Winter Garden/Oakland Homes with Restaurant Community Features

Winter Garden/Oakland Homes with Restaurant Community Features

Nestled in the heart of Orange County, Florida, the charming communities of Winter Garden and Oakland offer a delightful blend of small-town charm and modern conveniences. Known for their picturesque landscapes and vibrant atmosphere, these areas are perfect for those seeking a welcoming place to call home. With lush greenery, scenic lakes, and an abundance of outdoor activities, Winter Garden and Oakland truly embody the essence of Florida living.

One of the standout features of this region is its unique homes with restaurant community features, which cater to the culinary enthusiasts and social butterflies alike. Imagine living in a community where you can step outside your front door and find an array of delightful dining options just a stone's throw away. From cozy cafes to upscale eateries, these neighborhoods are designed to foster a sense of community while satisfying your taste buds.

The historic downtown Winter Garden is a hub of activity, boasting charming boutiques, farmer’s markets, and a vibrant arts scene. Residents can enjoy leisurely strolls along the West Orange Trail, perfect for walking, biking, or simply soaking in the natural beauty. The close-knit community hosts various events throughout the year, encouraging neighbors to connect and build lasting friendships.

With easy access to major highways and proximity to Orlando’s attractions, Winter Garden and Oakland offer the perfect balance of tranquility and excitement. Whether you’re a first-time homebuyer or looking to relocate, these communities promise a lifestyle filled with warmth, flavor, and endless opportunities for connection. Embrace the charm of Winter Garden and Oakland—your dream home awaits!

Newest Winter Garden/Oakland Homes with Restaurant Community Features

$710,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden
$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
$615,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
**Virtual staging in formal living and dining rooms. Video available.** Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, 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
$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
$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
$260,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
** WOW** A rare opportunity to purchase a 7th (top) floor condo at the beautiful Grove Resort and Water Park! This 3-bedroom, 2-bathroom, with sleeper sofa, comes fully furnished and ready to go! Onsite management does all the work for you by obtaining bookings through major websites and travel companies, and whenever you want to stay just let them know and you can stay in your unit for up to 179 nights per year. Everything you need is in the unit, full kitchen, washer and dryer, dishes, linens, TV's in all rooms, screened-in balcony, and gorgeous view over the pond and Lake Austin! The Grove Resort has three pools located at The Springs Pools area, where the large hot tub is also situated! Nearby is the full service Valencia restaurant, and the 24/7 gym. A short walk down to Lake Austin brings you to a fishing dock, and you can also rent a swan paddle boat, or kayak!! The Surfari Water Park is a must for owners and guests! A large pool is central to the amenity, and there is a lazy river, water slides, a splash zone, the Flowrider surfing experience, and you can enjoy a meal or beverage at the Longboard Bar and Grill! For added fun pay a visit to Flip Flops games arcade which has over 6000 sf of games and a black light mini golf course!! If you need snacks or quick essentials, the Marketplace has food, drinks, Starbucks, and gifts!! The concierge located at the front desk area sells all park tickets and can arrange transportation to all the theme parks!!! The Grove Resort is a Disney Good Neighbor Hotel, so transportation is FREE every day to the Disney theme parks also!! Don't miss this one!!****

14501 Grove Resort Avenue Unit 1728, 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
$244,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Discover a high-value investment opportunity at The Grove Resort & Water Park, one of Orlando’s most successful condo-hotel destinations just minutes from Walt Disney World. This fully furnished 2-bedroom, 2-bath unit offers a spacious layout, modern finishes, and a private balcony that enhances guest appeal and repeat bookings. Designed for both personal enjoyment and strong rental performance, this property delivers year-round demand driven by Orlando’s booming tourism market and The Grove’s exceptional amenities. Guests enjoy multiple pools, private cabanas, a full water park with surf simulator and lazy river, onsite restaurants, spa, fitness center, arcade, lake activities, and daily entertainment—premium features that consistently boost occupancy and revenue. Investors benefit from a turnkey, professionally managed short-term rental program, ensuring seamless operations, high visibility, and stable returns. The resort’s reputation, location, and amenity package create a powerful combination of passive income potential and long-term appreciation. Whether expanding your portfolio or securing a reliable income-producing asset, this unit offers a strategic opportunity in one of Central Florida’s strongest hospitality markets.

14501 Grove Resort Avenue Unit 2135, Winter Garden
$170,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Calling ALL Snowbirds & Anyone Looking For A Florida Experience! * This Condo Is An INCREDIBLE VALUE For A Resort Style Stay For Up To Half The Year! Then Turn It Into Your Orlando Investment Dream For The Other Half Of the Year! * Imagine Waking Up To This Nature View From Up On This 5th Floor. Enjoy Your Morning Coffee Or * FIREWORKS * View At Night! Unit 1527 Is Located Immediately Next To The Condo Walkway, Which Overlooks Out Into Nature And Water View. Upon Entering This 2 Bedrooms/2 Bathrooms Condo, Be Greeted With A View Of The Balcony! The Condo Has A Grand Kitchen That Is Fully Stocked With Cooking Utensils & Coffee Machine. * Kitchen Has Stainless Steel Appliances And Long Granite Countertops With Tons Of Storage Space. *Living Room And *Dining Room Combo Has A Great Entertaining Space. Kickback & Watch A Movie While Peering Out Through The Window To See Disney's Nightly Fireworks! That's Incredible! *Bedrooms Are Fully Furnished With A Full Bathrooms And Massive Walk-In Closet. * Water Heater 2008 * HVAC 2021 * Condo Amenities Are Included! Water Parks, Gym, Water/Electricity, And MUCH More. Conveniently Located ~ 7 Miles To Walt Disney World, ~ 4 Miles To Flamingo Crossings Town Center, ~ 20 Miles From Winter Garden Village At Fowlers Grove & West Orange Trail, And ~10 Miles To Interstate 4 (I-4)! This Fully Furnished Condo Won’t Last! * Priced To Sell! * Book Your Showing Today!

14501 Grove Resort Avenue Unit 1527, Winter Garden
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