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Browse All Kissimmee FL Properties with Pool for Sale

$219,000
3 Beds 2 Baths Villas At Laguna Bay Condo SubDv. 34746 Zip Code
Fully Furnished, High-Demand Income-Producing Villa Near Disney! Experience effortless Florida living in this bright and beautifully maintained first-floor villa located in the sought-after Villas at Laguna Bay community. Offering the convenience of ground-floor access and a welcoming open-concept layout, this property is perfect as a primary residence, vacation retreat, or income-producing rental. The spacious living and dining area creates an inviting atmosphere ideal for relaxing or entertaining, while generously sized bedrooms with walk-in closets provide comfort and ample storage. New windows, new a/c, new interior paint, new furnishings and more! This turnkey property has been meticulously cared for and tastefully furnished, with everything included—making it truly move-in or rental ready from day one - just in time for the upcoming peak rental season. Surrounded by lush tropical landscaping and tranquil natural scenery, the community offers an exceptional resort-style experience with a sparkling pool and spa, clubhouse, recreational amenities, tennis court & playground. Ideally located just minutes from Walt Disney World, world-renowned attractions, premier shopping, dining, and golf, this prime location continues to attract strong demand. With reasonable HOA fees that include water and zoning that permits short-term rentals, this is an incredible opportunity to own a versatile, low-expense, income-generating property in one of Central Florida’s most desirable areas. Don’t miss your chance to own this exceptional villa—schedule your showing today!

5004 Laguna Bay Circle Unit 49, Kissimmee

$445,000
5 Beds 5 Baths Windsor At Westside; Windsor/Westside SubDv. 34747 Zip Code
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Upgraded laminate floor; new dryer/washer (2025); two new king bed and bunkbed Star War theme in loft; Harry Potter theme and Disney Cruise theme in tow rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river plash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between Champions Gate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8904 Sydney Avenue, Kissimmee

$1,995,000
5 Beds 5 Baths Celebration East Village Unit 4 SubDv. 34747 Zip Code
Under contract-accepting backup offers. Virtually Staged. Rarely does a Remodeled Estate-Style home of this caliber, in a WATER VIEW location this serene, become available in the heart of Celebration! Nestled within the exclusive enclave of Aquila Reserve, 1247 Aquila Loop is a one-of-a-kind, Custom David Weekley Colonial Revival ‘Treefair’ that redefines luxury living. As one of only seven homes in the neighborhood to boast a PRIVATE backdrop of both lush CONSERVATION and tranquil Water views, this residence offers a level of privacy and natural beauty that is simply unmatched. From the moment you step inside, the scale of the home is breathtaking. The open-concept floor plan is anchored by 20-foot cathedral ceilings, FULL DUAL-PANE DOUBLE HUNG PGT WINDOWS and 24x24 porcelain tile that flows seamlessly across the main level. The heart of the home is a true gourmet Chef's kitchen, meticulously designed with Glacier Marble countertops, custom Duchess cabinetry including roll-out and stack of drawers, as well as a suite of Professional-grade appliances including a Sub-Zero Professional refrigerator, Wolf 48" Free standing gas range burner with grill/griddle, and a Zephyr wine fridge. Whether you’re hosting a grand gala or an intimate brunch, this space is as functional as it is beautiful. The primary suite is a true sanctuary, located on the main floor and featuring expansive bay windows that frame the water views. It’s complemented by a walk-in closet with California Style organization and a spa-like bath featuring granite dual vanities, a jetted tub, and a walk-in shower. A second ensuite bedroom on the first floor provides the perfect retreat for guests or multi-generational living. Follow the sweeping staircase to the second floor, where Blue Ridge Precision Milled Appalachian Hardwood flooring runs throughout. This level offers three additional bedrooms, two bathrooms, and a versatile 14x16 flex space, plus a private bonus/media room perfect for movie nights or a quiet library. The exterior is designed for the Florida lifestyle, featuring a classic wrap-around front porch and a screened back porch where you can enjoy the sights and sounds of the conservation area. Peace of mind comes standard here, with significant recent investments including a 2023 NEW ROOF, and THREE CARRIER HVAC systems all installed in 2023, along with (2017) FULL DUAL-PANE DOUBLE HUNG PGT WINDOWS and DUAL RINNAI TANKLESS WATER HEATERS. This isn’t just a house; it’s a masterwork of design and comfort, waiting for its next chapter in Celebration’s most coveted corner.

1247 Aquila Loop, Celebration

$599,900
5 Beds 3 Baths Forest Unit 1 SubDv. 34746 Zip Code
Welcome to this truly unique and versatile property nestled in Kissimmee, Florida, offering three separate living units, modern upgrades throughout, and incredible income-producing potential. The main residence is a spacious 3-bedroom, 1-bathroom home with a flexible layout that can easily be converted into a 4-bedroom, 2-bathroom home to suit your needs. Step inside and you’ll immediately notice the modern stone countertops that anchor the fully renovated interior, blending timeless style with everyday functionality. Enjoy Florida living at its finest from the fully enclosed screened-in porch, perfect for relaxing or entertaining year-round. Attached to the main home are two private 1-bedroom, 1-bathroom apartment units, each complete with their own kitchenette, ideal for rental income, extended family, or guest accommodations. Live in one unit and let the others pay your mortgage, or maximize your returns by renting all three. The property sits on a full acre of beautifully maintained land surrounded by mature trees that provide natural shade and privacy. The lot is fully fenced for security and seclusion, and features a large U-shaped driveway with ample parking for residents and guests alike. The home also includes a whole-house water purification system, ensuring clean, high-quality water throughout every unit on the property. Whether you’re an investor looking for a strong cash-flowing asset or a homeowner seeking space, privacy, and flexibility, this one checks every box. Opportunities like this don’t last, so schedule your showing today!

