Homes for Rent near Windermere Preparatory School

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  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Condo for Rent

  8179 Maritime Flag St Unit 210, Windermere, FL 34786

  3 bedroom, 2 bath condo on second floor. Carpet in living areas. Large pantry in kitchen and second storage closet. Easy access to major road and minutes to Disney. Community offers many amenities. Open floor plan. W/D in unit.

  

  Licinio Cruz

  L & L REALTY GROUP

  (407) 901-9373

  8179 Maritime Flag St Unit 210, Windermere, FL 34786
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  Explore Windermere Preparatory School

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  /35

  $3,600 per month

  • 4 Beds
  • 3.5 Baths
  • 2,836 Sq Ft
  • House for Rent

  6904 Corley Ave, Windermere, FL 34786

  Rare Windermere rental offering five private quarters, including 4 designated bedrooms plus an additional flex space ideal for office, guest use, or playroom PLUS large loft on 2nd floor. Extraordinary floorplan features a Jack and Jill bathroom upstairs, open living areas, and excellent flow throughout.Set on a desirable corner lot, this 2,836 sq ft home includes laminated wood flooring,

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (407) 606-7838

  6904 Corley Ave, Windermere, FL 34786
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  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • House for Rent

  15149 Night Heron Dr, Winter Garden, FL 34787

  Welcome to the highly sought-after Summerlake community in Horizon West! This beautiful home offers 3 bedrooms, 2.5 baths, and nearly 2,200 square feet of open living space, complete with a spacious backyard perfect for relaxation or entertaining. The modern kitchen is a chef’s dream, featuring a large center island, stainless steel appliances, a gas stove, a walk-in pantry, and ample storage.

  

  Cui Li

  RATIO REAL ESTATE, LLC

  (321) 495-6951

  15149 Night Heron Dr, Winter Garden, FL 34787
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  $3,250 per month

  • 4 Beds
  • 3.5 Baths
  • 2,853 Sq Ft
  • House for Rent

  5922 Grassy Point Rd, Winter Garden, FL 34787

  Experience effortless living in this captivating 4-bedroom home, perfectly situated at the highly desirable crossroads of Windermere and Winter Garden. Enjoy immediate access to a vibrant, established community brimming with local shopping, dining, and easy connections to interstate highways just moments away. Settle in by the weekend and revel in the simplicity of having cable, internet, and

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (321) 414-9885

  5922 Grassy Point Rd, Winter Garden, FL 34787
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  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  5800 Marleon Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Experience luxury Florida living at its finest in this stunning one-story custom home, perfectly situated on nearly an acre in the sought-after Lake Cypress Cove community of Windermere. With approximately 3,000 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom split floor plan offers both privacy and an open, inviting

  

  Eric Bress, Jr

  ERIC BRESS REAL ESTATE LLC

  (407) 871-6125

  5800 Marleon Dr, Windermere, FL 34786
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  $13,500 per month

  • 5 Beds
  • 6.5 Baths
  • 5,104 Sq Ft
  • House for Rent

  4302 Isabella Cir, Windermere, FL 34786

  Welcome to Casabella at Windermere, a private gated community where Spanish-inspired architecture meets modern luxury. This solar-powered estate offers 5 bedrooms, 6.5 bathrooms, and nearly an acre of beautifully landscaped grounds. Designed for a turnkey lifestyle, the home features hardwood floors, soaring ceilings, and high-quality finishes throughout. The gourmet kitchen includes KitchenAid

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (407) 783-8539

  4302 Isabella Cir, Windermere, FL 34786
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  $1,554 - $2,170 per month

  Apollo Apartments

  Studio - 2 Beds

  7000 Kiran Patel Dr, Winter Garden, FL 34787

  Apollo boast four stunning buildings that usher in a variety of iving spaces, including spacious studios, stylish one-bedroom, and comfortable two-bedroom apartments. Discover elegant kitchen islands, oversized windows that fill your space with natural light, and modern fixtures that add a touch of sophistication to every room.

