Winter Garden Homes under $500,000

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code

Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes with really thought-out details to make you feel right at home. The Community also offers TONS of recreational items to choose from: You can choose from relaxing at the spa, working out in one or both of the two fitness centers provided. 3 swimming pools with food and drink service, mini golf, a lazy river, and a variety of much more. Come take a look at this one before its gone!

Winter Garden

$169,900

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3420, Winter Garden

14501 Grove Resort Avenue Unit 3221, Winter Garden

$169,900

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3221, Winter Garden

14501 Grove Resort Avenue Unit 1516, Winter Garden

$283,800

3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel SubDv. ⋅ 34787 Zip Code

GREAT NEW LISTING: PRICE $283,800.00. MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 3 BEDROOM/2 BATHROOM JASMINE DESIGN CONDO HAS GREAT WATER VIEWS FROM THE SCREENED BALCONY ON THE 5TH FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1516, Winter Garden

17152 Arrowhead Boulevard, Winter Garden

$449,000

4 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code

Spectacular fully renovated Mother-in-Law suite in 2026, with lake views! 4 bedrooms, 2 bathrooms total, completely independent from each other. Full renovation: brand new walls, floors, ceilings and bathrooms. All plans completed by a certified engineer and all inspections approved by Orange County, including the final inspection, move-in ready with zero worries! The property is divided into two units: each with 2 bedrooms, 1 bathroom, its own kitchen, laundry, A/C and individual water heater. Both units feature a private entrance, independent access to the backyard and their own driveway. No HOA, no restrictions, total freedom. Park your trailer, boat or work vehicle without asking anyone for permission. Perfect for a large or extended family, multi-generational living, or investors looking for a turnkey property with flexible use potential. Located in Winter Garden, just 11 minutes from Walt Disney World and with easy access to SR-429 and I-4, the best of peaceful lakeside living, with everything nearby. An opportunity that won't come around again!

17152 Arrowhead Boulevard, Winter Garden

$449,999

3 Beds ⋅ 2 Baths ⋅ East Garden Manor Rep SubDv. ⋅ 34787 Zip Code

UNIQUE PROPERTY OPPORTUNITY!! Nearly of an 1/4 ACRE with NO HOA!! Welcome to this charming 3-bedroom, 2-bathroom home in the heart of Winter Garden! Situated on an oversized lot, this property offers added space and flexibility rarely found in many communities. Inside, enjoy a cozy fireplace, a unique wood accent wall, and an updated kitchen featuring custom cabinetry and convenient hidden storage. Ceramic tile and bamboo flooring, double-pane windows, and a screened front porch add to the home's appeal. The spacious backyard offers two storage sheds, offering plenty of room for outdoor enjoyment, hobbies, and additional storage. Hot water tank 2 years old. Conveniently located walking distance to Downtown Winter Garden, the West Orange Trail. This home combines charm, functionality, and the freedom of homeownership without HOA restrictions!

226 Charlotte Street, Winter Garden

$489,900

3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code

NEWER CONSTRUCTION. SHOWS LIKE A MODEL HOME + BUILT IN 2024 + SCREENED LANAI + FULLY FENCED BACKYARD + MINUTES FROM DISNEY! Welcome to 13151 Calming Breeze Way, a beautifully maintained 3-BEDROOM, 2.5-BATH HOME offering 2,096 SQ FT of stylish living space in the desirable SERENADE AT OVATION community of Horizon West in Winter Garden! With its modern finishes, thoughtfully designed OPEN-CONCEPT FLOOR PLAN, and exceptional attention to detail, this home offers the appeal of newer construction with valuable upgrades already completed by the current owners! Inside, experience the bright, inviting atmosphere created by HIGH CEILINGS, LUXURY VINYL FLOORING, and spacious living areas designed for both everyday comfort and entertaining. The beautiful GOURMET-STYLE KITCHEN is the heart of the home, featuring STONE COUNTERTOPS, A LARGE CENTER ISLAND, generous cabinetry, and an effortless connection to the dining and gathering areas. The open bungalow-style layout creates a welcoming space for hosting friends or simply relaxing at home. Upstairs, the spacious PRIMARY SUITE offers a comfortable private retreat with a walk-in closet and en-suite bathroom. Two additional generously sized bedrooms provide flexibility for guests, a HOME OFFICE, or additional living space. One of this home's standout features is its beautifully enhanced outdoor living area! Unlike many newer homes where these improvements are still on the wish list, the current owners have already invested in a SCREENED-IN COVERED LANAI AND PRIVACY FENCING, creating an inviting backyard retreat. Enjoy morning coffee, outdoor dining, or relaxing evenings in your own private space. Additional upgrades include WINDOW BLINDS AND CEILING FANS, adding comfort and convenience from day one. LOCATION, LOCATION, LOCATION! Situated in the thriving HORIZON WEST / WINTER GARDEN area, this home offers exceptional convenience to WALT DISNEY WORLD, with Disney's theme parks, resorts, dining, and entertainment just a short drive away. Enjoy easy access to FL-429, nearby shopping, restaurants, and everyday essentials, along with the charm of Historic Downtown Winter Garden. Even better, SERENADE AT OVATION OFFERS A LOW HOA AND NO CDD FEE, making this an attractive opportunity for buyers seeking newer construction in one of Central Florida's most desirable and growing locations. Why wait for new construction when you can enjoy a beautifully finished, MOVE-IN READY HOME with the outdoor upgrades already in place? SELLER OFFERING $10,000 TOWARDS BUYERS CLOSING COSTS. Schedule your private showing and see for yourself why this home truly shows like a model! Mortgage savings may be available for buyers of this listing. Ask for details.

