Winter Garden Homes under $350,000

Winter Garden Homes under $350,000

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes, friendly community, and vibrant downtown area, Winter Garden offers a perfect blend of suburban tranquility and urban convenience. With its rich history and a growing population, this delightful city is becoming a sought-after destination for families, retirees, and everyone in between.

One of the most appealing aspects of Winter Garden is its diverse real estate market, particularly for those seeking homes under $350,000. Here, you can find a variety of affordable housing options that cater to different lifestyles and preferences. From cozy single-family homes nestled in peaceful neighborhoods to modern townhouses with contemporary amenities, Winter Garden has something for everyone.

The city's commitment to preserving its natural beauty is evident in its many parks, trails, and outdoor recreational areas. The West Orange Trail, a scenic 22-mile-long path, is perfect for walking, biking, or jogging, making it a favorite among residents. Additionally, the vibrant downtown area is brimming with boutique shops, delicious dining options, and community events that foster a strong sense of belonging.

With excellent schools, a low crime rate, and a welcoming atmosphere, Winter Garden is not just a place to live; it’s a place to thrive. Whether you’re a first-time homebuyer or looking to downsize, Winter Garden’s affordable homes under $350,000 provide an incredible opportunity to join this flourishing community. Discover the magic of Winter Garden and find your dream home today!

Newest Winter Garden Homes under $350,000

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

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

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

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 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

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