Winter Garden/Oakland Homes with Security Amenities

Winter Garden/Oakland Homes with Security Amenities

Welcome to the picturesque charm of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its stunning landscapes, vibrant community spirit, and rich history, this region offers a unique blend of small-town charm and modern convenience. With its lush parks, scenic lakes, and a thriving downtown area, residents enjoy a lifestyle that seamlessly combines relaxation and recreation.

Winter Garden is renowned for its historic downtown district, where you can stroll along cobblestone streets lined with delightful shops, cafes, and the famous Winter Garden Farmers Market. The friendly atmosphere invites you to explore local art, indulge in delicious cuisine, and participate in community events throughout the year. Just a stone's throw away, Oakland boasts a serene environment, with beautiful trails and parks that are perfect for outdoor enthusiasts and families looking to connect with nature.

When it comes to finding a home in this enchanting area, you’ll be pleased to know that many properties come equipped with top-notch security amenities. These homes are designed to provide peace of mind, featuring advanced security systems, gated communities, and neighborhood watch programs, ensuring a safe and secure environment for you and your loved ones.

Whether you’re searching for a cozy bungalow or a spacious family home, Winter Garden and Oakland offer a variety of real estate options that cater to your lifestyle needs. Embrace the charm of this remarkable region and discover the perfect place to call home, where community, safety, and beauty converge.

Newest Winter Garden/Oakland Homes with Security Amenities

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

**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

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

**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

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

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

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

Virtually Staged. Experience the highly sought-after KENTON FLOOR PLAN in the award-winning WATERLEIGH community, just MINUTES FROM DISNEY! Ideally situated on a QUIET CUL-DE-SAC with NO THROUGH TRAFFIC, this beautifully upgraded 4 BEDROOM, 3 BATHROOM home offers WOOD-LOOK TILE throughout the main living areas and LUXURY VINYL PLANK upstairs. A welcoming foyer with TRAY CEILING opens to a versatile FLEX ROOM, perfect for a home office or formal dining room. The OPEN-CONCEPT design centers around a stunning GOURMET KITCHEN featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7' ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, plus a built-in COFFEE BAR/DROP ZONE. The spacious family room overlooks the covered lanai and backyard. A FIRST-FLOOR BEDROOM & FULL BATH provide the perfect guest or multigenerational suite. Upstairs, the PRIMARY SUITE features a TRAY CEILING, spa-inspired bath with GARDEN TUB, GLASS-ENCLOSED SHOWER, DUAL QUARTZ VANITIES, and an OVERSIZED WALK-IN CLOSET. A large LOFT offers the perfect space for a media room or playroom. Bedrooms 3 and 4 share a bath with DOUBLE SINKS, while the oversized laundry room includes a UTILITY SINK, WASHER & DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & FANS, VIDEO DOORBELL, LOW-E DOUBLE-PANE WINDOWS, R-30 INSULATION, and RECLAIMED WATER IRRIGATION for outstanding energy efficiency. Enjoy MAINTENANCE-FREE LIVING with lawn care included and access to 4 RESORT-STYLE POOLS, 3 CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, FISHING PIER, PLAYGROUNDS, PARKS, WALKING TRAILS, and more. WATER SPRING ELEMENTARY and WATER SPRING MIDDLE SCHOOL are just a SHORT WALK AWAY, making everyday routines incredibly convenient. Zoned for HORIZON HIGH SCHOOL and ideally located near shopping, dining, Disney, and with easy access to 429, 417 & 408, this home offers the perfect blend of luxury, convenience, and lifestyle.

