Winter Garden Homes under $400,000

Winter Garden Homes under $400,000

Welcome to Winter Garden, Florida, a hidden gem nestled in Orange County that perfectly blends small-town charm with modern conveniences. Just a stone's throw away from the vibrant city of Orlando, Winter Garden boasts a picturesque downtown area filled with quaint shops, delicious eateries, and a lively farmers market that draws locals and visitors alike. The city's rich history is reflected in its beautifully preserved architecture and the scenic West Orange Trail, ideal for walking, biking, and enjoying the great outdoors.

For those seeking the perfect home in this enchanting locale, Winter Garden offers a variety of properties under $400,000, making it an attractive option for first-time homebuyers, families, and retirees alike. From charming single-family homes to cozy townhouses, there’s something for everyone in this thriving community. Many of these homes feature modern amenities, spacious layouts, and lovely outdoor spaces, ensuring you can enjoy the beautiful Florida weather year-round.

Additionally, Winter Garden is known for its top-rated schools, friendly neighborhoods, and a strong sense of community, making it an ideal place to raise a family or enjoy a peaceful retirement. With easy access to major highways, you can quickly reach the attractions of Orlando, while still coming home to the tranquility that Winter Garden offers.

Explore the possibilities of finding your dream home in Winter Garden, where affordability meets quality of life. Embrace the charm of this delightful city and discover all that it has to offer!

Newest Winter Garden Homes under $400,000

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
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
441 Sand Lime Road, Winter Garden
$165,000
1 Beds ⋅ 2 Baths ⋅ Village Grove SubDv. ⋅ 34787 Zip Code
For sale for first time ever. Best price in 34787 with convenient location to SR 50. New carpet and paint. very low hoa at $63 a month. Community pool is few doors down too. Priced to sell so move quick. You wont find one like this again. Minutes from everything Winter Garden. NEW ROOF 2022, AC is 2019.

441 Sand Lime Road, Winter Garden
1432 Scarlet Oak Loop, Winter Garden
$384,900
3 Beds ⋅ 3 Baths ⋅ Villas/Tucker Oaks SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained and thoughtfully upgraded home in the desirable gated community of Tucker Oaks in Winter Garden. Offering 3 bedrooms, 2.5 baths, and over 1,700 square feet of living space, this home combines modern updates, energy-efficient features, and comfortable Florida living. The kitchen was beautifully updated in 2023 with quartz countertops and backsplash, 42-inch soft-close cabinetry, a Kraus 30-inch single-bowl stainless steel sink, and a newer KitchenAid dishwasher. Porcelain tile flows throughout the first floor, while newer luxury vinyl flooring extends up the stairs and throughout the upstairs hallway and bedrooms, complemented by 6-inch baseboards. Major improvements include a 2025 roof, 2022 Carrier A/C with soft-start technology, 2025 water softener, and a dedicated generator outlet. Solar panels help reduce energy costs, while whole-house Vista Luminance V28 8-mil window film, installed in 2023, helps block up to 65% of total solar energy and rejects 99.9% of harmful UV rays. Both the primary and guest bathrooms have been remodeled and feature comfort-height toilets. The laundry room has also been upgraded with additional cabinetry for convenient storage. Step outside to enjoy the screened lanai overlooking the pond, with pebble-stone flooring installed in 2023 and no-see-um screening added in 2026. The fenced-in yard provides added privacy and creates a wonderful outdoor space for relaxing or entertaining while enjoying the peaceful pond views. The garage offers additional convenience with overhead storage racks and a pull-down ladder providing access to the garage attic. Tucker Oaks is a gated community offering a resort-style pool, clubhouse, playgrounds, basketball courts, dog park, sidewalks, and green spaces. The location is hard to beat, with convenient access to the Florida Turnpike and major roadways, while being just minutes from historic Downtown Winter Garden and the popular Plant Street corridor, where you'll find restaurants, shopping, Plant Street Market, the weekly farmers market, and local entertainment. The West Orange Trail is also nearby for biking, walking, and outdoor recreation. With a long list of recent improvements, energy-efficient features, a fenced yard with peaceful pond views, and an ideal Winter Garden location, this home is truly move-in ready and offers the lifestyle you've been looking for.

1432 Scarlet Oak Loop, Winter Garden
14501 Grove Resort Avenue Unit 3703, Winter Garden
$178,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to Your Premier Vacation Gateway at The Grove Resort & Water Park! Located just minutes from Walt Disney World and Orlando’s world-class attractions, this fully furnished 2-bedroom, 2-bathroom condo-hotel unit (#3703) offers the perfect blend of vacation luxury and income-generating potential! ***PRIME CENTRAL VIEW: Positioned directly facing the lush central garden and courtyard, providing a peaceful, scenic backdrop and elevated tropical views right from your private space. ***UNRIVALED RESORT AMENITIES: Guests and owners enjoy full access to the renowned Surfari Water Park, dual water slides, lazy river, FlowRider® surf simulator, zero-entry pools, spa, game room, and multiple on-site dining options. ***TURNKEY & HASSLE-FREE: Professionally managed with on-site rental program options, making personal vacation stays and short-term rentals seamless.*** Whether you're seeking a vacation home, a smart investment property, or a hybrid of both, Unit #3703 delivers unbeatable lifestyle and convenience in the heart of Central Florida's tourism corridor. Schedule your showing today!!

