Winter Garden Single Family Homes For Rent - 100 homes

Remarks: Imagine starting your mornings beneath towering oak trees in the heart of the Winter Garden Historic District, where life moves just a little slower and neighbors still wave as they pass by in their golf carts. Tucked away on a quiet dead-end street in the sought-after Winter Garden Golf Cart District, this spectacular rental offers a rare opportunity to live in one of the most beloved pockets of town—on a street where homes seldom become available for rent. Set on a massive lot with an incredible backyard oasis, the property is surrounded by lush landscaping and mature fruit trees, creating a private retreat that feels worlds away while still being just minutes from the vibrant heart of downtown. Inside, the solid block home welcomes you with timeless charm, featuring pristine terrazzo floors and a dramatic wood-burning fireplace that anchors the spacious family room—perfect for cozy evenings or gathering with friends. The home offers generous living spaces with large formal living and dining rooms, ideal for entertaining or simply spreading out and enjoying the comfort of home. Step outside to an enormous covered and screened rear porch where you can relax with your morning coffee, host weekend barbecues, or unwind as the Florida breeze moves through the trees and across the expansive backyard. Beyond the main home, the property continues to impress with a full two-car garage, plus a separate backyard workshop complete with power and A/C—perfect for hobbies, projects, or additional workspace. A large secured wrap-around covered storage shed provides even more room for tools, equipment, or recreational gear. Living here means embracing the lifestyle that has made Winter Garden one of Central Florida’s most desirable communities. Just a quick golf cart ride away, you’ll find the brick-lined charm of Plant Street, where local restaurants, boutiques, and entertainment create a lively small-town atmosphere. Spend evenings enjoying live music and craft beer at Crooked Can Brewing Company, or start your Saturdays exploring the famous Winter Garden Farmers Market, consistently ranked among the best in the region. With year-round events, incredible dining, unique shops, and the charm of historic downtown just minutes away, this home offers more than a place to live—it offers a lifestyle. Opportunities like this rarely come along in the Historic District. Schedule your showing today and start living the authentic Winter Garden life.

Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)

Listing Agent: Joshua Brown (407-936-5344)

Remarks: This spacious and beautifully maintained one-story home offers 3 bedrooms, 2 baths, and a 2-car garage with approximately 2,300 sq. ft. of living space. The thoughtfully designed floor plan features an open-concept layout perfect for both everyday living and entertaining. The large kitchen is a true centerpiece, complete with a generous granite island, stainless steel appliances, 42” cherry cabinets, a butler’s pantry, and a walk-in pantry, plus a bright breakfast nook. Granite countertops are featured throughout all bathrooms. The home also includes a formal dining room and an expansive family room that seamlessly connects to the kitchen for an airy, open feel. The primary suite boasts a large garden tub, creating a relaxing retreat. Tile flooring runs through all main living areas, with comfortable carpeting in the bedrooms. Additional highlights include an indoor utility room with washer and dryer included, and a private backyard with no rear neighbors. Enjoy resort-style community amenities, including a clubhouse, pool, fitness center, splash pad, boat dock, bike trails, picnic areas, and lake access. Lawn care is included for added convenience. Ideally located with easy access to the 429, Turnpike, and 408, providing a quick commute to Downtown Orlando, the airport, and surrounding attractions. Zoned for excellent schools and offering nightly views of Disney fireworks—this home truly has it all!

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Courtney James (321-228-6181)

Remarks: Beautiful 5BD/3BA home in the desirable Summerlake community of Winter Garden. This spacious 3,295 sq ft home features an open floor plan, large kitchen overlooking the family room, loft/bonus area upstairs, and a 3-car garage. Enjoy resort-style amenities including pool, fitness center, parks, and walking trails. Conveniently located near Hamlin Town Center, top-rated schools, shopping, dining, and easy access to FL-429 and Disney. Playground will be removed from the backyard.

