Winter Garden Homes under $500,000

Winter Garden Homes under $500,000

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County that perfectly blends small-town warmth with modern conveniences. Known for its picturesque landscapes and vibrant community, Winter Garden boasts a rich history and a thriving downtown area filled with quaint shops, delightful restaurants, and a lively farmers market that draws residents and visitors alike.

One of the most appealing aspects of Winter Garden is its diverse real estate market, particularly for those seeking homes under $500,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, Winter Garden offers an array of affordable housing options that cater to various lifestyles. From cozy single-family homes with lush backyards to modern townhouses with community amenities, there's something for everyone.

The city is also renowned for its excellent schools, beautiful parks, and recreational facilities, making it an ideal place for families to thrive. With easy access to major highways, residents enjoy a convenient commute to nearby attractions, including the world-famous Walt Disney World Resort, Universal Studios, and the stunning lakes that dot the area.

In Winter Garden, you’ll find a welcoming community that embraces a laid-back Florida lifestyle while providing all the conveniences of urban living. Discover your dream home in this idyllic city, where affordability meets charm, and experience the best that Central Florida has to offer. Come explore Winter Garden—your future home awaits!

Newest Winter Garden Homes under $500,000

159 9th Street, Winter Garden

159 9th Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code

Enjoy the best of Winter Garden living in this beautifully built 2024 home! This property features 3 bedrooms, 2 bathrooms, and 1,188 square feet of thoughtfully designed living space, this home features an open-concept floor plan that creates a bright and welcoming atmosphere. The spacious kitchen is the heart of the home, showcasing a large island, shaker cabinetry, granite countertops, and stainless steel appliances. The primary suite has a spa-like feel with en-suite bathroom and walk-in closet. Enjoy the convenience of a one-car garage and a covered patio, perfect for relaxing outdoors. NO HOA! Ideally located near all that downtown Winter Garden has to offer, including shopping, dining, entertainment, and the popular West Orange Trail. Modern construction, a convenient location, and the freedom of no HOA make this home one you won't want to miss!

159 9th Street, Winter Garden

7183 Summerlake Groves Street, Winter Garden

7183 Summerlake Groves Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Highlands/Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

Located in the desirable Horizon West area of Winter Garden, this home features an open floor plan, neutral finishes, and a functional layout designed for comfortable everyday living. New landscaping enhances the home’s curb appeal, creating a fresh and inviting first impression. Inside, the open living spaces offer versatility for a variety of lifestyles, while newly carpeted bedrooms provide a comfortable retreat. Enjoy the Florida lifestyle with a covered lanai and fenced backyard, offering additional space to relax or entertain. Situated directly across the street from Orange County National Golf Center, this home offers a convenient location for golf enthusiasts and easy access to top-rated schools, Hamlin Town Center, shopping, dining, and Walt Disney World. Experience all that Winter Garden and Horizon West have to offer in this well-located home.

7183 Summerlake Groves Street, Winter Garden

14501 Grove Resort Avenue Unit 3239, Winter Garden

14501 Grove Resort Avenue Unit 3239, Winter Garden

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

***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden

14026 Frasier Street, Winter Garden

14026 Frasier Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code

SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden

6707 Marmalade Alley, Winter Garden

6707 Marmalade Alley, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code

Virtually Staged. Virtually Staged. Welcome to modern living in the heart of Winter Garden! This beautifully upgraded 4-bedroom, 3.5-bath corner-unit townhome offers a spacious, thoughtfully designed floor plan with the primary suite conveniently located on the main level, featuring a beautiful shiplap accent wall, updated shower, custom closet organization, and French doors opening to the inviting front porch. Upstairs, you'll find three carpeted bedrooms, including a private ensuite, along with a versatile loft featuring laminate flooring. The kitchen boasts stainless steel appliances, granite countertops, and a stylish backsplash, opening to inviting living and dining spaces accented by beautiful wood beams and upgraded lighting. Additional enhancements throughout the home include upgraded interior doors, a water softener, and thoughtful storage solutions. Step outside to your own private retreat featuring an extended, fully paved and fenced courtyard with sealed pavers, ideal for entertaining, relaxing, or enjoying Florida evenings. The detached garage has a covered walkway to the home. Located in the desirable Hamlin Reserve community in Horizon West, this home offers convenient access to Hamlin Town Center, shopping, dining, entertainment, and everyday essentials. Enjoy nearby parks, walking trails, and outdoor recreation, with easy access to SR-429 and a short drive to Walt Disney World and Central Florida's world-class attractions. A wonderful opportunity to enjoy modern living, exceptional outdoor space, and a convenient Winter Garden location!

