Osceola Homes with Short Sale

Osceola Homes with Short Sale

Welcome to Osceola County, Florida—a vibrant and diverse region that perfectly balances the allure of nature with the excitement of urban living. Nestled in the heart of Central Florida, Osceola County is renowned for its picturesque landscapes, welcoming communities, and a wealth of recreational opportunities. From the enchanting shores of Lake Tohopekaliga to the thrilling attractions of nearby Kissimmee, residents enjoy a lifestyle that is both relaxed and exhilarating.

For those considering a home in this beautiful county, you’ll be pleased to know that Osceola offers a variety of real estate options, including homes available through short sales. A short sale can be a fantastic opportunity for homebuyers looking to invest in a property at a competitive price. These homes are typically sold for less than the amount owed on the mortgage, making them an attractive option for savvy buyers who are willing to navigate the process.

Osceola County’s real estate market is thriving, with charming neighborhoods that cater to families, retirees, and everyone in between. Whether you’re drawn to the bustling atmosphere of Kissimmee or the serene surroundings of St. Cloud, there’s a perfect home waiting for you. With a growing economy, excellent schools, and a strong sense of community, Osceola County is not just a place to live; it’s a place to thrive.

Explore the possibilities of homeownership in Osceola County today, and discover the potential that awaits you in this dynamic Florida gem!

Newest Osceola Homes with Short Sale

4 Beds ⋅ 2 Baths ⋅ Lancaster Park East Ph 1 SubDv.

Short Sale. Welcome to this Exquisite 4-bedroom 2 -Bath Home situated in Lancaster Park East. Discover the perfect combination of modern sophistication, comfort, and functionality in this beautifully appointed residence, located near Narcoossee Road and Highway 192—just minutes from Lake Nona. From the moment you arrive, you’ll be impressed by this home’s impeccable design, open layout, and stylish finishes. The heart of the home is a gourmet kitchen that truly inspires, featuring rich wood cabinetry with 42” upper cabinets, elegant quartz countertops, premium stainless steel appliances, a dishwasher, disposal, and an expansive center island perfect for casual dining and entertaining. The kitchen seamlessly flows into the great room, creating an inviting space filled with natural light, perfect for gatherings and everyday living. throughout the main living areas complements the home’s contemporary design, while the bedrooms feature plush carpeting, ceiling fans, and custom blind

1870 Castleton Drive, St Cloud (Magnolia Square)

3 Beds ⋅ 2 Baths ⋅ I M Mabbetts Add SubDv.

Virtually Staged. Short Sale. 3 BEDROOMS, 2 BATHROOMS, 1,488 HEATED SQ FT, FULLY RENOVATED HISTORIC BUNGALOW IN THE HEART OF KISSIMMEE! Sale is subject to THIRD-PARTY/LENDER APPROVAL. Built in 1925 and located within Kissimmee's HISTORIC DISTRICT, this charming home combines the character and architectural appeal of an earlier era with the comfort of today's updates. From the inviting COVERED FRONT PORCH and classic bungalow design to the bright, spacious interior, this is a home with personality from the moment you arrive. Inside, you'll find 3 BEDROOMS and 2 FULL BATHROOMS across 1,488 HEATED SQUARE FEET, with an open and comfortable layout featuring a living and dining combination, a WOOD-BURNING FIREPLACE, and updated flooring throughout. The renovated kitchen features QUARTZ COUNTERTOPS, NEWER APPLIANCES, an INDUSTRIAL-STYLE SINK, and plenty of workspace for everyday living and entertaining. Major improvements include a NEWER HVAC SYSTEM (2025), METAL ROOF, UPDATED PVC PLUMBING, UPDATED ELECTRICAL, NEWER WINDOWS, LUXURY VINYL FLOORING, and updated tile bathrooms. The home sits on a crawlspace foundation and also offers a driveway, fenced outdoor space, rear patio area and additional storage shed. Conveniently located near DOWNTOWN KISSIMMEE, shopping, restaurants, major highways, schools and area attractions, this property offers a unique opportunity to own an updated piece of Kissimmee history. SHORT SALE — 3 BEDROOMS, 2 BATHROOMS, 1,488 HEATED SQ FT, FULLY RENOVATED HISTORIC BUNGALOW with a METAL ROOF, 2025 HVAC, UPDATED PLUMBING & ELECTRICAL, QUARTZ COUNTERTOPS and a PRIME KISSIMMEE LOCATION. THIRD-PARTY/LENDER APPROVAL REQUIRED.

