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Windermere, FL Homes for Sale

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  • /41

    $574,995

    • 4 Beds
    • 2 Baths
    • 1,798 Sq Ft

    9319 Woodbreeze Blvd, Windermere, FL 34786

    WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

    Steven Looper CHARLES RUTENBERG REALTY ORLANDO

    9319 Woodbreeze Blvd, Windermere, FL 34786
  • /95

    $2,199,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 3,525 Sq Ft

    505 Jennifer Ln, Windermere, FL 34786

    Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside.What unfolds within is architectural

    Ahmad Hassan COMPASS FLORIDA LLC

    505 Jennifer Ln, Windermere, FL 34786
  • /27

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    14368 Desert Haven St Unit 4106, Windermere, FL 34786

    Don't miss 14368 Desert Haven St, recently enhanced with a partial flooring replacement, providing an updated surface throughout. The kitchen is equipped with stainless steel appliances for functional meal preparation. This residence includes a primary bedroom with a spacious walk-in closet, and its connecting bathroom provides double sinks and a separate tub and shower, contributing to its

    Karen Albright OPENDOOR BROKERAGE LLC

    14368 Desert Haven St Unit 4106, Windermere, FL 34786
  • /33

    $585,000

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    13430 Hopkinton Ct, Windermere, FL 34786

    ***Charming Windermere Home in Lakes of Windermere – Peachtree! ***Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations. Step

    Lynn London EXP REALTY LLC

    13430 Hopkinton Ct, Windermere, FL 34786
  • /29

    $659,000

    • 5 Beds
    • 3.5 Baths
    • 2,960 Sq Ft

    12936 Droxford Rd, Windermere, FL 34786

    The seller will install a brand-new roof prior to closing, ensuring the property is fully updated and move-in ready on closing day.Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonus room and much more! The well-established neighborhood is out of a Norman Rockwell painting, lined with trees, 15 minutes from Disney, and loaded with charm. All you will

    Leo Rico UNITED REAL ESTATE PREFERRED

    12936 Droxford Rd, Windermere, FL 34786
  • /81

    $5,000,000

    • 6 Beds
    • 9 Baths
    • 8,305 Sq Ft

    9721 Carillon Park Dr, Windermere, FL 34786

    Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and

    Dianna Desboyaux DOUGLAS ELLIMAN

    9721 Carillon Park Dr, Windermere, FL 34786
  • /3

    $1,130,000

    • 8 Beds
    • 5 Baths
    • 4,830 Sq Ft

    6152 Golden Dewdrop Trail, Windermere, FL 34786

    More pictures coming soon. Beautiful and spacious 8-bedroom, 5-bathroom corner home offering 4,830 sqft of living space. This well-designed property features a generous layout with plenty of room for comfortable living and entertaining. The fenced backyard provides a great outdoor space, perfect for relaxing or enjoying time outside. Located on a desirable corner lot, offering added space and

    Vitor Silva VESTI LLC

    6152 Golden Dewdrop Trail, Windermere, FL 34786
  • /57

    $3,400,000

    • 4 Beds
    • 4 Baths
    • 4,877 Sq Ft

    9731 Chestnut Ridge Dr, Windermere, FL 34786

    Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

    Monica Lochmandy ISLEWORTH REALTY LLC

    9731 Chestnut Ridge Dr, Windermere, FL 34786
  • /65

    $3,200,000

    • 6 Beds
    • 6.5 Baths
    • 6,308 Sq Ft

    13448 Bellaria Cir, Windermere, FL 34786

    Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting

    Shawn Kennedy KENNEDY REALTY GROUP LLC

    13448 Bellaria Cir, Windermere, FL 34786
  • /26

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,161 Sq Ft

    11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786

    Windermere Renovated Condo | Elevator | Resort Amenities | Near Disney & Shopping Renovated and move-in ready, this light-filled second-floor condo with elevator access is ideally located in one of Windermere’s most convenient areas—just minutes from Disney, Winter Garden Village, and directly across from Lakeside Village Center offering everyday shopping and dining. Designed for effortless

