Winter Garden Homes under $400,000

Winter Garden Homes under $400,000

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County that beautifully blends the allure of small-town living with modern conveniences. Known for its picturesque downtown area, Winter Garden boasts a vibrant community atmosphere, where you can stroll along tree-lined streets, explore boutique shops, and savor delicious meals at local eateries. With its rich history and stunning natural surroundings, this city is an idyllic place to call home.

For those searching for affordable housing options, Winter Garden offers a variety of homes priced under $400,000, making it an attractive choice for first-time buyers, families, and investors alike. These homes come in diverse styles, from cozy single-family residences to modern townhouses, ensuring that you'll find the perfect fit for your lifestyle and budget. Many of these properties feature spacious yards, updated interiors, and access to the area's top-rated schools, parks, and recreational activities.

Winter Garden is also conveniently located near major highways, providing easy access to Orlando's bustling attractions and the beautiful landscapes of Central Florida. Whether you're looking to enjoy a day at the theme parks or a serene weekend in nature, Winter Garden offers the best of both worlds.

With its friendly community, rich culture, and affordable housing options, Winter Garden is not just a place to live – it's a place to thrive. Come explore the opportunities that await you in this delightful city, where your dream home is just a step away!

Newest Winter Garden Homes under $400,000

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
14501 Grove Resort Unit 1723, Winter Garden
$344,900
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
THE PERFECT COMBINATION AT THE GROVE RESORT! TOWER 1. TOP FLOOR. CORNER UNIT. LAKE AUSTIN & NATURE PRESERVE VIEWS. PLUS, ENJOY MAGIC KINGDOM & EPCOT FIREWORKS FROM YOUR PRIVATE PRIMARY SUITE SOLARIUM! Welcome to Unit 1723, a beautifully positioned 3-bedroom, 3-bathroom condo-hotel residence with a solarium, offering 1,544 sq. ft. of comfort, convenience, and breathtaking scenery at The Grove Resort & Water Park. LOCATION MAKES ALL THE DIFFERENCE! Situated on the 7th and highest floor of Tower 1, this desirable corner residence combines beautiful water and nature preserve views with the convenience of the resort's main building. Enjoy easy access to the lobby, concierge, restaurant, bar, and fitness center without leaving your tower. Inside, discover an inviting open-concept living and dining area, a fully equipped kitchen, spacious bedrooms, and a private solarium sitting area off the primary suite, where you can gather with family to watch the Magic Kingdom and EPCOT fireworks. Direct balcony access from the primary suite, a full-size in-unit washer and dryer, and ample resort parking add everyday convenience. Just minutes from Walt Disney World, The Grove is a designated Walt Disney World Good Neighbor® Hotel, featuring Surfari Water Park with its FlowRider® Surf Simulator, lazy river, swimming pools, hot tubs, on-site dining, recreational activities on Lake Austin, and resort transportation to Disney and Universal theme parks. Whether you're looking for a Florida vacation retreat or a professionally managed short-term rental opportunity, Unit 1723 offers an exceptional blend of location, comfort, memorable views, and resort living. This condo-hotel property is subject to resort rental and occupancy restrictions and is not intended for permanent residency. Buyers should verify all applicable association and resort requirements.

14501 Grove Resort Unit 1723, Winter Garden
14501 Grove Resort Avenue Unit 2539, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST-PRICED UNIT CURRENTLY AVAILABLE AT THE GROVE RESORT! This 5th-floor Birch residence is located in desirable Tower 2, the newest tower at The Grove and featuring the resort's most updated décor and finishes. Enjoy a peaceful garden view from this fully furnished resort residence just minutes from Walt Disney World. The Grove Resort & Water Park offers an exceptional combination of vacation ownership and resort amenities, including Surfari Water Park, multiple pools, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, market and coffee shop, and on-site resort management. An outstanding opportunity for buyers looking for an entry point into one of Orlando's most established condo-hotel resorts at the best price currently offered. Financial information and ownership details available upon request.

