Winter Garden Homes under $250,000

Winter Garden Homes under $250,000

**Discover Winter Garden, Florida: Your Ideal Home Awaits!**

Nestled in the heart of Orange County, Winter Garden is a charming city that beautifully blends small-town charm with modern living. Known for its picturesque streets, vibrant downtown area, and rich history, Winter Garden offers a unique lifestyle that appeals to families, retirees, and everyone in between. With its convenient location just a stone's throw away from Orlando, residents can enjoy the best of both worlds: the tranquility of suburban life and the excitement of city amenities.

One of the most appealing aspects of Winter Garden is its diverse housing market, particularly for those seeking homes under $250,000. This emerging area features a variety of affordable options, from cozy single-family homes to quaint townhouses, making it an ideal choice for first-time homebuyers or investors looking for value. These properties often come with spacious yards, community amenities, and access to local parks, ensuring you can enjoy the great Florida outdoors right at your doorstep.

Winter Garden is also known for its top-notch schools, friendly neighborhoods, and a strong sense of community. The city hosts a variety of events throughout the year, including farmers' markets, festivals, and outdoor concerts, providing plenty of opportunities to connect with neighbors and create lasting memories.

If you’re searching for an affordable home in a vibrant community, Winter Garden, Florida, is the perfect place to start your journey. Embrace the warmth of this delightful city and discover the home of your dreams today!

Newest Winter Garden Homes under $250,000

87 Windtree Lane Unit K, Winter Garden

87 Windtree Lane Unit K, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 03 SubDv. ⋅ 34787 Zip Code

**Great location, attractive pricing, and plenty of potential in Windtree Gardens Community in Winter Garden ** Tucked away at the back of the community, this private first-floor, 2-bedroom, 2-bath condo offers a peaceful setting and a fantastic opportunity to make a home your own. With a functional layout, a screened porch for enjoying the outdoors, and the convenience of an in-unit washer and dryer, the home provides a great foundation for thoughtful updates and personal touches. The community offers a variety of amenities, including a swimming pool, clubhouse, and basketball court, along with pest control service and two dedicated parking spaces. The location is a standout! Just minutes from SR 429, Florida's Turnpike, and charming Historic Downtown Winter Garden, you'll enjoy convenient access to shopping, dining, entertainment, and major commuter routes while being close to one of Central Florida's most beloved downtown destinations. This condo is a great choice for buyers who appreciate privacy, convenience, community amenities, and the chance to add their personal style. Condo also has a strong rental opportunity for savvy investors. Bring your vision and discover the possibilities at 87 Windtree!

87 Windtree Lane Unit K, Winter Garden

14501 Grove Resort Avenue Unit 1528, Winter Garden

14501 Grove Resort Avenue Unit 1528, Winter Garden

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

14501 Grove Resort Avenue Unit 1440, Winter Garden

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

14501 Grove Resort Avenue Unit 1218, Winter Garden

14501 Grove Resort Avenue Unit 1218, Winter Garden

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

341 Southern Pecan Circle Unit 202, Winter Garden

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

14501 Grove Resort Avenue Unit 3631, Winter Garden

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 Avenue Unit 2539, Winter Garden

14501 Grove Resort Avenue Unit 2539, Winter Garden

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

14501 Grove Resort Avenue Unit 3636, Winter Garden

14501 Grove Resort Avenue Unit 3636, Winter Garden

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

14501 Grove Resort Unit 2304, Winter Garden

14501 Grove Resort Unit 2304, Winter Garden

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

14501 Grove Resort Avenue Unit 3703, Winter Garden

14501 Grove Resort Avenue Unit 3703, Winter Garden

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

14501 Grove Resort Avenue Unit 3201, Winter Garden

14501 Grove Resort Avenue Unit 3201, Winter Garden

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

988 Stucki Terrace, Winter Garden

988 Stucki Terrace, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westside Townhomes Phase 2 19/100 Lot 5 Blk 11 SubDv. ⋅ 34787 Zip Code

Beautiful Family-Oriented Townhouse in a Great Location! Well-maintained and move-in ready, this home offers low-maintenance living with a low HOA fee. Conveniently located approximately 10–17 miles from Walt Disney World, Disney Springs, and many of Orlando’s top entertainment destinations. Easy access to major highways makes commuting and exploring the area convenient. A wonderful opportunity for a family, second home, or investment property. More photos coming soon!

988 Stucki Terrace, Winter Garden

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