Location: Winter Garden
Do Not Show Listings
314 DOUGLAS WAY #900, WINTER GARDEN, FL 34787
$1,60022 Days on yellowkey MLS ID: O6393613
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1989Community: Townhomes Winter GardenHalf Duplex
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Spacious 2-bedroom, 2-bath end-unit duplex located in the well-situated Townhomes of Winter Garden community. This unit offers a practical and comfortable layout with generously sized bedrooms, two full bathrooms, and the added privacy of an end-unit location. Hard-surface flooring runs throughout the home, featuring ceramic tile and laminate for easy maintenance and a clean, modern feel. A washer and dryer are conveniently located inside the unit for everyday convenience. The community is ideally positioned just off Park Avenue and SR 50 (E Colonial Drive), placing residents within close proximity to a wide selection of shopping centers, grocery stores, restaurants, and daily services. With quick access to the Florida Turnpike, SR 429, SR 408, and US 27, this location provides excellent connectivity to Downtown Orlando, Clermont, and surrounding areas, making it a great option for commuters and those looking to stay close to Winter Garden’s growing amenities and attractions.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Melquisedec Martins (407-952-6948)
12154 PLUMPTON DR, WINTER GARDEN, FL 34787
$2,80022 Days on yellowkey MLS ID: S5146362
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1688 Built: 2023Community: Encore/Ovation Ph 4BSingle Family
Remarks: Beautiful Home for Rent in Winter Garde Fl. Looking for the perfect place to call home? This spacious and modern property in Winter Garden, Fl has everything you need! Features: 3 comfortable bedrooms, 2 full bathrooms plus 1 half bath. Bright and open living spaces, fully equipped kitchen, private back yard perfect for relaxing or entertaining. Enjoy Florida living at its best in peaceful and family-friendly neighborhood.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Luis Montoya Tua (407-954-1985)
17049 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787
$2,99553 Days on yellowkey MLS ID: L4959570
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2048 Built: 2025Community: Northlake/Ovation Ph 1Single Family
Remarks: Ready for immediate move in! Beautiful 4 Bed, 3 Bath home with high end custom finishes Available Immediately! Small to medium pets are allowed. This neighborhood also include a community pool, clubhouse, playground, and dog park! This home features an open floorplan with tons of natural light. There are 4 large bedrooms and a gorgeous master suite with a huge walk in closet. There is a front porch for sitting and relaxing and a screened rear patio as well as a 2 car garage and extra long driveway. All appliances are included and are almost brand new, even the washer and dryer. This property is directly managed by the owner's team so you don't have to deal with waiting days to hear back from large management company for applications or repair requests. This home will be available for many years as a rental so you can move in and stay longterm without having to worry about the home being sold. This property is close to everythign including resturants, shopping, schools, golf, the parkway and the interstate. Schedule your showing today while this beautiful home is still availble!!!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Ben Becton (863-617-0232)
15523 BAY BRIDGE ST, WINTER GARDEN, FL 34787
$2,70080 Days on yellowkey MLS ID: O6376958
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1691 Built: 2026Community: Tribute At OvationTownhouse
Remarks: This newly constructed townhome features 3 bedrooms, 2.5 bathrooms, and a 2-car garage. The main level includes an open-concept layout with a kitchen equipped with ample counter space, cabinet storage, and additional pantry/storage areas. The adjacent living and dining spaces receive natural light from multiple windows. The upper level contains the primary bedroom with an attached full bathroom, plus two additional bedrooms and a second full bathroom. The property includes a 2-car attached garage. The community offers amenities including a pool, dog park, and playground, with convenient access to parks, shopping centers, restaurants, and major roadways. Contact for a private showing or additional details.
Listing is courtesy of: WEBB FLORIDA REALTY LLC (407-779-4695)
Listing Agent: Mayco Sampaio (407-766-5999)
14366 ORCHARD HILLS BLVD, WINTER GARDEN, FL 34787
$2,95036 Days on yellowkey MLS ID: S5145483
0 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2486 Built: 2017Community: Orchard Hills Ph 2Single Family
Remarks: Beautiful and Spacious 2-story home located in Orchard Hills Community in Winter Garden. The home features 4 bedrooms, 3.5 baths, with approximately 2486 sq.Ft of living space. The home has 2 master suites, one on each floor. The home features a nice-sized loft. All appliances included. LAWN CARE INCLUDED. The home is located close to SR-429, SR-535, US-192, and SR-545 in the Winter Garden area. It is near Walt Disney World, Orange County National Golf Center, and Universal Studios. The home is in a community that features a clubhouse with a fitness center, resort-style swimming pool, and playground. Community amenities... also include sport court and numerous walking and biking paths.
