Winter Garden Single Family Homes For Rent - 107 homes

Remarks: Welcome to this delightful 2-bedroom, 1-bathroom cottage located in the Historic District of Winter Garden. Just two blocks from Plant Street, you'll enjoy easy walking access to local restaurants, coffee shops, and boutique shopping. This home features beautiful hardwood flooring throughout, with tile in the kitchen and bathroom for added durability and style. Off the main living area is a spacious flex room—perfect for a home office, playroom, or additional living space to suit your needs. The kitchen has ample cabinet space. Please note the fireplace is non working, decoration only. The property includes a detached one-car garage off the kitchen, connected to the home by a covered walkway, with washer and dryer hooks ups, offering both convenience and charm. The large front and backyard are shaded by mature trees, creating a serene and inviting outdoor space. Don’t miss the opportunity to make this unique home yours! *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application.

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Gina Jenkins (407-588-2645)

Remarks: Welcome to this sophisticated, modern and spacious, elegant two-story home in the beautiful neighborhood of Independence in the Horizon West area. Across the pond, this 2,524-square-foot home offers an open concept living space. As you enter through the front door, you are greeted with gorgeous tile floors. The kitchen features beautiful modern espresso cabinetry, a large pantry, stainless steel appliances, and an oversized island overlooking the family room and dining area. This open floor plan provides a great space for entertaining and includes dual primary bedrooms on the main and second levels. The expansive primary suite features a walk-in closet, separate sinks with beautiful cabinetry, a soaking tub and a luxurious walk-in shower. Other features completing this exquisite home include three bedrooms and an upstairs loft on the second level, plus a two-car garage. Capturing some of the best living in Florida, the Independence neighborhood provides a resort-style swimming pool, walking trails, basketball courts, tennis courts, fitness center and a private community boat ramp. Conveniently 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 Clearden Floor Plan in the Highly Desirable Waterleigh Community! Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home located in the sought-after Waterleigh community in Winter Garden. Designed for both comfort and functionality, this spacious two-story home features an open-concept layout perfect for everyday living and entertaining. The first floor offers a private guest suite with a full bathroom, ideal for visitors, multigenerational living, or a home office. The gourmet kitchen showcases stainless steel appliances, quartz countertops, abundant cabinet space, and a large island overlooking the spacious dining and family room, creating the perfect space to gather with family and friends. Upstairs, the generous primary suite features a spacious walk-in closet and an en-suite bathroom with dual vanities. Two additional bedrooms, a full bathroom, a versatile loft, and a conveniently located laundry room complete the second floor. Additional features include a two-car attached garage, central air conditioning, and plenty of storage throughout. Residents of Waterleigh enjoy an exceptional resort-style lifestyle with multiple swimming pools, two clubhouse amenity centers, fitness centers, dog parks, playgrounds, mini-golf, beach volleyball courts, sports fields, walking trails, scenic lakes, and beautifully maintained green spaces. Waterleigh offers an exceptional lifestyle with the added convenience of having both an elementary school and a middle school located within the community, making it an ideal place for families. Residents also enjoy easy access to Publix, Hamlin Town Center, shopping, dining, medical facilities, and Walt Disney World.

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

Listing Agent: Daniela Gomes (305-965-4591)

Remarks: This beautiful 4-bedroom, 3.5-bath home for rent in the highly desirable area of Winter Garden offers a perfect blend of comfort, space, and style. Featuring a 2-car alley-load garage in the back and a welcoming front porch, this home boasts an impressive 2-story foyer and a private downstairs bedroom with a full bath—ideal for guests, in-laws, or a home office. The open-concept layout seamlessly connects the family room, kitchen, and dining area, all filled with natural light from large windows. Enjoy the Florida lifestyle on the angled covered lanai accessed through sliding glass doors. Wood-look tile flows throughout the first floor, which also includes a convenient powder bath near the garage entrance. Upstairs, a spacious loft offers a perfect spot for relaxing or entertaining, along with three more bedrooms, including a private owner’s suite located at the back of the home for added privacy.

Listing is courtesy of: ROBERT SLACK LLC (954-448-4287)

Listing Agent: Aparna Narla (703-867-3835)

Remarks: Welcome to your single-family home in the highly sought-after community of Osprey Ranch! Located in the heart of charming Winter Garden, this beautiful 4-bedroom, 3-bath residence with a 2-car garage offers the perfect blend of comfort, convenience, and community — an ideal place to raise a family. Enjoy living just minutes from world-class theme parks, top-rated local schools, major roadways, dining, shopping, parks, and vibrant farmers' markets. Families will appreciate the excellent educational opportunities nearby, making this location truly special. Inside, you'll find a spacious, gourmet-style kitchen with a large center island, flowing into the open-concept dining area and expansive family room — perfect for entertaining and everyday living. The first floor features a comfortable bedroom with a walk-in closet and a full bathroom, offering flexibility for guests or multi-generational living. Upstairs, the privately located owner’s suite includes a beautiful bathroom with dual sinks and a generous walk-in closet, creating a relaxing retreat. Step outside to enjoy your open-air patio — ideal for weekend barbecues, or relax on the welcoming front porch after a long day. Don't miss the opportunity to live in one of Winter Garden’s most desirable neighborhoods! Schedule your private tour today and experience the perfect place to call home.