Listing is courtesy of: REALTY ONE GROUP ESTATES (954-947-2383)

Listing Agent: Ian Merino (954-806-4349)

Remarks: Welcome to this CUSTOMZIED and MODERN property! 2,084 square feet of living space featuring four bedrooms, including a CUSTOM HOME OFFICE, and two and a half bathrooms. The open-concept layout includes a bright and inviting living area, contemporary design elements, elegant PANEL WALLS, CUSTOM BUILT-IN FURNITURE, and LED LIGHTINNG upgrades on the main floor. The home is fully furnished with SMART TVs, STYLISH DECOR, and high-end finishes throughout. The dedicated office is ideal for remote work or study, while the KID´S BEDROOM is tastefully decorated with two MONTESSORI style beds. The primary suite provides a peaceful retreat, perfect for rest and relaxation. Enjoy the convenience of a two-car garage and a prime location just minutes from top-rated schools, shopping, restaurants, banks, and more. Families will especially appreciate being near excelent schools, making this an ideal choice for those prioritizing quality education and a family-friendly environment. Schedule your appointment today. Association approval is not required. Renters Insurance is required.

Listing is courtesy of: CELEBRITY GLOBAL REALTY LLC (407-530-9264)

Listing Agent: Eduardo Pavone (407-232-1241)

Remarks: Welcome to this One Bedroom in a great location with access to everything Winter Garden has. Near theme parks, shopping centers, banks, hospitals, and a lot of entertainment. Rent includes Water, Electricity and Internet, and kitchen access. Schedule your appointment today!

Listing is courtesy of: VESTI LLC (407-749-5489)

Listing Agent: Maykol Romo (321-287-2378)

Remarks: Welcome to this sophisticated, modern and elegant two-story home, in the beautiful neighborhood of Summerlake Groves in the Horizon West area. On a fenced corner lot, this 3,377-square-foot home offers an open concept living space with an abundance of natural lighting. As you enter through the front door, you are greeted with gorgeous tile floors and direct views of the backyard. The gourmet kitchen features beautiful modern cabinetry, a large walk-in pantry, stainless steel appliances, and an oversized island overlooking the family room and dining area. This floor plan includes a great space for entertainment, high ceilings, a den/office space, the primary bedroom on the second level and a guest suite on the main level. Capturing some of the best living in Florida, the triple sliding glass door blends indoor and outdoor living space, where you can enjoy your tropical backyard oasis while enjoying stunning sunset views. The expansive primary suite features a walk-in closet, separate sinks with beautiful cabinetry and an oversized luxurious walk-in shower. Other features completing this exquisite home include three bedrooms, a formal dining space, a loft space and two-car garage. Conveniently within minutes from Disney World, Orange County National Golf Course, restaurants, shopping, hospitals and zoned for top-rated schools. Schedule your private showing and start enjoying the Florida lifestyle!

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)

Listing Agent: Llin Lu, Pa (954-907-3868)

Remarks: Beautiful 4/3 Home in desirable Summerlake community. Home features include nicely designed open floor plan when you walk in, with tile in wet areas and main living space, which opens to large kitchen with generous island, granite countertops, 42 inch cabinetry, stainless steel appliances, and a walk in pantry. The kitchen opens to a lovely living and dining area with surround sound system installed for family entertaining and get togethers. There is a large storage area downstairs, and a master with on suite downstairs. Large laundry room with sink, and the entire home is alarm system ready. The upstairs features a huge loft for entertaining or office use, three oversized bedrooms, and two bathrooms which include a large master, with walk in closet, and an on suite with a garden tub, a glass enclosed shower, and double granite his/hers sinks. Summerlake community amenities include a fitness center, basketball and tennis courts, playgrounds, clubhouse, resort style swimming pool, dog park, and walking/running trails. This home is move in ready with freshly painted walls and brand plush new carpet. Come on home.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Lisa Hamilton (407-924-3378)