13151 Calming Breeze Way, Winter Garden

$425,000

4 Beds ⋅ 2 Baths ⋅ Fries Survey Of Winter Garden SubDv. ⋅ 34787 Zip Code

Virtually Staged. LOCATION, LOCATION, LOCATION! Just ONE BLOCK SOUTH OF PLANT STREET in the heart of historic Downtown Winter Garden, this is the kind of opportunity that doesn’t come around every day! With a 6,933-square-foot lot, an existing four-bedroom, two-bathroom home, and a mother-in-law suite, this property offers something increasingly difficult to find: a prime downtown address with incredible possibilities for the future. In real estate, you can change almost anything about a property, but you can never change its location. And this one is exceptional! Situated just steps from the charm, character, and energy of Downtown Winter Garden, you’ll find yourself surrounded by some of Central Florida’s most beloved restaurants, coffee shops, boutiques, breweries, and community gathering spots. Spend your Saturday mornings exploring the award-winning Winter Garden Farmers Market, enjoy an afternoon along the West Orange Trail, or take an evening stroll down Plant Street for dinner and live entertainment. This is the walkable, golf-cart-friendly downtown lifestyle so many buyers dream about! The existing residence offers 1,685 square feet of living space with four bedrooms, two bathrooms, and the added flexibility of a mother-in-law suite. Whether you’re looking for a home with room for extended family, a property to personalize, or a place to establish your roots in one of Central Florida’s most desirable communities, there’s plenty of opportunity to make this address your own. But perhaps the most exciting feature isn’t just what’s standing on the property today. It’s the LAND and the LOCATION! With approximately 6,933 square feet just one block from Plant Street, this parcel presents a compelling opportunity for buyers who recognize the long-term appeal of owning property in the heart of Downtown Winter Garden. Bring your creativity, explore renovation possibilities, or investigate future improvements and redevelopment options, subject to city zoning and approval requirements. As Downtown Winter Garden continues to attract buyers seeking character, convenience, and a true sense of community, opportunities to secure property this close to the center of it all are especially appealing. Whether you’re a homeowner with a vision, an investor seeking a desirable location, or someone who’s always dreamed of living steps from Plant Street, this property deserves your attention. THE LOCATION IS ALREADY PERFECT. THE POSSIBILITIES ARE YOURS TO EXPLORE. Don’t miss your opportunity to own a piece of Downtown Winter Garden!

215 S Woodland Street, Winter Garden

$355,000

3 Beds ⋅ 2 Baths ⋅ Daniels Crossing SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the desirable Daniels Crossing community of Winter Garden! Featuring a bright, open floor plan, fresh modern finishes, and a comfortable living and dining area, this home offers the perfect blend of style and functionality. Enjoy peaceful pond views from your backyard, creating a relaxing setting to unwind and enjoy Florida living. The split-bedroom layout provides added privacy, while the attached 2-car garage offers convenience and extra storage. Residents can also enjoy the community pool. Conveniently located near shopping, restaurants, major roadways, and the popular Winter Garden Village, this home offers both comfort and an excellent location. Don't miss the opportunity to make this home yours!

271 Daniels Pointe Drive, Winter Garden

$499,000

3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code

Like-new and just five years young, this beautifully cared-for home showcases thoughtful upgrades and attention to detail throughout. Featuring 3 bedrooms, 2.5 baths, and a dedicated office space, the inviting layout offers room to live, work, and unwind. The open kitchen features a gas range, spacious walk-in pantry, and adjacent dining area, making everyday meals and entertaining effortless. Upstairs, the generously sized primary bedroom includes a walk-in closet with custom built-ins for exceptional organization. Enjoy your own private retreat in the fenced backyard, thoughtfully enhanced with maintenance-free landscaping. A two-car garage with an EV charger, tankless gas water heater, and water softener system add everyday convenience. Community amenities include a pool, three playgrounds, two dog parks, and community mailboxes. Conveniently located near Flamingo Crossings Town Center for shopping, dining, and primary care/ER services, as well as Disney, this meticulously maintained home offers comfort, convenience, and thoughtful details inside and out.

15032 Lebeau Loop, Winter Garden

14501 Grove Resort Avenue Unit 2627, Winter Garden

$194,900

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code

This stunning 3-bedroom, 3-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second and third bedrooms and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 2627, Winter Garden

$163,000

2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code

Charming single-story townhome in Townhomes of Winter Garden featuring 2 bedrooms and 2 full baths. Interior features low-maintenance laminate flooring throughout the main living areas and bedrooms, paired with an efficient open floor plan. Conveniently located just minutes from historic downtown Winter Garden, Plant Street dining, shopping, and major commuter routes including SR-429 and the Florida Turnpike. Easy to show—schedule through Showing Time today!

373 Eron Way Unit 47, Winter Garden

Winter Garden Homes under $500,000

Newest Winter Garden Homes under $500,000

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