Winter Garden/Oakland Homes with Garden View

Winter Garden/Oakland Homes with Garden View

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is celebrated for its charming small-town atmosphere, rich history, and stunning natural landscapes. With its picturesque streets lined with historic buildings, Winter Garden boasts a thriving downtown filled with delightful shops, restaurants, and a bustling farmer's market that showcases the best local produce.

One of the standout features of this region is the abundance of homes with breathtaking garden views. Imagine waking up every morning to the sight of lush greenery, colorful blooms, and serene outdoor spaces that invite tranquility and relaxation. These homes are designed to blend seamlessly with the natural beauty surrounding them, offering residents a personal oasis right in their backyards. Whether you’re sipping your morning coffee or hosting a gathering with friends, the garden views provide a stunning backdrop for every occasion.

In addition to its scenic beauty, Winter Garden and Oakland are perfectly situated, providing easy access to major highways and attractions, including the world-renowned theme parks of Orlando. Residents can enjoy a balanced lifestyle, with the serenity of suburban living and the excitement of city life just a short drive away.

This region is not just a place to live; it's a community where neighbors become friends, and families create lasting memories. With homes that embrace the splendor of nature and a welcoming atmosphere that invites you to explore, Winter Garden and Oakland are truly a hidden gem in Florida. Come discover your dream home with a garden view today!

Newest Winter Garden/Oakland Homes with Garden View

$340,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes from Walt Disney World. This spacious 3-bedroom, 3-bath condominium is located on the 3rd floor of Building 2, offering exceptional convenience to the main lobby and resort amenities. Designed for vacation enjoyment and investment potential, the residence features a spacious open floor plan, well-appointed kitchen, comfortable living and dining areas, and three bedrooms and baths providing plenty of room for family and guests. Enjoy your own Orlando vacation retreat and take advantage of rental income . The Grove offers an impressive resort experience with Surfari Water Park, multiple pools, a lazy river, FlowRider surf simulator, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, and complimentary transportation to Walt Disney World. Whether your goal is creating memorable Florida vacations, generating rental income, or enjoying the best of both, this Building 2 location offers convenience, flexibility, and investment potential in one of Orlando’s most popular vacation destinations. Vacation when you want. Earn rental income when you don’t.

14501 Grove Resort Avenue Unit 2342, Winter Garden
$239,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code
Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden
$2,600,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful custom home on Hancock Lake was built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat w/lift and 2 jet ski lifts. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and whimsical Disney characters embedded in the rock facade. Relax to lake views, or pull down the projector screen for a movie. After your show, stay tuned for the nightly fireworks over the lake from the Disney park. The home has a freshly painted exterior and interior with crown trim throughout. Spectacular front entrance with impressive light fixtures and an abundance of natural light where you'll catch the first glimpse of the lake. The Kitchen is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating merging with the open Family Room where sliders open to the patio and lake. A cabana bath and Den/Office/possible bedroom are down a separate wing behind the Kitchen providing additional patio access. The first level’s primary suite has private patio access and a lovely bay window styled seating area. Previous Owners used this room as a media room complete with surround sound that remains intact. The loft has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. Upstairs are two additional ensuites, 3 more bedrooms (two with balconies) and a laundry room. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$1,999,000
6 Beds ⋅ 7 Baths ⋅ Avalon Ridge SubDv. ⋅ 34787 Zip Code
Built in 2024 and completely upgraded beyond builder standards, this 6-bedroom, 5-full-bath, 2-half-bath home in Avalon Ridge gives you the feel of a custom home without having to start from scratch. From the moment you walk in, you can see how much thought was put into every space. The home features custom woodwork, built-ins, upgraded flooring, designer lighting, window treatments, and fully customized closets throughout. The main floor is open, bright, and made for both everyday living and entertaining. A custom lounge near the entrance includes built-in cabinets, lighting, beverage refrigerators, extra storage, and a sitting area. The living room, dining area, and kitchen flow together and open to the covered outdoor space through large sliding glass doors. The kitchen features a large island, quartz countertops, stacked cabinets, stainless steel appliances, and plenty of storage. The same custom wood details continue into the surrounding living spaces, giving the entire first floor a finished and connected look. The primary suite is located downstairs and includes a large bathroom with dual sinks and a fully customized walk-in closet with glass doors, built-in shelving, display space, and a center island. Upstairs, there are additional bedrooms, a Jack-and-Jill bathroom, flexible rooms that can be used as guest rooms or offices, and a dedicated movie room with custom built-ins. Every closet in the home has been redone to create more usable storage. The home also includes upgraded vanities, trim, interior finishes, and wiring already in place for an electric vehicle charger. Complete plans for a custom pool are included with the sale, so the next owner can move forward with the project without having to begin the design process from the beginning, subject to approvals. Photos of pool virtually staged. Custom built-ins, installed light fixtures, window treatments, and curtains are included. Furniture and décor are not included in the list price and will be sold separately as a complete furniture package. This is a nearly new home with the upgrades, storage, and finished look that are hard to find in a standard new-construction home.

16077 Barkly Ridge Court, Winter Garden
$244,000
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
$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
$499,900
3 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to Longleaf at Oakland by Pulte! Built in 2020, this move-in-ready three-bedroom, 2.5-bath home offers 1,811 square feet of stylish living space featuring brand-new luxury vinyl plank flooring throughout, fresh interior paint, quartz countertops, stainless steel appliances and an open-concept layout designed for comfortable everyday living and effortless entertaining. Located less than five minutes from the new Oakland Town Center, you’ll be close to an exciting new lifestyle destination featuring chef-driven restaurants, boutique shopping, fitness and wellness concepts, medical services, outdoor gathering spaces and everyday conveniences. Historic Downtown Winter Garden, the West Orange Trail and major highways are also just minutes away. Residents of Longleaf at Oakland enjoy a community pool, playground and beautifully maintained green spaces, all within one of West Orange County’s most desirable communities. Don’t miss the opportunity to own this beautifully updated, move-in-ready home in one of Oakland’s most sought-after neighborhoods. Schedule your private showing today!