Remarks: Almost NEW, 2.5 year old Gorgeous home, Arlington model with many upgrades, Awesome location in the heart of Horizon West right off the 429 at Independence and Avalon. This 4 bedroom, 4 bathroom and 3100sf. all 4 bedrooms downstairs, large loft 16x16 upstairs with separate walk in-closet and full bath could be used as another bedroom #5. The Great room, all with tall ceilings, triple panel slider to the covered lanai and fenced back yard, open to the dining area and the extended gourmet Kitchen. The extended kitchen wraps around adding 50% more, built in stove top, built in microwave and oven, HUGE extended island large enough to 6, and large walk in pantry. Behind the pantry is the laundry room with appliances, and the mud room next to the garage if you need a place to drop things and not bring in the house. The garage also has a large side area for hobbies/work/and more storage 9x20. The master bedroom is a large 15x18 with double door entry, two closets-one large walk-in, separate toilet room, dual sink vanities on granite, a free standing decor tub next to the large walk-in shower. the split floorplan has bed #2 #3 on the front side of the home to share a bath and bedroom 4 is opposite back corner giving good separation for more privacy, again with another full bath at its door. This home has 1 ac unit on a damper system for more efficiency, and fiber optic cable internet and lawn care is included. This community is right near the 429 exit at Independence, near the hospital and tons of new shops and restaurants. information deemed reliable but not guaranteed. Please email for more info.

Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)

Listing Agent: Bryce Rysewyk (407-340-1754)

Remarks: Furniture not included! Rent with purchase option available. This stunning two-story home, located in the desirable Storey Grove community in Winter Garden, offers the ideal combination of comfort, space, and modern design. With over 307 square meters of built area, this impressive 5-bedroom, 3-bathroom residence sits on a rare 0.13-acre lot, providing exceptional opportunities for both indoor and outdoor living. The open-concept floor plan is perfect for everyday living and entertaining, featuring a contemporary kitchen with stainless steel appliances, spacious living and dining rooms, and ample space for family and friends. The expansive backyard offers a serene environment for relaxing, playing, or hosting gatherings. Located in the heart of Winter Garden—one of Central Florida's most vibrant and rapidly growing areas—residents enjoy easy access to top-tier schools, shopping, restaurants, parks, and major highways. Don't miss this opportunity — schedule your visit today!

Listing is courtesy of: MANAGER PROP (689-240-5055)

Listing Agent: Tiago Ferreira (407-603-3350)

Remarks: Stunning Corner-Lot Home in Waterleigh | Horizon West Experience the perfect blend of elegance and comfort in this beautiful Laurel model home, located in the highly sought-after Waterleigh community in Winter Garden. Situated on an expansive corner lot, this residence offers 1,689 sq. ft. of thoughtfully designed living space featuring 3 bedrooms, 2 bathrooms, and a 2-car garage. Home Highlights: Designer Upgrades: Enjoy a modern aesthetic with an extraordinary upgrade package, including laminate flooring and smooth-finish faux wood blinds throughout. Gourmet Kitchen: Equipped with a stainless steel appliance gallery, ivory eased-edge cabinetry, and a vented-out microwave. Owner's Suite: Features a luxurious bathroom with gaily ornamental eased-edge wall tiling. Convenience Included: Full-size washer and dryer are provided for your comfort. Resort-Style Living: Waterleigh offers an unparalleled lifestyle with world-class amenities: 3 resort-style swimming pools & fitness centers. Sport courts (Tennis, Soccer, Beach Volleyball). Dog parks, playgrounds, walking trails, and a fishing pier. Clubhouse with a banquet hall, BBQ outdoor kitchen, and pavilion. Location & Maintenance: Prime Location: Minutes from Disney World, Hamlin Shopping Plaza, Flamingo Crossings, and Winter Garden Village with easy access to Highway 429. Daily Essentials: A brand-new Publix Supermarket is conveniently located at the community entrance. Worry-Free: Full landscaping services are included in the rent, provided by the HOA. Don’t miss this incredible opportunity to live in one of Horizon West’s premier communities. Schedule your showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Luciana Amorim Panajotti (917-853-0353)

Remarks: FOR RENT – LIKE NEW! Move-in ready and ideal for those seeking comfort, convenience, and an exceptional lifestyle in one of Winter Garden’s most desirable communities. Beautiful 3-bedroom, 2.5-bath home with a spacious loft and attached 2-car garage, located in the final phase of the highly sought-after Watermark community. This energy-efficient, Energy Star certified property offers excellent insulation, helping to reduce utility costs while maximizing comfort. The home features a functional and well-designed layout, perfect for both everyday living and entertaining. The loft provides additional flexible space ideal for a home office, media room, or play area. Enjoy resort-style living with access to outstanding community amenities, including two tennis courts, clubhouse, fitness center, playground, splash pad, park, scenic lake, outdoor amphitheater, and a resort-style pool. Prime location just minutes from top-rated schools, parks, and Lakeside Village Shopping Center, with Publix conveniently nearby. Property is vacant and ready for immediate occupancy. Don’t miss this opportunity to live in one of Winter Garden’s premier communities—schedule your showing today!

Listing is courtesy of: ALLUX REAL ESTATE LLC (407-802-7310)

Listing Agent: Denise Batista (407-802-7310)

Remarks: Your Dream Home Awaits! Welcome to this beautifully designed two-story single-family residence, built in 2020, where modern elegance meets everyday comfort. This exceptional home features 4 spacious bedrooms, 2 full bathrooms, and a convenient half bath, offering the perfect layout for both relaxation and entertaining. Step inside to discover an open-concept floor plan filled with natural light, contemporary finishes, and thoughtfully designed living spaces ideal for today’s lifestyle. Enjoy the unique flexibility of leasing this home either fully furnished or unfurnished, allowing you to tailor the space to your personal style and needs. Ideally located in a desirable area, this home offers both convenience and tranquility. Move-in ready starting February 28th—don’t miss the opportunity to make this stunning property your next home and create unforgettable memories

Listing is courtesy of: PAK HOME REALTY (909-351-5105)

Listing Agent: Ivanna Mendoza Heredia (417-335-1572)

Remarks: **** MOVE-IN READY SINGLE STORY MODERN 4 BEDROOM HOME IN WATERLEIGH **** Welcome to this beautifully maintained 4 BEDROOM | 3 BATHROOM single-family home located in the highly desirable Waterleigh community of Winter Garden, offering over 2,100 SQFT OF OPEN-CONCEPT LIVING with WATER and CONSERVATION VIEWS. This thoughtfully designed SINGLE-STORY FLOORPLAN features a seamless flow between the kitchen, dining, and living areas — perfect for both everyday living and entertaining — highlighted by a SPACIOUS KITCHEN WITH LARGE ISLAND | STAINLESS STEEL APPLIANCES | WALK-IN PANTRY and abundant natural light throughout. The home offers GENEROUSLY SIZED BEDROOMS including a comfortable primary suite, along with well-appointed bathrooms and modern finishes. Step outside to enjoy a COVERED PAVERED LANAI ideal for relaxing or hosting, plus a private backyard space. Additional features include a 2-CAR GARAGE and excellent overall condition. Located in Waterleigh, residents enjoy access to RESORT-STYLE AMENITIES INCLUDING CLUBHOUSES, POOLS, FITNESS CENTERS, TENNIS COURTS, AND WALKING TRAILS in a prime location near Disney, major highways, shopping, dining, and top-rated schools. **** COMFORT, LOCATION, AND LIFESTYLE ALL IN ONE — A MUST-SEE RENTAL OPPORTUNITY ****

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Marisol Goncalvez De Ayala (321-314-3494)

Remarks: *****Brand-New Home with Premium Upgrades and Lake View in Silverleaf – Be the First Resident! ***** . Welcome to this stunning brand-new residence and be the first resident on the main streets of the highly desirable Silverleaf community. This exceptional home offers modern design, premium upgrades, and a prime location, making it the perfect choice for those seeking comfort, style, and quality living. The upgraded first floor features custom wood paneling, decorative LED light panels, designer chandeliers, decorative mirrors, and a built-in wine refrigerator, creating elegant living spaces. The open-concept layout provides seamless flow between areas and abundant natural light, enhancing the home’s modern and inviting atmosphere. Also on the first floor, you’ll find a customized and modern suite, ideal for use as a home office, guest accommodation, or a comfortable space for individuals with mobility needs—adding versatility and functionality to the home. The primary suite is a private retreat, offering comfort and privacy, with a beautifully designed en-suite bathroom perfect for relaxation and everyday convenience. Step outside to a backyard with direct lake views, offering a peaceful and scenic outdoor setting. ***For added privacy and comfort, a Fence and Screening will be installed in the backyard. As a unique bonus, you can enjoy Disney fireworks views right from the comfort of your home.*** A rare opportunity to live in a brand-new home with premium upgrades, lake views, and an exceptional location. Schedule your showing today! *Note: Renters insurance is required. Grounds care fee is additional.