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Amanda Yuan (407-353-2867)
16021 TOLLINGTON ALY, WINTER GARDEN, FL 34787
$3,50023 Days on yellowkey MLS ID: O6393427
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2689 Built: 2025Community: Encore/Ovation Ph 1Single Family
Remarks: Beautiful home with a stunning contemporary design, premium upgrades, and an unbeatable location just minutes from Disney Parks, top-rated schools, and premier shopping destinations. Property is featured with 4 bedrooms and 3 bathrooms - In law suite on first floor is , modern open floorplan with high ceilings and abundant natural light. Laundry room fully equipped with washer and dryer and a stand alone sink. The community is a resort-style living, families can enjoy top-tier community amenities including pool, fitness center, playground, and a dog park. The house is currently tenant occupied until April 3rd 2026. The house will be ready to show as of April 4th 2026. Be aware there's road constructions around the area.
Listing is courtesy of: KICANTO REALTY (305-744-2297)
Listing Agent: Cristiane Leon (305-744-2297)
13465 SAGESTONE DR, WINTER GARDEN, FL 34787
$2,65023 Days on yellowkey MLS ID: O6393123
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1567 Built: 2023Community: WaterleighTownhouse
Remarks: Discover this beautifully crafted, townhouse located in the highly desirable Waterleigh community of Winter Garden. The thoughtfully designed kitchen, seamlessly connected to a spacious living and dining area, features a granite island, 42-inch cabinetry, stainless steel appliances, and a generously sized pantry. Rent includes maintenance of all common areas, providing added convenience and peace of mind. While all information and measurements are believed to be accurate, prospective tenants and their agents are encouraged to independently verify. Experience comfort, style, and functionality—this exceptional residence is ready to become your next home.
Listing is courtesy of: DOUBLE M GROUP COMPANY (407-777-0070)
Listing Agent: Marcelo Moura (239-628-8008)
WINTER GARDEN, FL 34787
$2,10072 Days on yellowkey MLS ID: O6378945
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 2005Community: Southern PinesCondo
Remarks: Prime Location & Resort-Style Living! Welcome home to this beautifully appointed first-floor, 2-bedroom, 2-bath condo in the highly sought-after GATED community of Southern Pines. The desirable open, split floor plan offers both space and privacy, enhanced by wood laminate flooring throughout the living, dining, and kitchen, tile in the baths, and plush carpeted bedrooms. The kitchen features granite countertops, and the home includes an in-unit washer and dryer for added convenience. Relax year-round in the bright solarium just off the living room—perfect for morning coffee or unwinding after a long day. Water, sewage, basic cable, and internet are all included, making this home as practical as it is comfortable. Enjoy resort-style amenities right outside your door, including a community pool, fitness center, indoor basketball court, tennis court, sand volleyball, playground, business center, game room with pool table, gas grilling area, and a private movie theater. Ideally located close to everything, but tucked away from the hustle and bustle. Located just minutes from the Florida Turnpike, SR-408, Winter Garden Village, and historic downtown Winter Garden, this condo offers the perfect blend of convenience, comfort, and community living.
