Osceola Homes for Sale

4 Beds ⋅ 2 Baths ⋅ Southwood Estates SubDv. ⋅ 34746 Zip Code

Private 2-Acre Custom Home in Southwood Estates — No HOA! Welcome to your own private retreat in Southwood Estates, a small, desirable development of custom-built homes with no HOA. Situated on 2 fully fenced acres, this 4-bedroom, 2-bath home offers privacy, space, and an abundance of thoughtfully designed features. A private security gate and wooded setting create a peaceful atmosphere while still providing convenient access to everyday amenities. The home is designed for both comfortable living and entertaining, featuring a spacious Florida room with a built-in wet bar and JennAir grill, perfect for gatherings year-round. Step outside to the covered, screened lanai, complete with a 4-person ThermoSpas hot tub, where you can relax and enjoy the tranquil surroundings. The primary suite offers dual walk-in closets and a separate dressing area outside the primary bathroom. Bedroom 2 features built-in shelving, while Bedroom 3 includes a built-in desk, upper and lower cabinets, and file drawers, making it ideal for a home office. A bonus room attached to Bedroom 3 provides even more flexibility for an office, hobby room, guest space, or additional living area. Storage is abundant throughout the home, with many closets, an inside utility room with sink and cabinets, and an oversized 2-car garage. The property also includes multiple outbuildings. A separate workshop features a vinyl-tiled floor, built-in vacuum system, work table, tool cabinet, drill press, and table saw. The workshop equipment is available for purchase separately or may be negotiable with a full-price contract. Two additional storage sheds—one metal and one wood—provide even more space for tools, equipment, and outdoor storage. If you’re looking for acreage, privacy, no HOA, abundant storage, and a home designed for both everyday living and entertaining, this unique Southwood Estates property is a must-see!

3385 Woodberry Court, Kissimmee

$484,999

7 Beds ⋅ 7 Baths ⋅ Wyndham Pointe SubDv. ⋅ 34747 Zip Code

WELCOME TO 8027 ACADIA ESTATES CT! Incredible opportunity to own a 7 BEDROOM, 6.5 BATHROOM POOL HOME in the highly desirable GATED COMMUNITY OF ACADIA ESTATES, ideally located in the heart of Kissimmee’s world-famous vacation corridor! Offering approximately 2,705 SQ FT, this spacious two-story home features an exceptional bedroom and bathroom configuration with plenty of room and privacy for family, guests and vacationers. The open floor plan connects the living, dining and kitchen areas, creating a comfortable space for gathering and entertaining. Step outside and enjoy your own private Florida retreat with a SCREENED POOL AND SPA, covered lanai and plenty of room to relax year-round. One of the property’s biggest advantages is its flexibility: SHORT-TERM RENTALS ARE ALLOWED, making this an outstanding option for investors looking for a vacation rental near Orlando’s major attractions, while also being perfectly suited as a primary residence or second home. Located in a smaller gated community just minutes from WALT DISNEY WORLD, Sunset Walk, Margaritaville, restaurants, shopping, golf and entertainment, the location is difficult to beat. The property is being offered WITHOUT FURNITURE; HOWEVER, EXISTING FURNISHINGS MAY BE NEGOTIATED SEPARATELY, providing additional flexibility for buyers interested in a more turnkey setup. With 7 BEDROOMS, 6.5 BATHROOMS, A PRIVATE POOL & SPA, SHORT-TERM RENTAL FLEXIBILITY AND A PRIME LOCATION NEAR DISNEY, this home offers an exceptional combination of space, versatility and investment potential. SCHEDULE YOUR PRIVATE SHOWING TODAY!