6707 Marmalade Alley, Winter Garden

9380 Bolshoi Alley, Winter Garden

9380 Bolshoi Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Tribute/Ovation SubDv. ⋅ 34787 Zip Code

SELLER PROVIDING UP TO $10,000 TOWARD BUYER CLOSING COSTS! Welcome to this nearly NEW townhome in the heart of highly desirable Horizon West! Built in 2025, this 3-bedroom, 2-and-a-half-bathroom residence offers the appeal of newer construction in one of Central Florida’s fastest-growing communities. Enjoy the convenience of having Publix and an expanding selection of shopping, dining, and everyday essentials just across the street! The unit is equipped with upgraded QUARTZ countertops, tile throughout the first floor & a cozy private courtyard. The home’s prime location also provides easy access to State Road 429, making commuting throughout Central Florida a breeze. Just minutes away, the popular Hamlin area offers an exciting mix of restaurants, retail, entertainment, and recreational opportunities. Whether you’re searching for a primary residence or a low-maintenance lifestyle, this townhome offers an excellent combination of location, convenience, and modern living. With construction completed in 2025, buyers can enjoy the benefits of a newer home without the wait of building from the ground up. Don’t miss your opportunity to own a nearly new townhome in the heart of Horizon West!

9380 Bolshoi Alley, Winter Garden

13537 Splashing Isla Drive, Winter Garden

13537 Splashing Isla Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome home to carefree villa living in the beautiful 55+ community of Del Webb Oasis. Follow a delightful pavered walkway past lush landscaping to reach the covered front porch. Stepping inside reveals a generous foyer with plank tile flooring that extends throughout all living/wet areas right up to carpeted bedrooms. Inside the spectacular kitchen you will find 42" uppers, gorgeous quartz countertops, subway tile backsplash, tall crown cabinet molding, waste-basket pull out, soft close drawers, double roll-out trays, whirlpool appliances, an island with storage and electric, excellent lighting and attractive matte black hardware. Just off the kitchen is the cafe or dining area which then flows into the gathering room or living room. Three clerestory windows provide natural light into the living room which also has a floor outlet and LED downlights illuminating well the ebb and flow of life lived to the fullest. The split floor plan places the primary suite at one end of the home with two guest bedrooms and a guest bath at the other end. With a window view into the peaceful backyard, the spacious primary bedroom adjoins an en suite bathroom complete with a shower (note the built-in seat and glass shower door), dual sinks, water closet, linen closet and enormous walk-in closet. Two guest bedrooms can serve as office, den, library, craft room or hobby space in addition to providing a comfortable space for visiting guests. An attractive tile-surround for the tub/shower in the guest bathroom complements the single vanity and finishes perfectly. Near the door leading to the 2-car garage is the laundry room with pocket door, washer/dryer, ventilated shelves, CAT6 Telecom Data Port and a transom-style window. Triple sliders open to the covered and extended pavered lanai. Keyless entry for the garage. 2" faux wood blinds at all functional windows. A 5" Carbon Clean MERV 16 filter with Cabinet enhances the HVAC system. Adjacent to the home is a paved walking trail. Community amenities include an active, sprawling Clubhouse, resort-style pool as well as pickle ball and tennis courts. HOA fees also include exterior maintenance, landscaping, irrigation repairs, exterior painting and roof replacement. Schedule your visit to see all that this home has to offer today!

13537 Splashing Isla Drive, Winter Garden

5705 New Independence Parkway, Winter Garden

5705 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code

WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden

13006 Serene Glade Road, Winter Garden

13006 Serene Glade Road, Winter Garden

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

Winter Garden, Florida | Former Model Home | 3 Bedrooms | 2.5 Bathrooms FORMER MODEL HOME • DESIGNER UPGRADES • WINTER GARDEN THIS ONE WILL GET YOUR BUYERS’ ATTENTION! Welcome to 13006 Serenade Glade, an exceptional 3-bedroom, 2.5-bath former model home where luxury, style, and thoughtful upgrades come together beautifully. This is not your typical resale! Built to impress and showcased as a model, this home features extensive upgrades, elevated finishes, designer details, and a beautifully appointed interior that immediately stands out from the competition. The open and inviting floor plan offers an effortless flow for entertaining, while the spacious living areas create the perfect combination of comfort and sophistication. The kitchen is a true focal point, complemented by upgraded finishes and a seamless connection to the living and dining spaces. The primary suite offers a private retreat, while the additional bedrooms provide excellent flexibility for guests, family, or a home office. Every detail was selected to make this home stand out—and it shows. From the upgraded flooring and lighting to the enhanced fixtures and finishes, this former model home delivers the polished look buyers are searching for without the hassle or expense of doing the upgrades themselves. Located in desirable Winter Garden, this is a fantastic opportunity for buyers looking for a home that feels special from the moment they walk through the door. FORMER MODEL HOME • 3 BEDROOMS • 2.5 BATHROOMS EXTENSIVELY UPGRADED • DESIGNER FINISHES • MOVE-IN READY Bring your buyers—this is one they’ll remember