Listing is courtesy of: MARTI PURDY PROPERTIES INC (407-614-6177)
Listing Agent: Marti Purdy (407-761-0848)
15146 WINDFLOWER ALY, WINTER GARDEN, FL 34787
$2,45045 Days on yellowkey MLS ID: O6386816
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 2024Community: Osprey Ranch Ph 1Townhouse
Remarks: Beautiful Corner Unit 3-Bedroom Townhouse for Rent in Winter Garden Welcome to this stunning two-story corner unit townhouse located in the highly desirable area of Winter Garden. As a corner unit, this home offers additional privacy, extra natural light, and an enhanced sense of space — making it an even more attractive and comfortable place to live. Designed for modern living, this spacious 3-bedroom home delivers the perfect combination of style, functionality, and location, ideal for families and professionals alike. The thoughtfully designed open floorplan creates a bright and inviting atmosphere, seamlessly connecting the expansive living room and dining room. The corner positioning allows for more windows and abundant natural light, making the living areas feel even more open and welcoming. This layout is perfect for both everyday living and entertaining guests. The beautiful kitchen is a true highlight, featuring solid wood cabinets, elegant stone countertops, and all appliances included. With generous counter space and ample storage, it is both stylish and practical for cooking and hosting. Upstairs, you will find three generously sized bedrooms. The primary suite offers a spacious walk-in closet and a private full bathroom, creating a relaxing retreat at the end of the day. The two additional bedrooms include built-in closets and share a well-appointed full bathroom. A convenient half bathroom is located on the main floor for guests. This home also includes a 2-car attached garage, providing secure parking and extra storage space. Located in a prime area near major roads for easy commuting and close to highly rated schools, this property combines comfort with convenience. You’ll be just minutes from shopping, dining, parks, and everything Winter Garden has to provide. If you are looking for privacy, natural light, space, and an excellent location, this beautiful corner unit townhouse is ready to welcome you home. Schedule your showing today and secure this exceptional rental opportunity.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Umberto Da Cunha Neto (407-690-3539)
15002 WINDFLOWER ALY, WINTER GARDEN, FL 34787
$2,350153 Days on yellowkey MLS ID: O6360807
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 2024Townhouse
Remarks: Discover this charming, like-new 3-bedroom semi-detached house, all with walk-in closets and carpeting, located in the heart of Horizon West in Winter Garden. The residence features a welcoming front porch, a modern kitchen with granite countertops and complete appliances, plus a separate, fully equipped laundry room. A garage with an automatic gate provides added convenience. Enjoy the convenience of living in a prime area, close to excellent schools, supermarkets, shopping centers, and various leisure options. Don't miss this opportunity schedule your visit today and transform this beautiful house into your new home!
15010 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$3,40069 Days on yellowkey MLS ID: O6371081
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2322 Built: 2024Community: Harvest At OvationSingle Family
Remarks: Welcome to this beautiful single-family home located in the highly desirable Harvest at Ovation community in Horizon West/Winter Garden, one of Central Florida’s fastest-growing areas. This spacious residence offers 4 bedrooms, 3 full bathrooms, and 1 half bath, including a downstairs suite, ideal for guests or multi-generational living. The home features a modern, functional layout with well-distributed living spaces, abundant natural light, and contemporary finishes throughout. Enjoy an unbeatable location just minutes from Disney, top-rated schools, grocery stores, restaurants, and shopping, with convenient access to FL-429 and US-192, Horizon West, Winter Garden Village, and Orlando. Please be aware that pest control ($25) and landscaping ($167) are not included in the rental price. Schedule your private showing today and make this beautiful townhome your next home!
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Ricardo Castillo Molina (407-624-9270)
16917 TESLA ALY, WINTER GARDEN, FL 34787
$2,60026 Days on yellowkey MLS ID: O6392623
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1568 Built: 2020Community: Waterleigh Ph 3ATownhouse
Remarks: NO CARPETS! Beautiful townhome in PERFECT Community - Waterleigh at Horizon West Winter Garden. Rent includes Lawn Care and All 4 Community Amenities Access! All Appliance included. Great school zone. Waterleigh is an amazing community, tons of amenities, including TWO large resort style clubhouses with fitness centers, TWO resort style pools and additional two outdoor pool amenity, soccer fields, mini golf, dog parks, playground, tennis, volleyball, etc. Only 5 mins to Orange County National Golf Center and SR429. Easy/close to access 535, 545, US192. Publix village just on front of community! Only few minutes to the Hamlin Town Shopping center, Walmart, Publix, Luxury Cinema, Banks, Starbucks, Restaurants, Winter Garden Village. Only short drive to downtown Windermere and Winter Garden. 10+ minutes to Walt Disney World. Schedule a showing TODAY!
Listing is courtesy of: YORK MILLS REALTY LLC (626-328-8535)
Listing Agent: Jacky Liu (407-921-5670)
12763 CHARMED DR, WINTER GARDEN, FL 34787
$4,10054 Days on yellowkey MLS ID: O6384328
0 Days Off yellowkey (back on 3/21/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2587 Built: 2024Community: Waterleigh Ph 4B & 4CSingle Family
Remarks: Welcome to your SEMI-FURNISHED home in one of Winter Garden's most desirable communities! This property offers a perfect blend of comfort and convenience. Enjoy the benefit of A-rated schools right within the community—both the elementary and middle schools—with no need for additional transportation. Plus, the high school, just a short distance away, is also highly rated, making this an ideal location for families seeking exceptional education at every level. The community offers a wealth of amenities, including a pool, fitness center, tennis courts, playgrounds, mini golf, and year-round events for all ages. Here, you're not just getting a home—you're embracing a lifestyle. This spacious home features 5 bedrooms and 4 bathrooms, with an open kitchen and living area perfect for family gatherings. The semi-furnished setup makes it move-in ready. The large backyard provides plenty of space for outdoor activities or relaxation. With easy access to major roads, shopping, dining, and parks, everything you need is right at your door. Don’t miss this unique opportunity to live in a community where convenience, comfort, and top-tier education come together. Schedule your showing today!
Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)
Listing Agent: Bruna Canesin Motta (407-580-1367)
165 WINDTREE LN #U, WINTER GARDEN, FL 34787
$1,75027 Days on yellowkey MLS ID: O6392506
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1985Community: Windtree Gardens Condo Ph 06Condo
Remarks: Wonderful renovated unit in Windtree Gardens. 2 brm 2 bath, 1st floor unit with screen enclosed front porch. No carpet in unit. Unit has 2 assigned parking spots. 1 small pet OK. Requirements are 600+ credit score and income 2.5 times rent with no evictions on record.
Listing is courtesy of: ZEAL REALTY (407-789-2051)
Listing Agent: Cheryl Good (321-356-7377)
13346 DANIELS LANDING CIR, WINTER GARDEN, FL 34787
$2,15041 Days on yellowkey MLS ID: O6388207
0 Days Off yellowkey (back on 3/19/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1151 Built: 2005Community: Daniels Lndg A-JTownhouse
Remarks: Available May1st! GATED cute neighborhood in the sought-after area of WINTER GARDEN VILLAGE MALL and so much more around the newer side of this HISTORIC CHARMING DISTRICT TOWN. Included in the rent amount: BASIC CABLE with HBO, BASIC INTERNET. This lovely UPDATED townhome is spacious, tile throughout 1st floor and on 2nd floor where the suites are. All bedrooms with walk-in closets, laundry is on the upper floor. The main floor features a large open Living/Dining great room, bright, natural light coming from a window with a view to the open patio, Stainless Steel Appliances, plenty of cabinets and closet pantry. The gated community offers a pool and fitness room.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Claudia D'Aquino (407-715-8810)
11032 GREAT ROCK ST, WINTER GARDEN, FL 34787
$2,60029 Days on yellowkey MLS ID: O6391704
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1567 Built: 2021Community: Waterleigh Ph 2ETownhouse
Remarks: The Ibis at Waterleigh is a spacious town home with 3 bedrooms, 2.5 baths with stainless steel appliances. This home invites you from the time you enter. This lifestyle Community includes over the top amenities with 2 beautiful clubhouses with 2 resort style pools,2 fitness centers, putt-putt golf, beach volleyball, tennis, lake view BBQ/picnic area, dog-park and so much more. Come out and see all of our beautiful decorated models and view the community that is a “must see” in Winter Garden/Horizons West.
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Marcos Paulo Nero, Llc (407-923-5128)
15585 GENTLE RAIN DR, WINTER GARDEN, FL 34787
$3,50038 Days on yellowkey MLS ID: O6389221
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2200 Built: 2025Community: Osprey Ranch Ph 1Single Family
Remarks: Live in one of the most convenient locations in Winter Garden. This beautiful home in the highly desirable Osprey Ranch community is just minutes from Flamingo Crossings Town Center, Walt Disney World, AdventHealth ER on Hartzog Road, and a wide variety of restaurants, shopping, and everyday conveniences. With quick access to SR-429 and US-192, commuting around Orlando, Horizon West, and Kissimmee is simple and efficient. Available for rent at $3,500 per month, this spacious Nicola II floor plan offers over 2,200 sq. ft., 4 bedrooms, 3 bathrooms, and 10’ ceilings, creating a bright and open feel throughout the home. The modern kitchen features quartz countertops, 42” upper cabinets, stainless steel appliances, a waterfall island upgrade, and a stone backsplash, flowing seamlessly into the open living and dining areas. A 12’ sliding glass door leads to a fully fenced backyard with premium PVC fencing and brick pavers, perfect for relaxing or entertaining outdoors. The first floor also includes a private guest suite with a walk-in closet, ideal for visitors or multigenerational living. Upstairs you'll find a versatile loft, two secondary bedrooms, and a spacious primary suite with large rear-facing windows, a generous walk-in closet, and a well-appointed bathroom. Osprey Ranch residents enjoy access to resort-style amenities, including a community pool and cabana, splash pad, playground, and dog park. Schedule your private showing today. All showings must be scheduled in advance with the listing agent.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Denio Gomes (203-609-4882)
12063 HOLYSTONE ST, WINTER GARDEN, FL 34787
$2,49090 Days on yellowkey MLS ID: O6374014
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1451 Built: 2023Community: Waterleigh Ph 4ATownhouse
Remarks: Charming Townhome for Rent with Courtyard Views in Waterleigh Welcome to this beautifully maintained interior-unit townhome located in the highly desirable, Waterleigh community. Offering 3 bedrooms and 2.5 bathrooms, this home features a spacious open-concept first floor, perfect for both everyday living and entertaining. The property has been recently updated with brand-new luxury vinyl plank (LVP) flooring throughout (no carpet) providing a modern look and easy maintenance, an attached one-car garage, offering both convenience and extra storage. Residents of Waterleigh enjoy lawn care included and access to outstanding resort-style amenities, including multiple swimming pools, scenic walking trails, a 6-hole mini golf course, sand volleyball courts, and more. Ideally located, the community offers top-rated schools, parks, and recreational areas within the neighborhood, as well as grocery stores and shopping conveniently located at the entrance of the community. This home delivers the perfect combination of comfort, convenience, and lifestyle.
Listing is courtesy of: ALLUX REAL ESTATE LLC (407-802-7310)
Listing Agent: Denise Batista (407-802-7310)
5783 CITRUS PARK DR, WINTER GARDEN, FL 34787
$2,95029 Days on yellowkey MLS ID: O6391947
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1846 Built: 2026Community: Parkview/HamlinTownhouse
Remarks: Experience elevated living in this brand-new luxury townhome ideally located in the heart of Hamlin, Winter Garden—one of Central Florida’s rapidly growing communities. This exceptional residence offers 3 spacious bedrooms, 2 full bathrooms, 1 half bath, and a 2-car garage, thoughtfully designed for both comfort and sophistication. The open-concept layout showcases a seamless flow between living, dining, and entertaining spaces, highlighted by a sleek, modern kitchen fully equipped with premium appliances. Natural light fills the home, creating a bright and inviting atmosphere throughout. Upstairs, the primary suite provides a private retreat, while additional bedrooms with flexibility for family, guests, or a refined home office. Designed with today’s lifestyle in mind, this smart home includes washer and dryer, along with internet and cable, delivering convenience and connectivity at every level. Located within a pet-friendly community, this home sits in the highly desirable Parkview at Hamlin. Indulge in a lifestyle of unmatched convenience with immediate access to fine dining, shopping, major supermarkets including Walmart, Publix, top-rated schools, Medical School, AdventHealth Hospital, and Orlando Health Hospital, all just minutes away. Commuting is effortless with quick access to SR-429, placing all of Central Florida within easy reach.
Listing is courtesy of: GOLDEN KEY REAL ESTATE SOLUTIONS LLC (407-801-8283)
Listing Agent: Marcia Vieira (781-706-8190)
12664 CHARMED DR, WINTER GARDEN, FL 34787
$2,500135 Days on yellowkey MLS ID: O6358668
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1568 Built: 2024Community: WaterleighTownhouse
Remarks: 2024 BEAUTIFUL TOWNHOME Nestled in the heart of the highly sought-after Winter Garden community. Bright and spacious 3 bedrooms and 2.5 bathrooms townhome in WATERLEIGH. Ceramic tiles on the first floor, Kitchen has granite counter tops, all new stainless steel kitchen appliances (dishwasher, refrigerator, electric stove, and microwave) and breakfast bar, large WALK IN Pantry. Kitchen and Living room are in a well planned open space concept opening to a small patio. There is also a half bath and mud room on the first floor. The second floor is completely carpeted and houses all three bedrooms, two full bathrooms and in unit washer and dryer included in the rent. Residents of this Winter Garden neighborhood enjoy access to a range of community amenities (included in rent), such as, sparkling community pool, playgrounds, fitness center and bike/walking trails.The community is known for its friendly atmosphere and is a great place to make lasting connections with neighbors. Situated in the heart of Winter Garden, this rental property is just minutes away from the historic downtown district, where you can explore charming shops, dine at a plethora of restaurants offering delicious foods, and enjoy community events. It's conveniently located near top-rated schools, major highways, and a variety of shopping centers, making it an excellent choice for families and commuters alike. Close to Orlando theme parks, shopping centers, supermarkets, and nearby hospitals. Additional Information: Rent includes lawn maintenance, pet-friendly (with landlord approval), washer and dryer included, ONE car connected garage and 2 space driveway for convenient parking and storage. Don't miss the opportunity to make this exceptional Winter Garden first time rental property your new home. With its prime location, modern amenities, and stylish design, it offers the perfect blend of comfort and convenience. *Landscaping provided by HOA"
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Luciana Lima Chaves (407-683-2474)
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