom is located on the main floor across from the updated second bathroom, which, like the primary, features stone countertops and modern finishes. Stylish lighting fixtures throughout the home add a contemporary touch, making this property truly move-in ready. Residents of Stonefield enjoy a secure gated community with resort-style amenities, including resort style pool, clubhouse, fitness center, tennis courts, fishing dock and walking / biking trails surrounded by exotic landscaping. Located just 15 minutes from Disney, Universal, Orlando’s top attractions, 20 minutes from Orlando International Airport, hospitals, schools, medical offices, markets and steps from The Loop’s dining with plenty of shopping for everyday needs. This home perfectly blends convenience, comfort and lifestyle. Live a life of ease, style and abundance of opportunity.

Listing is courtesy of: LPT REALTY LLC (386-204-6398)

Listing Agent: Scarlett Napolitano (407-808-6757)

Remarks: This inviting 3-bedroom, 2-bath condo in Flora Ridge offers a bright and spacious layout designed for comfortable everyday living. The living and dining areas flow seamlessly into a screened-in balcony, while the kitchen features ample cabinet space and a practical layout. All three bedrooms are generously sized, with carpeted flooring for added comfort, and both bathrooms are tiled for easy maintenance. Located near the community pool and just minutes from shopping, dining, schools, and major roads, this condo offers convenience and a family-friendly environment in a well-maintained and secure gated community.

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

Listing Agent: Mariana Nossa (407-455-9565)

Remarks: Discover this spectacular residence located in the exclusive gated and guard-secured community of Tapestry in Kissimmee. Featuring 3 bedrooms, 2 bathrooms, and an office, this 1,706-square-foot home is designed for those seeking comfort, style, and a lifestyle filled with exceptional amenities. From the moment you enter, the home welcomes you with an open-concept layout, bright living spaces, and a seamless flow between the main living areas, creating the perfect setting for both everyday living and entertaining. The office offers a versatile space ideal for working from home, studying, or adapting to your personal needs. The spacious bedrooms provide comfort and privacy, while the contemporary finishes and functional design create a warm and inviting atmosphere throughout the home. Living in Tapestry means enjoying resort-style amenities designed for the entire family, including a beach-entry pool with cabanas, splash and recreational areas, a state-of-the-art fitness center with yoga and movement studio, an elegant clubhouse with catering kitchen for special events, outdoor terrace, sports courts, BBQ pavilions, dog park, and walking and biking trails. All of this is nestled within a private 24-hour guard-gated community, conveniently located near major highways, Orlando attractions, the airport, shopping, dining, and excellent schools. Whether you are searching for a primary residence, vacation home, or investment opportunity, this beautiful property offers an exceptional chance to experience the Florida lifestyle at its finest. Schedule your private showing and experience everything this beautiful home.

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

Listing Agent: Neyla Alvarez (407-780-8786)

Remarks: READY TO MOVE !! UPDATED IN 2020, new wood kitchen cabinets, Italian granite kitchen countertops, new tile titles in downstairs living room, . SEE ATTACHED FEATURES SHEET. CORNER UNIT. 4 bedrooms, 3 bathrooms, TWO MASTER SUITES. 1 master on the ground floor AND 1 master on the upper floor. The downstairs master bathroom has been completely remodeled in 2023. The great room has French doors, The air conditioning has been changed approximately 1 year; This beautiful townhouse can be a short term rental or a main home. Conveniently located near schools, restaurants, theme parks, shopping and major highways. Venetian Bay is a 24 hour guarded community offering resort style amenities: 4 swimming pools (main pool is heated), sun deck, 4 children's play areas, clubhouse with kitchen, fitness center, game room, volleyball sand, basketball, tennis courts, picnic areas, fishing. dock and more. This gem won't last long. Call today for your private showing!O MOVE !!!

