Winter Garden, FL Homes for Rent with Pool

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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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  Explore Winter Garden

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  $6,500 per month

  • 5 Beds
  • 6 Baths
  • 4,025 Sq Ft
  • House for Rent

  10472 Petrillo Way, Winter Garden, FL 34787

  Now available for RENT, FOR SALE OR with a LEASE-PURCHASE OPTION. With nightly views of the Disney fireworks and access to top-rated schools, this is more than just a home — it’s a lifestyle you’ll love coming home to. Welcome to 10472 Petrillo Way, located in the serene Winding Bay Preserve community of Winter Garden. This stunning K. Hovnanian Grayson Model home, built in 2022, and offers the

  

  Alexis Bress

  EXP REALTY LLC

  (321) 405-1259

  10472 Petrillo Way, Winter Garden, FL 34787
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  $1,444 - $3,016 per month

  Integra Avalon

  1 - 3 Beds

  17825 Avalon Grove Loop, Winter Garden, FL 34787

  Experience the pinnacle of modern living at Integra Avalon, where every apartment blends sophistication and elegance. Nestled in the serene Four Corners Winter Garden, Florida, Integra Avalon embodies a refined lifestyle enhanced by premium amenities, state-of-the-art facilities, and a vibrant community atmosphere. Indulge in an unparalleled living experience where comfort and luxury seamlessly

  17825 Avalon Grove Loop, Winter Garden, FL 34787
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  $4,200 per month

  • 4 Beds
  • 3 Baths
  • 3,077 Sq Ft
  • House for Rent

  14556 Porter Rd, Winter Garden, FL 34787

  Live the resort lifestyle in sought-after Winter Garden! Your stunning 4-bedroom home with a private pool awaits.This beautifully updated 4-bedroom, 3-bathroom house is in one of Winter Garden's most desirable communities. Enjoy a private, caged pool, perfect for relaxing and entertaining. Inside, the home is entirely carpet-free, featuring high-end, water-resistant wood laminate flooring

  Ye Kang ONE STOP SERVICE REALTY INC

  14556 Porter Rd, Winter Garden, FL 34787
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  $1,621 - $2,455 per month

  Vida Winter Garden

  1 - 3 Beds

  1223 E Plant St, Winter Garden, FL 34787

  Indulge in modern and spacious living at Vida Winter Garden, offering 15 thoughtfully designed floor plans tailored to suit various lifestyles. Choose from studio, 1, 2, and 3-bedroom options, where open-concept designs create optimum space and comfort in every home. The authentic lifestyle you're after and the perfect place to put down your own roots. Enjoy life in a welcoming and diverse Winter

  1223 E Plant St, Winter Garden, FL 34787
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  $2,950 per month

  • 3 Beds
  • 2.5 Baths
  • 2,070 Sq Ft
  • Townhouse for Rent

  8078 Glenlloyd Ave, Winter Garden, FL 34787

  Welcome to this beautifully maintained 3-bed, 3-bath Townhome in the heart of Winter Garden’s highly desirable community. Built with contemporary styling and thoughtful upgrades, this residence offers an open-concept floor plan that seamlessly blends living, dining, and kitchen areas—perfect for entertaining or relaxing with family.Interior HighlightsSpacious kitchen with a large center

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  8078 Glenlloyd Ave, Winter Garden, FL 34787
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  $1,630 - $2,095 per month

  Prose Horizons Village

  1 - 2 Beds

  16810 Easthampstead Rd, Winter Garden, FL 34787

  Welcome home to Prose Horizons Village, a brand-new multifamily community located in Winter Garden, FL. Our spacious one and two-bedroom apartment homes feature modern stainless steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout, and full-sized washers and dryers in every apartment home. With convenient, must-have amenities like a fitness center,

  16810 Easthampstead Rd, Winter Garden, FL 34787
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  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Townhouse for Rent

  8926 Bismarck Palm Dr, Winter Garden, FL 34787

  Welcome to this pristine, barely lived-in 3 bedroom, 2.1 bath luxury townhome by Toll Brothers, located in the heart of Hamlin, Winter Garden. This immaculate home is ready for you to move right in, offering a spacious layout with gorgeous wood floors throughout, and an upgraded kitchen featuring high-end cabinetry, a large island perfect for gatherings, a natural gas cooktop, and a built-in

