Winter Garden Homes under $350,000

Winter Garden Homes under $350,000

Welcome to Winter Garden, Florida—an enchanting city nestled in the heart of Orange County. Known for its charming downtown area and vibrant community spirit, Winter Garden offers a delightful blend of historic charm and modern amenities. With its lush landscapes, scenic lakes, and a warm climate, it's no wonder that this picturesque city has become a sought-after destination for families, retirees, and everyone in between.

One of the most appealing aspects of Winter Garden is its affordability, particularly when it comes to housing. For those seeking a home under $350,000, Winter Garden presents an array of options that don’t compromise on quality or comfort. From cozy single-family homes to inviting townhouses, there’s something for everyone in this charming locale. Many of these homes feature modern finishes, spacious layouts, and beautiful outdoor spaces, perfect for enjoying the Florida sunshine.

Living in Winter Garden means embracing a lifestyle filled with outdoor activities, cultural experiences, and community events. The West Orange Trail, a favorite among locals, offers miles of scenic pathways for walking, biking, and jogging. The historic downtown area is brimming with unique shops, delightful restaurants, and a vibrant farmers’ market that showcases local produce and crafts.

With its rich history, friendly atmosphere, and affordable housing options, Winter Garden is not just a place to live—it's a place to call home. Discover the charm of this wonderful city and find your perfect home today!

Newest Winter Garden Homes under $350,000

14501 Grove Resort Avenue Unit 1528, Winter Garden
$215,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo I SubDv. ⋅ 34787 Zip Code
MOTIVATED SELLER... BRING OFFER! Welcome to a beautifully appointed 3-bedroom luxury condo-hotel residence at The Grove Resort & Water Park, offering exceptional views, a spacious layout, and true turnkey ownership just minutes from Disney and the Orlando theme parks. This well-designed unit features a generous open-concept living and dining area, ideal for entertaining or relaxing after a day at the parks. The thoughtfully separated bedroom layout provides comfort and privacy for owners and guests alike, making it especially attractive for short-term rentals. Offered fully equipped for immediate use, this residence is designed to perform as both a personal vacation retreat and an income-producing investment. Beyond the residence, owners and guests enjoy access to one of Central Florida’s most amenity-rich resorts. The Grove Resort & Water Park features a full-scale water park with lazy river and water slides, multiple resort-style pools, a surf simulator, full-service spa, fitness center, on-site shopping, and a variety of restaurants with indoor and outdoor dining. The resort also includes Lake Austin for fishing and paddle boating, conference and event facilities, and complimentary shuttles to Disney. The property is supported by a professional, on-site management team, providing a seamless and hands-off ownership experience while maintaining high guest satisfaction. This unique condo-hotel opportunity allows owners to enjoy personal use while generating rental income when not in residence. A rare combination of space, views, resort amenities, and location, this unit stands out among competing offerings—ideal for buyers seeking flexibility, lifestyle, and long-term value in a premier destination.

14501 Grove Resort Avenue Unit 1528, Winter Garden
14501 Grove Resort Avenue Unit 1440, Winter Garden
$159,999
2 Beds ⋅ 2 Baths ⋅ The Grove Resort And Spa SubDv. ⋅ 34787 Zip Code
Welcome to Resort-Style Living at Its Finest! Nestled on the 4th floor of Building 1 at the highly acclaimed Grove Resort & Water Park, unit #1440 offers a turnkey 2-bedroom, 2-bathroom condo designed for effortless relaxation and high-value performance. Step inside to discover a bright, open floor plan that flows seamlessly to a private balcony—the perfect spot to enjoy Florida’s warm breezes and tranquil views. Building 1 boasts an enviable location within the resort, placing you just steps from the main lobby, dining options, and world-class amenities, so guests and owners spend less time walking and more time enjoying the retreat. Whether you are looking for a personal vacation sanctuary or a lucrative investment asset, this property delivers an unmatched lifestyle package. The Grove Resort features the exciting Surfari Water Park—complete with a dual-waterslide tower, lazy river, and FlowRider® surf simulator—alongside peaceful heated pools, a full-service spa, fitness center, on-site dining, and watersports on Lake Austin. Positioned just minutes from Walt Disney World®, Universal Studios, premier shopping outlets, and dining destinations, this condo combines luxury living with an irresistible location for vacationers and homebuyers alike.

14501 Grove Resort Avenue Unit 1440, Winter Garden
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
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
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 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
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