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 beautifully blends historic charm with modern living. Known for its picturesque downtown area, Winter Garden boasts a vibrant community filled with delightful shops, cozy cafes, and a thriving farmers market that draws locals and visitors alike. The stunning West Orange Trail, perfect for walking, biking, and enjoying the great outdoors, winds through the city, offering residents a scenic escape just minutes from their homes.

Winter Garden is not only a wonderful place to live but also offers an impressive selection of homes priced under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, there’s something for everyone in this affordable market. From charming single-family homes with lush gardens to modern townhomes featuring open floor plans, the options are diverse and inviting.

The city's family-friendly atmosphere, combined with top-rated schools and numerous parks, makes it an ideal place to raise children. Additionally, with its close proximity to Orlando, Winter Garden residents enjoy easy access to world-renowned attractions, shopping, and dining, all while coming home to the peacefulness of suburban life.

Embrace the opportunity to call Winter Garden home and discover the perfect property that fits your lifestyle—all without breaking the bank. With its unique blend of community spirit, natural beauty, and affordability, Winter Garden is truly a hidden gem in Florida’s real estate market.

Newest Winter Garden Homes under $500,000

17138 Arrowhead Boulevard, Winter Garden
$499,900
2 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Prime location! Spring fed lakefront charm. Well-built and maintained 2 bedroom, 2 bath 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. A2zoning, A schools and No HOA.

17138 Arrowhead Boulevard, Winter Garden
2199 White Feather Loop, Oakland
$489,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code
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, Oakland
1444 Kenny Court, Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ Kenny Court SubDv. ⋅ 34787 Zip Code
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 ⋅ Tucker Oaks Condo SubDv. ⋅ 34787 Zip Code
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 ⋅ Brandy Creek SubDv. ⋅ 34787 Zip Code
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 ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
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 ⋅ Stone Creek Unit 4 SubDv. ⋅ 34787 Zip Code
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
345 E Maple Street, Winter Garden
$295,000
2 Beds ⋅ 1 Baths ⋅ J W Jones Add SubDv. ⋅ 34787 Zip Code
VALUE IS IN THE LAND AND LOCATION! Discover the possibilities in an established Golf Cart Winter Garden neighborhood, conveniently located near historic Downtown Winter Garden, with its charming shops, restaurants, farmers market, and community events. Enjoy proximity to Plant Street and the city's planned East Winter Garden revitalization improvements. An existing tenant-occupied residence is situated on the property, with a roof approximately three years old (2023). Whether considering the existing residence or exploring future possibilities, this property offers an opportunity in a growing Central Florida community. Buyer to independently verify zoning, permitted uses, and highest and best use with the City of Winter Garden.

345 E Maple Street, Winter Garden
1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
1069 Mildred Dixon Way, Winter Garden
$275,000
3 Beds ⋅ 2 Baths ⋅ Horizon Oaks SubDv. ⋅ 34787 Zip Code
Welcome to 1069 Mildred Dixon Way in Winter Garden, Florida! This well-maintained three-bedroom, two-bathroom block home offers comfortable living, a functional floor plan, and the freedom of NO HOA. Situated on a spacious lot with a fully fenced backyard, this property provides room to enjoy outdoor living, entertain guests, garden, or create your own private Florida retreat. The solid block construction and roof replacement in 2019 add to the home’s appeal. Step inside to a light-filled interior featuring tile flooring, an open and inviting atmosphere, and a comfortable living room with a ceiling fan, ideal for relaxing after a long day or gathering with family and friends. The adjoining eat-in dining area creates a convenient space for everyday meals and casual entertaining. The kitchen features granite countertops, rich cherry cabinetry, ample counter space, and appliances, offering practical functionality and plenty of room for meal preparation. The thoughtful layout connects the main living spaces, creating a welcoming environment for daily living. The spacious primary bedroom provides a comfortable private retreat with a ceiling fan and walk-in closet. The adjoining primary bathroom features a single vanity and a tub-and-shower combination. Two additional bedrooms offer flexible space for family members, guests, a home office, or hobbies. Both feature ceiling fans and carpeting and share a second full bathroom with a vanity and tub-and-shower combination. Additional highlights include a one-car garage, a generously sized yard, fenced outdoor space, and the added convenience of no mandatory HOA restrictions or fees. Whether you’re a first-time homebuyer, downsizing, or searching for an investment opportunity, this home offers versatility and value in an established Winter Garden neighborhood. Enjoy the convenience of the greater Winter Garden area, with access to local shopping, dining, schools, parks, and everyday essentials. The historic Downtown Winter Garden offers charming shops, restaurants, community events, and access to the popular West Orange Trail, while major roadways provide connectivity to surrounding Central Florida destinations. No HOA, solid block construction, a fenced backyard, a functional three-bedroom layout, and a roof replaced in 2019 make this home a wonderful opportunity to enjoy the Winter Garden lifestyle.