    Nilufer Rohleder COLDWELL BANKER REALTY

    11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786
  • /91

    $3,699,888

    • 4 Beds
    • 5.5 Baths
    • 6,054 Sq Ft

    12812 Jacob Grace Ct, Windermere, FL 34786

    Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

    Alireza Partovi EXP REALTY LLC

    12812 Jacob Grace Ct, Windermere, FL 34786
  • /91

    $3,950,000

    • 6 Beds
    • 7 Baths
    • 5,709 Sq Ft

    12132 Montalcino Cir, Windermere, FL 34786

    Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

    Caroline Perotti BELLA VIEW REALTY LLC

    12132 Montalcino Cir, Windermere, FL 34786
  • /81

    $7,595,000

    • 5 Beds
    • 6.5 Baths
    • 6,937 Sq Ft

    5074 Isleworth Country Club Dr, Windermere, FL 34786

    A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 6,900 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the

    Armaan Memarpouri MEMARPOURI REALTY LLC

    5074 Isleworth Country Club Dr, Windermere, FL 34786
  • /26

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,974 Sq Ft

    12353 Via Derna Place, Windermere, FL 34786

    The house does not include furniture.Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse, with furniture available for negotiation, located in the desirable Carrington at Windermere community. This residence provides a well-designed open-concept floor plan that seamlessly blends comfort and functionality, ideal for both everyday living and entertaining. The home features

    Tiago Ferreira AUTHENTIC REAL ESTATE TEAM

    12353 Via Derna Place, Windermere, FL 34786
  • /50

    $680,000

    • 5 Beds
    • 3.5 Baths
    • 2,976 Sq Ft

    6712 Thornhill Cir, Windermere, FL 34786

    With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual

    Brad Young HOMEVEST REALTY

    6712 Thornhill Cir, Windermere, FL 34786
  • /81

    $2,899,000

    • 5 Beds
    • 4 Baths
    • 3,737 Sq Ft

    10203 Trout Rd, Orlando, FL 32836

    Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

    Darlene O'Hara HOMEVEST REALTY

    10203 Trout Rd, Orlando, FL 32836
  • /90

    $3,700,000

    • 5 Beds
    • 7 Baths
    • 7,153 Sq Ft

    6857 Valhalla Way, Windermere, FL 34786

    Perfection has an address along with comfortable Florida living. Located on the 17th fairway of Jack Nicklaus-designed Golden Bear Club's golf course, this stunning home offers 5 bedrooms with the master on the 1st floor, 5 full baths, 2 half baths, home theatre, game room, office, and 2nd floor gathering room overlooking a stunning balcony. Invest in quality in this Rick Watson built masterpiece

    Mely Carrero EMPIRE NETWORK REALTY

    6857 Valhalla Way, Windermere, FL 34786
  • /38

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft

    12210 Langstaff Dr, Windermere, FL 34786

    WELL MAINTAINED TOWNHOME IN WINDERMERE! 3 BEDROOM 2.5 BATHROOMS! Located in the sought after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Courtyard leading to a Detached 2 Car Garage with Rear Entry Alleyway that backs up to a

    Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

    12210 Langstaff Dr, Windermere, FL 34786
  • /32

    $410,000

    • 3 Beds
    • 2.5 Baths
    • 1,569 Sq Ft

    7249 Shadeview Aly, Windermere, FL 34786

    This enchanting home located near all of Florida’s theme parks, necessities, and more can be yours today! What a stunning home located in a great neighborhood, feel safe in this community that also has a community pool and a playground! Minutes away from Disney, several shopping centers, spectacular schools, and more feel wonderful living close to everything one would need! Stepping into the

    Blanca Armada REMAX PREMIER PROPERTIES

    7249 Shadeview Aly, Windermere, FL 34786
  • /30

    $2,175,000 New Construction

    • 4 Beds
    • 5 Baths
    • 3,136 Sq Ft

    436 E 7th Ave, Windermere, FL 34786

    Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

    DENILEY VALDES TALENT REALTY SOLUTIONS

    436 E 7th Ave, Windermere, FL 34786
  • /70

    $374,400

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    14236 Oasis Cove Blvd, Windermere, FL 34786

    If watching Magic Kingdom fireworks from your own home sounds like a dream, this is where it becomes your reality. Welcome to Oasis Cove, a gated, resort-style community located just a few miles from Walt Disney World. This beautifully updated 3-bedroom, 2.5-bath residence stands out as one of the most upgraded and move-in ready homes in the community. As you walk in, you are welcomed by a

    Raquel Saunders WRA BUSINESS & REAL ESTATE

    14236 Oasis Cove Blvd, Windermere, FL 34786
  • /26

    $4,395,000

    • Land
    • 1 Acre
    • $4,395,000 per Acre

    12418 Park Ave, Windermere, FL 34786

    WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of

    Michael Julian JULIAN PROPERTIES, INC.

    12418 Park Ave, Windermere, FL 34786
  • /27

    $1,100,000 Open Sat 11AM - 2PM

    • 6 Beds
    • 4 Baths
    • 4,176 Sq Ft

    8236 Procida Isle Ln, Windermere, FL 34786

    This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light-filled foyer with a private office at the front of the home. Beautiful wood-look tile flooring flows seamlessly throughout the main level. The stunning gourmet kitchen features 42” cabinets, gas appliances, light

    Babi Hennemann WRA BUSINESS & REAL ESTATE

    8236 Procida Isle Ln, Windermere, FL 34786
  • /45

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 3,315 Sq Ft

    8724 Peachtree Park Ct, Windermere, FL 34786

    Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a

    Marcelo Machado LA ROSA REALTY LLC

    8724 Peachtree Park Ct, Windermere, FL 34786
  • /35

    $2,200,000

    • 8 Beds
    • 8.5 Baths
    • 4,735 Sq Ft

    11545 Brickyard Pond Ln, Windermere, FL 34786

    Luxury Lakefront Estate – Windermere, FL Discover a truly extraordinary lakefront residence located at one of Windermere's most prestigious addresses. Situated on a sprawling 0.75-acre lot, this property impresses with its grandeur, elegance, and impeccable attention to detail. With 8 spacious bedrooms, 9 full bathrooms, and 1 powder room, the home was designed to offer absolute comfort and a

    Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    11545 Brickyard Pond Ln, Windermere, FL 34786
  • /46

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft

    6442 Golden Dewdrop Trail, Windermere, FL 34786

    Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much

    Yindy Reyes EMPIRE NETWORK REALTY

    6442 Golden Dewdrop Trail, Windermere, FL 34786
  • /65

    $2,500,000

    • 6 Beds
    • 4 Baths
    • 4,482 Sq Ft

    9648 Weatherstone Ct, Windermere, FL 34786

    Set within the private gates of Weatherstone on Lake Olivia, this stunning lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views.Boasting 6 bedrooms and 4

    Andy Neal THE AGENCY FL

    9648 Weatherstone Ct, Windermere, FL 34786
  • /66

    $3,699,000

    • 3 Beds
    • 5 Baths
    • 4,262 Sq Ft

    4812 Alexandra Garden Ct, Windermere, FL 34786

    Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a

    Rob Rahter STOCKWORTH REALTY GROUP

    4812 Alexandra Garden Ct, Windermere, FL 34786
  • /9

    $5,995,000 New Construction

    • 5 Beds
    • 6 Baths
    • 6,000 Sq Ft

    13377 Lake Butler Blvd, Winter Garden, FL 34787

    Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

    Dawn Briggs BLUE MAGNOLIA REALTY LLC

    13377 Lake Butler Blvd, Winter Garden, FL 34787
  • /40

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    8648 Powder Ridge Trail, Windermere, FL 34786

    LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door.Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a

    Renan Serretiello NOVA REAL ESTATE SERVICES INC

    8648 Powder Ridge Trail, Windermere, FL 34786
  • /68

    $15,500,000

    • 10 Beds
    • 17 Baths
    • 13,425 Sq Ft

    12488 Park Ave, Windermere, FL 34786

    Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself

    Julie Christensen ONE LUXURY INTERNATIONAL LLC

    12488 Park Ave, Windermere, FL 34786
  • /31

    $579,900

    • 4 Beds
    • 3 Baths
    • 2,229 Sq Ft

    6897 Northwich Dr, Windermere, FL 34786

    Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel

    Blake Blahut REALTY ONE GROUP INSPIRATION

    6897 Northwich Dr, Windermere, FL 34786
  • /45

    $2,299,000

    • 5 Beds
    • 4 Baths
    • 3,461 Sq Ft

    5067 Sawyer Cove Way, Windermere, FL 34786

    STUNNING CUSTOM ESTATE in the EXCLUSIVE GATED community of Sawyer Sound - a private enclave of 20 luxury homes, ideally located across the street from Windermere Prep, and close to excellent dining and premiere entertainment. Built under the meticulous supervision of its owners, one of whom is an accomplished interior designer, this home showcases curated exceptional quality finishes and

    Denise Crabbe REVEL REALTY LLC

    5067 Sawyer Cove Way, Windermere, FL 34786
  • /31

    $875,000

    • 4 Beds
    • 3.5 Baths
    • 3,124 Sq Ft

    5413 Walsh Pond Ct, Windermere, FL 34786

    Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in

    Brenda Jebailey HAVEN PROPERTY GROUP LLC

    5413 Walsh Pond Ct, Windermere, FL 34786
  • /2

    $3,000,000 New Construction

    • 5 Beds
    • 5 Baths
    • 2,565 Sq Ft

    19 Main St, Windermere, FL 34786

    Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes!Experience modern lakefront living in the heart of the golf cart–friendly Town of Windermere. This brand-new construction home is currently under construction with an anticipated completion date of late Summer 2026. The residence will offer approximately 2,500 square feet of living space and

    Milena Fernandes GOLDEN GROUP REALTY LLC

    19 Main St, Windermere, FL 34786
  • /38

    $870,000

    • 5 Beds
    • 3.5 Baths
    • 3,724 Sq Ft

    8767 Iron Mountain Trail, Windermere, FL 34786

    The Melville floor plan features a functional and well-designed layout with formal living and dining areas, a spacious primary suite, an open-concept family room and a versatile flex space that can be used as a game room or adapted to suit a variety of lifestyle needs. Located in the desirable Windermere Trails community, the property offers convenient access to area lakes, daily essentials,

    Gilson Rodrigues KARDOSH REALTY

    8767 Iron Mountain Trail, Windermere, FL 34786
  • /56

    $749,999

    • 4 Beds
    • 3.5 Baths
    • 3,360 Sq Ft

    13609 Ancilla Blvd, Windermere, FL 34786

    Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony,

    Fernanda Soares Santos de Oliveira WRA BUSINESS & REAL ESTATE

    13609 Ancilla Blvd, Windermere, FL 34786
  • /16

    $895,000

    • 4 Beds
    • 3 Baths
    • 2,224 Sq Ft

    13542 Gorgona Isle Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly

    Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    13542 Gorgona Isle Dr, Windermere, FL 34786
  • /47

    $1,999,999

    • 4 Beds
    • 4.5 Baths
    • 4,013 Sq Ft

    6036 Greatwater Dr, Windermere, FL 34786

    Classic elegance defined in this stately Keene’s Pointe residence, set along the 17th Fairway of the renowned Jack Nicklaus Signature Golf Course. An impressive grand foyer with warm hardwood flooring greets guests to a traditional-style home with office and formal plus family living spaces on the first floor, along with a guest suite. The primary bedroom and two other secondary bedrooms are

    Rob Rahter STOCKWORTH REALTY GROUP

    6036 Greatwater Dr, Windermere, FL 34786

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