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: Welcome to 8816 Dunes Court #302, a top-floor 2-bedroom, 2-bathroom condo located just 8 minutes from Walt Disney World in the heart of Central Florida. Whether you're searching for a vacation home near Disney, a short-term rental investment property, an Airbnb opportunity, or a full-time residence, this resort-style condo checks all the boxes. Inside, you'll find an open and inviting layout with high ceilings that create a bright, spacious atmosphere. Step onto your private balcony and enjoy peaceful views of the community pond and its stunning fountain, offering a relaxing retreat after a day at the parks or exploring the area. Located within a highly desirable resort-style community, residents and guests enjoy access to two swimming pools, two tennis and pickleball courts, a volleyball court, fitness center, arcade room, playground, and BBQ picnic areas. The unbeatable location places you minutes from Disney World, major attractions, championship golf courses, shopping, dining, entertainment, and Orlando's world-famous theme parks. Perfect as a vacation rental, second home, investment property, or primary residence, this Disney-area condo offers the ideal combination of location, amenities, and lifestyle. Don't miss your opportunity to own a piece of Central Florida paradise just minutes from the magic.

Listing is courtesy of: MCKINNEY REALTY CO (407-750-0208)

Listing Agent: Matt Mckinney (407-750-0208)

Remarks: TURNKEY SHORT-TERM RENTAL OR PRIMARY RESIDENCE | POOL & SPA | LOW HOA | Welcome to this beautifully maintained, move-in-ready and fully furnished vacation home, currently operating as a very successful active short-term rental in one of Kissimmee’s most desirable locations near Disney and Margaritaville. Situated in the quiet community of Oak Island Cove with low HOA fees, this property offers an exceptional opportunity for both investors and second-home buyers, with strong rental income potential, excellent guest reviews, and a fully established, ready-to-go short-term rental business in place. This immaculate four-bedroom, three full bath home features two spacious primary suites and has been very well maintained. The home offers a comfortable open-concept layout with a modern kitchen, generous living and dining areas, and thoughtful design throughout for optimal guest experience and continued rental performance. Interior paint and kitchen cabinets were updated in 2023, and the home was fully furnished and professionally decorated in 2023, making it completely turnkey for immediate continued use. Enjoy your private outdoor retreat with a resurfaced pool completed in August 2022 and a hot tub that conveys with the sale, perfect for relaxing after a day at the parks. Additional improvements include a roof replacement in 2018 and plantation shutters throughout the home. Zoned for short-term rentals and located just minutes from world-class attractions, shopping, dining, and entertainment, this property combines prime location, strong income, and low-maintenance ownership. Schedule your private showing today and experience this exceptional investment opportunity.

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: Alena Nicole Kolyadchik (407-545-9000)

Remarks: Location, location! The seller is motivated to assist with some closing costs, which can be used to lower the interest rate or pay for closing expenses. Don't miss this opportunity to live in Tapestry community First time buyers ,investors Spectacular 4/3 with a beautiful landscaping exclusively designed for the property, it is located in one of the best areas of Kissimmee, with good access to I4, Osceola pkwy, 417, 528 and turnpike, access to everything you need for your daily living. It is a 24 hour guarded gate community with excellent amenities In addition, the house has a covered and completely fenced patio to generate privacy in your patio and your parties. Don't miss out on this opportunity.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Juan Oberto (407-810-3694)

Remarks: Beautiful 2-Story Home in Gated Community – Great for Living, Vacation, or Rental Income This is a wonderful opportunity to own a fully furnished 2-story home located in a quiet, gated community with 24/7 security and great amenities. The home is in excellent condition and is currently being used as a short-term rental with a 5-star rating on Airbnb. It’s located in a very convenient area — just minutes away from Walmart, Disney parks, Highway 192, and Plaza del Sol. Whether you're looking for a permanent home, a vacation spot, or an investment property, this one offers a lot of value and flexibility. The home is already listed and performing well on Airbnb. If the buyer is interested, we’re happy to transfer the current and upcoming Airbnb bookings to make the transition smooth and help you start earning right away. Inside, the home is clean, spacious, and comes fully furnished, so it’s truly turn-key — ready for living or renting without any extra effort. The community offers plenty of amenities for guests and residents, including a swimming pool, clubhouse, gym, and more. It’s a safe, family-friendly neighborhood that’s also appealing to tourists due to its close proximity to major attractions. Whether you plan to live here full-time, use it as a vacation getaway, or continue running it as a short-term rental, this home is a smart choice in a great location.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Juan Garcia Betancur (407-535-0909)