1756 Tangle Wood Drive, Kissimmee

$385,000
3 Beds 2 Baths Siena At Celebration Condo A SubDv. 34747 Zip Code
Welcome to Siena at Celebration, one of Celebration’s most desirable condominium communities. This spacious 3-bedroom, 2-bath residence offers 1,529 square feet of comfortable living space featuring soaring cathedral ceilings, abundant natural light, and an open-concept floor plan. The kitchen features white cabinetry, quartz countertops, stainless steel appliances, and a tile backsplash, opening seamlessly to the dining and living areas. Luxury vinyl flooring enhances the main living spaces, while the flexible third bedroom can serve as a guest room, home office, or additional living area. The primary suite includes a large walk-in closet and private en-suite bath. A full-size washer and dryer and assigned parking space are included for added convenience. Residents enjoy access to Siena at Celebration amenities including a resort-style pool, clubhouse, fitness center, playground, and all of the amenities that make Celebration one of Central Florida’s most sought-after communities. Enjoy miles of walking and biking trails, nearby shopping and dining, Celebration Town Center, AdventHealth Celebration, and easy access to Walt Disney World, Orlando International Airport, and major highways. Whether you’re looking for a primary residence, second home, or investment opportunity, this property offers the perfect combination of comfort, convenience, and the Celebration lifestyle.

760 Siena Palm Drive Unit 205, Kissimmee

$267,000
2 Beds 3 Baths Regal Oaks At Old Town SubDv. 34746 Zip Code
Welcome to Regal Oaks Resort, where comfort, convenience, and resort-style living come together in this 2-bedroom, 2.5-bathroom townhouse. Offered fully furnished, this property is ready for immediate enjoyment as a vacation home, investment property, or personal retreat. Step inside to find a spacious and inviting open-concept layout designed for both relaxation and entertaining. The fully equipped kitchen flows seamlessly into the dining and living areas, creating the perfect gathering space for family and friends. One of the standout features of this home is the private west-facing lanai, providing sunny afternoons and stunning evening sunsets. Unwind after a day of adventure in your own private hot tub, an ideal space to relax and enjoy Florida's beautiful weather year-round. The upstairs level offers two generously sized bedrooms, each with its own ensuite bathroom, providing privacy and comfort for owners and guests alike. A convenient main-floor powder room adds additional functionality. Located just a short walk from Regal Oaks' resort amenities, residents and guests enjoy access to a community pool, clubhouse, fitness facilities, restaurant, and recreational areas. Situated minutes from world-famous attractions, shopping, dining, and entertainment, this location offers exceptional convenience while maintaining a peaceful resort atmosphere. Whether you're looking for a vacation getaway, income-producing property, or both, this fully furnished townhouse presents an outstanding opportunity in one of Central Florida's most desirable resort communities.

2606 Roadster Lane, Kissimmee

$449,000
5 Beds 5 Baths Windsor At Westside; Windsor/Westside SubDv. 34747 Zip Code
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| END UNIT Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: End Unit Star War loft; Frozen and Nemo theme rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8932 Sydney Avenue, Kissimmee

$559,000
3 Beds 3 Baths Celebration Island Village Ph 1a SubDv. 34747 Zip Code
Welcome to your dream home and lifestyle in Celebration's Island Village. This beautifully designed 3-bedroom, 2.5-bath townhome combines modern finishes with the charm and sense of community that Celebration is known for. Inside you'll find several builder upgrades including luxury vinyl plank flooring throughout the main living area, stairs and master bedroom, upgraded tile in the bathrooms and a tile backsplash in the kitchen. The home has an open-concept floor plan perfect for entertaining, a stylish kitchen featuring quartz countertops and a large center island for the family and friends to gather around. The covered front porch provides a welcoming place to sit and enjoy the tree-lined streets, while the private rear courtyard offers the perfect setting for grilling, gathering with friends, or watching the Sunday game. Located within walking distance of the neighborhood school, this home also places you just steps from Island Village's outstanding amenities, including a resort-style pool, clubhouse, parks, playgrounds, scenic walking trails, and local favorites like the neighborhood coffee shop, restaurant, and ice cream shop. Located just minutes from Walt Disney World, residents of Celebration enjoy the unique advantage of being close to endless entertainment, dining, and recreation while still enjoying the charm and tranquility of Celebration living. Whether you're looking for a full-time residence or a place to enjoy the celebrated Florida lifestyle, this home offers the perfect opportunity to experience everything Celebration has to offer. Seller is offering $10k towards buyers closing costs and prepaids.