1069 Mildred Dixon Way, Winter Garden
14501 Grove Resort Avenue Unit 1218, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, where vacation ownership meets the full Orlando resort lifestyle! This beautifully furnished 2-bedroom, 2-bath condo-hotel residence offers a spacious, comfortable retreat just minutes from Walt Disney World and Central Florida’s world-famous attractions. Designed for both relaxation and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances, generous cabinetry and counter space, in-suite washer and dryer, and a private screened balcony—the perfect place to enjoy your morning coffee or unwind after a day at the parks. The spacious primary suite offers a private bath with dual vanities, soaking tub and separate shower, while the second bedroom and full bath provide plenty of room for family and guests. At The Grove, the resort itself is part of the experience. Spend the day at Surfari Water Park featuring a 695-foot lazy river, dual water slides, zero-entry pool, kids’ activity pool and exciting FlowRider® Double surf simulator. Looking for a slower pace? Relax at The Springs Pools with three full-size pools and an oversized hot tub, enjoy the natural beauty of Lake Austin, work out in the 24-hour fitness center, or take advantage of the resort’s restaurants, bars, family activities and recreation. The resort also offers transportation to Walt Disney World, Universal Orlando and SeaWorld, making it easy for guests to experience everything Orlando has to offer. Disney Springs is approximately 11 miles away, with SeaWorld, Universal Orlando, Epic Universe and countless dining, shopping and entertainment destinations all within easy reach. Ownership is made even more convenient by an association fee that includes many of the expenses normally handled separately, including electricity, water, sewer, trash, cable, internet, pest control, security, common-area and building maintenance, and recreational facilities.* Whether you're searching for your own Florida vacation getaway, a second home near the theme parks, or a furnished resort property with vacation-rental potential, Unit 1218 offers the opportunity to own where millions of visitors come to vacation every year. Come for the parks. Stay for the resort. Own a piece of the Orlando vacation lifestyle at The Grove Resort & Water Park.

14501 Grove Resort Avenue Unit 1218, Winter Garden
14017 Title Way, Winter Garden
$429,900
3 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 2 SubDv. ⋅ 34787 Zip Code
Rare CORNER-UNIT townhome with DISNEY FIREWORK VIEWS in the heart of Horizon West! Offering 3 bedrooms and 2.5 bathrooms, this home benefits from additional natural light, added privacy, and SCENIC VIEWS of the nearby pond. Inside, you’ll find an inviting layout featuring modern tile flooring throughout the first level and a thoughtfully designed kitchen with premium stainless steel appliances. Upstairs, the spacious primary suite features an updated bathroom with a beautifully REMODELED SHOWER. Two additional bedrooms allows flexibility for guests, family, or a home office. One of the property’s most appealing features is its large private courtyard, providing plenty of space for outdoor dining, entertaining, or simply relaxing. From home, you can also enjoy views of Disney’s nightly FIREWORKS! The corner-unit location creates a more open setting that is difficult to find among traditional interior townhomes. Just a short walk away, residents can enjoy community amenities including a swimming pool, playground, and splash pad. Located in one of Central Florida’s most desirable and growing communities, Horizon West offers an excellent combination of neighborhood amenities and everyday convenience. Nearby shopping, restaurants, entertainment, and major roadways make getting around the Orlando area easy. Whether you’re spending an evening in the courtyard or enjoying the surrounding community, this home offers a comfortable and convenient Central Florida lifestyle.

14017 Title Way, Winter Garden
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