Listing is courtesy of: CELEBRITY GLOBAL REALTY LLC (407-530-9264)

Listing Agent: Eduardo Pavone (407-232-1241)

Remarks: Nice 4 bed 3 bath home with a . It yas a nice large fenced in yard. Dogs and cats welcome.

Listing is courtesy of: WINDERMERE INTERNATIONAL REALTY (407-421-6241)

Listing Agent: Hans Welbergen (407-701-6814)

Remarks: Stunning residence for rent in one of the most desirable communities in Winter Garden, celebrated for its picturesque lakes, prime location, and vibrant lifestyle. Built by Taylor Morrison, this exceptional two-story home showcases a thoughtfully designed and distinctive floor plan, highlighted by soaring ceilings that create a bright, open, and elegant living space. Featuring 3 spacious bedrooms and 3.5 bathrooms, the home offers refined comfort and functionality, along with a 2-car garage and beautifully appointed living areas ideal for both everyday living and entertaining. Perfectly situated just minutes from premier shopping, dining, and the renowned Cinépolis Luxury Cinemas, this home delivers the perfect balance of convenience and upscale living. A truly inviting home, ready to welcome its next residents.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Viviane Rocha (407-558-1180)

Remarks: Spectacular 5/4 with 3 car garage home. This home has all the bells and whistles for your enjoyment, Modern kitchen with open floor plan to family/living room and access to large screened in patio. Fenced backyard. Upstairs has a large Loft and 4 bedrooms including the spacious master bedroom/master bathroom. This home is a must see located in Watermark Sub-division with to many features to list. Disclosure: The property will be available for move-in after 05/15/2026. Property is currently occupied. An appointment to tour the property will be required.

Listing is courtesy of: HAMPTON & HAMPTON MGMT LEASING (407-219-3297)

Listing Agent: Jessica Martinez Cestero (407-219-3297)

Remarks: Elevate your lifestyle in this impeccably designed home at Lakeside at Hamlin, offering a premier rental experience in the heart of Winter Garden. Perfect for families seeking proximity to Disney and Top-Rated Schools, this residence features a modern open layout with a stunning gourmet kitchen, quartz finishes, and smart appliances for effortless living. The functional design includes a private guest bedroom and full bathroom on the main level, three additional full baths, and a second-floor laundry room for ultimate convenience. Enjoy a secure, low-maintenance lifestyle with a fully fenced yard, a two-car garage with ample storage, and high-speed internet included. Located near the SR-429, Orlando Health Hospital, and the vibrant Hamlin shopping district, this home 'move-in ready' retreat with easy access to everything Central Florida.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Liliana Nino Velandia, Pa (305-310-8685)

Remarks: Beautiful 3-bedroom, 2.5-bath home in the highly desirable Summerlake community in Hamlin. Currently tenant-occupied showings by appointment only. Featuring a freshly painted exterior, this stunning two-story home offers a bright and spacious open layout with laminate flooring downstairs and carpet upstairs. Enjoy the convenience of a downstairs laundry room and an attached garage. Step outside to a private, fenced backyard—perfect for relaxing or entertaining. Lawn maintenance is included for easy living. Residents enjoy resort-style amenities, including: * Community pool * Basketball & tennis courts * Dog park * Scenic lake views * Elementary school within the community Located in the heart of Hamlin, just minutes from shopping, dining, entertainment, and major highways. Perfect for comfortable, convenient living in one of the area’s most sought-after neighborhoods.

Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)

Listing Agent: Samir Naim (818-268-9917)

Remarks: Beautiful 4-bedroom, 4-bathroom home located in a desirable luxury community. This spacious floor plan features a formal living room, dining area, and a large kitchen with an oversized island, ideal for entertaining. The home includes one bedroom and full bathroom on the first floor. The second floor offers a generous loft, along with three additional bedrooms including the primary suite. Interior features include a wood-railed staircase, engineered wood flooring in loft and hallways, and carpet in all bedrooms. Enjoy outdoor living with a screened patio. Community amenities include a clubhouse, resort-style pool, fitness center, playground, beach volleyball court, paddle boards, and more.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Andre Grubert (407-346-7625)