2253 Celebration Boulevard, Celebration

$949,000
11 Beds 10 Baths Reunion West Ph 1 West & Ament Ctr Rplt SubDv. 34747 Zip Code
Step into the Disney-area investment opportunity you’ve been waiting for: an 11 BEDROOM, 10 BATHROOM LUXURY VACATION RETREAT in amenity-rich Encore at Reunion, designed to deliver unforgettable guest experiences, room for everyone, and the rental potential investors want. Perfectly located just MINUTES FROM WALT DISNEY WORLD and Orlando’s world-famous theme parks, this frequently booked home is ideal as a personal vacation retreat, large-group rental property, or rare home that can help pay for itself. With a MOTIVATED SELLER and AGGRESSIVE PRICING, this fully furnished investment home offers the scale, features, and location that stand out in Orlando’s vacation rental market. The property has potential for UP TO $120K IN ANNUAL INCOME. Its bedroom count, ensuite-heavy layout, themed entertainment, quality furnishings, and proximity to DISNEY, UNIVERSAL & SEAWORLD, create the kind of large-group appeal that drives bookings. Designed for large groups and multi-generational travel, the home features 11 BEDROOMS, 10 FULL BATHROOMS, 9 BEDROOMS WITH FULL ENSUITES, and THREE PRIMARY SUITES, with two downstairs and one upstairs for flexibility and privacy. The ADDED 11TH BEDROOM further enhances rental capacity, while the spacious layout comfortably accommodates large vacation groups. From the moment you arrive, the home delivers strong curb appeal with a SPANISH TILE ROOF, STONE FACADE, and BRICK PAVER DRIVEWAY. Inside, it is sold FULLY FURNISHED with quality furnishings & COMPLETELY TURNKEY, allowing the next owner to step directly into ownership with minimal setup. The AIR-CONDITIONED STAR WARS THEMED GAME ROOM impresses with immersive murals and professional-level games including TWO NASCAR ARCADE DRIVING GAMES, POP-A-SHOT BASKETBALL, AIR HOCKEY, PING PONG, and FOOSBALL. Additional themed spaces include MICKEY MOUSE AND STAR WARS THEMED BEDROOMS, creating the memorable vacation experience guests want! The large gourmet kitchen is built for high-use vacation rental living w/GRANITE COUNTERS, 42” SHAKER-STYLE CABINETS, a TILED ISLAND FOR DURABILITY, TWO STAINLESS STEEL REFRIGERATORS, TWO STAINLESS STEEL DISHWASHERS, a coffee/wine bar, and fully stocked kitchen. The home also features upgraded bathrooms with GRANITE COUNTERS and GLASS-ENCLOSED SHOWERS, ceiling fans throughout, large storage closets, owner’s storage, TANKLESS WATER HEATERS, and TWO A/C UNITS. Recent upgrades add peace of mind and enhance the guest experience, including a NEW POOL HEATER, NEWER A/C, upgraded lighting, refreshed decor, stylish fixture updates, and the ADDED 11TH BEDROOM. Step outside to a private resort-style backyard with a HEATED POOL, HEATED HOT TUB, large covered lanai, expansive paver outdoor space, fenced backyard, and tropical landscaping. This outdoor space offers the private retreat expected from a luxury Orlando vacation home. Located just a 5-MIN WALK TO ENCORE CLUB AMENITIES, enjoy the Encore waterpark, pools, clubhouse, restaurant and bar, fitness center, game room, courts, soccer fields, and available concierge services, park shuttles. The HOA helps simplify ownership with access to Reunion amenities, security, 24-HOUR MANNED GATED ENTRY, internet, cable, landscaping, irrigation, daily valet trash, pest control, and community grounds maintenance. Whether you are searching for a large Disney-area vacation home or fully turnkey short-term rental this home offers the best of both worlds. Schedule your private showing today before it is gone!

7657 Wilmington Loop, Kissimmee

$450,000
3 Beds 2 Baths Windsor Point Ph 2 SubDv. 34741 Zip Code
Beautiful 3-Bedroom Home in a Gated Community – Available September 2026 Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering comfort, style, and exceptional outdoor living. From the inviting front porch to the impressive rear screened lanai, every detail has been designed for relaxed Florida living. Inside, you'll find a bright and welcoming interior enhanced by large windows that fill the home with natural light, ceiling fans, and laminate flooring in select areas. The spacious living area seamlessly connects to the outdoor space through sliding glass doors, creating the perfect setting for entertaining and enjoying Florida's indoor-outdoor lifestyle. The kitchen features wood cabinetry, a cozy breakfast nook, and comes fully equipped with appliances, offering both functionality and style for everyday living. The primary suite is a private retreat showcasing elegant crown molding, a tray ceiling, and dual walk-in closets. The en-suite bathroom offers dual vanities and a spacious glass-enclosed shower. The secondary bedroom also features a walk-in closet, providing additional storage and convenience. Step outside and enjoy the ultimate Florida lifestyle. The screened lanai features a beautifully designed summer kitchen complete with a built-in grill, granite countertops, sink, and generous space for outdoor dining and entertaining. The backyard offers plenty of room to add a future swimming pool. Recent improvements provide peace of mind and added value, including a new roof, new air-conditioning system, fresh exterior paint, screen enclosure, and new paver installation. Located in a desirable gated community, residents enjoy access to a community pool, playground, sidewalks, and beautifully maintained common areas. Conveniently situated near shopping, dining, schools, major highways, and Orlando's world-famous attractions. This home will be available starting September 2026.

2922 Willow Creek Lane, Kissimmee

$1,895,000
5 Beds 7 Baths Reunion Ph 01 Prcl 01 Unit 03 SubDv. 34747 Zip Code
Welcome to 7453 Gathering Drive, a truly one of a kind luxury residence in the heart of Reunion Resort. This exceptional 5 bedroom, 6.5 bathroom home comes with an active Reunion Membership and offers the rare combination of luxury, privacy, premier location, and refined personal ownership. Unlike a typical vacation rental home, this residence was lovingly used as a family’s personal retreat and was rarely rented, which is clearly reflected in the care, condition, and quality throughout. From the moment you enter, you will notice the super over the top finishes, elegant crown molding, thoughtfully updated interiors, and polished details that create a timeless and elevated feel. The home is being offered fully furnished, including the beautiful Z Gallerie furniture package, creating a true turnkey opportunity for the next owner to enjoy immediately. Designed for comfort, entertaining, and elevated resort living, the floor plan offers spacious bedrooms, beautifully appointed bathrooms, generous living areas, and a seamless indoor and outdoor lifestyle. The backyard overlooks the golf course, offering peaceful views, added privacy, and a relaxing setting that feels tucked away while still being in one of Reunion Resort’s most premier locations. While this home can be rented as a short term rental, it is especially well suited for a buyer looking for a private second home, primary vacation residence, or luxury family retreat where they can enjoy the best of Reunion Resort without compromising on quality, design, or location. Reunion Resort is one of Central Florida’s most sought after luxury resort communities, known for its championship golf, beautiful surroundings, resort style amenities, dining, pools, water park, tennis, pickleball, fitness, and close proximity to Walt Disney World and Orlando’s world class attractions. Whether you are looking for a private second home, a luxury vacation retreat, or an exceptional furnished residence in one of Reunion’s best locations, 7453 Gathering Drive delivers a level of quality, finish, and ownership pride that is truly hard to find.