Remarks: Welcome to one of the most compelling luxury investment opportunities in Story Lake—where upscale design, prime location, resort amenities, and exceptional income potential come together to deliver robust returns on investment. Here, ROI meets luxury, making this offering stand out for both personal enjoyment and strategic financial gain. This stunning 7-bedroom residence creates a bold first impression. It sits on a premium lot with no direct rear neighbors and offers a tranquil view of the pond. The property is fully furnished & professionally decorated, completely turnkey and ready for immediate enjoyment or rental. The thoughtfully designed interior features rectangular tile flooring throughout the first floor in the foyer, kitchen, baths, dining & living areas, and laundry room. A well appointed home chef’s kitchen offers grey subway tile backsplash, Extended cabinetry with crown molding, grey stainless steel appliances, a spacious pantry, massive center island, and upgraded pendant lighting. The adjacent dining room is elegantly furnished for entertaining and large group stays. The living room is professionally decorated to impress. It features a stunning polished porcelain tile accent wall behind the TV, high-end furnishings, and large sliding glass doors that open directly to the pool area. The first floor also includes: A guest suite with an adjacent full bath & quartz vanity, A dedicated owner’s storage closet, and a spacious laundry room equipped with a washer & two dryers. The garage has been converted into a game & media room, complete with a media projector & comfortable seating, dedicated split HVAC system, popcorn machine, and video games. Upstairs, you’ll find 6 additional bedrooms & 4 full baths; all professionally decorated with premium themed décor elevating the guest experience. Each bedroom is equipped with its own flatscreen TV, enhancing the experience. The rear primary suite offers a view of the pool & wooded area. It features a luxurious ensuite bath with a soaking tub, a separate walk-in shower, a quartz double vanity, a private water closet, and a big walk-in closet. Second-floor highlights include a Princess-themed room, a Mickey Mouse-themed room, and a Toy Story-themed room. There are also two additional spacious bedrooms at the front of the home, including a second primary suite with double queen beds, dual sinks, & a large walk-in shower. Step outside to your private retreat. Enjoy a heated pool and spa, plus a grill and added seating. Resort-Style Amenities allow Owners & guests to enjoy access to one of the most sought-after amenity packages in the area. Offerings include a resort-style clubhouse & community center, an expansive pool complex with a lazy river, water slides, and a splash pad, outdoor entertainment areas for guests and gatherings, a fitness center, jogging trails, a game room, and a theater. For an additional fee, guests can also enjoy: a Mini golf course, Kayak rentals & lake access, Ice cream shop, and a Full-service bar. In addition, the HOA provides basic lawn maintenance & includes basic cable + high-speed internet. These amenities enhance guest satisfaction, occupancy rates, and overall rental performance. From an investment perspective, this home excels: 7-bedroom capacity maximizes occupancy; water view and no rear neighbors drive premium bookings; high-end themed décor supports stronger nightly rates and guest retention; turnkey condition means immediate income potential.

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: David Dorman (407-948-8295)

Remarks: LOCATION, LOCATION, LOCATION! Beautiful fully furnished 3-bedroom, 3-bath townhouse located in a desirable gated community with NO lease restrictions — perfect for short-term rentals, long-term rentals, Airbnb, or Vrbo investment opportunities. Features 1 assigned parking space and access to community amenities including a pool and park. Ideally located just 10–14 minutes from Disney Theme Parks and close to shopping malls, restaurants, hospitals, pharmacies, and top-rated schools. Excellent opportunity for investors or vacation homeowners seeking strong rental income potential!

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Andrea Vanegas, Llc (786-658-1547)