  Michelle Dunkley RE/MAX PRIME PROPERTIES

  8926 Bismarck Palm Dr, Winter Garden, FL 34787
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  $1,495 - $2,705 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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  $5,300 per month

  • 5 Beds
  • 4.5 Baths
  • 3,736 Sq Ft
  • House for Rent

  15702 Shorebird Ln, Winter Garden, FL 34787

  A BEAUTIFUL and IMMACULATE 5/4 single-family home is available for IMMEDIATE occupancy in the desirable Lakeshore Preserve community located in Winter Garden! This home was built by Toll Brothers in 2017. It features an open floorplan, large living spaces, natural lighting, ceiling fans, high ceilings on both levels of the home, crown molding, tray ceilings in selected rooms and gorgeous

  Cleve Loveland LOVELAND PROPERTIES

  15702 Shorebird Ln, Winter Garden, FL 34787
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  $1,554 - $2,190 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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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Townhouse for Rent

  16306 Prairie School Dr, Winter Garden, FL 34787

  Stunning Townhome in Prime Winter Garden Location – Hawksmoor Community, Near HamlinStep into this beautifully designed two-story townhome offering 3 spacious bedrooms and 2.5 bathrooms—where contemporary style meets energy-efficient living. The heart of the home is the modern kitchen, featuring granite countertops, 42” upper cabinets, stainless steel appliances, and an oversized island

  Babi Hennemann WRA BUSINESS & REAL ESTATE

  16306 Prairie School Dr, Winter Garden, FL 34787
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  $1,754 - $2,482 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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  $3,295 per month

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft
  • House for Rent

  669 Groves End Ln, Winter Garden, FL 34787

  Welcome home to this beautiful move in ready two story house located in wonderful Regency Oaks . This 4 bed/ 2.5 bath home features a crystal clear blue pool and a large 2 car garage. Formal living room, dining room and laundry are all centrally located on the first floor. Laundry room comes complete with washer, dryer, sink and storage cabinet. Cook up delicious meals in this gorgeous dream

  Justin V LaManna HOMEVEST REALTY

  669 Groves End Ln, Winter Garden, FL 34787
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  $1,599 - $2,115 per month

  Prose Avalon Pointe

  1 - 2 Beds

  14505 Tristan Cir, Winter Garden, FL 34787

  Welcome home to Prose Avalon Pointe, Orlando's newest multifamily community. Our spacious one- and two-bedroom apartments for rent in Winter Garden, FL, feature modern stainless steel appliances, walk-in closets, dining-sized kitchen islands, hardwood flooring throughout and full-sized washer and dryers in every apartment home. And with convenient, must have amenities like a fitness center,

  14505 Tristan Cir, Winter Garden, FL 34787
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  $2,800 per month

  • 4 Beds
  • 3 Baths
  • 1,512 Sq Ft
  • Townhouse for Rent

  14547 Pleach St, Winter Garden, FL 34787

  Welcome to this beautifully renovated townhome in the highly desirable community of Independence! This spacious property offers 4 bedrooms and 3 full bathrooms, including a convenient second master suite on the first floor. Interior highlights include porcelain tile flooring on the first floor, wood laminate on the second floor and stairs, a fully renovated kitchen with hardwood cabinets, quartz

  Reina Mendez REILE REALTY CORP

  14547 Pleach St, Winter Garden, FL 34787
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  $1,635 - $3,456 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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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,683 Sq Ft
  • Townhouse for Rent

  6322 Tabebuia Pkwy, Winter Garden, FL 34787

  Step into modern living with this brand new 3 bedroom, 2.5 bath townhome in the Silverleaf Oaks community of Winter Garden. Perfectly located just minutes from Disney and Central Florida’s best attractions, this home blends comfort, style, and convenience. Inside you will find a bright open floor plan with luxury vinyl plank flooring, quartz countertops, stainless steel appliances, and a spacious

  Homayoun Kamalimoghaddam LPT REALTY, LLC

  6322 Tabebuia Pkwy, Winter Garden, FL 34787
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  $1,670 - $3,182 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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  $3,400 per month