14501 Grove Resort Avenue Unit 2539, Winter Garden
14066 Avenue Of The Groves, Winter Garden
$330,000
2 Beds ⋅ 3 Baths ⋅ Signature Lks-Pcl 01d Ph 01 SubDv. ⋅ 34787 Zip Code
Welcome to resort-style living in the sought-after community of Independence. This beautifully renovated, move-in-ready townhouse seamlessly combines modern updates, luxury amenities, and Disney-area convenience. Enjoy serene, unobstructed views with no front-facing neighbors—the ideal setting to watch Magic Kingdom’s dazzling nightly fireworks. Inside, you will find a newly updated kitchen, fresh luxury vinyl flooring throughout, a spacious open layout, and two bedrooms with ensuite bathrooms. Step outside to your private courtyard featuring newly installed synthetic turf, ideal for outdoor entertaining. A detached two-car garage provides ample parking and additional storage. Unit comes with soft water filtration system. Independence residents enjoy premier community amenities, including tennis and basketball courts, a clubhouse, a fitness center, two resort-style pools, walking parks, playgrounds, and a dedicated dog park. The HOA fee conveniently covers high-speed internet, cable, pest control, roof maintenance, exterior painting, amenity access, and all common-area landscaping. Contact us today to schedule your private showing!

14066 Avenue Of The Groves, Winter Garden
14501 Grove Resort Avenue Unit 3636, Winter Garden
$175,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to effortless resort living and an incredible SHORT-TERM RENTAL OPPORTUNITY at The Grove Resort & Water Park! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2-bath condo-hotel is TURNKEY READY and already part of the resort’s rental pool with onsite management, making ownership especially convenient. Owners are permitted PERSONAL USE for up to 179 days per year, offering the flexibility to enjoy the property yourself while also taking advantage of its VACATION-RENTAL POTENTIAL. Set within the GATED RESORT COMMUNITY, this condo is located in a high-rise building with ELEVATOR ACCESS and puts an incredible array of amenities right outside your door. Step inside to find a bright, inviting interior with LUXURY VINYL PLANK FLOORING throughout the main living areas. The open Kitchen features QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES and a convenient breakfast bar, all overlooking the spacious Living Room with plenty of room for a Dining Area. Sliding glass doors extend the living space outdoors to a SCREENED, COVERED BALCONY, creating a relaxing spot to enjoy your morning coffee or unwind after a day at the parks. The AC WAS UPDATED in 2017, adding to the home's appeal as a well-maintained vacation property.The SPLIT-BEDROOM FLOOR PLAN provides privacy for owners and guests alike. The generous PRIMARY SUITE features a walk-in closet, an en suite Bath, and a COMFORTABLE SITTING AREA with its own PRIVATE ACCESS to the balcony. The en suite Bath offers dual sinks with QUARTZ COUNTERTOPS, a garden tub, step-in shower and private water closet. On the opposite side of the condo, the spacious SECOND BEDROOM offers a walk-in closet and its own EN SUITE BATH. A dedicated Laundry Room with washer and dryer adds everyday convenience.The Grove Resort & Water Park is a 106-acre destination with an IMPRESSIVE COLLECTION OF AMENITIES, including SURFARI WATER PARK, featuring a 695-foot lazy river, dual water slides, a FlowRider surf simulator, kids' activity pool and ZERO-ENTRY POOL. The resort also offers MULTIPLE POOLS including the lakefront Springs Pools with three full-size pools, hot tub and children's splash area, along with a 24-hour FITNESS CENTER, restaurants, family activities, LAKE AUSTIN ACCESS and more. CABLE AND INTERNET are also included, while resort transportation provides SHUTTLE SERVICE to Walt Disney World, Universal Orlando and SeaWorld. Lake Austin provides another way to enjoy the outdoors, with a LAKESIDE PIER offering beautiful nature views, catch-and-release fishing and resort watersports. When it is time to venture out, the resort is just SIX MILES FROM WALT DISNEY WORLD, putting Orlando's WORLD-FAMOUS ATTRACTIONS within easy reach. Beyond the resort, enjoy the growing Horizon West area with FLAMINGO CROSSINGS TOWN CENTER, Historic Downtown Winter Garden, the West Orange Trail and Plant Street offering opportunities for dining, shopping, entertainment and enjoying the FLORIDA LIFESTYLE. Families will appreciate the access to A-RATED SCHOOLS, including WATER SPRING ELEMENTARY, WATER SPRING MIDDLE and HORIZON HIGH SCHOOL.Whether you're looking for a vacation home, a personal getaway or a TURNKEY SHORT-TERM RENTAL INVESTMENT, this furnished Grove Resort condo provides an EXCEPTIONAL OPPORTUNITY to own a piece of the Orlando vacation lifestyle—with onsite management, RESORT AMENITIES, and the flexibility to enjoy it yourself. Come discover the possibilities at The Grove!

