Winter Garden/Oakland Homes with Gated Community - Guard Community Features

Winter Garden/Oakland Homes with Gated Community - Guard Community Features

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where charming small-town vibes meet modern convenience. Nestled just a stone's throw from the vibrant city of Orlando, this picturesque area boasts a rich history, beautiful landscapes, and a thriving community spirit. With its lush parks, scenic lakes, and delightful downtown filled with eclectic shops and dining options, Winter Garden and Oakland offer an idyllic setting for families, retirees, and everyone in between.

One of the most appealing aspects of this region is the availability of stunning homes within gated communities. These exclusive neighborhoods provide a sense of security and privacy, ensuring peace of mind for residents. Many of these guard-gated communities feature beautifully designed homes that range from modern masterpieces to charming traditional styles, catering to a variety of tastes and preferences.

Residents of these gated communities enjoy a host of amenities, including resort-style pools, fitness centers, and meticulously maintained landscapes. The sense of community is palpable, with neighbors often coming together for social events and activities that foster lasting friendships.

Living in Winter Garden and Oakland means having access to top-rated schools, outdoor recreational opportunities, and a vibrant arts scene, making it the perfect place to call home. Whether you're seeking a tranquil retreat or a bustling community atmosphere, the gated homes in this area provide the best of both worlds. Discover the charm of Winter Garden and Oakland, where your dream home awaits!

Newest Winter Garden/Oakland Homes with Gated Community - Guard Community Features

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

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code

Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden

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

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decorative tile backsplash. The Whirlpool stainless steel appliances—including a built-in natural gas cooktop and a refrigerator—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the extended covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a rain shower head and a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. The additional spare bedroom and bathroom, along with the enclosed flex room, provide ample space for everyone. The upgraded laundry room with built-in cabinetry, quartz countertop, utility sink, and a Whirlpool washer and dryer make daily tasks a breeze. Designer-curated finishes elevate every corner of this home, including wood-look tile flooring throughout, pendant light pre-wire and under cabinet lighting in the kitchen, 2” faux wood blinds, and brushed nickel hardware and plumbing fixtures. The 2-car garage offers extra tandem storage space with an epoxy finish on the floor, ensuring that every part of your home is both beautiful and practical. With its stunning design and thoughtful touches, the Mystique home provides the perfect blend of luxury and functionality for today’s lifestyle.

13056 Sandcastle Drive, Winter Garden

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

3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code

Most evenings, unforgettable sunsets spill across the pool and water, casting a breathtaking glow over this premier cul-de-sac homesite. Positioned on an oversized lot with an expansive side yard, this residence enjoys one of Stoneybrook West’s most coveted viewpoints—serene water vistas paired with sweeping Back 9 scenery, including uninterrupted sightlines to the 13th green and 14th tee. Welcome home to an immaculate 3-bedroom, 2-bath split-plan retreat that is truly move-in ready. Step inside and immediately feel the care, quality, and comfort woven throughout. Thoughtful upgrades include brand-new plantation shutters, a custom built-in kitchen nook with outlet, updated light fixtures and fans, and a new refrigerator. Major systems add peace of mind with a roof, HVAC, hot water heater, and interior paint all less than 3 years old. The open living area impresses with a striking white stone accent wall and durable wood-like tile flooring that flows seamlessly through the home. The primary suite features a barn-door entry to the bath and an exceptionally spacious walk-in closet. Outside, your private oasis awaits: a covered lanai overlooking a stunning saltwater pool with sun shelf and water features, all less than 5 years old. The backdrop is pure magic—tranquil water, golf course views, and sunsets that feel like a nightly masterpiece. The fully fenced yard offers fresh tree trimming and an extra-large side yard, ideal for pets, play, or future enhancements. Perfectly situated on a quiet cul-de-sac next to the residents’ gate, this home blends privacy with convenience. Community amenities are exceptional: golf course, playgrounds, pickleball, tennis, basketball, hockey court, resort-style pool, gym, and the Stoneybrook restaurant. Zoned for highly rated schools and just minutes from Winter Garden Village with easy access to the 429, the location is unbeatable. Additional highlights include built-in garage storage and shelving, a fenced yard, and standout curb appeal. This home delivers comfort, style, and a lifestyle that’s hard to match. Call today for a private showing!

2420 Balforn Tower Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden

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

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

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

3 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome home! The neighbors call this one of the best kept secrets in Oasis. One of the few homes in the community that have an amazing view of the Disney fireworks from your screened-in porch. The seller has spared no expense in making this home move-in ready. As soon as you walk in, you'll be greeted by high ceilings, beautiful tile floors and plenty of light. This home features the maximum amount of recessed lighting offered by the builder in every single room. This home has a gourmet kitchen, featuring an oversized kitchen island and plenty of cabinet/countertop space and a KitchenAid refrigerator. The corner pantry features a custom closet by design buildout. This beautiful kitchen will bring out your inner chef. In addition, the kitchen overlooks the dining room and living room, ideal for entertaining. The home features custom smart blinds throughout the first floor. The seller spared no expense in upgrading this property, featuring custom closets by design in the main bedroom, mudroom and laundry room as well as the garage. This home comes with full home water purification system. Fully paid-off solar panels at closing. The upstairs loft and third bedroom have exotic wood throughout. Minutes from Walt Disney World Resort, Hamlin Town Center and downtown Winter Garden. Contact the listing agent today to schedule.

13355 Sunny Retreat Lane, Winter Garden

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