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 charm meets modern living. Known for its picturesque landscapes and rich history, Winter Garden boasts a delightful blend of small-town appeal and urban conveniences. With its historic downtown area brimming with unique shops, local eateries, and a lively farmers market, residents enjoy a vibrant community atmosphere that’s hard to beat.

One of Winter Garden's most enticing features is its accessibility to the stunning natural beauty of Florida. With numerous parks and recreational spaces, including the scenic West Orange Trail, outdoor enthusiasts can indulge in biking, hiking, and leisurely strolls while soaking up the sunshine. The city’s commitment to preserving its lush surroundings makes it a haven for families and nature lovers alike.

For those looking to plant roots in this enchanting city, Winter Garden offers an array of homes priced under $500,000, making it an attractive option for first-time buyers, growing families, or anyone seeking a serene lifestyle without breaking the bank. From charming single-family homes to modern townhouses, there’s a diverse selection to suit every taste and budget.

With its friendly community, excellent schools, and proximity to major attractions like Walt Disney World, Winter Garden is not just a place to live; it’s a place to thrive. Discover your dream home in this delightful city and experience the warmth and charm that Winter Garden has to offer!

Newest Winter Garden Homes under $500,000

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
341 Southern Pecan Circle Unit 202, Winter Garden
$220,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
WINTER GARDEN GEM! NEW KITCHEN • NEW APPLIANCES • NO CARPET • PRIVATE GARAGE • RESORT-STYLE AMENITIES! Welcome to 341 Southern Pecan Circle, Unit 202, Winter Garden, FL 34787! Discover this beautifully updated, move-in-ready 1-bedroom, 1-bathroom condo featuring modern upgrades, open-concept living, a private garage, and outstanding resort-style community amenities in desirable Winter Garden, Central Florida! Step inside to enjoy bright, inviting living and dining areas filled with natural light, fresh interior paint, and NO CARPET THROUGHOUT! Attractive wood-look flooring enhances the living areas and bedroom, complemented by easy-to-maintain tile flooring in the kitchen and bathroom. The NEW KITCHEN showcases beautiful cabinetry, attractive countertops, a spacious breakfast bar, stainless steel appliances, and a NEW REFRIGERATOR AND MICROWAVE! The open layout provides an inviting space for everyday living and entertaining. The spacious bedroom offers generous closet space, while the UPDATED BATHROOM features attractive tile finishes and a convenient vanity. Additional conveniences include an IN-UNIT WASHER AND DRYER and a PRIVATE GARAGE for parking and extra storage. ENJOY RESORT-STYLE LIVING! This amenity-rich community features a sparkling swimming pool, fitness center (gym), basketball court, tennis courts, sand volleyball court, playground, and car wash station. The COMMUNITY CLUBHOUSE also offers a community kitchen, computer room, nursery room, and meeting room, providing excellent spaces for recreation, convenience, and community activities. DESIRABLE WINTER GARDEN LOCATION! Enjoy convenient access to shopping, dining, entertainment, parks, major roadways, and the greater Orlando area. IDEAL FOR LOW-MAINTENANCE LIVING OR INVESTMENT! Whether you're seeking a primary residence, seasonal retreat, convenient home for work or studies, or a potential rental investment, this updated Winter Garden condo offers comfort, functionality, and lifestyle amenities. Rental opportunities are subject to association rules and restrictions. NEW KITCHEN • NEW APPLIANCES • UPDATED BATHROOM • NO CARPET • PRIVATE GARAGE • IN-UNIT LAUNDRY • RESORT-STYLE AMENITIES! SCHEDULE YOUR PRIVATE SHOWING TODAY!

341 Southern Pecan Circle Unit 202, Winter Garden
159 9th Street, Winter Garden
$369,900
3 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
Built in 2024, this well-kept 3-bedroom, 2-bath home in the heart of Winter Garden gives you modern construction without the new-build wait. The open-concept layout connects the kitchen, with its stainless appliances, to the living and dining areas. The owner’s suite has a private en-suite bath, and two more bedrooms work well for guests or a home office. An attached garage and a newer roof and systems mean low-maintenance living from day one. You’re minutes from Plant Street’s dining, the Saturday Farmers Market and the West Orange Trail, with easy access to SR-429 and the Turnpike. Schedule your showing today!

159 9th Street, Winter Garden
6270 Sunny Time Avenue, Winter Garden
$432,290
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! This FH townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a rear-facing 2-car garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Tilden White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, gathering room, and powder room, is finished with elegant Shaw wood-look luxury vinyl plank for both style and easy maintenance. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. In the bathrooms and laundry room, you’ll find beautiful tile. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6270 Sunny Time Avenue, Winter Garden
9469 Meadow Hunt Way, Winter Garden
$485,000
4 Beds ⋅ 3 Baths ⋅ Watermark At Horizon West SubDv. ⋅ 34787 Zip Code
HOME AVAILABLE TO MOVE IN - This 4 bedroom 2.5 bath home is located in the highly desirable Hamlin Community has a GREAT SCHOOL ZONE in the Winter Garden Area!!! This recently built home features street front parking, open living space downstairs with plenty of room for entertaining, all dearooms upstairs and is wired to charge your lesla. Ine nome is minutes tom great senools, great eating at the namin center and in walking distance to the new development "The Mark". The community features clubhouse, dog park, pool, a playground, tennis court. The local snops reature a variety or restaurants, Danks, nealt orices, a rudiix grocery store, Anyume neness gym, and minutes trom Disney!

9469 Meadow Hunt Way, Winter Garden
2107 Gopher Tortoise Terrace, Oakland
$364,900
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Beautifully maintained fully furnished six-year-old townhome in the charming town of Oakland! This 2-bedroom, 2.5-bath home features a covered front porch, abundant natural light, and thoughtful upgrades throughout. The open great room welcomes you with Shaw luxury vinyl tile flooring, neutral colors, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen features 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, plus an LG French-door refrigerator. A generous pantry with a California Closets shelving system provides exceptional organization. The adjoining dining area features upgraded lighting and access to a private 19-by-15-foot paver courtyard through a full-glass door with built-in blinds. A convenient desk nook with granite countertops, drawers, and cabinetry offers space to work from home. The first-floor laundry room includes a California Closets laundry station and access to ample storage beneath the stairs. A half bath is conveniently located off the stair landing. Upstairs, both spacious bedrooms feature walk-in closets and private bathrooms. The primary suite offers a beautifully organized California Closets system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s bathroom features granite countertops and a tiled tub/shower combination with an accent inlay. The private courtyard connects to a two-car garage with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village. Bring your pups—this community has no dog breed restrictions!

2107 Gopher Tortoise Terrace, Oakland
14501 Grove Resort Avenue Unit 3631, Winter Garden
$164,900
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 3631, Winter Garden
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