  7000 Kiran Patel Dr, Winter Garden, FL 34787
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  $3,990 per month

  • 5 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  2732 Balforn Tower Way, Winter Garden, FL 34787

  Welcome to rent this amazing opportunity in Stoneybrook West a Golf gated community offering a perfect blend of modern design and comfortable living. Upgraded bathrooms, NO carpet, ceramic tile, a In-laws about 250 SQFT private space and full bathroom and upstairs 4 bedrooms, 2 bathrooms. You will love ample family room and kitchen with a dining area overlooking a conservation area and a screen

  Zaira Mejia SPACES & STYLES GROUP

  2732 Balforn Tower Way, Winter Garden, FL 34787
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  $1,669 - $3,625 per month

  Homestead at Hamlin

  1 - 3 Beds

  15100 Free Range Run, Winter Garden, FL 34787

  There’s no place like Home(stead). Inspired by nature’s bounty, our thoughtfully designed one, two, and three-bedroom apartment residences blend perfect neutral tones and ample natural light to create spaces that help you discover the joy of simply being.

  15100 Free Range Run, Winter Garden, FL 34787
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  /20

  $18,000 per month

  • 7 Beds
  • 6 Baths
  • 4,834 Sq Ft
  • House for Rent

  4303 Isabella Cir, Windermere, FL 34786

  Best Value in Casabella — Fully Furnished & Move-In Ready!Step into effortless luxury in this beautifully furnished residence, where elegant design meets everyday comfort. Soaring windows fill the space with natural light, highlighting stylish interiors and thoughtfully curated furnishings throughout.The open-concept layout is perfect for both relaxing and entertaining, with a chef’s

  Elisa Mroz WRA BUSINESS & REAL ESTATE

  4303 Isabella Cir, Windermere, FL 34786
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  $1,895 - $2,795 per month

  Arya at Windermere 55+ Active Adult Living

  1 - 2 Beds

  1231 Arya Way, Ocoee, FL 34761

  Enjoy a vibrant lifestyle at Arya at Windermere, a 55+ community in Ocoee, FL offering unparalleled luxury amenities, including a massage room, steam room, outdoor putting green and a micro market. Arya features open concept 1 and 2-bedroom apartments with chef-inspired kitchens, granite countertops, stainless steel appliances, breakfast bar, wood-style plank floors, walk-in shower, washer and

  1231 Arya Way, Ocoee, FL 34761
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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,523 Sq Ft
  • Townhouse for Rent

  7702 Anselmo Ln, Windermere, FL 34786

  For rent is this nice modern townhome with a 2 car garage. Solid floor throughourt. Ni carpet. Great area with Windermere schools.

  Hans Welbergen WINDERMERE INTERNATIONAL REALTY

  7702 Anselmo Ln, Windermere, FL 34786
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  $1,527 - $2,477 per month

  Talcott at Windermere

  1 - 3 Beds

  5820 Nature View Dr, Windermere, FL 34786

  With thoughtful design and exclusive amenities, Talcott at Windermere, is your premier destination for luxury living in Windermere, Florida! Our luxury one, two, and three-bedroom apartments, ranging up to 1,380 square feet, redefine luxury with a range of modern interior features. Step into a home with soaring 9 foot ceilings, a stylish two-tone paint scheme, wood-style flooring, and AirPlay

  5820 Nature View Dr, Windermere, FL 34786
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  $3,000 per month

  • 4 Beds
  • 2 Baths
  • 2,211 Sq Ft
  • House for Rent

  13218 Charfield St, Windermere, FL 34786

  PET FRIENDLY **4 BEDROOMS **2 Bathrooms ** 2-car Garage **FENCED BIG YARD **COMMUNITY POOL (walking distance). The MAIN homeis on the FIRST FLOOR with ELEGANT *9FT CEILINGS * & *LOTS OF WINDOWS!!! and **ONLY the 4th Bedroom** which also can be used as aSECLUDED OFFICE with immediate access from the MAIN DOOR is located UPSTAIRS. EXTRA OUTDOOR ROOMS to Enhace your Florida

  Avi Maganda EMPIRE NETWORK REALTY

  13218 Charfield St, Windermere, FL 34786
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  $1,670 - $3,840 per month

  Addison At Windermere

  1 - 3 Beds

  13644 Tortona Ln, Windermere, FL 34786

  Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

  13644 Tortona Ln, Windermere, FL 34786
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  $3,095 per month

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • House for Rent

  12824 Penshurst Ln, Windermere, FL 34786

  Beautiful 3 bedrooms, 2.5 bathroom, plus an office/den. This one-story, Single-family home, is located in the highly desired community of Lakes of Windermere. This home offers a split floor plan, 2 bedrooms in the front of the home with a full bathroom in between, and a linen closet. The Dining room features a built-in wine rack, the open and airy kitchen has plenty of storage plus all

  Linda Jaramillo DON ASHER & ASSOCIATES, INC.

