Winter Garden/Oakland Condos for Sale

Winter Garden/Oakland Condos for Sale

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant local culture, these areas offer a delightful blend of suburban tranquility and urban convenience. With lush greenery, scenic lakes, and a rich history, Winter Garden and Oakland are perfect for those seeking a serene lifestyle without sacrificing access to modern amenities.

Winter Garden is famous for its historic downtown, where you can stroll along cobblestone streets lined with boutique shops, delightful cafes, and local eateries. The city hosts a variety of events throughout the year, including farmers' markets and festivals, fostering a strong sense of community. Just a stone's throw away, Oakland boasts a quaint, small-town charm with its beautiful parks and scenic views, making it an ideal spot for outdoor enthusiasts.

For those considering a move to this enchanting area, there are fantastic condos for sale that cater to a variety of lifestyles. Whether you’re a first-time homebuyer or looking to downsize, Winter Garden and Oakland offer modern, well-appointed condos that provide the perfect blend of comfort and convenience. Enjoy easy access to amenities, including shopping, dining, and recreational facilities, all while being surrounded by the natural beauty of Central Florida.

With its welcoming atmosphere and vibrant community spirit, Winter Garden and Oakland are not just places to live—they're places to thrive. Discover your dream condo today and become a part of this remarkable region!

Newest Winter Garden/Oakland Condos for Sale

$290,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Luxury Condo for Sale at The Grove Resort & Water Park, Just 5 Minutes from Walt Disney World! 3 Bedrooms / 3 Bathrooms | Fully Furnished |Ideal 1031 Exchange Property Discover the height of vacation luxury in Orlando's newest and most exclusive community, The Grove Resort &Water Park. This spacious sixth-floor unit (#3642) features 3 bedrooms and 3 bathrooms, designed for comfort and style, with stunning views ofthe meticulously maintained courtyard and beyond. The property is fully adapted for individuals with disabilities, ensuring accessibility andcomfort for all residents and guests. Key Features: Location: Just 5 minutes from Walt Disney World, one of the world’s top destinations.Accessibility: The condo and common areas are fully accessible for individuals with disabilities, ensuring ease of movement and comfort for all.Amenities: Enjoy multiple swimming pools, a full-service spa, water park, and a breathtaking 20-acre lake ideal for fishing, boating, and relaxing.The resort also offers a modern fitness center, conference rooms, and a wide variety of bars and restaurants. Investment Opportunity: When notin use, place your unit in the professionally managed turnkey hotel rental program to help offset ownership costs and enjoy hassle-free propertymanagement. Perfect for 1031 Exchange: Benefit from Orlando’s booming vacation rental market while owning a personal retreat. This propertyis more than just a vacation home—it’s a lifestyle choice. With the hotel rental program, owners can enjoy privacy, convenience, and the incomepotential of Orlando’s thriving vacation rental market.

14501 Grove Resort Avenue Unit 3642, Winter Garden
$290,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$387,900
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo I SubDv. ⋅ 34787 Zip Code
Property in excellent condition ready to go, very good source of extra revenue, do not let I pass, very rare 3 bedrooms for this vacation condo.

14501 Grove Resort Avenue Unit 1409, Winter Garden
$219,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code
**Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden
$270,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this newly updated 2 bedroom / 2 bathroom first floor condo in Winter Garden, where low-maintenance living meets comfort and convenience. This beautifully updated first-floor condo features fresh interior paint and new flooring, creating a bright, modern, and move-in-ready space. The open-concept floor plan offers comfortable living and dining areas, making it perfect for everyday living or entertaining. The well-designed layout provides a seamless flow, while large windows bring in an abundance of natural light. This condo hasa detached garage for easy parking near your home. Residents enjoy the outstanding amenities of this sought-after community, including a resort-style swimming pool, fitness center, clubhouse, playground, walking paths, and beautifully maintained green spaces. The HOA also provides low-maintenance living, allowing you more time to enjoy everything Winter Garden has to offer. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, shopping, dining, entertainment, major highways, and Orlando's world-famous attractions, this home offers an unbeatable combination of location and lifestyle. Whether you're a first-time homebuyer, seasonal resident, downsizing, or looking for an investment opportunity, this move-in-ready condo delivers exceptional value in one of Central Florida's most desirable communities.