14501 Grove Resort Avenue Unit 3636, Winter Garden
10114 Salt Point Drive, Winter Garden
$395,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2e SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-bedroom, 2.5-bathroom townhome in the desirable Waterleigh community in Winter Garden! The thoughtfully designed two-story layout offers comfortable living spaces for everyday enjoyment and entertaining. Enjoy Waterleigh’s resort-style amenities, including community pools, clubhouses, fitness centers, playgrounds, and scenic walking trails. Conveniently located near shopping, dining, Walt Disney World, and major highways, this home offers an appealing combination of comfort and convenience. Schedule your private showing today!

10114 Salt Point Drive, Winter Garden
14501 Grove Resort Unit 2304, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Short Sale. Experience the Ultimate Orlando Resort Lifestyle & Investment Opportunity! Welcome to The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations, ideally located just minutes from Walt Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. Enjoy a fully furnished, turnkey 2-bedroom, 2-bath condominium that offers the perfect blend of comfort, style, and investment flexibility. The spacious open-concept floor plan features a beautifully appointed kitchen, bright great room, oversized windows, and a private balcony overlooking the peaceful courtyard. The split-bedroom layout provides privacy, while two spa-inspired bathrooms feature garden tubs, tiled showers, and dual vanities. With a sleeper sofa in the living room, the residence comfortably accommodates up to six guests. Step outside your front door and discover an extraordinary resort experience. The spectacular Surfari Water Park features a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Additional amenities include multiple pools and hot tubs, a 20-acre activity lake with private dock, fishing, fitness center, full-service spa, arcade, game room, and an array of on-site dining options including Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, and Byte. Convenient shuttle transportation to Disney World, Universal Studios, and SeaWorld adds even more appeal for vacation guests. As a short-term rental property, owners may enjoy personal use, while professional on-site management can handle bookings, housekeeping, maintenance, and guest services. Whether you're looking for a personal Orlando getaway, a vacation home, or a hands-off investment opportunity, this property offers an exceptional combination of resort amenities, flexibility, convenience, and income potential. Experience the magic of Orlando while owning your own piece of the vacation lifestyle at The Grove Resort & Water Park!

14501 Grove Resort Unit 2304, Winter Garden
1323 Azalea Way, Winter Garden
$189,000
3 Beds ⋅ 2 Baths ⋅ Westside Twnhms Ph 03 SubDv. ⋅ 34787 Zip Code
This 3-bed, 2-bath townhome is just minutes from Historic Downtown Winter Garden, Plant Street Market, farmers markets, boutique shops, and local dining. Enjoy easy access to major highways, top-rated schools, Walt Disney World, and Central Florida’s theme parks. Whether you’re adding to your rental portfolio or looking for a property in a highly desirable area, this one offers location, lifestyle, and investment potential all in one.