  12824 Penshurst Ln, Windermere, FL 34786
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  /25

  $1,505 - $2,750 per month

  IMT Sonoma Hills

  1 - 3 Beds

  14619 Casita Ridge, Winter Garden, FL 34787

  IMT Sonoma Hills’ stunning one, two and three-bedroom apartments will take your breath away with a new level of luxury for West Orlando. Inside each home are five-star features and amenities, including spacious walk-in closets, gourmet kitchens with granite countertops, soaring ten-foot ceilings and sophisticated designer finishes. Start a tour of IMT Sonoma Hills and it won’t take long to

  14619 Casita Ridge, Winter Garden, FL 34787
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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Townhouse for Rent

  17097 Water Spring Blvd, Winter Garden, FL 34787

  This brand-new 3-bedroom, 2.5-bath townhome in Winter Garden offers the perfect blend of comfort and convenience near the magic of Disney. The spacious master suite provides a private retreat, while the community amenities—including a pool, fitness center, sports courts, and dog park—create a vibrant lifestyle for all. Ideally located near Publix and within the Orange County school zone, 17097

  Mariana Nossa WRA BUSINESS & REAL ESTATE

  17097 Water Spring Blvd, Winter Garden, FL 34787
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  $1,519 - $4,094 per month

  Kestra

  1 - 3 Beds

  10387 Vista Oaks Ct, Orlando, FL 32836

  Welcome to KestraWhen it comes to choosing an apartment, expected shouldn't be the status quo. At Kestra, we've redefined the norm and raised the bar, providing residents with the opportunity to live a more distinctive lifestyle. To discover something unexpected. To outgrow average and to excel at living. To connect with home, naturally.

  10387 Vista Oaks Ct, Orlando, FL 32836
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  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,834 Sq Ft
  • House for Rent

  10726 Reams Rd, Windermere, FL 34786

  Renovated earlier this year, this beautiful 3-bedroom, 2.5-bathroom home combines modern updates with the charm of Windermere Trails living.. With 1,834 sq. ft. of thoughtfully designed living space across two levels, this home offers a perfect blend of modern upgrades and everyday comfort. Step inside to a bright, open floor plan featuring brand-new luxury vinyl flooring on the main level and

  Jessica Souza Meuli WRA BUSINESS & REAL ESTATE

  10726 Reams Rd, Windermere, FL 34786
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  $1,738 - $2,547 per month

  Windermere Cay

  1 - 3 Beds

  8200 Jayme Dr, Winter Garden, FL 34787

  So close yet a world away. Windermere Cay, the premier luxury and 100% Smoke-Free community is NOW OPEN! We are conveniently located on Reams Road, adjacent to Walt Disney World, just minutes from Orlando International airport, area theme parks, Winter Garden Village, Millenia Mall, and much more. Our four-story buildings offer elevators, high-end details, finishes, and an exclusive resident

  8200 Jayme Dr, Winter Garden, FL 34787
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  /45

  $3,950 per month

  • 5 Beds
  • 3 Baths
  • 3,436 Sq Ft
  • House for Rent

  13145 Moro Ct, Winter Garden, FL 34787

  Welcome to your new home in Winter Garden! This spacious 5-bedroom, 3-bath home is designed for comfort and convenience. With a versatile layout that includes two living rooms, a formal dining room, and a large upstairs loft, there’s plenty of room for everyone to spread out.The kitchen and main living areas feature tile flooring, while the bedrooms and loft have plush carpet for a cozy feel.

