Winter Garden Homes with Short Sale

Winter Garden Homes with Short Sale

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community, Winter Garden seamlessly blends small-town charm with modern amenities. With its historic downtown area boasting quaint shops, delightful eateries, and a scenic waterfront, residents enjoy a lively atmosphere that fosters connection and engagement.

Winter Garden is not just a beautiful place to live; it’s also a city rich in recreational opportunities. The West Orange Trail runs through the area, offering miles of trails for walking, biking, and enjoying the great outdoors. For families, the city hosts various parks and community events throughout the year, ensuring there’s always something fun to do.

For those considering a move to this delightful city, you’ll find an enticing opportunity in the real estate market with homes available through short sales. Short sales can be a fantastic way to acquire a property at a competitive price, allowing you to invest in your dream home while navigating the complexities of the market. Winter Garden’s real estate landscape features a variety of homes, from charming historic houses to modern family residences, catering to diverse tastes and budgets.

Whether you’re drawn to Winter Garden for its beautiful scenery, friendly community, or promising real estate opportunities, you’ll find that this city has something special for everyone. Explore the charm of Winter Garden and discover your next home today!

Newest Winter Garden Homes with Short Sale

$419,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code
Short Sale. ***SHORT SALE***Built in 2024, this like new 2 bedroom plus den, 2 bathroom home offers modern finishes, thoughtful upgrades, and a private setting tucked toward the back of the community with no rear neighbors. The flexible den features French doors, making it ideal for a home office, hobby room, or additional living space. The open concept layout is filled with natural light and centers around a beautifully appointed kitchen with white cabinetry, white Ice subway tile backsplash, white quartz countertops, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. The primary suite features an upgraded walk in shower, while ceiling fans in the living room, both bedrooms, and the den provide added comfort throughout the home. Enjoy Florida living from the covered front porch with space for seating or unwind on the screened lanai overlooking the peaceful backyard with exceptional privacy. The 2 car garage includes two overhead storage racks for added organization. Located just minutes from Walt Disney World, Flamingo Crossings, Horizon West shopping and dining, major roadways, and everyday conveniences, this home combines a desirable location with low maintenance, move in ready living.

13640 Splashing Isla Drive, Winter Garden
$224,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange Trail. Inside, you'll find a thoughtfully updated interior offering easy, low-maintenance living. Perfect for first-time buyers, downsizers, or investors looking for a move-in ready property in one of Central Florida's most sought-after towns. With its prime location close to shopping, dining, parks, and major roadways, this townhouse offers an unbeatable opportunity to enjoy the best of downtown Winter Garden living without the downtown price tag. Schedule your showing today!

359 Douglas Way Unit 54, Winter Garden
$459,300
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code
Short Sale. Welcome to this beautiful two-story home offering 3 bedrooms, 2.5 bathrooms. The first-floor features spacious living and dining areas that flow seamlessly into the well-appointed kitchen, complete with granite countertops, 42-inch cabinetry, and a large walk-in pantry providing ample storage. Upstairs, you'll find a huge loft space that can serve as a second living area, home office, playroom, or media room. The convenient upstairs laundry room makes everyday chores a breeze. The spacious primary suite features dual sinks, a walk-in shower, and plenty of room to unwind. Enjoy resort-style living with outstanding community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, tennis courts and playground. Ideally located just minutes from Walt Disney World, shopping, dining, and entertainment at Hamlin Town Center, this home offers the perfect combination of comfort, convenience, and lifestyle. This is a bankruptcy sale and there is a 15,000 dollar buyers premium due at closing.

9362 Woodcrane Drive, Winter Garden
$469,000
4 Beds ⋅ 4 Baths ⋅ Mezzano SubDv. ⋅ 34787 Zip Code
Short Sale. Great home, great shape, let's talk

7030 Twilight Bay Drive, Winter Garden
$182,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned within a well-established Winter Garden community, this updated 2-bedroom, 2-bath condo offers a NEW ROOF, and an easy, comfortable lifestyle in one of Central Florida’s most desirable areas. Approaching the home, you’ll appreciate the tucked-away cul-de-sac location with paved private streets and sidewalks that create a calm, residential feel. Step inside through the front entrance and you’re immediately welcomed into a bright, open living space where natural light enhances the clean layout and efficient use of square footage. The living room feels inviting and functional, offering enough space to relax, entertain, or simply enjoy a quiet evening at home. Continuing through the home, the upgraded kitchen with GRANITE counter tops, anchors the main living area with modern appliances, ample cabinetry, and practical counter space. Its open connection to the living room allows for easy conversation while cooking, hosting, or enjoying everyday routines, making the space feel connected and intentional. The primary bedroom is set apart as a comfortable retreat, featuring brand-new carpeting and a private en-suite bathroom. The bathroom has been thoughtfully renovated with updated finishes that feel fresh and clean without excess. The secondary bedroom is well-sized and flexible, ideal for guests, a home office, or additional living space, with a second fully updated bathroom conveniently nearby. Throughout the condo, the layout flows efficiently from room to room, offering smart storage, comfortable proportions, and a low-maintenance design well suited for full-time living or long-term ownership. Assigned parking adds convenience, while the community’s shared amenities—including a COMMUNITY POOL—enhance the overall lifestyle. Located just minutes from downtown Winter Garden, residents enjoy close proximity to local shops, dining, farmers markets, and the West Orange Trail. Easy access to major highways makes commuting throughout Central Florida simple, whether heading toward downtown Orlando, major employment centers, or nearby attractions. This location is ideal for buyers exploring Orlando homes for sale or those planning an Orlando relocation home in a walkable, community-oriented area. While not intended as a short-term rental investment, this Winter Garden property represents a strong opportunity within the Central Florida real estate market for buyers seeking comfort, location, and value. Contact us today for a private tour or more details on this exceptional opportunity.