7453 Gathering Drive, Reunion

$425,000
4 Beds 3 Baths Gleneagles SubDv. 34744 Zip Code
One or more photo(s) has been virtually staged. SELLER OFFERING $5,000.00 TOWARDS CLODING COST &/OR RATE BUY-DOWN. Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home featuring TWO PRIMARY SUITES, a private screened pool, and an exceptional floor plan designed for comfortable living, entertaining, and investment potential. From the moment you arrive, you'll appreciate the charming screened front porch, the perfect place to enjoy your morning coffee, unwind in the evening, or greet guests in comfort year-round. Step inside and discover a home that has been thoughtfully updated with today's buyer in mind. Featuring luxury vinyl plank flooring throughout, freshly painted white kitchen cabinetry, brand-new stainless-steel appliances, designer matte black fixtures, and a modern boho-inspired design, every detail has been carefully selected to create a warm, stylish, and inviting atmosphere. The fully renovated bathrooms showcase stunning floor-to-ceiling ceramic tile, creating a spa-like experience rarely found at this price point. New Water Heater, Roof Replaced in 2022, A/C System (2013), Screened Front Porch, Move-In Ready. Whether hosting family gatherings, pool parties, or simply unwinding after a long day, this outdoor space offers the Florida lifestyle buyers dream about. RESORT-STYLE COMMUNITY AMENITIES • Gated Community • Golf Course Community • Clubhouse • Fitness Center • Community Pool • Tennis Courts • Playgrounds • Scenic Walking Trails • Beautifully Maintained Common Areas INVESTOR FRIENDLY: Short-term rentals are permitted, making this property an excellent opportunity for homeowners, vacation home buyers, or investors seeking strong rental income potential. PRIME CENTRAL FLORIDA LOCATION: Conveniently located nearby: Orlando International Airport, Lake Nona Medical City, Florida Turnpike and Major Highways, Walt Disney World, Universal Studios, and Orlando's World-Famous Attractions, Shopping Centers and Retail Destinations, Restaurants and Entertainment, Schools and Childcare Facilities. One of the standout features of this home is its incredible family-friendly location. Remington Christian Academy and Kidsville Daycare Academy are located approximately a 2-minute walk from the property, providing unmatched convenience for families with children. Whether you're searching for a primary residence, vacation home, or investment property, this home delivers the perfect combination of modern upgrades, resort-style amenities, income-producing potential, and an unbeatable location. This is the move-in-ready Florida lifestyle you've been waiting for. Schedule your private showing today before this incredible opportunity is gone!

2705 Willow Glen Circle, Kissimmee

$345,000
3 Beds 2 Baths Ventura At Windsor Hills Condo Ph 3 SubDv. 34747 Zip Code
NOW OFFERED AT $345,000 + $5,000 SELLER CONCESSION toward buyer closing costs, prepaid expenses, interest rate buy-down or other allowable buyer costs! PLUS, for QUALIFIED BUYERS, ask about the 1% PREFERRED LENDER'S CREDIT. Welcome to an exceptional opportunity in the highly sought-after Windsor Hills Resort, one of Central Florida's premier vacation destinations. Perfectly positioned just minutes from Walt Disney World, this beautifully renovated 3-bedroom, 2-bath condominium at 2778 Almaton Loop #303 offers the ideal blend of luxury, comfort, and investment potential. Offered fully furnished with stylish, updated décor and furnishings, this turnkey residence is ready for immediate enjoyment as a personal retreat, vacation home, or income-producing short-term rental. The thoughtfully designed floor plan features spacious living areas, abundant natural light, and effortless single-level living. At the heart of the home, the open-concept living and dining area creates an inviting space for entertaining family and guests. The upgraded kitchen showcases modern cabinetry, generous counter space, and seamless connectivity to the main living areas. The private owner's suite serves as a relaxing sanctuary with an ensuite bath and ample closet space, while two additional bedrooms provide comfortable accommodations for guests, family members, or flexible workspace options. Beyond the residence, Windsor Hills delivers an unparalleled resort lifestyle. Residents and guests enjoy world-class amenities including a lagoon-style pool with water slide, fitness center, clubhouse, movie theater, game room, sports courts, playgrounds, and 24-hour gated security. Every day feels like a luxury vacation. Located less than two miles from Disney and moments from Orlando's renowned attractions, championship golf courses, upscale shopping, and dining destinations, this property offers both convenience and exceptional value. Whether you're seeking a highly desirable vacation rental investment, a second home, or your own Florida getaway, this move-in-ready residence presents a rare opportunity to own within one of the area's most successful and recognized resort communities. Experience the best of resort-style living and schedule your private showing today.

