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Windermere, FL Homes for Sale

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  • /39

    $449,980

    • 3 Beds
    • 2.5 Baths
    • 1,767 Sq Ft

    13369 Gorgona Isle Dr, Windermere, FL 34786

    Back on the Market! The Buyer was not able to obtain financing; you now have a new opportunity to own this gorgeous Townhome! Wow! Gorgeous, newly updated three-bedroom luxury townhome with a scenic water and fountain view. This spacious, light-filled home is open, bright, clean and move-in ready. This home features a new HVAC system with programmable thermostat, new flooring, trim and fresh

    Wendy Fischer PREMIER SOTHEBYS INT'L REALTY

    13369 Gorgona Isle Dr, Windermere, FL 34786
  • /38

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    12804 Salomon Cove Dr, Windermere, FL 34786

    Experience elevated living in this beautifully updated Windermere townhome, where timeless design meets modern convenience. Fresh interior paint, plush new carpeting, new water heater, and a full array of new appliances—including refrigerator, dishwasher, stove, washer, and dryer—offer effortless, move-in-ready comfort.An elegant arched entry adds architectural charm, while the eat-in kitchen

    Beverly Bray Bluewater Realty Services LLC

    12804 Salomon Cove Dr, Windermere, FL 34786
  • /35

    $1,399,000

    • 5 Beds
    • 4.5 Baths
    • 3,082 Sq Ft

    106 Palm St, Windermere, FL 34786

    Set on a large, tree-lined lot just moments from historic downtown Windermere, this fully reimagined residence blends modern luxury with timeless charm—delivering a level of craftsmanship and detail that truly stands out. Every inch of this home has been thoughtfully redesigned, including a newly configured floor plan, all new interior doors and trim, and beautiful wide-plank flooring throughout.

    Jill Healey KELLER WILLIAMS WINTER PARK

    106 Palm St, Windermere, FL 34786
  • /22

    $1,460,000

    • 4 Beds
    • 4 Baths
    • 3,997 Sq Ft

    9548 Crown Prince Ln, Windermere, FL 34786

    Situated on a premier half-acre lot in highly desirable area of Windermere, this fully renovated 4-bedroom, 4-bath home offers a hard to find 'like-new' living experience. Every detail has been thoughtfully updated, featuring a chef’s kitchen with brand-new Thermador appliances, custom cabinetry, luxury vinyl plank flooring, and designer lighting throughout. The versatile floor plan includes an

    Jessica Oliveira LA ROSA REALTY LLC

    9548 Crown Prince Ln, Windermere, FL 34786
  • /32

    $1,495,000

    • 6 Beds
    • 4.5 Baths
    • 5,316 Sq Ft

    17521 Black Rail St, Windermere, FL 34786

    *** Now priced under $1.5M offering strong value at approximately $281/SF compared to similar Windermere homes*** PRIME opportunity for a LIKE NEW spacious MOVE-IN READY Windermere pool home just 1.5 miles from Windermere Preparatory School, and conveniently located near other top-rated public and private schools. Offering over 5,300 sq ft of thoughtfully designed living space, this 6 bedroom/4.5

    Rebecca Puig CHARLES RUTENBERG REALTY ORLANDO

    17521 Black Rail St, Windermere, FL 34786
  • /39

    $1,359,999

    • 5 Beds
    • 4.5 Baths
    • 4,257 Sq Ft

    11044 Hawkshead Ct Unit 2, Windermere, FL 34786

    Stunning home in the Reserve at Lake Butler Sound-Windermere. This luxury living at its finest located in the prestigious 24 hour guarded community. The property features 5 bedrooms, 4.5 bathrooms, a 3-car garage, and a private heated pool, perfect for relaxing or entertaining. The owner has invested more than $100,000 upgrades..... newly renovated kitchen boasts brand new cabinetry and