  Stacey Payne PREFERRED REAL ESTATE BROKERS

  13145 Moro Ct, Winter Garden, FL 34787
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  $1,554 - $2,790 per month

  Citra at Windermere

  1 - 3 Beds

  11353 Citra Cir, Windermere, FL 34786

  Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay Lake

  11353 Citra Cir, Windermere, FL 34786
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  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,075 Sq Ft
  • Condo for Rent

  7863 Sugar View Ct Unit 7863, Orlando, FL 32819

  This fully furnished 2 bed 2 bath Condo is located in the desirable Dr Phillips area and has quick access in walking distance to the Dr Phillips luxurious YMCA, shopping and the world Famous restaurant row. This condo with screened balcony overlooking a relaxing conservation is a must see. The home comes with a 1 car garage and small driveway for parking. This home has been completely tiled

  Donald Robinson KING CORNERSTONE REALTY

  7863 Sugar View Ct Unit 7863, Orlando, FL 32819
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  $1,733 - $4,480 per month

  Zen

  1 - 3 Beds

  9835 Namaste Loop, Orlando, FL 32836

  Theres a home waiting for you at ZEN! This luxurious midrise apartment community features one, two and three-bedroom apartment homes, located near the Grand Cypress Golf Course.Peaceful yet invigorating, ZEN exceeds traditional apartment living in every way. Our modern residences offer designer touches, sufficient craftsmanship and eco-friendly aspects that are not only beautiful, savvy and

  9835 Namaste Loop, Orlando, FL 32836
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  $3,299 per month

  • 4 Beds
  • 3.5 Baths
  • 2,836 Sq Ft
  • House for Rent

  12992 Holdenbury Ln, Windermere, FL 34786

  Available for immediate move in! Windermere Terrace is one of the most sought after developments and is nestled among the lakes of Florida. Great spacious floor plan with 4 bedrooms, and 3.5 baths, featuring a downstairs Master bedroom! Kitchen features granite counters, Stainless-steel appliances with 36-inch cabinets and huge island offering tons of counter space. This home also has a sunny

  Steve Simpson 407 PROPERTIES

  12992 Holdenbury Ln, Windermere, FL 34786
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  $1,726 - $6,073 per month

  Venetian Isle

  1 - 3 Beds

  6506 San Francesco Way, Windermere, FL 34786

  A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication youll find awe-inspiring day and night.

  6506 San Francesco Way, Windermere, FL 34786
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  $5,200 per month

  • 5 Beds
  • 4 Baths
  • 2,872 Sq Ft
  • House for Rent

  6926 Cucamelon Ct, Windermere, FL 34786

  A rare opportunity to lease a beautiful home either furnished or unfurnished with solar panels! This property shines with lifestyle features in the very sought-after neighborhood of Sanctuary Lakes in Windermere upon entering, this home is luxury, convenience and the genuine feeling of home with integrated smart home features. Offering a formal dining room and 1st floor en suite for guests or can

  Dana Adams CENTURY 21 CARIOTI

  6926 Cucamelon Ct, Windermere, FL 34786
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  /23

  $1,704 - $3,296 per month

  Corban Horizon West

  1 - 3 Beds

  15000 Stratus Loop, Winter Garden, FL 34787

  Take the next step in life at Corban Horizon West. A place that draws inspiration from the warmth of the neighborhood and the endless possibilities that surround it, our homes offer a refreshing experience guaranteed to exceed your expectations for modern living. Timeless yet contemporary. Comfortable yet connected. Our residences are a wonderful blend of tasteful design, thoughtful amenities and

  15000 Stratus Loop, Winter Garden, FL 34787
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  $15,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,339 Sq Ft
  • House for Rent

  6844 Valhalla Way, Windermere, FL 34786

  Beautiful and fully furnished home in Keene's Pointe golf community. Guard gated community. A Tuscan style luxury home with a large covered back patio with fireplace and large pool overlooking the 14th green Bear Club. Master and extra suite on first floor and three more suites upstairs. This house has a very big loft, perfect for entertaining.

  Marilene Auge CHARLES RUTENBERG REALTY ORLANDO

  6844 Valhalla Way, Windermere, FL 34786
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  $1,738 - $3,392 per month

  The Lodge at Hamlin

  1 - 3 Beds

  6151 Lake Lodge Dr, Winter Garden, FL 34787

  It’s human nature to want everything at your fingertips. It’s rare to find it. Tucked between the water, sunshine, and cypress trees, discover The Lodge at Hamlin. With nature surrounding you at home and a lakefront village at your doorstep, your hunt for the perfect lifestyle begins and ends here.

