Winter Garden Homes under $500,000

Winter Garden Homes under $500,000

Welcome to Winter Garden, Florida—a vibrant city nestled in the heart of Orange County, where charming small-town vibes meet modern conveniences. Known for its picturesque landscapes and rich history, Winter Garden boasts a thriving community that is perfect for families, young professionals, and retirees alike. With its historic downtown brimming with boutique shops, delightful cafes, and a variety of dining options, residents enjoy a lifestyle that seamlessly blends leisure and activity.

One of the most appealing aspects of Winter Garden is its diverse selection of homes, particularly those under $500,000. This makes it an ideal destination for first-time homebuyers or anyone looking to invest in a beautiful property without breaking the bank. From cozy single-family homes to stylish townhouses, the real estate market here caters to various tastes and preferences. Many homes feature modern amenities, spacious layouts, and beautiful outdoor spaces—perfect for enjoying Florida’s sunny weather.

Outdoor enthusiasts will find plenty to love about Winter Garden. The city is home to the West Orange Trail, a 22-mile-long recreational path perfect for biking, jogging, or leisurely strolls. With nearby parks and lakes, residents can enjoy a variety of outdoor activities, including fishing, picnicking, and nature walks.

With its affordable housing options, vibrant community spirit, and a wealth of recreational opportunities, Winter Garden truly offers the best of Florida living. Explore your future home in this charming city, where every day feels like a vacation!

Newest Winter Garden Homes under $500,000

5522 New Independence Parkway, Winter Garden
$499,900
3 Beds ⋅ 2 Baths ⋅ O6451777 MLS
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
8163 Red Stopper Lane, Winter Garden
$455,000
3 Beds ⋅ 3 Baths ⋅ O6451594 MLS ⋅ 8163 BLDG.
Discover the best of Winter Garden living in the highly desirable Summerlake community, where resort style amenities, convenient access to Orlando attractions, and beautiful neighborhood surroundings come together. Located at 8163 Red Stopper Lane, this beautifully maintained 3 bedroom, 2.5 bathroom home offers an inviting open concept floor plan designed for comfortable everyday living and entertaining. Step inside to a spacious main living area featuring ceramic tile flooring, abundant natural light, and a thoughtfully designed layout. The kitchen features granite countertops, 42 inch cabinetry with crown molding, a decorative tile backsplash, stainless steel appliances, a breakfast bar, and a generous pantry. The adjoining dining area provides additional space for gathering with family and friends. Upstairs, the spacious primary suite offers a special Florida experience with views of the Walt Disney World fireworks illuminating the night sky! The primary bathroom features dual sinks, stone countertops, an upgraded tiled shower, and a large walk in closet. Two additional bedrooms and a full guest bathroom complete the upstairs living space. Outside, enjoy your own private fenced courtyard with attractive pavers and a covered lanai, perfect for morning coffee, outdoor dining, or relaxing in the Florida sunshine. An attached two car garage provides convenient parking and additional storage. Summerlake is known for its exceptional community amenities, including a resort style swimming pool, clubhouse, fitness center, tennis courts, basketball courts, playground, dog park, zip line, and scenic walking trails. Located in the sought after Horizon West area of Winter Garden, residents enjoy convenient access to Hamlin Town Center for shopping, dining, and entertainment, along with nearby golf courses, parks, and outdoor recreation. Historic Downtown Winter Garden offers charming boutiques, local restaurants, a popular farmers market, and access to the West Orange Trail. With Walt Disney World, major Orlando attractions, and important Central Florida roadways nearby, this location offers an exceptional combination of neighborhood charm and everyday convenience. Whether you are looking for a primary residence or a seasonal Florida retreat, this Summerlake property offers the lifestyle and location that make Winter Garden one of Central Florida's most desirable places to call home. Schedule your private showing and discover everything this home and community have to offer!