    Jennie Ho MAY HO REALTY

    11044 Hawkshead Ct Unit 2, Windermere, FL 34786
  • /31

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    5849 Soter Ln, Windermere, FL 34786

    Beautiful 3-bedroom, 2.5-bathroom townhome in the desirable Horizon West area. This spacious two-story home features an open-concept layout with a bright living and dining area that flows into the kitchen, perfect for everyday living and entertaining. Upstairs you’ll find a large primary suite with private bath and walk-in closet, along with two additional bedrooms and a full bathroom. Convenient

    Juliet Saldarriaga ORLANDO HOME DEALER LLC

    5849 Soter Ln, Windermere, FL 34786
  • /26

    $1,396,000

    • 6 Beds
    • 4.5 Baths
    • 3,794 Sq Ft

    13596 Gorgona Isle Dr, Windermere, FL 34786

    Stunning Two-Story Pool Home in Prime Windermere LocationWelcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space, and comfort. With 6 generously sized bedrooms and an open, airy design, this home is ideal for families seeking both elegance and functionality.The primary suite is a true retreat, featuring a

    Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    13596 Gorgona Isle Dr, Windermere, FL 34786
  • /68

    $1,369,000

    • 4 Beds
    • 3.5 Baths
    • 3,809 Sq Ft

    8375 Bowden Way, Windermere, FL 34786

    The kitchen has been recently upgraded with brand-new white quartz (Calacatta Belardo) countertops and backsplash, creating a bright, modern, and spacious feel. This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm,

    Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

    8375 Bowden Way, Windermere, FL 34786
  • /36

    $455,000

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    13742 Bravante Aly, Windermere, FL 34786

    Welcome to low maintenance living in the heart of Windermere’s sought after Vineyard Square community. A modern townhome built in 2017 with an OPEN FLOOR PLAN designed for easy everyday living and entertaining. Step inside to a bright and airy oasis with soaring ceilings on the main level, tile flooring throughout the first floor living areas, and generous windows that fill the home with natural

    Dustin Bragg MARK SPAIN REAL ESTATE

    13742 Bravante Aly, Windermere, FL 34786
  • /64

    $444,900

    • 3 Beds
    • 2.5 Baths
    • 1,997 Sq Ft

    13712 Summerport Village Pkwy, Windermere, FL 34786

    Location!!! Great price!!! Top-rated school district!!! and a Renovated!!! Property ready for you to move in or invest. High rental demand and low inventory, ideal for investors or families.Fresh paint inside and out, new carpets, new indoor A/C with warranty, rear entry 2-car garage with epoxy flooring, and a spacious driveway. Kitchen island, granite counters, breakfast bar, stainless

    Carines Hernandez Bustillo AGENT TRUST REALTY CORPORATION

    13712 Summerport Village Pkwy, Windermere, FL 34786
  • /31

    $1,475,000

    • 4 Beds
    • 4.5 Baths
    • 4,257 Sq Ft

    6443 Cartmel Ln, Windermere, FL 34786

    Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted Reserve at Lake Butler Sound community, this meticulously crafted residence epitomizes luxury living. Boasting classical architecture and spanning 4,257 square feet, this property offers a sophisticated retreat with unparalleled amenities. Upon entry, a raised travertine and marble foyer sets the tone for the

    Julie Bettosini STOCKWORTH REALTY GROUP

    6443 Cartmel Ln, Windermere, FL 34786
  • /100

    $1,490,000

    • 5 Beds
    • 4 Baths
    • 3,492 Sq Ft

    11339 Camden Park Dr, Windermere, FL 34786

    Luxury Pond-View Home in Keene’s Pointe – WindermereLocated in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom residence offers an exceptional combination of space, comfort, and scenic surroundings.The home features a thoughtfully designed floor plan with a private den/office, formal living and dining rooms, and expansive living areas