13006 Serene Glade Road, Winter Garden

87 Windtree Lane Unit K, Winter Garden

87 Windtree Lane Unit K, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 03 SubDv. ⋅ 34787 Zip Code

**Great location, attractive pricing, and plenty of potential in Windtree Gardens Community in Winter Garden ** Tucked away at the back of the community, this private first-floor, 2-bedroom, 2-bath condo offers a peaceful setting and a fantastic opportunity to make a home your own. With a functional layout, a screened porch for enjoying the outdoors, and the convenience of an in-unit washer and dryer, the home provides a great foundation for thoughtful updates and personal touches. The community offers a variety of amenities, including a swimming pool, clubhouse, and basketball court, along with pest control service and two dedicated parking spaces. The location is a standout! Just minutes from SR 429, Florida's Turnpike, and charming Historic Downtown Winter Garden, you'll enjoy convenient access to shopping, dining, entertainment, and major commuter routes while being close to one of Central Florida's most beloved downtown destinations. This condo is a great choice for buyers who appreciate privacy, convenience, community amenities, and the chance to add their personal style. Condo also has a strong rental opportunity for savvy investors. Bring your vision and discover the possibilities at 87 Windtree!

87 Windtree Lane Unit K, Winter Garden

5685 New Independence Parkway, Winter Garden

5685 New Independence Parkway, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code

INDEPENDENCE Community! This END unit is nothing like you have ever seen in the neighborhood before!! Offering stylish finishes, thoughtful improvements, and an exceptional location, this MOVE IN READY home is the perfect blend of comfort, functionality, and modern living. EXTENSIVELY UPDATED!! This home features a freshly painted exterior and interior (2024), updated trim, new 6-inch baseboards, 3-inch door casings, and upgraded lighting, ceiling fans, and fixtures throughout (2024). In 2023, the home received luxury vinyl plank flooring on the main level and in the upstairs bathrooms, a fully remodeled kitchen, an updated laundry area, and a new water heater. The high-efficiency TRANE 20-SEER A/C system (2020) adds year-round comfort and efficiency. Luxury Vinyl Plank flooring added to the stairs and upstairs this year! (2026) NO CARPET!! New refrigerator (2026!) The stunning remodeled kitchen is the heart of the home, featuring quartz countertops, solid wood cabinetry with soft-close drawers and crown molding, a farmhouse sink, a walk-in pantry, and an oversized island complete with a wine fridge. Stainless steel appliances complete this stylish and functional space, offering plenty of storage and room to gather. The open-concept layout flows seamlessly into the dining area and spacious living room, where abundant natural light creates a warm and inviting atmosphere. A convenient half bath on the main level adds to the home's everyday functionality.Upstairs, you'll find three comfortable bedrooms and two upgraded bathrooms featuring refreshed vanities, new mirrors, updated lighting, and comfort-height, skirted self-cleaning toilets. Outside, enjoy the added privacy and curb appeal of this end-unit townhome, complete with a covered front porch, block and stucco construction extending to the roof, and a two-car rear-facing garage with additional ceiling storage installed in 2021. The outdoor living space is just as inviting, featuring a private, fenced paver patio with green space beyond the fence—perfect for morning coffee, relaxing evenings, or entertaining guests. Additional improvements include all-new appliances (2021), new window screens and blinds (2021), a wired security system, and energy-efficient lighting throughout. Located in a highly rated A-rated school district, Independence offers desirable community amenities and a welcoming neighborhood atmosphere. Conveniently situated in the heart of Winter Garden/Horizon West, you'll enjoy easy access to shopping, dining, entertainment, theme parks, SR-429, and other major roadways. With extensive updates, modern finishes, added privacy, and an outstanding location, this beautifully maintained townhome is ready for its next owner. Don't miss your opportunity to make this exceptional property your own—schedule your private showing today!

5685 New Independence Parkway, Winter Garden

5522 New Independence Parkway, Winter Garden

5522 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code

Independence ** Rare floor plan for Independence with 3 bedrooms and +/-17x12' DEN or living room space ** FRESHLY painted neutral soft white interior and BRAND NEW LAMINATE FLOORING in the 3 bedrooms ** 19x10' Florida Room with AC and heat ** Primary bedroom has 2 walk in closets with built in white shelving & ensuite primary bath with two sinks, granite counters, garden tub and separate shower ** The kitchen has a large cooking island with granite counters and includes the stainless steel stove, refrig and dishwasher ** Laundry room with built in white shelving and washer and dryer included ** Ceiling fans in every room ** Great completely fenced back yard with Florida room and brick paver patio area 2018 ** 2 car attached garage ** Lovely front porch with brick patio pavers ** Beautiful Florida Room Other upgrades include: NEW Trane A/C SYSTEM 10/2025, NEW white vinyl fence and gates 2/2024, NEW exterior brass whole house water shutoff valve 3/2026, NEW garage door system, SPRINGS 2/2021 and garage door opener 10/2024 ** LOW HOA fees $194.69 incl cable & internet which currently includes HBO and Max! Incredible amenities including 2 community pools, play areas, a lg community park plus other neighborhood green space and play areas thru-out the neighborhood, loads of sidewalks & conservation thru-out... All room measurements are approximate from the Builder floor plan. Buyer to verify measurements. Square footage is from Orange County Appraiser records ** Refrigerator ice maker is not working **

5522 New Independence Parkway, Winter Garden

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