  • 4 Beds
  • 3.5 Baths
  • 2,988 Sq Ft
  • House for Rent

  15114 Gaulberry Run, Winter Garden, FL 34787

  2,988 sqft - 4B / 3.5B Best Property in Independence, next to Disney. Come live among multimillion dollar homes fronting Sky Lake Hancock (private ramp for residents). Best schools in Orange County (elementary inside the subdivision). Just painted and available August 23, 2025. See the Disney fireworks everyday from your home. Two excellent gyms, community pools and clubhouses. Come enjoy life in

  Claudia Salcedo CHARLES RUTENBERG REALTY ORLANDO

  15114 Gaulberry Run, Winter Garden, FL 34787
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  $1,805 - $2,820 per month

  Birchstone Waterleigh

  1 - 3 Beds

  9405 Ascend Falls Dr, Winter Garden, FL 34787

  Welcome to Birchstone Waterleigh, where luxury meets tranquility in the heart of Winter Garden, FL. Designed for those who seek the extraordinary, our community offers an elevated living experience with refined interiors, resort-inspired amenities, and thoughtfully curated experiences. From impeccably crafted apartments to exclusive social spaces, every detail embodies sophistication and

  9405 Ascend Falls Dr, Winter Garden, FL 34787
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  $2,700 per month

  • 3 Beds
  • 21.5 Baths
  • 1,683 Sq Ft
  • Townhouse for Rent

  6409 Breeze Filled Ln, Winter Garden, FL 34787

  Welcome to this brand new home in Silverleaf Oaks in Winter Garden! Enjoy this two story 3 bedrooms with 2.5 bathrooms and 2 car garage. Located in Horizon West community with proximity to top rated schools, and right in the heart of Orlando’s attractions, you will enjoy an array of amenities, including a resort-style pool, cabana, and playground, dog park, open green space and walking trails.

  Milena Valle VIVA ORLANDO REALTY INC.

  6409 Breeze Filled Ln, Winter Garden, FL 34787
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  $1,729 - $3,014 per month

  Solay Horizon West

  1 - 3 Beds

  9005 Solay Rd, Winter Garden, FL 34787

  Enjoy UP TO 8 WEEKS FREE on Select Homes! Live like youre on vacation every day at our brand new community, offering spacious apartments and the largest amenity offering in the area. With a dedicated onsite team, we are committed to providing exceptional customer service. Call or come by today!

  9005 Solay Rd, Winter Garden, FL 34787
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  $3,750 per month

  • 5 Beds
  • 3 Baths
  • 3,846 Sq Ft
  • House for Rent

  739 Cascading Creek Ln, Winter Garden, FL 34787

  AVAILABLE NOW...Fantastic, gated community with pool, playground, sports field, and community boat ramp/dock. This beautiful home is immaculate and offers 5 bedrooms and 3 full baths. The kitchen is nestled in the back, with an expansive breakfast bar overlooking the family room & boasts features such as 42" cabinets, all appliances. Sliding doors lead to the back yard. The master bedroom is a

  Claudia Montes LPT REALTY, LLC

  739 Cascading Creek Ln, Winter Garden, FL 34787
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  $2,575 - $3,295 per month

  Silverleaf Oaks

  3 - 5 Beds

  6496 Tabebuia Pkwy, Winter Garden, FL 34787

  Brand-new homes in a prime Winter Garden location near trails, shopping and public lagoons.Silverleaf Oaks features brand-new 3 to 5-bedroom, 2.5 to 3-bathroom homes. Located just outside Orlando, each home offers Smart Home technology, granite countertops and 2-car garages. Residents enjoy easy access to nearby retailers, scenic trails and public lagoons in Winter Garden. Silverleaf Oaks

  6496 Tabebuia Pkwy, Winter Garden, FL 34787
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  $5,500 per month

  • 6 Beds
  • 5 Baths
  • 3,632 Sq Ft
  • House for Rent

  5404 Golden Apple Dr, Winter Garden, FL 34787

  Welcome to 5404 Golden Apple Drive, an extraordinary 6-bedroom, 5-bathroom residence nestled in the Horizon West community of Winter Garden, FL. Built in 2021 by Dream Finders, this stunning home offers a perfect blend of luxury, comfort, and modern convenience, making it an ideal choice for those seeking a high-end rental experience. As you step inside, you'll be captivated by the expansive

  Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

  5404 Golden Apple Dr, Winter Garden, FL 34787
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  $1,800 - $3,180 per month

  Ascend Waterleigh Village

  1 - 3 Beds

  16200 Ascend Village Ln, Winter Garden, FL 34787

  Retreat to a life of ultimate luxury at Ascend Waterleigh Village, a brand-new community offering one, two, and three bedroom apartments in a beautiful lakeside neighborhood. Our open floor plans offer the perfect mix of form and function, with features ranging from modern kitchens with stainless steel appliances and prep islands to spacious bedrooms with oversized walk-in closets. As a resident,

  16200 Ascend Village Ln, Winter Garden, FL 34787
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  $2,550 per month

  • 3 Beds
  • 2.5 Baths
  • 2,036 Sq Ft
  • Townhouse for Rent

  13921 Easdale Alley, Winter Garden, FL 34787

  Discover your new home in the heart of Winter Garden! This stunning townhome offers modern living with a perfect blend of comfort and style.Key Features:Spacious Layout: Enjoy an open family/dining room combo with elegant tile and plush carpet flooring throughout.Gourmet Kitchen: Featuring all stainless steel appliances, a convenient breakfast bar, and a spacious pantry, this kitchen

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  13921 Easdale Alley, Winter Garden, FL 34787
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  $1,791 - $3,022 per month

  Vintage Horizon West

  1 - 3 Beds

  9223 Vintage Hills Way, Winter Garden, FL 34787

  Comfortable, sleek, and modern, Vintage Horizon West is your piece of paradise. Our spacious one, two & three-bedroom apartment homes provide comfort you'll love and the luxury you deserve. Enjoy a uniquely convenient neighborhood and a prime location offering access to Orlando's theme parks, shopping, dining, and entertainment. Each well-appointed floor plan boasts modern features and finishes

  9223 Vintage Hills Way, Winter Garden, FL 34787
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  $1,950 per month

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Condo for Rent

  1546 Broken Oak Dr Unit 201, Winter Garden, FL 34787

  Look no more! You have just found your home. This beautiful 2 bedroom and 2 bath with 1 car garage condo. No Carpets!!! Open floor plan with a living room/dining room combo. No neighbors above you or below you. This one you can't miss! Located in the gated community of Tucker Oaks, featuring a huge community pool. basketball courts, playground, BBQ & picnic area, fenced dog park, and walking

  Elisa Seixas WRA BUSINESS & REAL ESTATE

  1546 Broken Oak Dr Unit 201, Winter Garden, FL 34787
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  $1,653 - $3,310 per month

  The Haven at Lake Britt

  Studio - 3 Beds

  15145 Havencrest Cir, Winter Garden, FL 34787

  BRAND-NEW! Apply by September 30th and receive up to 2 months free! Looking for your next luxury, pet-friendly apartment home? Make your move even sweeter with these exclusive offers. For a limited time only. Tour today for details. Now leasing luxury apartments and two-car garage townhomes for rent in Winter Garden, FL, near Disney! Discover The Haven at Lake Britt, a brand-new upscale apartment

  15145 Havencrest Cir, Winter Garden, FL 34787
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  $2,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,544 Sq Ft
  • Townhouse for Rent

  15667 Boggy Oak Cir Unit B, Winter Garden, FL 34787

  Welcome to this beautifully maintained townhouse located in the highly sought after gated community of Tucker Oaks. This home features a 2-car garage, a kitchen island with pot rack, and a custom shower in the laundry area! Enjoy peaceful park views from your private patio, perfect for relaxing evenings.Upstairs, the owner’s suite boasts a tray ceiling, dual sink vanity, and a large walk-in

  Caridad Pool CHARLES RUTENBERG REALTY ORLANDO

  15667 Boggy Oak Cir Unit B, Winter Garden, FL 34787
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  $1,599 - $2,844 per month