2778 Almaton Loop Unit 303, Kissimmee

$499,990
3 Beds 4 Baths Pleasant Hill Lakes Unit 9 SubDv. 34746 Zip Code
Under contract-accepting backup offers. Welcome to a home designed around the way Florida living was meant to be enjoyed. From the moment you step through the front door, your eyes are immediately drawn through a dramatic wall of glass to the sparkling screened pool beyond, creating a breathtaking first impression that sets the tone for everything this exceptional custom-built residence has for you. Perfectly situated on an expansive .52-acre homesite in the sought-after Pleasant Hill Lakes community, this is the rare property that combines privacy, character, and space in a way that newer cookie-cutter neighborhoods simply cannot. Lovingly maintained by its original owners and recently refreshed with numerous updates, this 3-bedroom, 3.5-bathroom home showcases timeless architecture centered around seamless indoor-outdoor living. Natural light fills the home through oversized sliding glass doors, while soaring ceilings create an open and airy atmosphere throughout the main living spaces. At the heart of the home, the updated kitchen features beautiful new cabinetry and flows effortlessly into the breakfast nook and spacious family room, creating the perfect gathering space for everyday living and entertaining. A charming fireplace anchors the living area, adding warmth and character to the home's inviting ambiance. Formal dining and a dedicated office provide flexibility for hosting guests, working remotely, or enjoying additional living space. The primary suite serves as a private retreat, offering an oversized bedroom with vaulted ceilings, direct pool access through sliding glass doors, a large walk-in closet, and a beautifully renovated spa-inspired bathroom complete with dual vanities, a dedicated makeup station, a soaking jacuzzi tub, and a separate walk-in shower. Step outside and discover the lifestyle that truly sets this home apart. The oversized screened pool enclosure creates a private backyard oasis, complete with a dedicated pool bath and a newly refinished pool deck. Whether hosting weekend gatherings, enjoying your morning coffee, or unwinding under the Florida sunshine, this outdoor living space was designed to be enjoyed year-round. Recent improvements provide peace of mind and modern appeal, including a new HVAC system (2026), second HVAC system (2023), newer roof (2023), new kitchen cabinetry, renovated primary bathroom, fresh interior and exterior paint, new flooring in the primary bedroom, updated landscaping, and a refinished pool deck. The washer, dryer, and refrigerator are all included, making this home truly move-in ready. Additional highlights include an oversized 8+ car driveway, spacious 3-car garage, mature landscaping, and ample room for boats, recreational vehicles, or additional parking. Located within the established Pleasant Hill Lakes community, residents enjoy larger estate-style homesites, mature oak trees, custom architecture, wide streets, and a remarkably low HOA. Conveniently located near Disney, Lake Nona, Orlando International Airport, Downtown Kissimmee, The Loop, major highways, shopping, dining, and entertainment, this location offers an ideal balance of privacy and convenience. Homes offering this combination of land, architecture, updates, pool-focused design, and location rarely become available. This is more than a home. It is an opportunity to enjoy the space, character, and Florida lifestyle today's buyers are searching for but seldom find.

2827 Shadow Wood Court, Kissimmee

$437,900
4 Beds 3 Baths Reunion Ph 1 Prcl 1 Unit 1 SubDv. 34747 Zip Code
Under contract-accepting backup offers. Virtually Staged. 7407 Devereaux St offers something increasingly hard to find in Central Florida: a home where much of the maintenance is already handled for you. Located behind the 24-hour guarded gates of Reunion, the HOA includes internet, cable TV, lawn mowing, edging, fertilization, and even scheduled tree trimming - meaning fewer vendors to coordinate, fewer bills to manage, and more time to enjoy where you live. Whether you’re looking for a primary residence, vacation home, short-term rental, or long-term investment, this community in Reunion offers the flexibility to fit your goals. When it’s time to leave the community, you’re minutes from ChampionsGate’s restaurants, Publix, Target, Starbucks, and everyday conveniences. Want dinner out? Head to Ford’s Garage for burgers, Trevi’s at Omni Orlando Resort for Italian, or grab drinks with friends without venturing far from home. Disney, Disney Springs, golf courses, water parks, and some of Central Florida’s most visited destinations are all within easy reach, while home remains tucked behind one of the area’s most recognizable gated communities. Enjoy! *Some marketing images have been AI-assisted and virtually staged to illustrate the property’s potential layout, design, use of space, and possible aesthetic enhancements. Certain photos may include digitally enhanced visualization of furnishings, décor, finishes, landscaping, or cosmetic elements for marketing and illustrative purposes only. Actual property conditions, features, finishes, fixtures, and appearance may vary, and buyers are encouraged to independently inspect the property to verify all present conditions.*

7407 Devereaux Street, Reunion

$245,000
4 Beds 2 Baths Poinciana Nbrhd 02 Village 08 SubDv. 34759 Zip Code
Welcome to 252 Fig Court, a well-maintained 4-bedroom, 2-bath home offering 1,414 square feet of thoughtfully designed living space. Featuring a desirable split bedroom floor plan, this residence provides the perfect balance of privacy and functionality. The spacious primary suite is tucked away from the secondary bedrooms and includes an ensuite bathroom with dual vanity sinks and a walk-in closet, creating a comfortable retreat at the end of the day. The additional three bedrooms are conveniently located on the opposite side of the home and share a full secondary bathroom, making the layout ideal for guests, family members, or flexible work-from-home needs. At the center of the home, the kitchen features a large bar-top breakfast counter that seamlessly connects to the living and dining areas, creating an open and welcoming space for everyday living and entertaining. Durable laminate flooring enhances the main living spaces with both style and easy maintenance, while plush carpeting in the bedrooms adds warmth and comfort. A designated laundry area adds convenience to daily routines. The efficient floor plan maximizes every square foot, offering bright living spaces, comfortable bedrooms, and practical storage throughout. Whether you're looking for room to spread out, a home with a functional layout, or a property that offers comfortable Florida living, 252 Fig Court delivers. Enjoy the benefits of a 4-bedroom design, open gathering spaces, and a private primary suite, all within a home designed to support a variety of lifestyles. Located in Kissimmee, this home offers convenient access to shopping, dining, entertainment, and major commuter routes throughout Central Florida. If you've been looking for a home that combines functional living spaces, a desirable split-bedroom design. Schedule your private showing today and discover everything this Kissimmee property has to offer.