8163 Red Stopper Lane, Winter Garden
10606 Words Drive, Winter Garden
$420,000
4 Beds ⋅ 3 Baths ⋅ O6448083 MLS ⋅ 10606 BLDG.
Investor Opportunity in Desirable Storey Grove!Tenant-occupied 4-bedroom, 2.5-bath home featuring an open-concept living area and a primary suite on the first floor. The home offers a generous front yard and a spacious backyard between the house and the detached two-car garage, providing plenty of room for outdoor gatherings and entertaining. Residents can also enjoy the community pool and amenities. Currently leased through March 31 2027, offering immediate rental income for investors. Sale is subject to the existing lease, and the buyer must honor the lease through the end of its term.

10606 Words Drive, Winter Garden
14501 Grove Resort Avenue Unit 1528, Winter Garden
$215,000
3 Beds ⋅ 3 Baths ⋅ O6451566 MLS
MOTIVATED SELLER... BRING OFFER! Welcome to a beautifully appointed 3-bedroom luxury condo-hotel residence at The Grove Resort & Water Park, offering exceptional views, a spacious layout, and true turnkey ownership just minutes from Disney and the Orlando theme parks. This well-designed unit features a generous open-concept living and dining area, ideal for entertaining or relaxing after a day at the parks. The thoughtfully separated bedroom layout provides comfort and privacy for owners and guests alike, making it especially attractive for short-term rentals. Offered fully equipped for immediate use, this residence is designed to perform as both a personal vacation retreat and an income-producing investment. Beyond the residence, owners and guests enjoy access to one of Central Florida’s most amenity-rich resorts. The Grove Resort & Water Park features a full-scale water park with lazy river and water slides, multiple resort-style pools, a surf simulator, full-service spa, fitness center, on-site shopping, and a variety of restaurants with indoor and outdoor dining. The resort also includes Lake Austin for fishing and paddle boating, conference and event facilities, and complimentary shuttles to Disney. The property is supported by a professional, on-site management team, providing a seamless and hands-off ownership experience while maintaining high guest satisfaction. This unique condo-hotel opportunity allows owners to enjoy personal use while generating rental income when not in residence. A rare combination of space, views, resort amenities, and location, this unit stands out among competing offerings—ideal for buyers seeking flexibility, lifestyle, and long-term value in a premier destination.

14501 Grove Resort Avenue Unit 1528, Winter Garden
14501 Grove Resort Avenue Unit 1440, Winter Garden
$159,999
2 Beds ⋅ 2 Baths ⋅ S5159866 MLS ⋅ 1 BLDG.
Welcome to Resort-Style Living at Its Finest! Nestled on the 4th floor of Building 1 at the highly acclaimed Grove Resort & Water Park, unit #1440 offers a turnkey 2-bedroom, 2-bathroom condo designed for effortless relaxation and high-value performance. Step inside to discover a bright, open floor plan that flows seamlessly to a private balcony—the perfect spot to enjoy Florida’s warm breezes and tranquil views. Building 1 boasts an enviable location within the resort, placing you just steps from the main lobby, dining options, and world-class amenities, so guests and owners spend less time walking and more time enjoying the retreat. Whether you are looking for a personal vacation sanctuary or a lucrative investment asset, this property delivers an unmatched lifestyle package. The Grove Resort features the exciting Surfari Water Park—complete with a dual-waterslide tower, lazy river, and FlowRider® surf simulator—alongside peaceful heated pools, a full-service spa, fitness center, on-site dining, and watersports on Lake Austin. Positioned just minutes from Walt Disney World®, Universal Studios, premier shopping outlets, and dining destinations, this condo combines luxury living with an irresistible location for vacationers and homebuyers alike.

14501 Grove Resort Avenue Unit 1440, Winter Garden
17138 Arrowhead Boulevard, Winter Garden
$499,900
2 Beds ⋅ 2 Baths ⋅ O6450444 MLS
Prime location! Spring fed lakefront charm. Well-built and maintained 2 bedrooms, 2 baths home high and dry. Nice layout inside out with private pond and lake access. Outdoor pet enclosure for your furry friends. The enclosed metal garage can protect all your toys. Mature landscaping. Established neighborhood. Tons of natural life with fishing opportunities. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge. Close proximity to all major amusement parks. A2 zoning, A schools and No HOA.