725 Mabbette Street, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Anthem Park Tr G Rep SubDv.

Short Sale. Just TWO YEARS OLD and designed for easy living, this beautifully maintained END-UNIT TOWNHOME offers the space, natural light, and features that make it feel more like a single-family home. EXTRA WINDOWS along the side of the home fill the living spaces with natural light, creating a bright and welcoming atmosphere from the moment you walk through the door. The main level features an OPEN-CONCEPT LAYOUT with NO CARPET DOWNSTAIRS, making everyday living and entertaining simple. One of the home's most versatile features is the generous STORAGE AREA BENEATH THE STAIRS—ideal for additional storage, a cozy reading nook, a play space, or a dedicated spot for your pet. Upstairs, a LARGE LANDING provides valuable FLEXIBLE SPACE with enough room for a comfortable chair, small desk, or reading area. The thoughtful layout keeps the BEDROOMS AND LAUNDRY ROOM TOGETHER for added convenience. The PRIMARY SUITE offers a PRIVATE EN-SUITE BATHROOM, creating a comfortable retreat at the end of the day. Step outside and discover a COMMUNITY FILLED WITH AMENITIES, including a RESORT-STYLE POOL, PLAYGROUND, BASKETBALL COURT, TENNIS COURTS, GAZEBOS, PICNIC AREAS, WALKING PATH, and COMMUNITY DOCK. The location adds even more convenience, with the NEIGHBORHOOD ELEMENTARY SCHOOL VERY CLOSE and US 192 JUST MINUTES AWAY, putting shopping, dining, entertainment, and everyday essentials close to home. With its NEARLY NEW CONSTRUCTION, END-UNIT LOCATION, ABUNDANT NATURAL LIGHT, FLEXIBLE STORAGE, CONVENIENT UPSTAIRS LAUNDRY, and AMENITY-RICH COMMUNITY, this townhome offers a fantastic opportunity to enjoy a LOW-MAINTENANCE FLORIDA LIFESTYLE without giving up the feeling of space and comfort.

5170 Quakers Place, St Cloud (City of St Cloud)

4 Beds ⋅ 2 Baths ⋅ Peppertree At Cyp Wds U1 SubDv.

Short Sale. This exceptional 4-bedroom, 2-bathroom single-story home is in pristine, move-in ready condition, offering effortless, stairs-free living paired with the convenience of an attached 2-car garage. The interior is dramatically highlighted by striking cathedral and vaulted ceilings that enhance the natural light and create an open, expansive atmosphere throughout the living spaces. At the heart of the home, the impressive kitchen comes fully outfitted with elegant granite countertops and a sleek suite of stainless steel appliances, offering a stylish, high-performing hub for all your daily culinary and entertaining needs. Spotlessly prepared and meticulously maintained from top to bottom, this turnkey residence is completely ready for a stress-free transition into a comfortable lifestyle.

414 Spice Court, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Soleil At Westside SubDv.

Short Sale. Welcome to Soleil at Westside! This beautiful two-story home features a spacious open-concept floor plan, ideal for modern living and entertaining. The property offers 4 bedrooms, 2.5 bathrooms, a well-appointed kitchen with solid surface countertops, and a bright living area. Located in a resort-style gated community with top-tier amenities including a community pool, clubhouse, fitness center, playground, and park. Conveniently situated near major highways, dining, shopping, and Orlando's world-famous attractions. POTENTIAL SHORT SALE: Sale of this property is subject to third-party approval by the seller's mortgage lender(s).