252 Fig Court, Kissimmee

$305,000
3 Beds 2 Baths Poinciana Village 2 Nbhd 1 SubDv. 34758 Zip Code
Under contract-accepting backup offers. $5,000 credit towards buyer closing cost.....Price Drop!!!!This fully renovated, 3/2 Block home with 2 car garage is on .37 acres in Poinciana Village community in Kissimmee home is exactly what you have been looking for. Purchasing this property will leave you worry free for many years to come and gives you a feel of luxury with quartz countertop and modern soft close cabinets in each bathroom and kitchen; and luxury vinyl flooring throughout the entire house (except kitchen and bathrooms that are tiled). Knowing that your roof, Hot Water Heater and HVAC system (indoor and outdoor) were replaced in 2026, will put your mind at ease. This already low HOA includes cable, internet and access to all the amenities that you would need to be to enjoy Florida days such as pool, fitness center and basketball court to name a few! LOCATION...LOCATION....LOCATION!!! Property is conveniently located to shopping center and grocery stores such as Wal-Mart, Publix, Bravo Supermarket, Aldi's, Spouts Farmers Market, Burlington, Five Below, TJ Maxx, First Watch, Panda Express, Crunch Fitness, and much more. This property provides all the space that you will need for entering friends and family. Bring your grill and toys to enjoy this oversized fully fenced back yard with an oversized back patio. The luxurious owners' suite with huge walk-in closet (his and her closet facing each other), specious walk-in shower with brand-new rain shower head and deep soak tub. The open kitchen which offers lots of cabinets, modern farm style sink and brand-new stainless-steel appliances (fridge, microwave, stove, dishwasher). The open concept kitchen also features a breakfast bar overlooking the adjacent family room with sliding glass doors that lead to the oversized backyard. You will enjoy the comfort of having an actual laundry room in your home! 100% financing available with preferred lender. Lender will reimburse for inspection and appraisal fees at closing.

931 Van Loon Court, Kissimmee

$308,000
3 Beds 2 Baths Ventura At Windsor Hills Condo Ph 1 SubDv. 34747 Zip Code
Mins to Disney! Magical 3BR + FREE Waterpark | 200Mbps WiFi | Elevator Access | Walk to Pool The Experience Step into your family’s fairytale! Our beautifully updated 3BR/2BA condo in the prestigious Windsor Hills Resort is the closest you can get to the magic of Disney without staying on-property. Whether you’re exploring the Hundred Acre Wood in the living room or blasting off to infinity in our Toy Story suite, we’ve created a "Disney Bubble" designed for comfort, convenience, and zero stress. The Space – 4 Immersive Themed Worlds: Beauty & the Beast Primary Suite: A regal retreat for parents featuring a King bed, private en-suite bath, and Smart TV. Toy Story Adventure Room: "To infinity and beyond!" Features twin-over-full bunk beds—the ultimate home base for little rangers. Mickey & Minnie Classic Suite: A cheerful Queen bedroom celebrating the world’s most famous mice. Winnie the Pooh Living Space: Relax in a cozy, Hundred Acre Wood-inspired lounge with a 65" Smart TV for family movie nights. Covered Patio: The perfect spot to relax with a cold drink and enjoy the Florida breeze while the kids recharge for the next park day. High-Tech & Family-First Features: Blazing Fast 200+ Mbps WiFi: Seamless 4K streaming and lag-free video calls for remote work or gaming. Dual Elevator Access: We are on the 3rd floor skip the stairs! Perfect for strollers, groceries, and luggage. Walkable Location: One of the closest units to the Clubhouse. A short, easy stroll to the waterslides and pool! Baby Gear Included: Pack 'n Play and high chair provided at no extra cost. Resort Amenities (100% FREE Access): Lagoon Pool & Waterpark: Dueling waterslides, splash pad, and oversized hot tub. Entertainment: On-site movie theater, arcade, and kids' zone. Active Life: State-of-the-art fitness center, tennis, basketball, and sand volleyball. Essentials: On-site marketplace, ice cream shop, and 24/7 gated security. Fully Equipped Kitchen – Mickey Style: From quick park-bound breakfasts to late-night snacks, we have you covered: Coffee Bar (Keurig + Drip), Mickey waffle maker, toaster, and blender. Full-sized fridge with ice maker and dishwasher. In-unit Washer/Dryer (with starter pods!). Note: For food safety, we do not provide pantry items like salt, pepper, or spices. What’s Included (Stress-Free Starter Pack): We provide a starter pack of home essentials so you can settle in immediately: Toilet paper & paper towels Trash bags, dish pods, & hand soap Fresh linens & plush towels Need more? The on-site convenience store has your back! Guest Access: You will enjoy contactless check-in with a secure digital lock. You have full, private access to the entire condo.