11031 Jackson Cove, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The beautifully designed 4 bedroom with an enclosed flex room, 3 bathroom, 2 car garage Coral Grand home offers the perfect blend of luxury, comfort, and functionality. As you step inside, you are greeted by a grand foyer that opens to the second floor, creating an inviting and open atmosphere. To your one side, a spacious secondary bedroom and full bath provide ideal accommodations for guests. Adjacent, an enclosed flex room offers endless possibilities – whether it’s a private office, hobby room, or a cozy reading nook. Travel deeper into the heart of the home, and you’ll find an expansive open concept layout that seamlessly connects the gathering room, kitchen, and cafe. Large windows throughout the main living areas flood the space with natural light, creating a warm and welcoming ambiance. The chef’s dream kitchen is a showstopper, complete with a built-in cooktop, stainless steel appliances, quartz countertops, and soft-close cabinetry. Step outside to enjoy the covered lanai, complete with two sliding glass doors that create a seamless transition between indoor and outdoor living. The owner's suite, located conveniently on the first floor, provides a private retreat with ample space, and is complemented by a luxurious en-suite bathroom with a spa-like walk-in shower with rain shower head, a quartz-topped dual vanity, a private water closet, and an expansive walk-in closet. The laundry room is also thoughtfully located on the first floor, complete with built-in cabinetry and a quartz trimmed utility sink, adding to the home’s convenience and ease of living. Upstairs, you’ll find two additional bedrooms, a full bathroom, and a spacious loft, offering plenty of room for everyone. Shaw wood-look luxury vinyl plank spans the first floor living areas and owner’s suite, beautiful tile flooring adds durability in the bathrooms, and laundry room, and plush, stain-resistant carpet covers the upstairs loft and secondary bedrooms. For those who appreciate the convenience of technology, this home comes equipped with a smart thermostat, video doorbell, and LED downlights, ensuring your home is as connected as it is beautiful. Experience the luxury of modern living with timeless design – schedule a tour today and see all that this exceptional home has to offer!

346 Crystal Wood Drive, Winter Garden

5 Beds ⋅ 6 Baths ⋅ Waterleigh Ph 1 SubDv. ⋅ 34787 Zip Code

Virtually Staged. SPECTACULAR LAKEFRONT HOME with 99 Feet of Shoreline! Start Enjoying LIFE ON THE LAKE in this Special Home built with the HIGHEST LEVEL OF UPGRADES! Enter this 4,641 sq ft Home with 5 Bedroom Suites and 6 Full Baths through a PRIVATE COURTYARD. Double Doors with Leaded Glass Welcome you to a life of LUXURY! First Floor has Soaring 12 Foot Ceilings, Tray Ceilings, 7 ¼” Baseboards and four Ten Foot Tall Sliders that open to the nearly HALF ACRE Premium Lot with Wide Open Lake Views! Build a DOCK and enjoy Boating, Fishing, Kayaking or try the WATER SKI COURSE on 420 Acre Lake Hickorynut just minutes from DISNEY! Outstanding Features include: Premium Lot that is over 200 Feet Deep, a true GOURMET Kitchen with all WOLF Appliances: Sub-Zero 36” SS Refrigerator, Sub-Zero 36” SS Freezer, Wolf E Series Wall Oven, Convection Steam Oven, Warming Drawer and Wolf Induction Cooktop. The DOUBLE Stacked Raised Panel Cabinetry features a HIDDEN Pantry with CUSTOM Shelving! The Great Room has a Custom Built-In and a Butler Pantry was added near the Dining Room. Oversized Covered Patio is enhanced with Electronic RETRACTABLE Screens, and the Pool Bath is just steps away. Impressive FIRST FLOOR PRIMARY SUITE with Hickory Flooring opens to Spa Bath with DOUBLE Vanities, FREESTANDING TUB, Spacious Shower and Large WALK-IN CUSTOM Closet PLUS a LAUNDRY ROOM with Sink and a STORAGE Closet! Private Suite 2 has Lake Views, Custom Built-In Shelving, Large Bath and Custom Closet. Private Suite 5 overlooks the Courtyard. The CUSTOM Staircase with Oak treads leads upstairs to 2 more Bedroom Suites with 10’ ceilings and Custom Closets, a LARGE Bonus Space wired for SURROUND SOUND is an Ideal THEATER ROOM and a large Covered Balcony with Electronic Screens that is a perfect spot for Relaxing while Enjoying the Sunset over the Lake! Upstairs Laundry Room with original plumbing has been converted to Mini Kitchen – great opportunity for a Mother-In-Law Suite! Outstanding Upgrades Include Engineered Hickory Flooring in entire 2nd Floor and Bedrooms, WATER FILTRATION system, Gutters, Drop Zone with Cabinetry, SOLID CORE Doors throughout home and UV Light in AC Units. Property is very ENERGY EFFICIENT with Double Pane Lo E Windows, Radiant Barrier and Extra Insulation in the Concrete Block. Waterleigh is a Lifestyle Community with 4 Community Pools, 3 Clubhouses with Fitness Centers, Tennis, Pickleball, Mini Golf, Parks, Playgrounds, Community Fishing Dock and MORE! HOA Does all Yard Maintenance. Schools Include Panther Lake Elementary, Water Spring Middle and NEW Horizon High School. Close to Shopping, Dining, NEW Publix, DISNEY and convenient to 429, 1-4 and 417!