17138 Arrowhead Boulevard, Winter Garden
2199 White Feather Loop, Winter Garden
$489,900
3 Beds ⋅ 3 Baths ⋅ W7890380 MLS
Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Winter Garden
1444 Kenny Court, Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ O6448407 MLS
Welcome to this inviting 3-Bedroom, 2-Bath single-story home in a DESIRABLE LOCATION near Winter Garden, offering a spacious CORNER LOT, NO HOA and plenty of room to make the most of Florida living! Set on NEARLY A QUARTER ACRE, the property features MATURE SHADE TREES, a large driveway with ample parking and a welcoming setting. Inside, BEAUTIFUL LVP FLOORING and NEW LEVELOR BLINDS throughout, create a fresh, cohesive look, while NEW AC (2026) and a ROOF REPLACED IN 2022 add peace of mind. The OPEN FLOOR PLAN allows the Living Room, Dining Room and Kitchen to flow together seamlessly, creating a comfortable setting, while NATURAL LIGHT fills the space, enhancing the bright and airy feel. The Kitchen offers plenty of SOLID WOOD WHITE CABINETRY, solid-surface countertops and a center island with breakfast bar seating. A RECENTLY UPDATED TILE BACKSPLASH adds a stylish finishing touch, while STAINLESS STEEL APPLIANCES—including a GAS STOVE—make meal preparation a pleasure. A window above the sink brings in NATURAL LIGHT and provides a view of the backyard, and a CONVENIENT LAUNDRY ROOM is located just off the Kitchen. Down the hallway, you’ll find THREE BEDROOMS, each featuring a STYLISH CEILING FAN and WALK-IN CLOSET for comfortable living and convenient storage. The Primary Suite presents a private retreat with its own en suite Bath, complete with a MODERN VANITY AND TILED WALK-IN SHOWER. A SECOND FULL BATH with a modern vanity and tub/shower combination, is conveniently located near the additional Bedrooms.The Kitchen provides access to the backyard, where there's an OPPORTUNITY to create an outdoor space that reflects your own style, whether you envision a GARDEN, entertaining area or a place to relax under the Florida sunshine. With its GENEROUS CORNER LOT, mature shade trees and NO HOA, there’s room to make this property your own. Enjoy a GREAT LOCATION, just 2 miles from the charm and character of HISTORIC DOWNTOWN WINTER GARDEN, where you can explore local shops and restaurants, browse the popular PLANT STREET MARKET, visit the SATURDAY FARMERS MARKET or catch a show at the GARDEN THEATRE. Outdoor enthusiasts will appreciate the nearby WEST ORANGE TRAIL, ideal for biking, jogging and leisurely strolls, and with CONVENIENT ACCESS to Florida's Turnpike and SR-429, you can easily reach Orlando’s WORLD-FAMOUS THEME PARKS. Families will appreciate the nearby GREAT SCHOOLS including, A-RATED William Maxey Elementary and West Orange High School, adding to the appeal. With its thoughtful updates, GENEROUS LOT and convenient access to everything WINTER GARDEN has to offer, this home is FULL OF POTENTIAL and ready for its next chapter. Call and schedule your private tour today!

1444 Kenny Court, Winter Garden
15613 Boggy Oak Circle Unit 110A, Winter Garden
$299,900
2 Beds ⋅ 2 Baths ⋅ O6450253 MLS ⋅ 110a BLDG.
MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!