2784 Almaton Loop Unit 301, Kissimmee

$510,000
5 Beds 5 Baths Cumbrian Lakes Resort Ph 1 SubDv. 34746 Zip Code
ASSUMABLE VA LOAN AT 5.75% FOR QUALIFIED BUYERS – SUBJECT TO LENDER APPROVAL & BUYER QUALIFICATION! Welcome to 4602 Cumbrian Lakes Drive, a beautifully maintained and fully furnished 5-bedroom, 5-bathroom pool home located in the gated Cumbrian Lakes community, just minutes from Walt Disney World, shopping, dining, and Central Florida’s top attractions. Originally built as the community’s model home, this spacious residence offers over 2,600 square feet of living space with soaring vaulted ceilings, an open and functional floor plan, and a premium conservation lot with peaceful nature preserve views and no rear neighbors. The community features scenic walking trails through the preserve, including a charming bridge overlooking the pond, providing the perfect setting to enjoy Florida’s natural beauty. Recent upgrades provide exceptional value and peace of mind, including a new Carrier A/C system and furnace (2024), roof replacement (2018), pool heater (2025), updated GFI outlets with USB ports (2024), luxury vinyl flooring, fresh interior and exterior paint, new pool enclosure screens, keyless entry, security system, and new televisions throughout. The thoughtfully designed floor plan features two bedrooms on the first floor, while upstairs you'll find the expansive primary suite complete with a spacious ensuite bathroom, dual closets, and a huge private balcony overlooking the conservation area, along with two additional guest bedrooms. The kitchen is equipped with stainless steel appliances and a breakfast area, while the generous living and dining spaces are ideal for entertaining and everyday living. Step outside to your private screened-in pool retreat featuring a child safety fence, outdoor shower, convenient pool bath, and newly installed grab bar. Short-term rentals are permitted, making this property an excellent primary residence, vacation getaway, or income-producing investment opportunity.

4602 Cumbrian Lakes Drive, Kissimmee

$350,000
4 Beds 2 Baths Indian Point Ph 7 SubDv. 34746 Zip Code
Back of the market. Cash or conventional financing only. Seller is seeking full-price offers. The listing price is firm. Please submit all offers with proof of funds or a current pre-approval letter. Welcome to your Florida dream home! This beautifully maintained 4-bedroom, 2-bathroom residence offers the perfect combination of comfort, investment potential, and resort-style living. Whether you're a snowbird searching for a second home, an investor looking to capitalize on Airbnb or VRBO opportunities (short-term rentals are permitted), or a first-time homebuyer, this property is an exceptional opportunity. Step inside to discover a spacious open-concept floor plan filled with natural light, creating an inviting atmosphere ideal for entertaining family and guests. The home comes partially furnished, making it move-in or rental-ready from day one. Your private backyard oasis features a large, heated pool and spa, perfect for year-round enjoyment and maximizing rental appeal. Recent updates provide added peace of mind, including a brand-new roof installed in 2025. Residents enjoy access to outstanding community amenities, including a playground, tennis courts, community pool, and cabana, all with an incredibly low HOA fee. Conveniently located just minutes from Disney, major highways, shopping, dining, and entertainment, this home offers the ideal balance of lifestyle, location, and income-producing potential. Don't miss this rare opportunity—schedule your private showing today!

121 S Roma Way, Kissimmee

$425,000
4 Beds 3 Baths Terra Verde Ph 02 SubDv. 34746 Zip Code
Welcome to this stunning fully furnished 4-bedroom, 3-bathroom home located in the highly sought-after Terra Verde Resort gated community. Whether you're searching for a primary residence, a vacation home, or an income-producing short-term rental property, this home delivers exceptional value and versatility. Featuring two spacious master suites, this well-maintained home provides comfort and privacy for owners and guests alike. One of the bathrooms has been fully renovated, adding a fresh, modern touch. The interior and exterior were professionally painted just one month ago, creating a clean, move-in-ready feel. Step outside to your private south-facing heated pool with an extended deck — perfect for outdoor dining, BBQ, and year-round entertaining. The home is also equipped with solar panels installed two years ago and a tankless water heater for added energy efficiency. Inside, the spacious living area features a one-year-old leather sectional with four built-in recliners. Property Features: 4 Bedrooms | 3 Bathrooms | Two Master Suites One Fully Renovated Bathroom Fully Furnished and Turnkey Private South-Facing Heated Pool with Extended Deck Solar Panels | Tankless Water Heater Recently Painted Interior and Exterior Leather Sectional with Four Recliners Two-Car Garage | Owner's Closet Located within Terra Verde Resort, residents enjoy 24-hour security and resort-style amenities, just minutes from world-famous theme parks, shopping, and dining. Schedule your private showing today!

156 Barefoot Beach Way, Kissimmee

$425,000
3 Beds 3 Baths Windsor Hills Ph 2 SubDv. 34747 Zip Code
Welcome to this beautifully maintained and upgraded 3-bedroom, 3-bathroom pool townhome located in the highly sought-after Windsor Hills Resort, just minutes from Walt Disney World. Offered fully furnished, this turnkey property is ideal as a primary residence, vacation home, or income-producing short-term rental investment. This exceptional home stands out within the community thanks to its numerous quality upgrades and thoughtful enhancements. The updated kitchen features upgraded cabinetry, granite countertops, and stainless-steel appliances, creating a stylish and functional space for owners and guests alike. Luxury vinyl flooring extends throughout the entire home, providing durability, easy maintenance, and a modern look with no carpet anywhere. A major improvement includes a NEW AC system installed in June 2020, offering peace of mind and energy efficiency. Upstairs, guests will love the tastefully themed Disney bedroom, while each bedroom has been thoughtfully designed to create a magical and memorable Disney vacation experience. Step outside to your private screened-in pool, perfect for relaxing after a day at the theme parks. Whether you're seeking a high-performing vacation rental or a personal getaway near Disney, this home checks all the boxes. Located within the gated Windsor Hills Resort community, residents and guests enjoy world-class amenities including a lagoon-style resort pool, water park, thrilling water slides, movie theater, fitness center, game room, sports courts, onsite convenience store, bar and grill, playgrounds, and more. Just minutes from Walt Disney World, Universal Orlando Resort, shopping, dining, and entertainment, this property offers the perfect combination of location, comfort, and investment potential. Don't miss this opportunity to own your own piece of the magic—schedule your private showing today!