130 Southern Pecan Circle Unit 103, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$335,000
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully maintained end-unit townhome located in the desirable gated community of Tucker Oaks in Winter Garden, offering extra privacy, abundant natural light, and a premium pond-view lot with additional backyard space. Conveniently situated right next to the community amenities, this home combines comfort, style, and an exceptional location. Step inside to an inviting open-concept floor plan featuring a spacious living room, dining area, and kitchen that flow seamlessly together, making it perfect for both everyday living and entertaining. The kitchen is beautifully appointed with tall cabinetry, granite countertops, stainless steel appliances, and a large walk-in pantry, while a versatile flex room offers the perfect space for a home office, formal dining room, playroom, or additional living area. A beautifully renovated half bathroom and an indoor laundry room add convenience to the first floor. Upstairs, you'll find like-new carpet (2020) throughout, two spacious guest bedrooms, a full guest bathroom, and a relaxing primary suite featuring an elegant tray ceiling and tranquil pond views. The en-suite bathroom offers a double-sink vanity, a garden tub/shower combination, and a generous walk-in closet. Additional features include a new air conditioning system (2026), new roof (2024), new water heater (2024) and a large garage with tall ceilings, providing excellent storage space. Enjoy peaceful mornings overlooking the pond and all the benefits of living in a gated community with nearby amenities including a pool and dog park. This move-in-ready home offers the perfect combination of thoughtful upgrades, functional living space, and an unbeatable location.

1668 Scarlet Oak Loop Unit C, Winter Garden
$219,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
**Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! Beautiful 3-bedroom/2-bathroom Jasmine floorplan available for sale at The Grove Resort and Water Park! This first floor apartment is fully-furnished and has everything you need for a wonderful vacation condo! This spacious unit has 14-foot ceilings in the main living space, giving a light, airy feel, and opens to an enclosed balcony where you can enjoy views of gardens and pond. Full kitchen has everything you need for cooking breakfasts, to family dinners, with a full washer and dryer in a room just off the kitchen. The living room also has a sleeper sofa for extra guests if needed. A short stroll brings you to either the central front desk area where you will find The Marketplace, the well-stocked convenience store, and the gift shop and concierge desk, or to the Springs Pools area where you can choose from three beautiful pools and the hot tub. The Valencia Restaurant, with additional outside seating, is open for breakfast, lunch, and dinner, 7 days a week, and is next to the 24/7 gym. Take a walk down to Lake Austin and try some fishing, or paddle a swan boat! From there you can visit the Surfari water park with its large pool, lazy river, water slides, and splash area! Try out the Flowrider surfing experience, or just watch while enjoying food and drinks from the Longboard Bar and Grill! Flip Flops is the 6000sf games arcade with glow-in-the-dark mini golf, so don't miss that! Free daily shuttles to the Disney parks are available for all owners and guests! This truly is a great place to own a vacation condo while the onsite management company rent out your unit when you are not there! Call for more details!!**

14501 Grove Resort Avenue Unit 2119, Winter Garden
$179,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
**Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! Beautiful Palm model 2-bedroom/2-bathroom condo for sale at The Grove Resort and Water Park! This fully-furnished unit has a lovely view over the central fountain and is bright and airy. This floorplan has the desirable two double beds in the second bedroom, providing extra sleeping accommodation for owners and guests. A sleeper sofa in the living room gives extra sleeping space if required. A full kitchen provides all you need for cooking a quick breakfast, or family dinner, and a laundry room is also conveniently situated just off the kitchen. The dining area and living room give plenty of seating for guests, or enjoy a quiet coffee out on the screened balcony. The unit is central to the resort, so all amenities are just a few minutes stroll away. You can enjoy the Surfari water park with its large pool, lazy river, water slides, and splash zone! The Longboard Bar and Grill are also inside the water park, along with the Flowrider surfing experience!! Don't forget to visit Flip Flops, the 6000sf games arcade, with glow-in-the-dark mini golf, or go down to the Springs Pools where you have your choice of three further pools, or relax in the hot tub! You can enjoy a meal at the Valencia Restaurant, or at the outdoor bar, or walk down to Lake Austin and try your hand at fishing, kayaking, or paddling a swan boat! The Front Desk is where you will find the Marketplace convenience store and gift shop, and the concierge for all your theme park tickets or excursions! The Grove Resort also provides FREE daily transportation to the Disney theme parks. Don't miss out on owning a wonderful vacation condo at The Grove, where you can enjoy your vacations, then let the onsite management company rent out your unit for income when you are not using it. Call for more details!!**

14501 Grove Resort Avenue Unit 3406, Winter Garden
$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

93 Windtree Lane Unit 102, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
$190,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
TOWER 3 LOCATION CLOSEST TO THE WATERPARK! Exceptional opportunity to own at The Grove Resort & Water Park, one of Central Florida’s premier vacation ownership destinations just minutes from Walt Disney World. This condo is a beautifully furnished Birch Plan residence offering a comfortable, turnkey layout designed for personal enjoyment and income-producing vacation rental use. The open living area, full kitchen, private bedrooms, and resort-style finishes create an inviting retreat for Owners and guests alike. The Grove offers an impressive amenity package including a water park, multiple pools, lazy river, restaurants, bars, spa, fitness center, lake activities, arcade, onsite market, and full-service onsite management. Owners may enjoy generous personal use while the onsite management team handles guest services, reservations, maintenance, and day-to-day rental operations. With its strong location, established resort setting, and continued appeal to Orlando visitors, this Birch Plan condo is a compelling choice for Buyers seeking lifestyle, convenience, and long-term Central Florida vacation ownership.

14501 Grove Resort Avenue Unit 3231, Winter Garden
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