15613 Boggy Oak Circle Unit 110A, Winter Garden
1210 Brandy Lake View Circle, Winter Garden
$450,000
3 Beds ⋅ 2 Baths ⋅ O6449523 MLS
Virtually Staged. Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable gated community of Brandy Creek in Winter Garden! Step inside to discover an inviting, open layout where the living area flows seamlessly into the kitchen and dining space, creating a comfortable setting for everyday living and entertaining. The kitchen features granite countertops and ample cabinetry for storage. French doors open to an extended screened-in lanai, providing the perfect space to relax, entertain, or simply enjoy the Florida lifestyle. The fenced backyard offers additional room for outdoor activities, pets, or gatherings with family and friends. The primary suite features a walk-in closet and an en-suite bathroom with dual sinks, a garden tub, and a separate shower. The additional bedrooms provide comfortable, flexible spaces for family, guests, or a home office. With generous living spaces and the opportunity to add your own personal touches, this home offers wonderful potential to make it truly your own. Beyond the home, Brandy Creek offers a peaceful setting with tranquil ponds, a scenic lake, and a community fishing pier. Just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to the popular West Orange Trail, Saturday Farmers Market, live music, boutique shopping, and an incredible variety of local restaurants. Convenient access to the Florida Turnpike and SR-429 makes commuting and exploring Central Florida a breeze. Whether you're enjoying a quiet evening on your screened lanai or exploring the charm of downtown Winter Garden, this home offers a wonderful combination of space, location, and lifestyle. Don't miss the opportunity to make it your own!

1210 Brandy Lake View Circle, Winter Garden
8067 Glenlloyd Avenue, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ O6447368 MLS ⋅ N/A BLDG.
Welcome home to this better-than-new townhome in Horizon West! Why pursue new construction when you can have UPDATES AND UPGRADES GALORE including a new primary bathroom barn door and shower, faucets and commodes in all bathrooms, carpet padding, soft-close cabinets, ceiling fans, hue lighting in the living room, and fresh touch-up paint inside and out. This townhome requires that you sacrifice nothing! The curb appeal is waiting to welcome you from the moment you pull up to the house. A massive covered front porch is ready for your morning coffee to be sipped and/or your evening beverage of choice. Step inside and forget that you are in a townhome as you take in the HUGE kitchen in the middle of the open concept downstairs living. Whether prepping meals, socializing, or landing an airplane, this kitchen island was made for enjoyment. This kitchen features stone countertops, loads of cabinetry, and stainless steel appliances all with a popular and tasteful color palette. A dining space on one side of the kitchen and a living room on the other, both lined with windows for natural lighting, make this space one to write home about. Head upstairs and find the primary suite on one side and the secondary bedrooms on the other. The primary bathroom has a brand new shower, dual vanity, and private water closet. You can even SEE DISNEY FIREWORKS from the bedroom and bathroom! The 2 remaining bedrooms share a bathroom that includes a shower/bathtub combination. Step out back to your private brick-paved courtyard ready for your outdoor enjoyment. The home and the 2-car garage are connected by an overhang across this courtyard for convenience and weather protection. This community is situated in the heart of Horizon West between Hamlin and Waterleigh for ample shopping and dining options, is super close to Disney, and right off of Highway 429 to bring you to all your favorite Central Florida destinations. Inquire today to make this gem your own!

8067 Glenlloyd Avenue, Winter Garden
1956 Portcastle Circle, Winter Garden
$429,000
4 Beds ⋅ 3 Baths ⋅ O6449142 MLS
Beautifully updated and move-in ready! Welcome to 1956 Portcastle Circle in Winter Garden's Stone Creek community. This bright and inviting two-story home features an open-concept main living area filled with natural light, tile flooring, recessed lighting, and a seamless flow between the kitchen, dining, and living spaces. The newly remodeled kitchen showcases shining cabinetry, light countertops, stainless steel appliances, updated fixtures, and a spacious breakfast bar with sink and dishwasher overlooking the main living area. Sliding glass doors lead directly to the backyard, creating an easy indoor-outdoor connection. Upstairs, brand-new carpet adds warmth and comfort throughout the bedrooms and hallway. The remodeled bathrooms feature fresh contemporary finishes, including updated vanities, fixtures, and elegant marble-look tile. A convenient downstairs powder room, spacious bedrooms, ample closet space, large windows, and a flexible open floor plan further enhance the home's appeal. Major updates also include a NEW ROOF, providing added value and peace of mind. Conveniently located near Winter Garden shopping, dining, entertainment, and major roadways, this beautifully refreshed home combines modern updates, functionality, and an excellent location.

1956 Portcastle Circle, Winter Garden
Start Your Search

How much is your home worth?

Get instant property value now!