1090 Boardwalk Place, Kissimmee

5 Beds ⋅ 3 Baths ⋅ Summerly SubDv.

Short Sale. Welcome to 416 Talisi Loop, a spacious 5-bedroom, 3-bathroom home offering 2,601 square feet of thoughtfully designed living space in St. Cloud’s Summerly community. Built in 2023, the home features a 2023 roof, HVAC system, and water heater, providing newer major systems and fewer immediate maintenance concerns compared with many older homes. The open-concept main level features a modern kitchen with solid-surface countertops, stainless steel appliances, a large island with seating, and an easy flow into the living and dining areas—ideal for everyday living and entertaining. A first-floor bedroom and full bathroom provide flexibility for guests, multigenerational living, or a private home office. Upstairs, the oversized primary suite includes a walk-in closet and private bathroom, while the additional bedrooms and versatile loft offer plenty of room for work, play, or relaxation. Additional highlights include an upstairs laundry room, attached two-car garage, irrigation system, and a spacious backyard ready for outdoor enjoyment. Summerly residents enjoy access to a community pool, playground, sidewalks, walking paths, and inviting outdoor gathering areas. Conveniently located near Lake Nona, shopping, dining, Orlando International Airport, and major roadways. This property is a short sale. The purchase price, terms, lender approval, and closing timeline are subject to the seller’s lender; buyers should allow additional time for the short-sale process. Schedule your private showing today!

416 Talisi Loop, St Cloud (Magnolia Square)

3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 6 SubDv.

Short Sale. SHORT-SALE OPPORTUNITY IN WINDSOR PALMS! This fully furnished 3-bedroom, 2-bath condo offers approximately 1,268 square feet in a gated resort community just minutes from Walt Disney World. Suitable for personal occupancy, a vacation home, or short- or long-term rental use, subject to applicable association rules, licensing, and governmental requirements. Documented 2023 updates include the A/C system, luxury vinyl flooring, interior paint, granite countertops, bathroom vanities and sinks, kitchen sink, dishwasher, and washer/dryer. Televisions were updated in 2025. Community amenities include gated entry, resort-style pool, clubhouse, sports courts, movie theater, arcade, and bar. Conveniently located near Disney-area attractions, shopping, dining, entertainment, major roadways, and Orlando-area airports. Sale price, terms, and closing timeline require the seller’s lender approval. Buyer must verify measurements, property condition, included furnishings, HOA fees and assessments, rental requirements, licensing, insurance, financing, and association information.

8107 Coconut Palm Way Unit 201, Kissimmee

4 Beds ⋅ 4 Baths ⋅ Cumbrian Lakes Resort Ph 3 SubDv.

Virtually Staged. Short Sale. One or more photos have been virtually staged. Welcome to this beautiful home located in the exclusive gated community of Cumbrian Lakes, one of Kissimmee's most sought-after neighborhoods for short-term vacation rentals and investment properties. This spacious home features an open-concept floor plan, making it ideal as a primary residence, vacation home, or income-producing investment property. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances, a large breakfast island, and seamless flow into the living room, dining area, and covered lanai—creating the perfect space for entertaining. Step outside to your private screened pool, where you can relax and enjoy Florida's year-round sunshine. High ceilings fill the home with abundant natural light, while the split-bedroom floor plan provides added privacy. The garage has been professionally converted into a climate-controlled living space with air conditioning and heating, adding approximately 440 square feet of additional living area—ideal for a game room, home office, fitness room, or flexible living space. The spacious primary suite offers direct access to the lanai and pool and features an en-suite bathroom with a garden tub, separate walk-in shower, and walk-in closet. Bedrooms two and three share a Jack-and-Jill bathroom, while the fourth bedroom is conveniently located near another full bathroom. An additional half bathroom and an outdoor poolside shower provide extra convenience for family and guests. The covered lanai includes a ceiling fan and lighting, making it the perfect place to enjoy outdoor living throughout the year. Lawn maintenance is included in the HOA fee, offering added convenience and low-maintenance ownership. Ideally located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld Orlando, shopping, dining, major highways, and the SunRail station, this property offers exceptional convenience and accessibility. Cumbrian Lakes is a highly desirable gated community that allows short-term rentals, making it an outstanding opportunity for investors seeking strong rental potential or buyers looking for a vacation home in the heart of Central Florida. Don't miss this exceptional opportunity to own a property in one of Kissimmee's premier vacation rental communities!