  6151 Lake Lodge Dr, Winter Garden, FL 34787
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  $5,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,312 Sq Ft
  • House for Rent

  13106 Orange Isle Dr, Windermere, FL 34786

  Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

  Gladys Bezerra FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  /50

  $1,800 - $3,525 per month

  Lakewalk at Hamlin

  1 - 3 Beds

  14012 Shoreside Way, Winter Garden, FL 34787

  Warm lake breezes and sunshine define the luxe lakeside lifestyle of the Lakewalk apartment residences that will wrap the shoreline of Lake Hancock next to the Town Center’s shopping, dining and entertainment. We offer 1 bedroom, 2 bedroom, and 3 bedroom apartment homes with the most up-to-date luxurious furnishings. If you are looking for relaxing, luxury living, look no further than Lakewalk at

  14012 Shoreside Way, Winter Garden, FL 34787
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  $2,995 per month

  • 4 Beds
  • 2 Baths
  • 2,063 Sq Ft
  • House for Rent

  9149 Palm Tree Dr, Windermere, FL 34786

  Hard to find 4 bedroom 2 Bath Pool home in Windermere with over 2000 Square feet. Close proximity to Olympia High School. Nice open floor plan and a large, screened porch off the back of the back overlooking the pool. Fully privacy fenced back yard and pets are considered. This property is very clean and include upgrades such as Granite and travertine floors. Large 2 car Garage and plenty of

  Charles Woolley BHHS FLORIDA REALTY

  9149 Palm Tree Dr, Windermere, FL 34786
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  $1,401 - $2,355 per month

  Windermere at Lakes Edge Apartments

  1 - 3 Beds

  2415 Treasure Landing Pkwy, Ocoee, FL 34761

  Theres no place like these coastal-inspired homes at Windermere at Lake's Edge in Ocoee, FL. Come experience the difference in our spacious one-, two-, and three-bedroom apartments and townhomes complete with private patios, washers and dryers, and vinyl plank flooring. As a resident of our community, youll enjoy modern amenities like a resort-style swimming pool, grilling station, and fitness

  2415 Treasure Landing Pkwy, Ocoee, FL 34761
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  /20

  $5,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,483 Sq Ft
  • House for Rent

  11905 Camden Park Dr, Windermere, FL 34786

  This rare opportunity for a lovely two-story rental home in Keene's Pointe is now available to show and move in ready today - October 1, 2025. Terrific floor plan boasts 4BR/4.5 Baths + office + bonus room and a 3 Car Garage. Primary Suite is located on the man floor with all other bedrooms on the second floor along with the bonus room. Enjoy the great privacy this location offers as well as a

  Angela Durruthy KEENE'S POINTE REALTY

  11905 Camden Park Dr, Windermere, FL 34786
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  /25

  $1,640 - $2,578 per month

  Casa Mirella

  1 - 3 Beds

  101 Casa Mirella Way, Windermere, FL 34786

  Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind

  101 Casa Mirella Way, Windermere, FL 34786
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  /15

  $2,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,385 Sq Ft
  • Townhouse for Rent

  11377 Evesham Dr, Windermere, FL 34786

  Available Now! Stunning 2BR/2.5BA in the desirable community of Preston Square in Windermere. The main level includes a Great Room that opens to a private brick-paver courtyard, ideal for entertaining. The kitchen boasts granite countertops, dinette area, and A half bath, laundry room with washer and dryer included, and access to the attached 2-car garage. Upstairs, the primary suite offers a

  Barry Jamieson JAMIESON PROPERTIES, INC.

  11377 Evesham Dr, Windermere, FL 34786
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  $1,932 - $2,820 per month

  Overture Hamlin 55+ Active Adult Apartment...

  1 - 2 Beds

  5795 Citrus Village Blvd, Winter Garden, FL 34787

  Schedule your in-person or virtual tour today! Walk-ins are also welcome!

  5795 Citrus Village Blvd, Winter Garden, FL 34787
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  /18

  $2,550 per month

  • 3 Beds
  • 2.5 Baths
  • 1,724 Sq Ft
  • Townhouse for Rent

  7230 Shadeview Alley, Windermere, FL 34786

  Beautiful 3/2.5 townhouse at Ashlin Park in the heart of Windermere. Community Pool, Club House, Playground, Conservation areas, ponds, access to bike trail and just at walking distance from Restaurants and market places. Right next to the 535 road, one mile away from Publix and commercial development with many new restaurants. MUST SEE!

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  7230 Shadeview Alley, Windermere, FL 34786

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