Winter Garden/Oakland Homes under $250,000

Winter Garden/Oakland Homes under $250,000

Welcome to the enchanting area of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant region is a perfect blend of small-town charm and modern conveniences, making it an ideal place to call home. Known for its picturesque landscapes, lush parks, and a rich historical backdrop, Winter Garden offers a welcoming community that thrives on its Southern hospitality.

As you explore this delightful region, you will discover a variety of homes that cater to different lifestyles and budgets. For those seeking affordable options, there are several charming homes available for under $250,000. These properties provide an excellent opportunity for first-time buyers, families, or investors looking to grow their portfolio. Many of these homes feature cozy layouts, inviting yards, and access to the area's top-rated schools, parks, and recreational facilities.

Winter Garden is particularly renowned for its vibrant downtown area, where you can stroll along the historic streets lined with boutique shops, delightful cafes, and a bustling farmers' market. Just a short drive away, the serene beauty of Oakland offers a peaceful retreat, with scenic views of lakes and nature trails perfect for outdoor enthusiasts.

Living in Winter Garden and Oakland means enjoying the best of both worlds—proximity to Orlando's attractions while relishing the tranquility of suburban life. With a strong sense of community and a plethora of activities to engage in, this region is truly a hidden gem in Florida. Don’t miss your chance to find your dream home in this charming area!

Newest Winter Garden/Oakland Homes under $250,000

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
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
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
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
988 Stucki Terrace, Winter Garden
$230,000
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
14501 Grove Resort Avenue Unit 3403, Winter Garden
$170,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program and a prime location near Central Florida’s top attractions, this turnkey condo offers an easy, hands-off ownership opportunity while giving you your own place to enjoy when visiting Orlando.

14501 Grove Resort Avenue Unit 3403, Winter Garden
1315 Eastern Pecan Place Unit 202, Winter Garden
$204,900
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a fully equipped kitchen and grilling area. The community also offers a park and playground, providing something for everyone to enjoy. This 1bed/1 bathroom with a flex room boast commercial grade luxury vinyl plank flooring, crown molding throughout, granite counter tops throughout the kitchen and bathroom, dedicated dining room, indoor laundry room with washer and dryer included, neutral interior wall paint, excellent natural light, ensuite bathroom, ample size primary suite walk-in closet, and more. Conveniences to be noted in the association fees are: Water, Cable, Trash, Pest Control, Roof, Exterior Building Maintenance, and Pool. Live just minutes from Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail. Getting around Central Florida is easy with quick access to SR-429, the Florida Turnpike, SR-408, and SR-50. Everyday shopping is also close by, with Publix and Costco Just minutes away. Low maintenance living at it's finest. Come see this condo today.

1315 Eastern Pecan Place Unit 202, Winter Garden
14501 Grove Resort Avenue Unit 3534, Winter Garden
$199,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Beautiful bright and airy 3-bedroom, 2-bathroom condo in the Grove Resort and Water Park Resort!!! Ideal for snowbirds who want to stay a few months in the winter, and have the onsite rental management company rent out the unit to vacationers when not in use! Buyers have the best of both worlds when owning at The Grove! Stay up to 179 nights per year in your unit, and the management do the rest of the work and enable you to earn when you are not there! This unit has a lovely south-facing balcony on the fifth floor, plus it has all the comforts of home - spacious living room, TV's in main room and all bedrooms, full kitchen, full washer and dryer, and screened-in balcony to enjoy quiet time! The resort has amazing amenities - the Springs Pools area has three heated pools plus a hot tub! Located nearby is the Valencia Restaurant, the 24/7 gym, and the boardwalk takes you to Lake Austin where you can fish off the dock, or paddle a swan boat! A short stroll takes you to the Surfari Water Park with a large heated pool, lazy river, water slides, and splash area! Try your skill on the Flowrider surfing experiences where instructors will help you ride the waves! Enjoy delicious food and drinks at the Longboard Bar and Grill, while listening to the relaxing music played on the hidden speakers! All ages can enjoy the Flip Flops games arcade, which also has a 9-hole mini golf course! At the Front Desk area you will find the Marketplace, selling convenience items, food, drinks, Starbucks coffees, and gifts. The concierge will help you with theme park tickets, and if you need transportation to the Disney theme parks, there is a FREE daily shuttle! For more information please give me a call!!!***