1323 Azalea Way, Winter Garden
15515 Campden Street, Winter Garden
$359,900
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this Gorgeous Home, where CONVENIENCE, and LOW-MAINTENANCE LIVING come together in a fantastic Winter Garden location making it easy to enjoy the vibrant Winter Garden lifestyle!! Step inside this to FRESHLY PAINTED 3 bedroom, 2.5 bath home. Featuring highly desirable WOOD-LOOK CERAMIC TILE throughout the main living areas, including the spacious living room, dining area, and kitchen.The kitchen features a NEW REFRIGERATOR, while a convenient downstairs half bath and large storage closet add to the home’s functionality. Upstairs, the VERSATILE LOFT adds valuable additional living space and is perfect for a home office, media room, playroom, fitness area, or cozy second family room. Plus the convenience of an UPSTAIRS LAUNDRY ROOM. The SPACIOUS Primary suite has 2 WALK-INCLOSETS and an ensuite bathroom with DUAL SINKS. The secondary bedrooms are also spacious and the 2nd bedroom also has a WALK-IN CLOSET as well. Enjoy added peace of mind with a NEW A/C installed in 2022, ROOF approximately 3 years NEW, gutters, and fresh exterior paint completed in 2025. Enjoy Florida living with access to the COMMUNITY POOL, perfect for cooling off, relaxing, and enjoying sunny Central Florida days without the maintenance of a private pool. The HOA provides exceptional value and low-maintenance living, including pest control, lawn, exterior maintenance, roof replacement approximately every 10 years, exterior painting, community pool, and tot lot. And then there's the LOCATION! Enjoy convenient access to the charm and energy of HISTORIC DOWNTOWN Winter Garden, where brick-lined streets are filled with locally loved restaurants, cafés, boutique shops, entertainment, and the popular Farmers Market. Grab a coffee, meet friends for dinner, spend an afternoon browsing the shops, or simply enjoy the welcoming small-town atmosphere. Outdoor enthusiasts will love the 22-mile West Orange Trail, which travels directly through the heart of Downtown Winter Garden. Whether you enjoy biking, running, walking, or simply getting outside, the trail offers miles of recreation and is one of the area's signature lifestyle amenities. This is more than just a home, it’s a lifestyle!

15515 Campden Street, Winter Garden
14501 Grove Resort Avenue Unit 2219, Winter Garden
$269,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 2219 at The Grove Resort & Water Park Orlando, where resort-style living meets an exceptional ownership opportunity just minutes from Central Florida’s world-famous attractions. This beautifully appointed 3-bedroom, 2-bath residence comes fully furnished and ready to enjoy. The spacious open-concept layout provides plenty of room for owners and guests, while the private balcony overlooking a peaceful water view creates the perfect setting to relax after a day enjoying everything Orlando has to experience. The primary suite features a spacious bathroom with a separate walk-in shower and soaking tub, offering the comfort and convenience expected from a full-service resort residence. Owners have access to The Grove’s extensive resort-style amenities, including water attractions, multiple swimming pools, dining options, fitness facilities, spa services, recreational areas, and much more. For owners seeking a hands-off approach, The Grove offers an optional professional resort management and rental program, providing the convenience of having the property managed and rented when not being personally enjoyed. Whether you are looking for a Florida vacation home, a furnished resort property, or an investment opportunity with professional management available, Unit 2219 offers a unique combination of comfort, convenience, and resort amenities in the Orlando area.