4806 Cumbrian Lakes Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ The Townhomes At Anthem Park SubDv.

Short Sale. Short Sale Opportunity! Beautifully upgraded and move-in ready, this stunning two-story townhome features 3 bedrooms, 2.5 bathrooms, and a one-car garage. The home showcases thoughtful designer upgrades throughout, including a custom wood-slat kitchen island, a striking feature wall with a floating entertainment center, elegant matte plumbing fixtures, quartz countertops, stainless steel appliances, and a custom mural that adds charm to the secondary bedroom. The open-concept floor plan is perfect for both everyday living and entertaining. Conveniently located near shopping, dining, major highways, and Central Florida attractions. Potential short sale. Sale is subject to lender approval.

4870 Spangle Drive, St Cloud (City of St Cloud)

4 Beds ⋅ 2 Baths ⋅ Concorde Estates Ph 1b SubDv.

Short Sale. Ideally located in one of Kissimmee's fastest growing areas, this beautiful home offers the perfect combination of convenience, comfort, and lifestyle. Just minutes from Valencia College, top rated elementary schools, shopping centers, restaurants, grocery stores, hospitals, parks, and Orlando's world famous attractions, this location is ideal for both homeowners and investors. Perfectly positioned directly across from a beautiful pond, the home enjoys peaceful water views that create stunning sunrises and breathtaking sunsets, adding a sense of tranquility to everyday living. This spacious single story residence features 4 bedrooms, 2 full bathrooms, and over 2,000 square feet of living space with an open and functional layout, a generously sized kitchen, a spacious primary suite, and a two car garage. Step outside to a fully fenced backyard that offers privacy and the perfect setting for relaxing or entertaining family and friends. Residents also enjoy access to outstanding community amenities, including a swimming pool and fitness center, all with a low HOA fee, making this home an exceptional opportunity to enjoy the best of Central Florida living.

3108 Westbrook Road, Kissimmee

8 Beds ⋅ 6 Baths ⋅ Windsor/Westside-Ph 2a SubDv.

Short Sale. Welcome to your own slice of paradise in the highly sought-after, guard-gated Windsor at Westside Resort! This beautifully updated and fully furnished 8-bedroom, 6-bath home offers over 4,041 square feet of spacious living designed for comfort, entertainment, and unforgettable vacation experiences. The versatile floor plan features a convenient first-floor primary suite, while two upstairs bedrooms include private en-suite baths for added privacy. Enjoy Florida living year-round in your private heated pool and spa, or gather family and guests in the incredible converted game room complete with gaming consoles, a pool table, and driving simulators. Located just minutes from Disney, this exceptional resort home provides access to world-class amenities, including a resort-style pool, lazy river, expansive clubhouse, fitness center, poolside cabana, sand volleyball courts, and tennis courts. Whether you're looking for a vacation retreat, primary residence, or income-producing investment property, this move-in-ready home offers the perfect blend of luxury, location, and resort-style living.

1836 Nice Court, Kissimmee

2 Beds ⋅ 1 Baths ⋅ St Cloud 2nd Town Of SubDv.

Short Sale. Fully Remodeled and Move-In Ready! This beautifully updated 2-bedroom, 1-bath home offers 816 square feet of thoughtfully designed living space and is the perfect starter home, investment property, or low-maintenance Florida retreat. Situated on a desirable corner lot in the heart of St. Cloud, you'll enjoy convenient access to Downtown St. Cloud, East Lake Tohopekaliga, shopping, dining, schools, and major roadways. Step inside to discover a bright, modern interior featuring luxury vinyl plank flooring throughout, recessed lighting, and a stunning new kitchen complete with quartz countertops, sleek cabinetry, and stainless-steel appliances. The spacious primary bedroom, energy-efficient ductless mini-split HVAC system in rooms, fully renovated kitchen and bath showcases stylish finishes and all-new plumbing. No HOA! Major system upgrades provide added peace of mind, including a new roof, updated electrical, and a new tankless water heater for improved energy efficiency. The generous corner lot offers plenty of outdoor space with room to relax, entertain, or personalize to suit your lifestyle. The home includes a car port and has white vinyl fencing (with a little under 10' in the back that is not fenced in- large lot 150x50'). With quality updates throughout and a fantastic location, this turnkey home is ready for its next owner. Don't miss your opportunity to make it yours—schedule your private showing today!

624 Illinois Avenue, St Cloud (City of St Cloud)

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