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

Listing Agent: Alexandre Zapparoli Llc (321-444-8701)

Remarks: s a beautiful 3 bedroom, 3 bathroom home offering the perfect blend of space and comfort. With a thoughtfully designed layout and inviting living areas, this home is ideal for both everyday living and entertaining. Nestled in a peaceful, well maintained community and just minutes from top-rated schools, shopping, and dining, it delivers both convenience and a relaxed Florida lifestyle.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Elaine Garcia (407-920-3616)

Remarks: Energy-Efficient Home in Silverleaf Reserve Winter Garden! This spacious Hurston model features an open-concept layout with a stunning kitchen, complete with a large island overlooking the dining area and family room-perfect for entertaining and everyday living. The upstairs loft offers flexible space to fit your lifestyle, whether as a home office, playroom, or media room. Located in the desirable Silverleaf Reserve community, you'll enjoy easy access to top-rated schools, dining, shopping, and entertainment in the heart of Winter Garden. Built with innovative energy-efficient features, this home helps reduce utility costs while providing year-round comfort and peace of mind.

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

Listing Agent: Carolina Medeiros (305-753-1943)

Remarks: Experience elevated Florida living in this exquisite, fully furnished luxury residence at 15704 Marina Bay Drive in the highly desirable Winter Garden area. Beautifully designed with sophisticated finishes, elegant furnishings, and a thoughtfully curated interior, this exceptional home offers a seamless blend of comfort, style, and convenience. From the moment you enter, you'll be welcomed by an expansive open-concept floor plan filled with natural light, creating an inviting atmosphere for both everyday living and elegant entertaining. The gourmet kitchen features premium finishes, ample cabinetry, and generous counter space, flowing effortlessly into the spacious dining and living areas. Every room has been professionally furnished with high-quality décor, providing a refined, turnkey living experience. The luxurious primary suite serves as a private retreat, offering a spa-inspired ensuite bath and generous closet space. Additional bedrooms are beautifully appointed to provide comfort and privacy for family members or guests. Thoughtful details throughout the home reflect quality craftsmanship and timeless design. Step outside to enjoy Florida's year-round lifestyle in the private outdoor living space, perfect for relaxing with your morning coffee, hosting friends, or unwinding after a long day. Every detail has been carefully considered to deliver a resort-inspired atmosphere that feels both elegant and welcoming. Ideally located just minutes from premier shopping, dining, golf, top-rated schools, major highways, and Orlando's world-renowned attractions, this exceptional home offers luxury living with unmatched convenience. Whether you're relocating, on an executive assignment, or seeking a high-end furnished residence, this turnkey home delivers an unparalleled rental opportunity. Simply bring your suitcase and enjoy the very best of luxury living.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: Luxury lease opportunity in the gated community of Canopy Oaks, offering an exceptional combination of space, privacy, and convenience in one of Winter Garden's most desirable locations. Ideally situated near major healthcare facilities, business centers, Downtown Winter Garden, Winter Garden Village, and Orlando's attractions and entertainment destinations, this A.R. Bailey Homes Delray model is designed for those seeking luxury living with easy access to everything Central Florida has to offer. Nestled within an intimate community of just 49 homesites, this impressive residence showcases timeless architecture and thoughtful design throughout. A striking exterior presentation features a paver driveway, concrete tile roof, stone-accented elevation, wood-look garage doors, and grand solid wood double-entry doors. Inside, expansive living spaces are filled with natural light and enhanced by architectural ceilings, elegant finishes, and a versatile floor plan designed for both everyday living and entertaining. The chef-inspired kitchen serves as the heart of the home, featuring a natural gas cooktop with exterior venting, built-in oven, upgraded appliances, pot filler, 42-inch cabinetry with crown molding, under-cabinet lighting, tile backsplash, walk-in pantry, and an oversized island overlooking the spacious great room with coffered ceilings. A gated wine cellar adds a distinctive feature rarely found in comparable properties. The first-floor primary suite offers a private retreat complete with dual granite vanities, a soaking tub, oversized walk-in shower with dual shower heads and bench seating, and a custom-designed closet system. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, or a private office. Upstairs, the home continues to impress with a second primary suite, two additional en-suite bedrooms, a spacious loft, guest powder bath, and a covered balcony, creating multiple private living areas throughout the residence. Designed to embrace Florida's indoor-outdoor lifestyle, dramatic corner-opening glass walls and expansive stackable sliding doors create a seamless connection to the covered lanai, enhanced by a motorized retractable screen. The oversized backyard offers privacy and abundant space for outdoor enjoyment. Additional features include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, a mudroom, reading nook, and extensive storage throughout. Residents enjoy access to community walking trails and a playground while benefiting from convenient access to healthcare facilities, shopping, dining, recreation, and major transportation corridors including the Florida Turnpike, SR 429, SR 408, and Interstate 4. Property is currently offered for sale (MLS# O6394059) and lease. Availability and terms are subject to change. Virtual pool rendering shown for illustrative purposes only. No pool currently exists on the property. Any depicted pool or outdoor improvements are conceptual and subject to design, permitting, and approval requirements.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Lisa Rutkowski (407-793-2416)

Remarks: Spacious and beautifully designed 5-bedroom, 3-bathroom home with a 3-car garage located in the heart of Winter Garden. Offering approximately 3,462 square feet of living space, this home features a versatile floor plan perfect for families of all sizes. The first floor includes a formal dining room, a spacious family room, a separate sitting room, and a well-appointed kitchen with granite countertops, ample cabinet space, and a breakfast nook. A full bedroom and bathroom are conveniently located downstairs, making it ideal for guests, extended family, or a home office. Upstairs, you'll find a large loft area, four additional bedrooms, and two full bathrooms. The oversized primary suite offers a spacious retreat complete with dual vanities, a garden tub, a separate shower, and generous closet space. Ideally located near top-rated schools, shopping, restaurants, major highways, and just minutes from downtown Winter Garden. Enjoy easy access to Walt Disney World, other world-famous Central Florida attractions, and all the conveniences the area has to offer. Don't miss the opportunity to make this spacious Winter Garden home your next residence. Schedule your showing today!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Amanda Yuan (407-353-2867)

Remarks: Beautiful 4-bedroom, 3.5-bath home available for immediate move-in! Home is unfurnished, easy application process with fast approval — move in right away! This spacious 3,020 sq ft residence features an open floor plan, updated kitchen with dual ovens and ample storage, and a bright living/dining area with pocket sliders leading to a large fenced backyard. The primary suite includes two walk-in closets. Located in a top-rated school zone with convenient access to shopping, dining, and major highways. Schedule your showing today!

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Gabriella Massaro (689-280-9558)

Remarks: Quintessential Florida living! Located in the highly sought after subdivision of Watermark Community. Beautiful 3 bedroom, 2.5 bathrooms with loft. Full open concept floor plan. The light filled kitchen has amply storage with 42" cabinets, large pantry, granite countertops, and stainless steel appliances. The master suite features a large walk-in closet, duel sink vanity and oversized walk-in shower. The loft is perfect for entertaining or can be used as a playroom. Solar panels provide relief on electric bills, high-speed internet and pest control are included to the lease. The community amenities are amazing. Features a zero-entry pool with slide and dumping bucket, large clubhouse that can be rented for events, basketball court, playground, fitness center, observation deck. Beautiful views of Disney's Worlds Magic Kingdom fireworks from your front lawn every night! The MARK Shopping Center is just a quick walk.. NY Brewery, Huey Magoo's, Walgreens, Starbucks, and plenty more! Zoned for Panther Lake Elementary School. Live like your on vacation.

Listing is courtesy of: DOUGLAS ELLIMAN (727-698-5708)

Listing Agent: Mike Daquino (631-872-3855)

Remarks: Experience luxury living in one of Winter Garden's most desirable communities! Built in 2023, this stunning 4-bedroom, 3-bath home features soaring double-height ceilings, an open-concept layout, abundant natural light, and a gourmet kitchen with a large island and stainless-steel appliances. Enjoy a private SUMMER KITCHEN, an upstairs laundry room, PAID OFF SOLAR PANEL and Disney's nightly fireworks right from your street. Located in the sought-after Hamlin school district, with Hamlin Elementary and Hamlin Middle School nearby, this home also offers resort-style community amenities, including a pool and pickleball courts. Just minutes from Hamlin Town Center, shopping, dining, major highways, and Walt Disney World. The property is under painting process. Updated photos will be available as soon as the project is completed.

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

Listing Agent: Carolina Medeiros (305-753-1943)

Remarks: Welcome to this beautiful home located in the highly desirable community of Winter Garden! This well-maintained property offers a spacious and functional floor plan with bright living areas, a modern kitchen featuring ample cabinet space and stainless steel appliances, and comfortable bedrooms designed for everyday living. The primary suite includes a private bathroom and generous closet space, while the backyard provides the perfect setting for relaxing or entertaining. Conveniently located near shopping, dining, major highways, schools, and local attractions, this home offers both comfort and convenience. Don't miss the opportunity to make this wonderful property your next home. Schedule your showing today! A mandatory Resident Benefit Package of $50/month is required and includes renters insurance (up to $100,000 in liability coverage and $10,000 for personal belongings), monthly air filter delivery to improve air quality and HVAC efficiency, move-in concierge services to assist with utilities and internet setup, credit building with rent payments reported to all three major credit bureaus, 24/7 maintenance hotline, identity theft protection with up to $1 million in coverage, and access to an online resident portal for payments and maintenance requests.

Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)

Listing Agent: Ursula Garcia Moraes (407-429-1417)

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: Beautifully renovated 4-bedroom home located in one of the area’s most desirable communities. This bright and inviting residence features abundant natural light, modern finishes, spacious living areas, and a functional floor plan ideal for everyday living and entertaining. The private backyard overlooks a peaceful green space, offering extra privacy and a relaxing setting with no immediate rear neighbors. Conveniently located near the community clubhouse and within walking distance of Water Spring Elementary and Water Spring Middle School, this home provides an exceptional combination of comfort, convenience, and lifestyle. Residents enjoy access to a wide variety of resort-style amenities, including a community pool, clubhouse, playgrounds, recreational areas, walking trails, and beautifully maintained common spaces. Move-in ready and ideally situated near schools, shopping, dining, major roads, and everything the area has to offer. A wonderful opportunity to live in a highly sought-after community!

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

Listing Agent: Ana Thurman (321-310-6382)

Remarks: Available for a one-year lease at $3,850/month, this two-story, 5/3 home with a private screened pool sits in the gated Wintermere Pointe community of Winter Garden. The layout offers a downstairs bedroom plus four bedrooms up, an open family room with sliding doors to the covered lanai and pavered pool deck, formal living and dining rooms, and two upstairs loft spaces. Residents are minutes from Winter Garden Village, downtown Winter Garden and the West Orange Trail, with quick access to SR-429 and Florida's Turnpike. HOA/association dues are included in the monthly rent. Square footage and room sizes are approximate and should be independently verified.

Listing is courtesy of: GLOBAL KEY REALTY, LLC (305-707-1080)

Listing Agent: Kevin Escribano (321-333-2959)

Remarks: MOVE-IN READY! PERFECT location in desirable Winter Garden! Greate school zone. NO CARPET! Renovated kitchen, countertops, floorings, light fixtures, baths shower/vanities/mirrors/lights...Beautiful home featuring 3 bedrooms plus 1 loft/retreat/office/bonus upstairs and 2.5 baths, 2 car garage on front. Screened covered lanai, sizable back yard. All appliance included. Open floorplan with spacious living room and formal dinning room. Large master bedroom features walk-in closet, dual new sinks and new shower tub. Park with playground in the community. Just walking distance to top graded Whispering Oak Elementary School and Publix and Stoneybrook West Village shopping center, Walgreen, Ladybird Academy, Medical Clinics, Restaurants, etc. 5 mins drive to Winter Garden Village and Winter Garden Hospital, including Target, Lowes, Bestbuy, ROSS, Marshalls & HomeGoods, Party City, Staples, Restaurants, Banks, etc. Only Few minutes to SR429 and avalon road. Near to Walt Disney World. Only short drive to downtown Winter Garden and Windermere. Schedule a showing TODAY!

Listing is courtesy of: YORK MILLS REALTY LLC (626-328-8535)

Listing Agent: Jacky Liu (407-921-5670)

Remarks: Life is not a dress rehearsal! Lease a HOME not an apartment!!!! Enjoy all the benefits of ownership in this gorgeous resort style community without all the headaches! Hamlin’s flagship community Watermark has convenient access to “A” rated schools, restaurants, shops and a never ending schedule of things to do in and around your new HOME! Amenities include a gorgeous resort pool, fitness center, tennis/pickleball courts, playground, clubhouse and more! Situated on a corner lot with a covered porch perfect for your rocking chairs and a refreshing glass of lemonade :) The downstairs is ALL living space with a 1/2 bath and the sleeping quarters upstairs. Much like a vintage floor plan, maximizing the square footage and privacy! The kitchen has stone counter tops, plenty of storage cabinets and a breakfast bar. The second floor opens up to a nice loft space with an accent wall perfect for homeschooling! A serene lake view can be enjoyed from the upstairs level. The primary suite has tray ceilings and an ensuite bath with double sinks, shower with bench and huge closet. The home has lots of windows and lightly colored finishings. A mix of luxury vinyl plank and tile means this home is move-in ready aside from personalization! 2 additional bedrooms share a bath and having the laundry on the second level makes chores a little less annoying! