Winter Garden, FL Homes for Rent under $2,000

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  Starting at $1,483

  Total Monthly Price

  • 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,

  Prose Horizons Village

  

  16810 Easthampstead Rd, Winter Garden, FL 34787
• Explore Winter Garden

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  Starting at $1,682 Per Month

  • Studio - 3 Beds

  1223 E Plant St, Winter Garden, FL 34787

  Welcome to Vida Winter Garden, where modern living meets timeless charm. Nestled in the vibrant Gateway District of Winter Garden, our community offers a unique blend of luxury, convenience, and small-town warmth. With thoughtfully designed apartments, resort-style amenities, and easy access to local attractions, Vida Winter Garden is more than just a place to live—it's a place to thrive. Whether

  Vida Winter Garden

  

  1223 E Plant St, Winter Garden, FL 34787
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  Starting at $1,444 Per Month

  • 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. Homes ranging from one, two-, and three-bedroom spaces incapsulate the luxury

  Integra Avalon

  17825 Avalon Grove Loop, Winter Garden, FL 34787
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  Starting at $1,899

  Total Monthly Price

  • 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

  Windermere Cay

  

  8200 Jayme Dr, Winter Garden, FL 34787
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  Starting at $1,585

  Total Monthly Price

  • 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.

  Apollo Apartments

  

  7000 Kiran Patel Dr, Winter Garden, FL 34787
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  Starting at $1,464 Per Month

  • 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

  Halston Waterleigh

  

  10091 Tuller Loop, Winter Garden, FL 34787
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  Starting at $1,421

  Total Monthly Price

  • 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,

  Prose Avalon Pointe

  

  14505 Tristan Cir, Winter Garden, FL 34787
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  Starting at $1,599 Per Month

  • 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, you'll find amenities

  Registry on Grass Lake

  

  14520 Avalon Rd, Winter Garden, FL 34787
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  Starting at $1,480

  Total Monthly Price

  • 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

  IMT Sonoma Hills

  

  14619 Casita Ridge, Winter Garden, FL 34787
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  Starting at $1,450 Per Month

  • 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

  Birchstone Waterleigh

  

  9405 Ascend Falls Dr, Winter Garden, FL 34787
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  Starting at $1,605 Per Month

  • 1 - 3 Beds

  16200 Ascend Village Ln, Winter Garden, FL 34787

  Retreat to a life of ultimate luxury at Waterleigh Village Luxury Apartments , 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

  Waterleigh Village Luxury Apartments

  

  16200 Ascend Village Ln, Winter Garden, FL 34787
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  Starting at $1,733

  Total Monthly Price

  • 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.

  Homestead at Hamlin

  

  15100 Free Range Run, Winter Garden, FL 34787
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  Starting at $1,499

  Total Monthly Price

  • 2 Beds

  521 S Park Ave, Winter Garden, FL 34787

  Garden City Apartments is nestled in the heart of Downtown Winter Garden, Florida. Within walking distance or a quick golf cart ride to Historic Plant Street, life is full of excitement with local arts and entertainment, trails and restaurants galore you will surely feel at home and safe living in our newly renovated industrial designed family-friendly apartments. We have a mix between

  Garden City Apartments

  521 S Park Ave, Winter Garden, FL 34787
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  Starting at $1,604 Per Month

  • 1 - 3 Beds

  9005 Solay Rd, Winter Garden, FL 34787

  LIMITED TIME OFFER: 2 Month's FREE + $1,000 Gift Card* on select homes. Live like you're 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!

  Solay Horizon West

  

  9005 Solay Rd, Winter Garden, FL 34787
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  Starting at $1,840 Per Month

  • 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

  Lakewalk at Hamlin

  

  14012 Shoreside Way, Winter Garden, FL 34787
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  Starting at $1,711

  Total Monthly Price

  • 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.

  The Lodge at Hamlin

  

  6151 Lake Lodge Dr, Winter Garden, FL 34787
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  Starting at $1,399

  Total Monthly Price

  • 1 - 3 Beds

  15122 W Colonial Dr, Winter Garden, FL 34787

  Learn more about our current specials! Welcome home to Country Gardens, a premier residential community offering spacious apartments for rent in charming Winter Garden, Florida. Ideally situated with quick access to major thoroughfares like SR-50, Florida's Turnpike, and the SR-408 East-West Expressway, our neighborhood offers a

  Country Gardens

  

  15122 W Colonial Dr, Winter Garden, FL 34787
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  Starting at $1,099 Per Month

  • Studio - 2 Beds

  15300 W Colonial Dr, Winter Garden, FL 34787

  Welcome to Winterwoods, apartments in Winter Garden, FL. Rest easy knowing you will be in a great neighborhood with convenient access to all that Winter Garden has to offer. Our single-story, garden-style West Winter Garden apartments feature private entrances and patios for your enjoyment. We offer Studio, 1 & 2 bedroom apartments in Winter Garden near Fowler Groves Winter Garden

  Winterwoods

  

  15300 W Colonial Dr, Winter Garden, FL 34787
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  Starting at $1,850

  Total Monthly Price

  • 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

  Corban Horizon West

  

  15000 Stratus Loop, Winter Garden, FL 34787
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  Starting at $1,591 Per Month

  • Studio - 3 Beds

  14680 Westerly Dr, Winter Garden, FL 34787

  Luxury apartment living has never been easier than in your dream apartment home at The Westerly Apartments in Horizon West. Offering pet-friendly homes with modern interiors, abundant amenity spaces and an unparalleled location near Orlando's theme parks.With exceptional craftsmanship and attention to detail, our rentals offer a variety of studio, one, two, and three-bedroom layout to meet your

  The Westerly

  

  14680 Westerly Dr, Winter Garden, FL 34787
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  Starting at $1,460 Per Month

  • 1 - 3 Beds

  1301 Inland Seas Blvd, Winter Garden, FL 34787

  Inland Seas Apartments

  

  1301 Inland Seas Blvd, Winter Garden, FL 34787
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  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  12597 Clear Sapphire Dr, Winter Garden, FL 34787

  Property Id: 2797772 12597 Clear Sapphire Dr in Winter Garden, FL! This beautiful, fully furnished private efficiency offers the perfect combination of comfort, convenience, and an excellent location. Ideally suited for one female occupant. Located just 12 minutes from Disney and only a few minutes from Flamingo Crossings, shopping, restaurants, and entertainment. The

  12597 Clear Sapphire Dr, Winter Garden, FL 34787
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  $1,855 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,145 Sq Ft
  • House for Rent

  1198 Maxey Dr, Winter Garden, FL 34787

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist today.

  1198 Maxey Dr, Winter Garden, FL 34787
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  $1,000

  Total Monthly Price

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  15043 Evergreen Oak Loop, Winter Garden, FL 34787

  Looking for a tenant to share this big house. (1) Exclusive usage of a very spacious Master Bedroom Suite with a joint family lounge on the 2nd floor: queen size bed set, round nightstand, hardwood rectangular table and chair, two-drawer metal file cabinet, 2 storage cabinet, hardwood full size bookshelf, full bathroom facilities (bathtub and shower, toilet, dual-sink vanity cabinet, mirrored

  15043 Evergreen Oak Loop, Winter Garden, FL 34787
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  $1,800

  Total Monthly Price

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  1345 Winter Green Way, Winter Garden, FL 34787

  1345 Winter Green Way, Winter Garden, FL 34787
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  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • Apartment for Rent

  1301 Eastern Pecan Place Unit 208, Winter Garden, FL 34787

  Welcome to this beautifully maintained 2-bedroom, 2-bath condominium located in the highly desirable gated community of Southern Pines in Winter Garden. This spacious second-floor unit offers 1,264 square feet of comfortable living space with an open-concept layout that seamlessly connects the living, dining, and kitchen areas, creating the perfect space for everyday living and

  Neyla Alvarez EXP REALTY LLC

  1301 Eastern Pecan Place Unit 208, Winter Garden, FL 34787
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  $1,895 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • House for Rent

  407 Douglas Way, Winter Garden, FL 34787

  Minimum Deposit $1,895. Monthly Rent $1,895. Available now!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome home to this beautiful 2-bedroom, 2-bathroom residence in the highly desirable Winter Garden area! This

  407 Douglas Way, Winter Garden, FL 34787
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  $1,675 Per Month

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Townhouse for Rent

  508 Varsity St, Winter Garden, FL 34787

  Location, location, location! Hip patio villas situated on a quiet oak lined street featuring tile flooring throughout, granite counter tops. Huge rear yard with open brick patio & two parking pads. All located within close proximity of the picturesque historic downtown Winter Garden. Wonderful cafes, restaurants, theatre and the new Plant Street market and Crooked Can Brewing Company. AMAZING!!

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  508 Varsity St, Winter Garden, FL 34787
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  $1,795 Per Month

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • House for Rent

  53 Windtree Ln, Winter Garden, FL 34787

  This 2 bedroom and 2 bath condo is located on the first floor and it comes with tiled flooring throughout, all appliances, and fresh paint. Two assigned parking spaces for your convenience and beautiful amenities like pool, and basketball courts. Located at just minutes from Downtown Winter Garden and close to shopping, public transportation, and restaurants. Clean and ready for a great resident;

  53 Windtree Ln, Winter Garden, FL 34787
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  $1,690 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  14978 Lebeau Loop, Winter Garden, FL 34787

  Apartment for rent: one bedroom, one bathroom, with all utilities included. The apartment is above the property’s garage, fully furnished, and has a separate entrance. Only 6 minutes from Disney

  christian dellolio AGENT TRUST REALTY CORPORATION

  14978 Lebeau Loop, Winter Garden, FL 34787
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  $1,925 Per Month

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

  1642 Scarlet Oak Loop, Winter Garden, FL 34787

  You will enjoy the community pool, basketball courts, BBQ area, playground and a pet park in this amenity-rich gated community. Unit is centrally located quick access to the 408 & 417 and 429; The Winter Garden Village is just minutes away.Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management South Orlando

  1642 Scarlet Oak Loop, Winter Garden, FL 34787
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  $1,650 Per Month

  • 1 Bed
  • 1 Bath
  • 942 Sq Ft
  • Condo for Rent

  417 Southern Pecan Cir Unit 207, Winter Garden, FL 34787

  Ready to move-in One-bedroom, one Jack-n-Jill bath. Fully renovated with fresh paint from top to bottom. Luxury Vinyl floors from stairs thru out the unit. the Bathroom has ceramic tile. The unit features a study/den perfect if you have a home office or need a craft room.

  Maria Lloret HOMESMART

  417 Southern Pecan Cir Unit 207, Winter Garden, FL 34787
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  $1,850 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  200 Southern Pecan Cir, Winter Garden, FL 34787

  Welcome to this beautifully maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan features spacious living areas, granite countertops, abundant natural light, and a versatile den—perfect for a home office, study, reading room, or additional flex space.Enjoy low-maintenance living with

  200 Southern Pecan Cir, Winter Garden, FL 34787
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  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  1300 Eastern Pecan Place Unit 207, Winter Garden, FL 34787

  Enjoy resort-style living in this spacious second-floor condominium featuring 2 bedrooms, 2 bathrooms, and 1,276 square feet of living space. Located in the gated Southern Pines community, residents have access to an impressive selection of amenities, including a community pool and heated spa, a fitness center, indoor basketball and racquetball courts, a tennis court, a playground, outdoor

  Lauren Foley JULIAN PROPERTIES, INC.

  1300 Eastern Pecan Place Unit 207, Winter Garden, FL 34787
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  $1,495 Per Month

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • House for Rent

  502 Dunbar Ave, Winter Garden, FL 34787

  SPECIAL $300 OFF THE 1ST MO RENT IF YOU SIGN A LEASE BEFORE 8/31SECTION 8 WELCOME! Remodeled 2 Bed/1 Bath with Modern Touches in Winter Garden! Step into the comfort of this delightful 2-bedroom, 1-bath gem nestled in Winter Garden. This recently remodeled residence now boasts modern elegance and a functional design.As you enter, you are greeted by an inviting separate

  502 Dunbar Ave, Winter Garden, FL 34787
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  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • House for Rent

  16042 Micelli Dr, Winter Garden, FL 34787

  Beautiful corner-lot property for rent in Winter Garden!The property features a separate 1-bedroom, 1-bath apartment (approximately 561 sq. ft.), AVAILABLE IMMEDIATELY for $1,600/month. The apartment has a private entrance, designated access, a washer and dryer, and electricity, water, and internet are included in the rent.Schedule your private showing today!

  Sheyla Fernandez Cardenas MELIN REALTY LLC

  16042 Micelli Dr, Winter Garden, FL 34787
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  $1,495 Per Month

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • House for Rent

  36 Windtree Ln, Winter Garden, FL 34787

  Great location! 2nd floor condo in Winter Garden offers 918 square feet of living space, split floor plan, tile, and two assigned parking spaces. Rental application is $75 per lease holder that will run a credit check, criminal background, and a rental history. We also do verify income, so between the lease holders combined together will have to make three times the monthly rent

  36 Windtree Ln, Winter Garden, FL 34787
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  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 738 Sq Ft
  • Condo for Rent

  234 Southern Pecan Cir Unit 202, Winter Garden, FL 34787

  Charming 1-bedroom, 1-bathroom apartment with a private 1-car garage, ideally located just minutes from the heart of Downtown Winter Garden. This inviting home features a functional layout, a private garage for convenient parking and additional storage, and an unbeatable location in one of Central Florida's most desirable communities. Enjoy being just minutes from local restaurants, coffee shops,

  Michele Saenz NOVA REAL ESTATE SERVICES INC

  234 Southern Pecan Cir Unit 202, Winter Garden, FL 34787
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  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • Condo for Rent

  108 Windtree Ln Unit Building N, Winter Garden, FL 34787

  Welcome to our available 2BR/2BA, 918 sqft condo, located on the second floor of the Windtree Gardens community in desirable Winter Garden FL. Upon entry, you'll be greeted by the open living space. The kitchen overlooks the living and dining rooms and contains a full suite of appliances including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop space. Off to the

  108 Windtree Ln Unit Building N, Winter Garden, FL 34787
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  $1,850 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  200 Southern Pecan Cir Unit 206, Winter Garden, FL 34787

  Welcome to this beautifully maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan features spacious living areas, granite countertops, abundant natural light, and a versatile den—perfect for a home office, study, reading room, or additional flex space.Enjoy low-maintenance living with

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  200 Southern Pecan Cir Unit 206, Winter Garden, FL 34787

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