    Martonio Pinto AMERICAN HORIZONS REALTY

    11339 Camden Park Dr, Windermere, FL 34786
  • /45

    $1,650,000

    • 5 Beds
    • 5.5 Baths
    • 3,837 Sq Ft

    1087 Jack Nicklaus Ct, Kissimmee, FL 34747

    tunning, custom Bears Den property on an exceptional corner walled lot, backing onto a park for extra privacy, WITH ACTIVE REUNION MEMBERSHIP, & has 5 beds & 5.1 baths. This Bears Den property is absolutely breathtaking, offering an array of luxurious amenities and a meticulously designed living space. The impressive upgrades, including the high ceilings and engineered wood floors, create a sense

    Penny Stokes Hilton TOP VILLAS REALTY LLC

    1087 Jack Nicklaus Ct, Kissimmee, FL 34747
  • /44

    $1,299,000

    • 4 Beds
    • 3 Baths
    • 2,614 Sq Ft

    11608 Claymont Cir, Windermere, FL 34786

    Keene's Pointe - 24-hour gated/attended golf community in Windermere, Florida. Experience refined living in this beautifully updated 4-bedroom, 3-bathroom residence. Designed for both comfort and elegance, this home features thoughtful upgrades throughout and exceptional indoor-outdoor living. Enter through the custom iron doors to discover porcelain flooring throughout the home and gorgeous

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    11608 Claymont Cir, Windermere, FL 34786
  • /46

    $445,000

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft

    7644 Ripplepointe Way, Windermere, FL 34786

    Welcome to Lake Burden, one of Windermere’s most desirable and well-established communities! This corner-lot townhome offers 3 bedrooms, 2.5 bathrooms plus office. This open-concept floor plan that flows seamlessly with a well-appointed kitchen with granite countertops and backsplash, and a walk-in pantry. Large living room features high ceilings and tons of windows for natural light. French

    Kelly Zannini HOMEVEST REALTY

    7644 Ripplepointe Way, Windermere, FL 34786
  • /18

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    11636 Water Run Aly, Windermere, FL 34786

    This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

    Jose Jimenez EXP REALTY LLC

    11636 Water Run Aly, Windermere, FL 34786
  • /78

    $3,499,999

    • 5 Beds
    • 4.5 Baths
    • 4,417 Sq Ft

    5001 Latrobe Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own a stunning estate home in the prestigious Isleworth Golf & Country Club, perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features five spacious bedrooms, four-and-a-half

    Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

    5001 Latrobe Dr, Windermere, FL 34786
  • /26

    $1,000,000

    • Land
    • 0.5 Acre
    • $2,000,000 per Acre

    2504 Windermere Reserve Ct, Windermere, FL 34786

    Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

    Carolina Dumit CORCORAN PREMIER REALTY

    2504 Windermere Reserve Ct, Windermere, FL 34786
  • /49

    $1,200,000

    • 4 Beds
    • 4 Baths
    • 2,787 Sq Ft

    1361 Whitney Isles Dr, Windermere, FL 34786

    Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

    Gabriel Mantovani ALVES AND HOWELL REALTY

    1361 Whitney Isles Dr, Windermere, FL 34786
  • /44

    $750,000

    • 4 Beds
    • 3.5 Baths
    • 3,413 Sq Ft

    11903 Cave Run Ave, Windermere, FL 34786

    Stunning move-in ready home in the highly sought-after Windermere Trails community, located in a top-rated school district and just 2 miles from Walt Disney World! This beautifully upgraded 4-bedroom, 3.5-bath home features a gourmet kitchen with an oversized center island, custom solid wood cabinetry, granite countertops, built-in ovens, and a spacious walk-in pantry — perfect for entertaining

    Yan Zheng LOKATION

    11903 Cave Run Ave, Windermere, FL 34786
  • /2

    $575,000

    • Land
    • 0.47 Acre
    • $1,223,404 per Acre

    9802 6th St, Windermere, FL 34786

    Corner residential lot in Gotha. Small town charm near Windermere. No HOA. Shaded with Oaks. Easy access to 408 and Florida Turnpike. Great location, desirable schools and convenient to shopping, hospital, restaurants and more.

    Judy Plett UPSIDE REAL ESTATE INC

    9802 6th St, Windermere, FL 34786
  • /35

    $814,000

    • 4 Beds
    • 3.5 Baths
    • 3,044 Sq Ft

    7123 Calm Cove Ct, Windermere, FL 34786

    Beautifully updated 4-bedroom, 3.5-bath two-story home located on a quiet cul-de-sac in the highly sought-after Ashlin Park community of Windermere. This spacious residence offers a functional layout with generous living and dining areas, perfect for both everyday living and entertaining. The kitchen and main living spaces flow seamlessly toward the backyard, where you’ll enjoy the privacy of no

    Brandon McCarter RE/MAX PRIME PROPERTIES

    7123 Calm Cove Ct, Windermere, FL 34786
  • /42

    $769,900

    • 5 Beds
    • 3.5 Baths
    • 3,390 Sq Ft

    6615 Helmsley Cir, Windermere, FL 34786

    Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined

    Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

    6615 Helmsley Cir, Windermere, FL 34786
  • /34

    $389,000

    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft

    14215 Desert Haven St, Windermere, FL 34786

    Welcome to this stunning, move-in-ready townhome in the highly sought-after Windermere community of Oasis Cove at Lakeview Village. Boasting over 2,000 heated Sq. Ft. of meticulously maintained living space, this residence offers the perfect blend of modern updates and functional design. The first floor features a bright, open-concept living and dining area that flows seamlessly into a spacious

    Brandi Crain Iron Valley R.E.Osceola

    14215 Desert Haven St, Windermere, FL 34786
  • /71

    $1,199,000

    • 4 Beds
    • 3 Baths
    • 2,599 Sq Ft

    8351 Bowden Way, Windermere, FL 34786

    Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal

    Sharon Brandt KELLER WILLIAMS REALTY AT THE LAKES

    8351 Bowden Way, Windermere, FL 34786
  • /47

    $929,900

    • 5 Beds
    • 3.5 Baths
    • 3,717 Sq Ft

    12941 Westside Village Loop, Windermere, FL 34786

    Experience the elegance of Westside Village in Windermere, where timeless design meets modern luxury. This five-bedroom, four-bath residence spans 3,717 square feet of thoughtfully designed living space, built in 2018. The foyer welcomes you with porcelain tile floors, vaulted ceilings, and chandelier lighting that set a tone of quiet sophistication. French doors open to a versatile home office,

    Keren Reyes CENTURY 21 CARIOTI

    12941 Westside Village Loop, Windermere, FL 34786
  • /18

    $539,000

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    12863 Holdenbury Ln, Windermere, FL 34786

    Experience refined living in this impeccably upgraded residence located in Lakes of Windermere.This elegant 3-bedroom, 2-bathroom home showcases a seamless blend of modern sophistication and everyday comfort, featuring a thoughtfully designed split floor plan and no carpet throughout for a clean, contemporary aesthetic.From the moment you enter, you’re welcomed by light-filled living

    Maria Castro-Aversano LPT REALTY, LLC

    12863 Holdenbury Ln, Windermere, FL 34786
  • /4

    $395,000

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft

    8638 Brookvale Dr, Windermere, FL 34786

    Great opportunity to own this wonderful townhouse in the beautiful Lake Reams community near Disney World! This townhouse features 3bedrooms, 2.5 bathrooms, a 2-car garage, and a spacious courtyard for outdoor gatherings, a fully equipped kitchen that opens up into a living room. All bedrooms are located upstairs for privacy. The primary bedroom offers high ceilings and a spacious walk-in

    Karina Aumaitre AK GLOBAL REALTY LLC

    8638 Brookvale Dr, Windermere, FL 34786
  • /46

    $899,900

    • 4 Beds
    • 3.5 Baths
    • 3,424 Sq Ft

    13302 Roskin Ln, Windermere, FL 34786

    Welcome to this impeccably maintained former model home in Windermere, beautifully positioned on a premium corner lot in a quiet, highly desirable community and zoned for top-rated schools. Offering over 3,400 square feet with 4 bedrooms and 3.5 bathrooms, this home stands out for its smart use of space, generous room sizes, and the refined “model home” presentation that feels clean, polished,

    Xiaoyu Su RATIO REAL ESTATE, LLC

    13302 Roskin Ln, Windermere, FL 34786
  • /3

    $1,172,945 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,764 Sq Ft

    Deerfield Plan at Palms at Windermere, Windermere, FL 34786

    The Deerfield floorplan is a spacious two-story home designed for growing families, featuring 5 bedrooms and 3.5 bathrooms. This layout offers an ideal combination of private retreats and open gathering spaces. The first floor includes the primary bedroom suite, complete with a luxurious bathroom and walk-in closet, a separate study perfect for working from home, and an expansive great room

    Dream Finders Homes Builder
    14207 Crest Palm Ave Unit 36467792, Windermere, FL 34786
  • /11

    $998,000

    • Land
    • 1.07 Acres
    • $932,710 per Acre

    13125 Filly Ct, Lake Butler, FL 34786

    A Once In A Lifetime Opportunity to build your dream home in the heart of Windermere within a Private, Equestrian-Friendly Community * The Farms in Windermere consists of 14 larger than 1 Acre Homesites * Flanked by nearly 11 acres of Fully Fenced and Manicured Pasture and Riding Field, Stables, 2 Spring Fed Ponds and Towering Oaks providing shade for the Lucky Horses that make The Farms their

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    13125 Filly Ct, Lake Butler, FL 34786
  • /75

    $9,999,000

    • 6 Beds
    • 8 Baths
    • 6,783 Sq Ft

    6149 Grosvenor Shore Dr, Windermere, FL 34786

    Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    6149 Grosvenor Shore Dr, Windermere, FL 34786
  • /30

    $6,490,000

    • 6 Beds
    • 5.5 Baths
    • 6,706 Sq Ft

    1002 Down Reserve Ct, Windermere, FL 34786

    Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment

    Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    1002 Down Reserve Ct, Windermere, FL 34786
  • /60

    $639,900

    • 4 Beds
    • 3.5 Baths
    • 2,812 Sq Ft

    5224 Lemon Twist Ln, Windermere, FL 34786

    Welcome to one of the lowest-priced single-family home in the highly desirable Summerport community in Windermere. This well-maintained home features 4 bedrooms, 3.5 baths, a formal dining room, a private office, and a versatile loft/bonus space. Recent updates include a new roof (2021), fresh interior paint, and two new HVAC units (2023). The open-concept layout offers a spacious kitchen with

    Carmen Aridas RE/MAX PRIME PROPERTIES

    5224 Lemon Twist Ln, Windermere, FL 34786
  • /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
  • /69

    $2,868,000 Open House 4/15

    • 6 Beds
    • 6 Baths
    • 4,920 Sq Ft

    13304 Bellaria Cir, Windermere, FL 34786

    Some residences are simply houses. Others are a statement. Welcome to Casa Pietra — an exceptional estate nestled within Bellaria, one of Windermere's most exclusive guard-gated communities, where only 64 homes share the privilege of calling this address home. Set on nearly 3⁄4 of an acre with serene water views, this meticulously curated two-story residence offers just under 5,000 square feet of

    Caroline De Castro Marcellini COMPASS FLORIDA, LLC

    13304 Bellaria Cir, Windermere, FL 34786
  • /29

    $725,000

    • 4 Beds
    • 2 Baths
    • 2,373 Sq Ft

    17514 Black Rail St, Windermere, FL 34786

    New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and

    He Gao U S GLORY REALTY

    17514 Black Rail St, 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

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