7674 Otterspool Street, Kissimmee

$279,000
2 Beds 3 Baths Encantada Ph 2 SubDv. 34747 Zip Code
Welcome to the perfect blend of location, lifestyle, and investment potential! Ideally situated just minutes from Disney and Central Florida’s world-renowned attractions, this beautifully maintained 2-bedroom, 2.5-bath townhome offers privacy, comfort, and proven income opportunity—all in one. Step inside to a thoughtfully designed first floor featuring a modern kitchen with granite countertops, a spacious living and dining area, and a convenient half bath—perfect for entertaining or relaxing after a day out. Sliding glass doors lead to your private lanai, where a hot tub and serene conservation views create a true backyard retreat with no rear neighbors. Upstairs, both bedrooms are generously sized and designed for comfort, each complete with its own en-suite bathroom, walk-in closet, and TV. The primary suite offers a peaceful escape, while the second bedroom provides ideal flexibility for guests or renters. This home is being sold FULLY FURNISHED and boasts a strong rental history, making it an exceptional opportunity for short-term or long-term investors—or anyone seeking a turnkey primary residence or vacation home. Additional highlights include smart home features for enhanced efficiency and security, a recently serviced AC system, a new thermostat, and fresh interior updates throughout. HOA dues cover exterior maintenance, landscaping, lawn care, cable and wifi/internet, providing a truly low-maintenance ownership experience. Opportunities like this—combining location, privacy, and income potential—don’t come around often. Schedule your private showing today and see firsthand why this property stands out from the rest!

3050 White Orchid Road, Kissimmee

$524,000
3 Beds 2 Baths North Point Ph 1b SubDv. 34744 Zip Code
Welcome to this stunning, well-cared-for home located in the highly sought-after North Pointe community of Kissimmee. This residence offers the perfect combination of comfort, quality upgrades, and resort-style outdoor living. Step inside to discover tile flooring throughout the entire home, creating a seamless, low-maintenance living space. Beautiful plantation shutters add timeless charm and refined character in every room. The home also includes a RainSoft salt-water purification system, providing clean, soft water throughout. The kitchen comes fully equipped with all major appliances, including washer, dryer, refrigerator, stove, microwave, and dishwasher — making this home truly move-in ready. Outdoors, your private oasis awaits with a screened and enclosed salt-water Black Diamond pool, perfect for entertaining, relaxing, and enjoying Florida’s sunshine year-round. Additional practical upgrades include overhead garage storage racks and storm panels with clips for enhanced storage and storm protection. For added peace of mind, the roof was replaced approximately five years ago. Furniture is available for purchase through a separate bill of sale, offering flexibility for buyers seeking a turnkey option. Prime Location & Nearby Convenience This home offers exceptional access to everyday conveniences and popular destinations: Lake Nona (medical city, dining, shopping, and entertainment) - approx. 6 miles Orlando International Airport (MCO) - approx. 7 miles Downtown St. Cloud, with local dining, shopping, and lakefront recreation - approx. 12 miles The Loop - approx. 12 miles Downtown Kissimmee - approx. 12 miles Walt Disney World - approx. 20 miles Easy access to major highways, parks, schools, medical facilities, and daily necessities This home delivers quality construction, thoughtful upgrades, and a prime Central Florida location — making it ideal for full-time residents, seasonal homeowners, or investors.

4461 Indigo Sky Lane, Kissimmee

$895,000
5 Beds 6 Baths Reunion West Village 03a SubDv. 34747 Zip Code
PRICE IMPROVEMENT! Exceptional Reunion Resort Golf View Pool Home – Fully Updated & Turnkey! Welcome to this stunning 5-bedroom, 5.5-bath luxury vacation home located in the world-renowned Reunion Resort. Perfectly positioned with breathtaking golf course views and conservation views, this property offers the rare advantage of having no neighbor on one side, creating enhanced privacy and a more exclusive resort-style setting. Designed for both personal enjoyment and high-performing short-term rental income, this beautifully furnished home features five spacious en-suite bedrooms, including a whimsical themed bedroom that guests love. Entertainment is taken to the next level with THREE dedicated recreation areas, including an incredible Space-Themed Game Room, a fun-filled Pikachu-Themed Game Room, and an exciting Monster-Themed Entertainment Space, providing unforgettable experiences for guests of all ages. The open-concept floor plan is bright, airy, and ideal for entertaining. The gourmet kitchen showcases granite countertops, stainless steel appliances, abundant cabinetry, and overlooks the spacious family room and pool area. Large windows and sliding glass doors bring in natural light while showcasing the spectacular golf and conservation views. The luxurious primary suite offers a private balcony overlooking the fairways and natural preserve, creating the perfect place to relax after a day at the parks or on the golf course. The spa-inspired primary bath features dual vanities, extensive cabinetry, a makeup station, and a large walk-in shower. Step outside to your private backyard oasis featuring a saltwater pool, built-in spa, waterfall feature, and LED lighting. Pool heating is available through both propane gas and solar heating for year-round enjoyment. This property has been extensively upgraded, including: • New luxury wood flooring throughout the entire home (2022) • New cooktop and oven (2025) • New primary A/C unit (2025) • Fully paid-off Tesla Solar System, providing significant energy savings and long-term value Whether you're looking for a primary residence, second home, or a high-performing vacation rental investment, this exceptional Reunion property delivers luxury, privacy, entertainment, and an unbeatable location. Conveniently located just minutes from Disney World, championship golf courses, shopping, dining, entertainment, and Orlando's major attractions. A rare opportunity to own a fully upgraded, income-producing resort home with golf views, privacy, and premium themed entertainment spaces in one of Central Florida's most desirable communities.

945 Desert Mountain Court, Reunion

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