  Registry on Grass Lake

  1 - 3 Beds

  14520 Avalon Rd, Winter Garden, FL 34787

  Welcome home to Registry on Grass Lake, our brand-new apartment community that prioritizes a connection to comfort & convenience through designer touches and thorough consideration of your needs. Enjoy your own space with our studio, one-, two-, and three-bedroom floor plans all thoughtfully curated to bring you the best of apartment living. Within Registry on Grass Lake, youll find amenities

  14520 Avalon Rd, Winter Garden, FL 34787
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  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Townhouse for Rent

  9473 Cinzel Alley, Winter Garden, FL 34787

  PERFECT Location in PERFECT Waterleigh Community at Horizon West in Winter Garden! CORNER LOT! Closed to Amazing community Park and Lake! 3 bedrooms + Loft/game room upstairs + 2.5 baths, 1814 sqft. Rent includes lawn maintenance and all appliance and all community amenities access. Graded school zone. Waterleigh is an amazing community, tons of amenities, including two clubhouses, four resort

  Jacky Liu YORK MILLS REALTY LLC

  9473 Cinzel Alley, Winter Garden, FL 34787
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  $1,514 - $1,929 per month

  Country Gardens

  1 - 3 Beds

  15122 W Colonial Dr, Winter Garden, FL 34787

  Stylish design at a price thats right! Country Gardens Apartment Homes is located in Winter Garden, Florida, with easy access to Florida's Turnpike and SR-50/Colonial Drive. You'll experience a top selection of amenities and features at this community, like a resort-style pool with sundeck, lake/pond views, and a heart-healthy cardio & fitness center. The leasing team is ready for you to come by

  15122 W Colonial Dr, Winter Garden, FL 34787
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  /22

  $4,800 per month

  • 5 Beds
  • 4.5 Baths
  • 3,793 Sq Ft
  • House for Rent

  14037 Pecan Orchard Dr, Winter Garden, FL 34787

  This beautiful 3,793 sq. ft. home in Orchard Park offers 5 bedrooms and 4.5 bathrooms, including a guest bedroom with an ensuite bath downstairs. The home features plantation shutters throughout, luxury vinyl flooring, new appliances, and freshly painted interiors. No carpet at all! The open kitchen, with granite countertops, oversized island, and walk-in pantry, is perfect for preparing meals

  Nadya Stringham NEARBY REALTY

  14037 Pecan Orchard Dr, Winter Garden, FL 34787
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  $1,725 - $2,750 per month

  Halston Waterleigh

  1 - 3 Beds

  10091 Tuller Loop, Winter Garden, FL 34787

  Step into a world of luxury at Halston Waterleigh, an upscale community in Winter Garden, Florida. Experience exquisite design, abundant natural light, advanced technology, and endless comfort in your new home. Enjoy a vacation-like atmosphere daily with our heated saltwater pool, expansive fitness center, and a variety of additional top-tier amenities. Schedule your personal tour today and

  10091 Tuller Loop, Winter Garden, FL 34787
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  $3,500 per month

  • 4 Beds
  • 4 Baths
  • 2,722 Sq Ft
  • House for Rent

  10031 Bedtime Story Dr, Winter Garden, FL 34787

  Welcome to 10031 Bedtime Story Drive—where comfort, convenience, and community come together in one incredible home. Perfectly positioned on a premium corner lot in the sought-after Storey Grove neighborhood, this spacious 4-bedroom, 4-bathroom residence offers over 2,700 square feet of upgraded living space on a generous quarter-acre lot with a 2-car garage. Inside, you’ll find fresh updates

  Tyler Somers KELLER WILLIAMS REALTY AT THE PARKS

  10031 Bedtime Story Dr, Winter Garden, FL 34787
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  $1,880 - $3,480 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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  $5,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,945 Sq Ft
  • House for Rent

  14423 Hampshire Bay Cir, Winter Garden, FL 34787

  Welcome to your new retreat in Bay Isle, Wintergarden, Florida! Tucked away in the exclusive gated community, this charming four-bedroom, four-bathroom home offered furnished. 3000 square feet of inviting living space, complete with a brand new finished pool and an extra-large yard. Step inside to discover a meticulously updated interior where every details thought of. From the elegant porcelain

  Lilivette Vasquez EXP REALTY LLC

  14423 Hampshire Bay Cir, Winter Garden, FL 34787

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