14501 Grove Resort Avenue Unit 2219, Winter Garden
2224 Gopher Tortoise Terrace, Oakland
$379,900
2 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
Set in Longleaf at Oakland, directly across from Oakland Nature Preserve and the 22-mile West Orange Trail, this END-UNIT TOWNHOME offers a rare combination of natural surroundings and everyday convenience. A covered front porch overlooking a large grassy area welcomes you home and provides a peaceful place to relax and enjoy beautiful Florida sunsets. ADDITIONAL WINDOWS fill the end-unit home with natural light and create a bright, open feel. UPGRADED luxury vinyl flooring flows throughout the first floor. The OPEN FLOOR PLAN brings the living spaces together, with spacious living and dining areas that flow naturally into the kitchen. UPGRADED 42-inch white cabinetry with crown molding, stone countertops, a tile backsplash, a generous island with additional seating and a LARGE WALK-IN PANTRY create an inviting and functional setting for everything from casual mornings to entertaining friends and family. Just beyond the main living area, a PRIVATE COURTYARD connects the home to the detached TWO-CAR GARAGE by a covered walkway. With the garage positioned separately from the home, the courtyard becomes a private extension of the living space for grilling, entertaining or unwinding outdoors. Offering 1,652 sf, the townhome features TWO BEDROOMS plus a large LOFT that can serve as a HOME OFFICE, MEDIA ROOM, PLAYROOM or additional living area, and 2.5 BATHROOMS. Both bedrooms are located on the second floor and have PRIVATE ENSUITE BATHROOMS, giving the second bedroom the comfort and privacy of a SECOND PRIMARY SUITE. The primary suite includes an expansive WALK-IN CLOSET, while the bathroom is finished with UPGRADED shower tile and an UPGRADED glass shower door. SMART HOME features, including a Ring doorbell, security camera and MyQ garage-door opener add everyday ease. ENERGY-EFFICIENT double-pane windows and a programmable Nest thermostat help keep energy use and monthly electric costs down. Tall oak trees enhance the community’s natural setting, along with a COMMUNITY POOL, PLAYGROUND and WALKING TRAILS. Just outside the community, you can spend mornings walking beneath the trees, head out for a bike ride or follow the WEST ORANGE TRAIL into HISTORIC DOWNTOWN WINTER GARDEN for dining, shopping and the award-winning Saturday Farmers Market. Here, you can feel connected to nature without leaving convenience behind. Florida’s Turnpike entrance is approximately one mile away, while everyday shopping, including the new Costco in Clermont, is less than 10 minutes from home. It is an ideal setting for enjoying a quieter community atmosphere while remaining connected to work, recreation and everything the surrounding area has to offer.

2224 Gopher Tortoise Terrace, Oakland
14169 Avenue Of The Groves, Winter Garden
$375,000
2 Beds ⋅ 3 Baths ⋅ Signature Lks-Pcl 01d Ph 01 SubDv. ⋅ 34787 Zip Code
Resort-style ease meets everyday comfort in this move-in ready Independence townhome that lives like a single-family home. Two bedroom, two and a half bath, with both bedrooms featuring private en suites.  Enjoy a welcoming front porch for morning coffee and an expansive private courtyard that truly feels like your own backyard, with direct access to a 2-car garage—giving you outdoor living space, privacy and functionality you don’t always find in townhome living. **And when the sun goes down, enjoy the magic of Magic Kingdom fireworks right from home.** Fresh exterior paint and newer roof, inside brand new carpet, newer Trane HVAC, upgraded LG Smart stainless steel appliances app controlled plus W/D (with added features like bio defense light) set a clean, modern tone. An open-concept layout features a kitchen with an island breakfast bar that flows seamlessly into the dining and living areas, keeping everyone connected. Soaring ceilings and abundant natural light from numerous windows create a bright, airy feel throughout. Smart-home conveniences include a Ring security system with remote monitoring and My Q remote-access garage controls, giving you added convenience whether you’re home or away. The HOA covers lawn care, so your weekends are truly yours. Step outside and you’ve got a Gazebo on corner to enjoy lakefront picnics, two clubhouses in close distance where lots of community parties happen with resort pools, fitness center, game room, holiday events, giant open lawns for sports and activities, walking and biking trails, multiple playgrounds and parks, basektball and tennis courts, dog parks, a community boat ramp onto Lake Hancock, access to a PokemonGo Pokestop, and that signature Indenpendence reflecting pond. (Lake Views from Master BD and front porch). All the polish of a model home, with the space and feel of a single family, plus the low maintenance lifestyle you want. Just minutes from shopping, groceries, and dining, with Walt Disney World approximately 20 minutes away. Everyday convenience and weekend magic, right at your doorstep. Organized community events, including festivals, pool events, food-truck nights and Independence's annual fireworks event.

14169 Avenue Of The Groves, Winter Garden
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