Winter Garden Homes with Short Sale Special Sale Provision

Winter Garden Homes with Short Sale Special Sale Provision

Welcome to Winter Garden, Florida—a vibrant city nestled in the heart of Orange County, just a stone's throw from the bustling attractions of Orlando. Known for its charming downtown area, Winter Garden boasts a rich history that dates back to the early 1900s. Today, it seamlessly blends small-town charm with modern conveniences, making it an ideal place for families, retirees, and everyone in between.

The city is renowned for its picturesque landscapes, featuring lush parks, scenic lakes, and an extensive network of walking and biking trails. The West Orange Trail—a favorite among locals—offers a delightful way to explore the area while enjoying the stunning natural beauty. With a thriving arts scene, numerous community events, and a variety of dining options, Winter Garden is a place where neighbors become friends and memories are made.

For those looking to invest in real estate, Winter Garden presents a unique opportunity with homes available under the Short Sale Special Sale Provision. This provision allows buyers to purchase properties that are priced below market value, providing a chance to secure a dream home at an attractive price. Whether you're searching for a cozy bungalow or a spacious family home, Winter Garden's diverse real estate offerings cater to various tastes and budgets.

Embrace the warmth and welcoming spirit of Winter Garden, where every day feels like a vacation. Explore the possibilities that await you in this enchanting city, and discover why so many are proud to call Winter Garden home!

Newest Winter Garden Homes with Short Sale Special Sale Provision

$189,000
2 Beds ⋅ 1 Baths ⋅ O6437162 MLS
Short Sale. Welcome to this charming 2-bedroom, 1-bath townhome offering an easy, low-maintenance lifestyle in Winter Garden. Just minutes from Downtown Winter Garden, this home puts you close to everything you love about the area while offering a peaceful place to call home. Inside, you’ll find a comfortable open layout with a spacious living area that connects naturally to the kitchen, creating a great space for everyday living and entertaining. Step outside to your private patio, the perfect spot to enjoy your morning coffee, relax after a long day, or spend time outdoors. Additional highlights include a newer roof, newer HVAC system, and low HOA fees. Location is a major plus! The West Orange Trail is just a short walk or bike ride away, while Downtown Winter Garden’s restaurants, local shops, entertainment, and popular farmers market are all nearby. Whether you're purchasing your first home, looking to downsize, or searching for a low-maintenance investment, this townhome offers an excellent opportunity to enjoy the Winter Garden lifestyle. Schedule your viweing today.

963 Stucki Terrace, Winter Garden
$214,000
2 Beds ⋅ 2 Baths ⋅ O6420014 MLS ⋅ 1 BLDG.
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
$449,300
3 Beds ⋅ 3 Baths ⋅ O6417277 MLS
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 ⋅ O6410364 MLS ⋅ Na BLDG.
Short Sale. Great home, great shape, let's talk

7030 Twilight Bay Drive, Winter Garden
$182,000
2 Beds ⋅ 2 Baths ⋅ O6371713 MLS ⋅ 373 BLDG.
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 ⋅ O6368187 MLS
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 ⋅ V4944858 MLS
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
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