2766 Bobcat Chase Boulevard, 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
$230,000
3 Beds ⋅ 2 Baths ⋅ The Grove Resort SubDv. ⋅ 34787 Zip Code
The Jasmine model is the MOST SPACIOUS condo in the sought after Grove Resort & Water Park. The condo 2233 is FULLY FURNISHED, DECORATED and equipped with everything you need and is located in NEWEST STERLING TOWER-II. Featuring an open concept living & dining area with a screened balcony overlooking lush gardens. The modern kitchen has quartz countertops, stainless steel appliances, and attached laundry room with full size washer and dryer. YOUR PERFECT VACATION HOME IS AT THE GROVE RESORT where you will enjoy privacy and convenience, including a concierge, multiple bars, restaurant, convenience store, spa, elaborate game room, stunning water park oasis, breathtaking 22-acre activity lake all professionally managed with turnkey hotel rental programs to help offset costs. The property is JUST 6 MILES FROM WALT DISNEY WORLD and close to all Central Florida’s attractions, shops, restaurants and major highways.

14501 Grove Resort Avenue Unit 2233, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve SubDv. ⋅ 34787 Zip Code
Luxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained CICERO Spanish Colonial floorplan offers an open-concept layout with 10' ceilings, 8' doors, wood-look tile flooring, and abundant natural light. The gourmet kitchen features a center island, 42" cabinets, Diamond white-quartz countertops, stainless steel appliances, natural gas cooking, a large pantry, and a new oversized single-basin sink. The first-floor owner's suite includes a spacious walk-in shower and dual vanities. Upstairs you'll find two generous bedrooms, a loft, and a charming wraparound balcony. A covered walkway connects the home to the attached two-car garage. Recent upgrades include new landscaping, French doors added to the kitchen, water-resistant laminate flooring throughout the upstairs, updated quartz countertops in the kitchen and guest bath, upgraded lighting and staircase chandelier, new refrigerator, washer and dryer, saltwater softener system, patio pavers, and added garage storage. The home has been meticulously maintained with annual HVAC servicing and regular tankless water heater maintenance. Enjoy resort-style living at Lakeshore Preserve with a lakefront clubhouse, fitness center, gathering room, catering kitchen, resort pool, kayaking, and paddleboarding. Ideally located in Horizon West, just minutes from Disney, Universal, shopping, dining, and major retail centers.

8873 Fountain Palm Alley, Winter Garden
$785,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Experience effortless luxury just 2 miles from Walt Disney World in this impeccably maintained, like-new 2024 residence located within the highly sought-after Del Webb Oasis community. Perfectly positioned directly across from the spectacular amenity campus, you'll enjoy the rare convenience of simply strolling across the street to indulge in world-class resort-style living every day. From the impressive 12,000-square-foot clubhouse featuring a coffee bar, resident lounge, and wine lockers to the zero-entry resort pool, hot tub, state-of-the-art fitness center, tennis and pickleball courts, every luxury is just moments from your front door. Designed with both elegance and functionality in mind, this stunning home welcomes you with an expansive open-concept floor plan that seamlessly connects the chef's kitchen, dining area, and spacious living room, creating the perfect setting for entertaining or relaxed everyday living. The gourmet kitchen is beautifully appointed with upgraded quartz countertops, a large eat-in breakfast bar island, 42-inch cabinetry, premium stainless steel appliances including a gas range, and an extra-deep double-basin sink. Beautiful upgraded flooring flows throughout the home, offering both timeless style and easy maintenance. Step outside to your own private outdoor retreat, where a screened-in pool and covered lanai create an inviting space to enjoy Florida's year-round sunshine. Whether sipping morning coffee on the charming front patio or unwinding with a glass of wine beside your sparkling pool in the evening, you'll appreciate the peaceful surroundings and exceptional privacy. The thoughtfully designed split-bedroom floor plan offers an ideal balance of comfort and privacy. Tucked away at the rear of the home, the luxurious primary suite is filled with natural light and features a spacious walk-in closet and an elegant spa-inspired bath complete with dual quartz vanities and an oversized walk-in shower. A generously sized secondary bedroom and beautifully finished guest bath are situated at the front of the home, providing a welcoming retreat for family and visitors alike. Additional highlights include a large laundry room, convenient drop zone, and an energy-efficient tankless water heater for endless hot water. Beyond the gates, you'll find yourself just minutes from Disney, championship golf, premier shopping, exceptional dining, and Central Florida's most desirable attractions. Combining an unbeatable location, refined finishes, and unparalleled walkability to Del Webb Oasis' extraordinary amenities, this exceptional home offers a truly elevated lifestyle where every day feels like a luxury vacation.

13175 Sunny Retreat Lane, Winter Garden
$415,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
Step into this beautifully designed 3-bedroom, 2.5-bath townhome located in the highly desirable Osprey Ranch community in Horizon West. Built recently and featuring 1,536 sq ft, this home offers modern finishes, an open-concept layout, and a bright, spacious living area perfect for entertaining. The kitchen includes elegant cabinetry, quartz countertops, and stainless-steel appliances. Upstairs, the primary suite provides a peaceful retreat with a walk-in closet and a well-appointed bathroom. Enjoy low-maintenance living with a private patio and one-car garage, plus access to top-rated schools, new retail, dining, and all the growth of Winter Garden. Minutes from Hamlin, SR-429, and Disney. A perfect blend of comfort, convenience, and modern living.

14942 Windflower Alley, Winter Garden
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