14501 Grove Resort Avenue Unit 3534, Winter Garden
14501 Grove Resort Avenue Unit 2221, Winter Garden
$184,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Li 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 2221, Winter Garden
14501 Grove Resort Avenue Unit 2542, Winter Garden
$205,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 22019039615 SubDv. ⋅ 34787 Zip Code
The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! This 5th-floor corner unit is the largest "Sable" model in the community, offering 1,544 sq ft with an open living/dining/kitchen area, a separate in-unit utility/laundry room, and a screened balcony. The kitchen features stainless steel appliances and granite counters. The primary suite includes an extra sitting area/solarium with direct balcony access, a bath with double sinks, a separate shower and soaking tub, and a large walk-in closet with a safe. Each bedroom includes a flat-screen TV. This condo-hotel offers an in-house hotel rental program that generates income to offset the cost of ownership — an ideal opportunity to own an Orlando/Disney-area vacation home just 6 miles from Walt Disney World. Resort amenities are exceptional. Surfari Water Park features the FlowRider Double Surf Simulator (one of only a few double units in the U.S.), dual water slides, a 695-foot lazy river, a zero-entry pool, and a kids' activities pool. The Springs Pools offer three full-sized pools, an oversized hot tub, a splash area, and private cabanas. Lake Austin provides catch-and-release fishing, watersports, and a lakeside pier overlooking the nature preserve. Additional amenities include a 24-hour fitness center, Flip Flop's Fun Center with a glow-in-the-dark indoor mini golf course and arcade, and a Kids' Activity Center. Dining options abound: The Springs Bar & Grill for relaxed poolside dining, Longboard Bar & Grill overlooking the FlowRider, Alfresco Market for outdoor cafe seating, and DYVE at The Terraces above the upscale pool area. The resort also offers daily transportation to Walt Disney World, Universal Orlando, and SeaWorld, plus complimentary resort-wide Wi-Fi. A rare chance to own a turnkey resort residence in one of the Orlando area's premier destinations.

14501 Grove Resort Avenue Unit 2542, Winter Garden
14501 Grove Resort Avenue Unit 1420, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing views from this two-bedroom, two-bathroom fully-furnished condo in the beautiful Grove Resort and Water Park Resort! Fourth floor views over the Springs Pools, with Lake Austin beyond that! Enjoy the morning sunrise with a coffee on your screened-in balcony!! These condos are fully managed by the onsite rental company, so when you are not using it, you can earn some income from guest bookings! These are ideal for snowbirds who wish to spend up to 179 nights per year in their unit, and then have the hands free experience of management renting it out when they are not using it! Full kitchen, full size washer and dryer, dining area, sleeper sofa, deep comfortable mattresses, all lend to a home from home for owners and guests! The Valencia Restaurant is located next to the Springs Pools area, which has three separate pools and a hot tub, and the 24/7 gym is also in this area. Take a stroll down the boardwalk to Lake Austin and paddle a swan boat, or try some fishing from the dock! A leisurely stroll takes you to the Surfari water park, with large heated pool, lazy river, water slides, splash area, and the Surfari surfing experience! The Longboard Bar and Grill is excellent for food and refreshing beverages while spending your day there! The Flip Flop games room has over 6000sf of exciting games and mini golf! The Marketplace sells all you need for snacks, food, small necessities, and the gift shop has souvenirs, clothes, sun cream, etc for essentials. The concierge located in the front lobby sells theme park tickets, and will book your seat on the FREE daily shuttle to the Disney Parks! Call NOW for more information!!***

14501 Grove Resort Avenue Unit 1420, Winter Garden
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