8750 Bayview Crossing Drive, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code

Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.

1061 Portmoor Way, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Imagine coming home to space, style, and ease—where every detail is already done. This move-in-ready Toll Brothers home offers 4 bedrooms, 3.5 baths, and 3,304 sq. ft. in one of Horizon West’s most desirable communities. From the Tuscan-inspired curb appeal and welcoming front porch to the bright, open living spaces, this home was designed for comfort, flexibility, and effortless entertaining. The chef’s kitchen features a large island and flows seamlessly into the family room and covered lanai. With two primary suites, including one on the main level, the floor plan is ideal for guests, multigenerational living, or a private owner’s retreat. The oversized backyard offers room to create your dream outdoor oasis, including space for a future pool. Enjoy resort-style amenities with lawn care included, a clubhouse, fitness center, parks, playgrounds, and a lakeside pool overlooking Panther Lake. Located minutes from top-rated schools, Hamlin Town Center, Disney, and everything Horizon West has to offer. Luxury without waiting. Space without compromise. This is where your next chapter begins.

15149 Canoe Place, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Winter Grv SubDv. ⋅ 34787 Zip Code

Welcome to Winter Grove in the charming city of Winter Garden. Ideally located just 1.2 miles from Winter Garden Village and approximately 2.8 miles from Historic Downtown Winter Garden, this intimate gated community offers the perfect blend of luxury, convenience, and privacy. Featuring spacious homesites and no CDD, residents enjoy easy access to premier shopping, dining, entertainment, and everything that makes this one of Central Florida’s most sought-after locations. Introducing the stunning Roseland model, a beautifully designed 5-bedroom, 5-bathroom residence with a 3-car garage, offering an exceptional balance of elegance, functionality, and thoughtfully curated finishes throughout. As you step through the impressive double glass entry doors, you are welcomed by a dramatic two-story foyer that immediately creates a grand first impression. Just off the entrance, an enclosed flex room provides endless possibilities—ideal as a home office, fitness room or additional living space—while the formal dining room creates the perfect setting for entertaining. Continuing through the home, a striking staircase featuring engineered hardwood plank treads and wrought iron balusters enhances the sophisticated design. Tucked beneath the staircase is a wine lover’s dream: a stylish wine cave complete with built-in cabinetry, quartz countertops, and designer tile backsplash. At the heart of the home, the open-concept kitchen is designed to impress, featuring built-in KitchenAid stainless steel appliances, including a gas-cooktop, oven, and beverage cooler. Beautiful two-tone soft-close cabinetry is paired with elegant quartz countertops, creating a timeless and refined aesthetic, while a spacious walk-in pantry provides abundant storage. The seamless flow between the kitchen, café, and gathering room creates an inviting and light-filled space, ideal for both everyday living and entertaining. Sliding doors lead to the covered lanai, which has already been pre-plumbed and pre-wired for a future outdoor kitchen, including electric, water, sewer, and natural gas connections—allowing the future owner to easily create their dream outdoor living space. Also located on the first floor is a spacious Multi-Gen Suite, perfect for guests or multigenerational living, complete with a walk-in closet and private bathroom. Upstairs, the luxurious owner’s suite occupies its own private wing, creating a peaceful retreat. An additional sitting area provides the perfect place to unwind or enjoy quiet moments. The spa-inspired owner’s bath showcases a freestanding soaking tub, oversized frameless glass shower and generous dual walk-in closets. The second floor also features additional well-appointed bedrooms, including two connected by a Jack-and-Jill bathroom and another with its own private en-suite bath, offering both comfort and privacy for family and guests. The upstairs laundry room, complete with cabinetry and a utility sink with quartz finishes, adds everyday convenience. Residents of Winter Grove also enjoy access to community amenities including a beautiful pond with walking trails. With an intelligently designed floor plan, carefully selected finishes, and a highly desirable location, this exceptional home offers the perfect blend of luxury, comfort, and lifestyle. Schedule your private tour today and experience this extraordinary home has to offer.