14501 Grove Resort Avenue Unit 3703, Winter Garden
15579 Honeybell Drive, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Welcome home to this gorgeous end unit townhome in the heart of Hamlin! With capabilities of fencing in the side yard, this townhome offers potential unlike any other. Step inside and admire the fresh color palette this home boasts. With light wood-plank tile flooring, light countertops, light cabinetry, and lots of windows, this open concept downstairs feels incredibly warm and inviting. Updated lighting and window drapes elevate the space even more. Functionality and convenience were also taken into consideration in this downstairs with a cabinet and counter-lined drop zone upon entry into the home from the garage and patio, a closet pantry, and hallway leading to the half bathroom. Head upstairs where you will find a split bedroom floor plan with the primary suite on one side and the secondary bedrooms and Jack-and-Jill styled bathroom on the other, the space separated even further by the upstairs laundry room. Step out back to the private fenced-in brick-paved patio that separates the house from the two-car garage. The community is situated right in the middle of Hamlin’s shopping, dining, and entertainment offerings, super close to Disney, and right off of Highway 429 to bring you to all of your favorite Central Florida destinations. Inquire today on how to make this gem your own!

15579 Honeybell Drive, Winter Garden
8049 Basilica Lane, Winter Garden
$399,900
3 Beds ⋅ 3 Baths ⋅ Ravenna Ph 1 SubDv. ⋅ 34787 Zip Code
OPEN-CONCEPT LIVING • OVERSIZED KITCHEN ISLAND • HARD-SURFACE FLOORING • SPACIOUS PRIMARY SUITE • PRIVATE PAVER PATIO • COMMUNITY POOL • WINTER GARDEN 34787 This Winter Garden townhome brings together the features that make a difference: a spacious open-concept layout, oversized kitchen island, abundant natural light, hard-surface flooring on the main level, staircase and upstairs hallway, generous storage, interior laundry, a spacious primary suite, private enclosed paver patio and access to the community pool. Welcome to 8049 Basilica Lane, a two-story residence offering 3 bedrooms, 2.5 bathrooms and approximately 1,860 sq ft, with thoughtfully connected indoor and outdoor spaces. The entry opens to a bright foyer featuring tile flooring, recessed lighting, a sidelight window and textured accent wall. From here, the floor plan transitions naturally into the kitchen, dining and living areas, creating one continuous gathering space. Large windows bring in natural light, while the open layout provides flexibility for different furniture and dining configurations. At the center of the main level, the kitchen features dark cabinetry, stainless-steel appliances, built-in microwave, range, dishwasher, pendant lighting and an oversized island with extended countertop seating. Generous cabinetry and counter space provide plenty of room for meal preparation and storage. Large-format tile flooring extends throughout the main gathering areas, creating a cohesive and low-maintenance surface. Continue upstairs via a hard-surface staircase with no carpet, where the upstairs hallway also features hard-surface flooring. Multiple closets provide additional storage, and a dedicated interior laundry closet offers space for a side-by-side washer and dryer with shelving above. The primary bedroom offers multiple windows, a tray ceiling and decorative wall detailing. The primary bathroom includes a long dual-sink vanity, extensive countertop and cabinet storage, a large wall mirror, tile flooring and an oversized glass-enclosed shower with tiled surround and built-in shower shelving. Step outside to a private enclosed paver patio designed to extend the living space outdoors. The fenced area provides room for lounge seating, outdoor dining and grilling, while shade coverings and string lighting add functionality for daytime and evening use. The community also offers a swimming pool with a spacious paver deck and lounge areas surrounded by Florida landscaping. Located in Winter Garden’s 34787 area, the property is convenient to Horizon West and Hamlin, with shopping, restaurants, grocery stores, entertainment and recreation nearby. Major Central Florida roadways provide connections to Walt Disney World, Windermere, Downtown Winter Garden and the greater Orlando area. Schedule your private showing today and come experience 8049 Basilica Lane in person!

8049 Basilica Lane, Winter Garden
14501 Grove Resort Avenue Unit 3201, Winter Garden
$245,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
FULLY FURNISHED/TURNKEY LUXURIOUS 3/3 Corner Unit at The Grove Resort & Spa, Orlando Welcome to your dream oasis at The Grove Resort & Spa Orlando! This magnificent corner unit boasts the LARGEST floor plan available, featuring 3 spacious bedrooms and 3 elegant bathrooms. Experience the ultimate blend of comfort and luxury in this stunning condo-hotel located just six miles from Walt Disney World® Theme Parks, The Grove Resort & Spa offers unparalleled access to Orlando’s world-famous attractions. Enjoy daily transportation to Walt Disney World®, Universal Orlando, and SeaWorld, making it effortless to explore all that Orlando has to provide. Indulge in a variety of resort amenities designed for both relaxation and adventure. The Surfari Water Park features thrilling water slides, a lazy river, and the exhilarating FlowRider® Double surf simulator. Unwind at The Springs Pools, with three full-sized pools, an oversized hot tub, and poolside bar service. At Lake Austin, engage in catch-and-release fishing, paddle boating, or simply savor the serene views of the surrounding nature preserve. Stay active with a fully-equipped fitness center and scenic jogging paths. Families will love Flip Flop’s Family Fun Center, offering the latest arcade games and a glow-in-the-dark mini golf course. This corner unit is designed with a modern touch, offering a spacious open-plan living area, a gourmet kitchen, and stylish furnishings throughout. Each bedroom is a private retreat, complete with luxurious bedding and ample storage. Owning a unit at The Grove Resort & Spa offers not only a luxurious vacation spot but also a fantastic stress-free investment opportunity. Don’t miss the opportunity to own a piece of paradise at The Grove Resort & Spa, where every day feels like a vacation. Contact us today to schedule a private viewing and experience the exceptional lifestyle that awaits you.

14501 Grove Resort Avenue Unit 3201, Winter Garden
14501 Grove Resort Avenue Unit 2608, Winter Garden
$255,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden
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