8027 Acadia Estates Court, Kissimmee

$559,000

4 Beds ⋅ 2 Baths ⋅ Pleasant Hill Heights Unit 2 SubDv. ⋅ 34746 Zip Code

Rare Opportunity – No HOA on Over an Acre! Enjoy the perfect combination of privacy, space, and convenience with this beautifully upgraded home situated on over one acre in a quiet neighborhood. Offering approximately 2,901 square feet of living space, plus an impressive 2,037-square-foot detached garage/workshop, this property is ideal for those who need room for vehicles, boats, RVs, recreational equipment, or a home-based business. The additional detached building also includes a private office/in-law suite, providing exceptional flexibility for multigenerational living, guest accommodations, or a dedicated workspace. Inside, you'll find gorgeous wood flooring, an upgraded kitchen, and quality finishes throughout the home, creating a warm and inviting atmosphere that's perfect for everyday living and entertaining. The main home features a durable tile roof, while the detached garage/workshop is topped with a shingle roof. Conveniently located just minutes from shopping, dining, and everyday amenities, this property offers the freedom of no HOA, abundant parking, and endless possibilities—all while enjoying the peace and tranquility of a spacious country-style setting with city conveniences nearby. If you've been searching for room to spread out without sacrificing location, this exceptional property is a must-see!

2749 S Stewart Street, Kissimmee

$299,900

3 Beds ⋅ 2 Baths ⋅ Westview Pod B Neighborhood 5 Ph 1 SubDv. ⋅ 34758 Zip Code

Come see this bright and inviting 3-bedroom, 2-bathroom home recently built in 2025 in Kissimmee. This move-in-ready residence blends modern design with everyday comfort, offering an easy, low-maintenance lifestyle just minutes from local shopping, dining, and major roadways. Step onto the covered front porch, an inviting spot for morning coffee, and through the front door into a bright, open-concept living space. The main living and dining areas feature a stylish tray ceiling that adds architectural interest, along with large windows that fill the rooms with natural light. Durable tile flooring runs throughout the main living areas, making cleanup a breeze. The kitchen is a true centerpiece, featuring crisp white cabinetry, sleek stainless-steel appliances, a tile backsplash, and a spacious island with bar seating, perfect for casual meals or entertaining guests. The adjacent dining area comfortably fits a full-size table, and the open flow into the living room makes this home ideal for gatherings with friends and family. The living room invites you through sliding glass doors to the backyard, creating a seamless indoor-outdoor connection. The primary suite offers a peaceful retreat with plush carpet, a ceiling fan, and plenty of natural light, while the second and third bedrooms provide flexible space for guests, family, or a home office. A dedicated large laundry room offers space for a full-size washer and dryer plus built-in shelving for extra storage. The two-car garage offers ample space for parking and storage, and the water softener conveys with the home for added value Outside, the home showcases attractive curb appeal with a paver driveway and walkway, stone accents at the entry, and a well-manicured lawn. Behind the home, unwind on the enclosed, covered lanai overlooking a large backyard and peaceful water view, a perfect spot to relax any time of the day. This home is part of Lennar at Esplanade, a new master-planned community in Kissimmee that welcomes pets, making it a great fit for owners with furry companions. Residents enjoy access to a community pool and clubhouse, a fitness center, dog park plus courts for tennis, pickleball and bocce ball, along with a spa for relaxing after a day of activity. The neighborhood sits close to Highway 17, putting the greater Orlando area within easy reach, and outdoor lovers will appreciate being a short drive from area lakes and nature trails for hiking and exploring, such as the Lake Marion Creek Wildlife Management area. Whether you're a first-time buyer, growing family, or investor, this property checks all the boxes: modern finishes, thoughtful design, and a location that puts you close to everything Central Florida has to offer. With green and energy-efficient construction plus thoughtful finishes throughout, this home offers the comfort of new construction without the wait. Come see the possibilities and make this house your own. Don't miss your chance to own this nearly new home. Schedule your private showing today!

4536 Ochos Rios Place, Kissimmee

$260,000

3 Beds ⋅ 2 Baths ⋅ Pine Island Villas At Bvl SubDv. ⋅ 34743 Zip Code

Welcome home, perfectly situated in the quiet, established community of Pine Island Villas in Kissimmee! Unbeatable location meets everyday convenience in this charming home. Positioned just off Buenaventura Boulevard with quick access to Osceola Parkway and Florida’s Turnpike, commuting across Central Florida is a breeze. Enjoy the convenience of being just minutes from local shopping plazas, dining options, top-rated medical centers, and essential services, all while remaining a short drive from Central Florida’s world-famous attractions and Orlando International Airport. Upgrades on this home are: Roof 2015 by HOA, HVAC unit 2018, Water Heater 2025, French doors and Sliding doors on 2021, exhaust vent 2023. Designed for easy, low-maintenance living, this property features a functional, light-filled layout ideal for a primary residence or a long-term investment. Don't miss this opportunity to enjoy comfort, connectivity, and peace of mind in a wonderful Kissimmee neighborhood. Schedule your private tour today!