325 Crystal Wood Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code

GREAT NEW PRICE: $410,990.00. MOTIVATED SELLER. GREAT OWNER FINANCING AVAILABLE. BEAUTIFUL FULLY FURNISHED LUXURY 3 BED 2 BATH CONDO WITH GREAT VIEWS. Take the opportunity to own a slice of paradise in one of the world's most sought-after vacation destinations. The Grove Resort and Waterpark is a haven of fun and relaxation, featuring a plethora of amenities including: A Thrilling Water Park; Relaxing Lazy River; Exciting Water Slides; Multiple swimming pools; tranquil spa; The picturesque Lake Austin for fishing and paddle boating, etc.. Indulge in a variety of dining experiences with both indoor and outdoor settings, engage in retail therapy with on-site shopping, stay active in the state-of-the-art fitness center, and unwind in the full-service spa. The resort also caters to business and events with its well-equipped conference rooms. Embrace the luxury. Dive into the excitement. Make it yours. Take advantage of this opportunity

14501 Grove Resort Ave Unit 1535, Winter Garden

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

Opportunity Knocks with an amazing Price!! Looking for an Investment Fully Furnished STR that is managed for you and pays for itself when you are not vacationing? HERE IT IS! *One of the nicer Views & easier location to get to at The Grove Resort* The Grove Resort is a family Vacation Destination in the Orlando Florida area with a great location near Walt Disney World Theme Parks like Magic Kingdom, Epcot Center, Animal kingdom, and Sea World, Universal Studios, the Premium Outlets, many Restaurants, Golfing, Places of worship, etc. The occupancy rate here is very high and is managed very well. This Unit located in Building 2 and on the 2nd Floor has 2 Bedrooms, 2 Bathrooms, Stackable Full Size Laundry closet, Living, Dining and Fully Stocked Kitchen area within 1,375 sq feet under AC. There is a long-screened balcony as well with a beautiful view of the Palm Trees, lake and garden. **Parking right by this unit in garage and enter in for just a short walk and this makes this unit very desirable** You have access to all amenities such as the heated pools, SPA, Flip Flops Arcade, GYM, Surfari Water Park with a Lazy River & Learn how to surf with the dual FlowRiderÂ® surf simulator plus the 2 story water adventure, three slides, water spouts, and a wading pool, massage room, walking paths, restaurants(Valencia, Springs Bar & Grill, Longboard Bar & Grill, Alfresco Market Place(Yummy Pizza made here), Bar and much more. Add to your short list to view while in Orlando. BONUS: There is daily transportation to Walt Disney World Theme Parks, Universal Orlando, Hollywood Studios & SeaWorld! Did I mention there is an APP with Resort Events information that has an array of exciting activities planned to make your stay even more fun like Karaoke, Fishing Tournament on Lake Austin, Slime Time, Scavenger Hunts, National Beer Day, National Cheddar Fries Day and more. Any Repairs and Replacements are included & the onsite hotel management handles all the check-in and check-out, cleaning, accounting, advertising, and everything else! You are able to vacation here up to 120 days a year. Call us to own a piece of paradise in Florida where you can Own, Enjoy, Cover expenses at a World Class Vacation Condo-Hotel!!

14501 Grove Resort Avenue Unit 2214, Winter Garden

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