373 Eron Way Unit 47, Winter Garden
$270,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time Residency Investor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large balcony, modern kitchen, and in-unit washer/dryer. High occupancy potential through the on-site rental program. Resort Amenities (included for guests): Surfari Water Park, surf simulator, water slides, laser river. Multiple resort-style pools, hot tubs & cabanas. Lake Austin access with fishing and water sports. Fitness center, arcade, full-service spa, on-site restaurants, bars, market, and conference center, 24/7 front desk, concierge, and gated community security. Prime Location, located in Winter Garden, FL, just minutes to Walt Disney World® and major Orlando attractions. Close to shopping, dining, and major highways. This unit is part of a condo-hotel program: no full-time residency allowed. Short-term rentals only. SHORT SALE – priced to sell fast! A great chance to secure a unit below market value in a high-demand tourist location. Ideal for investors looking for short-term rental income with professional management available on-site. Not suitable for full-time occupancy. Contact us today to schedule a showing and take advantage of this exceptional income-generating property!

14501 Grove Resort Avenue Unit 2527, Winter Garden
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Short Sale. ***SHORT SALE. ***ALL OFFERS MUST GO THROUGH SHORT SALE PROCESS WITH SELLERS LENDER FOR APPROVAL/DENIAL. MULTIPLE OFFERS RECEIVED AND ARE IN REVIEW. ** The Bellmore in Waterleigh! This elegant single-story four-bedroom, two-bath residence offers 2,984 total square feet of refined living on a premier corner lot with wooded privacy and pond access. Blending timeless design with modern upgrades, this home showcases luxury finishes inside and out. The gourmet kitchen is a centerpiece, featuring stainless steel appliances, a walk-in pantry, and an oversized island with abundant prep and seating space. It opens seamlessly to the spacious family room, creating a setting for gatherings. Designer touches include recessed wood-insert ceilings in the foyer and primary suite, a dramatic brick accent wall in the living room, upgraded lighting throughout and a striking chandelier in the foyer. The primary suite offers a custom closet organization system, while ceiling fans are thoughtfully placed in almost every room. Outdoor living rivals a private resort with a screened, heated saltwater pool and cascading waterfalls, surrounded by lush tropical landscaping. The covered lanai features a 10-foot drop-down projection screen for outdoor cinema nights, while brick pavers enhance the driveway, walkways, and patio. A 13.67-kilowatt solar system with net metering ensures energy efficiency. From the backyard, enjoy nightly views of the spectacular Disney fireworks—an unforgettable backdrop unique to Central Florida living. Optional luxury additions for additional purchase include a four-seat electric golf cart with charger, professional-grade garage storage racks and a complete home gym with free weights. Waterleigh is Winter Garden’s flagship planned community, offering two expansive clubhouses with resort-style pools, state-of-the-art fitness centers, tennis courts, miniature golf, walking trails, dog parks, community gardens and scenic lakes with fishing piers. Ideally near Disney, major highways, shopping and dining, Waterleigh combines convenience with unmatched amenities. Ranked as one of the top communities in the United States, Winter Garden is celebrated for its vibrant downtown, lifestyle amenities and exceptional quality of life—making this home a rare opportunity to own in one of the nation’s desirable areas. This one is a must-see. By appointment only. BUYER MUST ASSUME 50K SOLAR PANEL LOAN- BANK WILL NOT CONSIDER ANY OFFERS ASKING FOR BANK TO PAY OFF SOLAR PANELS. OCCUPIED- BY APPOINTMENT ONLY.

9605 Lost Creek Drive, Winter Garden
$450,000
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 2c SubDv. ⋅ 34787 Zip Code
Short Sale. BACK ON THE MARKET — THROUGH NO FAULT OF THE SELLER! Buyer financing fell through. Welcome Home! 14536 Golden Harbor – a beautifully designed 3-bedroom, 2.5-bathroom home offering 1,904 square feet of thoughtfully laid-out living space. Nestled on the desirable Watermark community on the Disney side of Winter Garden, this Meritage Angelou II model combines modern efficiency with everyday comfort. The home comes equipped with fully PAID OFF solar panels, already wired and ready for connection—making this an energy-smart choice for eco-conscious buyers. As you walk in you are greeted with open-concept living/ dining room area that is ideal for entertaining, with a spacious kitchen located at the rear of the home. Enjoy stainless steel appliances, crown-topped cabinetry, a walk-in pantry, and a generous granite island that flows seamlessly into the living and dining areas. You’ll also find a built-in office nook and a convenient half-bath on this level. Upstairs, a spacious loft adds flexibility—perfect as a second living area, playroom, or home office. The laundry area is thoughtfully tucked away, and the split-bedroom design offers added privacy. The primary suite includes a walk-in closet, dual vanity, and a walk-in shower. Two additional bedrooms are located toward the front of the home and extend access to a private, covered balcony—an ideal spot to catch Disney’s nightly fireworks with a glass of wine and a great book. Whether you're unwinding on the front porch, enjoying balcony views, or taking advantage of community amenities—including a resort-style pool, playground, fitness center, basketball court, and more—you’ll find the lifestyle here hard to beat. You are just walking distance to The Mark, a versatile retail neighborhood center, with stores, restaurants, gas station, and more! Best of all, you’re just minutes from Walt Disney World, Magic Kingdom, Epcot, and Hollywood Studios—each less than 20 minutes away.

14536 Golden Harbor Lane, Winter Garden
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