49 Pine Island Circle, Kissimmee

$539,000

4 Beds ⋅ 3 Baths ⋅ Villa Sol Ph 1 Village 5 SubDv. ⋅ 34744 Zip Code

Virtually Staged. One or more photo(s) was virtually staged. Welcome to this Spanish-Mediterranean single-family home located in the gated community of Villa Sol in Kissimmee! Offering 4 bedrooms, 3 full bathrooms, a 2-car garage, and 2,351 sq. ft. of heated living space, this single-story residence combines flexible living with pond views. A key feature of the home is the attached in-law suite with its own private exterior back entrance, bedroom, and full bathroom. Inside, an open floor plan is filled with natural light, featuring polished porcelain tile flooring, vaulted ceilings, and architectural archways. The kitchen includes granite countertops, a multi-level breakfast bar, light grey cabinetry, stainless steel appliances, and pendant lighting. The primary bedroom suite offers luxury vinyl plank flooring, vaulted ceilings, a walk-in closet, and sliding glass door access to the pool deck. The en-suite bath features a dual-sink granite vanity, light grey cabinetry, a corner jetted soaking tub, and a separate glass-enclosed shower. Step outside to your private rear screen enclosure featuring an in-ground pool and integrated spa overlooking serene water views on an oversized lot. Villa Sol community amenities include a gated entry, clubhouse, fully equipped fitness center, resort-style community pool, tennis courts, basketball court, and playground, with cable TV and high-speed internet included in the low HOA fee. Perfectly positioned in Kissimmee, this home offers quick access to SR-417, US-192, and Boggy Creek Road, putting Lake Nona, Medical City, and Orlando International Airport (MCO) just a short drive away. Zoned for East Lake Elementary, Neptune Middle, and Tohopekaliga High School, you are also minutes from local shopping centers, dining, Lake Tohopekaliga parks, golf courses, and Central Florida's major theme parks and attractions. Schedule your private tour today!

3133 Riachuelo Lane, Kissimmee

$695,000

8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph1 SubDv. ⋅ 34747 Zip Code

Discover this stunning 8-bedroom, 6-bathroom luxury home located in the highly sought-after Windsor at Westside Resort, just 15 minutes from Walt Disney World! This property sits on one of the most desirable lots in the community —just a one-minute walk to the magnificent clubhouse in Phase I. This turn-key, fully furnished vacation home is ready for short-term rental or personal use. It has been professionally decorated and can comfortably host up to 22 guests — an ideal choice for families, groups, and high-performing investors. Property Highlights: • Spacious 8 bedrooms and 6 full bathrooms • Beautiful lake views in front house and just a one-minute walk to the magnificent clubhouse in Phase I. • Luxury vinyl flooring throughout (no carpet) • Disney-themed game room with pool table and foosball at loft • Three custom-designed themed bedrooms: Star Wars, Harry Potter, and Frozen • And Five bedrooms with Fully furnished and tastefully decorated for wide guest appeal • Two sets of washers, dryers, and refrigerators for high guest turnover convenience. in 2022 new AC unit replaced • Large dining area with 16 chairs plus 4 bar stools for group gatherings • Screened patio with spa and no rear neighbors for extra privacy Resort Amenities: Windsor at Westside offers an exceptional 8,000 sq. ft. resort-style clubhouse featuring: • Heated pool and spa • Lazy river and water playground • Fitness center and game room • Restaurant, tiki bar, and on-site convenience store • Sand volleyball, tennis, and basketball courts • 24-hour gated security Prime Location: • Only 15 minutes to Walt Disney World • 6 miles to Orlando Premium Outlets • 10 miles to the Orange County Convention Center • Close to golf courses, supermarkets (Sam’s Club, Walmart), and restaurants • Approximately 30 minutes from Orlando International Airport (MCO)

2137 Malta Terrace, Kissimmee

$425,000

4 Beds ⋅ 3 Baths ⋅ Poinciana Village 2 Nbhd 3 SubDv. ⋅ 34758 Zip Code

*Offering interest rate buy down or closing cost credit through preferred lender!* An impressive residence in Poinciana offering the space, flexibility, and distinctive features that are increasingly hard to find. One of the larger homes currently available in the community, this property is situated on a generous corner lot and provides an exceptional amount of living and storage space ideal for a growing household, multi-generational living, entertaining, or simply anyone who wants room to spread out. From the moment you arrive, the home makes a statement with its expansive multi-car paver driveway, providing plenty of parking for residents and guests. The spacious garage adds even more versatility, with ample room for multiple vehicles, storage, recreational equipment, tools, and toys. Step inside and you're immediately greeted by a dramatic living area showcasing soaring approximately 20-foot ceilings that create an incredible sense of openness and scale. One of the home's standout architectural features is the custom staircase with decorative railings, adding character and elegance while overlooking the impressive main living space. The first floor also features a private home office, providing a dedicated space for working remotely, studying, managing a business, or creating a quiet flex room away from the main gathering areas. The spacious floor plan offers multiple areas for everyday living and entertaining, giving everyone room to enjoy the home comfortably. Upstairs, a large loft creates another valuable living space that can easily become a media room, game room, playroom, second family room, fitness area, or additional workspace. The oversized primary suite provides a private retreat with plenty of room for a full bedroom setup and sitting area, complemented by a generously sized primary bathroom designed for comfort and functionality. Outside, the covered lanai extends the living space and provides a shaded setting for outdoor dining, relaxing, grilling, and enjoying Florida's year-round lifestyle. Combined with the oversized corner homesite, there's plenty of opportunity to make the outdoor space your own. With its exceptional size, dramatic ceilings, custom staircase, private office, oversized loft, spacious primary suite, substantial garage and parking, covered lanai, and large corner lot, 331 Ashburton Way delivers the kind of space and versatility that makes a home truly adaptable for years to come. If you've been searching for a large Poinciana home with room for everyone—and everything—this one deserves to be at the top of your list.

331 Ashburton Way, Kissimmee

$439,999

4 Beds ⋅ 3 Baths ⋅ Lake Berkley Resort SubDv. ⋅ 34746 Zip Code

FULLY FURNISHED | PRIVATE POOL | GATED RESORT COMMUNITY | SHORT-TERM RENTALS ALLOWED Welcome to your Florida dream home! This beautifully maintained 4-bedroom, 2-bathroom fully furnished pool home is located in the highly desirable gated community of Lake Berkley Resort, offering an exceptional combination of comfort, location, lifestyle, and investment potential. From the moment you arrive, you’ll appreciate the inviting atmosphere and thoughtfully designed layout, perfect for relaxing, entertaining, or hosting vacation guests. Step outside and enjoy your private swimming pool, creating your own backyard retreat where you can soak up the Florida sunshine year-round. The location is truly unbeatable. Just minutes from Walt Disney World, Universal Orlando Resort, and SeaWorld Orlando, while also being close to premier shopping, dining, entertainment, golf courses, and countless Central Florida attractions. Medical facilities, retail centers, supermarkets, and everyday conveniences are also easily accessible, with Celebration Hospital by AdventHealth approximately 19 minutes away. Orlando International Airport is approximately 30–38 minutes away, depending on traffic. Lake Berkley Resort provides a peaceful, vacation-style environment with 24-hour gated security and resort amenities, making this property an attractive choice for both homeowners and investors. One of the property’s biggest advantages is its flexibility. Short-term rentals are permitted, making this a compelling opportunity for investors looking to generate rental income in one of the country’s most visited tourism destinations. At the same time, it can serve as a comfortable primary residence, a second home, or the perfect vacation getaway for family and friends. And because the home is FULLY FURNISHED, it’s ready to enjoy or rent with minimal preparation. Whether you’re looking for an investment property, a vacation home, or your own place in the heart of Central Florida, this property checks all the boxes: private pool, four bedrooms, resort-style community, gated security, excellent proximity to world-famous attractions, and outstanding rental potential. Don’t miss the opportunity to own a piece of the Florida lifestyle in one of the most convenient and sought-after areas near Orlando. Bring your suitcase and start enjoying Florida living from day one!

1017 Lake Berkley Dr, Kissimmee

$389,000

4 Beds ⋅ 2 Baths ⋅ Kindred Ph 1d SubDv. ⋅ 34744 Zip Code

Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable Kindred community. This move-in ready residence offers a bright open floor plan, a modern kitchen with a large island, stainless steel appliances, and a spacious owner’s suite with a walk-in closet. Enjoy the covered lanai and fully fenced backyard, perfect for entertaining or relaxing. Residents of Kindred enjoy resort-style amenities, including a community pool, clubhouse, fitness center, playgrounds, parks, walking trails, and more. Conveniently located near Lake Nona, Medical City, Florida’s Turnpike, shopping, dining, schools, and Orlando International Airport. Schedule your private showing today!

1795 Partin Terrace Road S, Kissimmee

$324,990

3 Beds ⋅ 2 Baths ⋅ Poinciana Village 2 Nbhd 1 SubDv. ⋅ 34758 Zip Code

Welcome to this beautifully updated POOL HOME featuring an open floor plan, vaulted ceilings, and a spacious layout designed for comfortable everyday living and entertaining. The kitchen offers solid-surface countertops, stainless steel appliances, ample cabinetry, and an open connection to the main living areas. The primary suite features a walk-in closet and a spacious bathroom with dual sinks, a walk-in shower, and a Jacuzzi-style garden tub. The home has been thoughtfully updated throughout, including refreshed bathrooms with attractive tile finishes, and offers a clean, well-maintained interior that is ready for its next owner. Step outside to your own private retreat with a screened-in lanai and swimming pool, offering plenty of space to relax, entertain, or enjoy Florida living year-round. The POOL was resurfaced in 2024, and the pool pump was replaced in 2023. Additional recent improvements include a NEW ROOF and WATER HEATER in 2024, new window blinds in 2026, and fresh interior and exterior paint in 2026. Located in Poinciana Village 2 with no CDD, residents enjoy access to community amenities including internet and cable, a fitness center, community pool, playgrounds, parks, and recreational facilities. Conveniently located near shopping, dining, schools, medical facilities, and major roadways. With numerous recent updates, a private pool, and generous indoor and outdoor living space, this home is ready for its next owner. Schedule your private showing today.

1025 Derbyshire Drive, Kissimmee

$725,000

6 Beds ⋅ 6 Baths ⋅ Sonoma Resort At Tapestry Ph 1 SubDv. ⋅ 34741 Zip Code

Super rare opportunity to own a professionally designed home in the exclusive guard-gated resort community of Sonoma Resort at Tapestry! Lightly and gently used as a vacation retreat, this immaculate 6-bedroom, 6-bath contemporary residence has been meticulously maintained and is offered fully furnished. The interior was specially designed by acclaimed Brazilian-born Orlando interior designer Flavia Gueiros, whose signature blend of modern design and a light-toned palette gives the home a bright, clean, and elevated aesthetic throughout. Soaring high ceilings, an open floor plan, and a seamless living/dining combination create an airy, light-filled atmosphere from the moment you step inside. Ceramic tile flooring runs throughout, and the chef's kitchen features an eating space, dry bar, and generous storage. Enjoy your own private in-ground pool and spa overlooking serene water and pond views. The screened, covered lanai extends the living space outdoors, complete with a built-in outdoor kitchen and grill—ideal for entertaining or unwinding in the Florida sunshine. Additional highlights include a two-car attached garage, upper-level laundry, masonry fencing, tile roof, and a full suite of modern appliances. Sonoma Resort at Tapestry offers 24-hour guard-gated security, a resort-style pool, clubhouse, and fitness center. Ideally positioned near Orlando's world-famous attractions, dining, and major roadways, this community also permits short-term rentals—an excellent option for investors or vacation-home buyers. Built in 2018 and move-in ready, this turnkey designer home is a true standout. Schedule your private showing today!

2667 Calistoga Avenue, Kissimmee

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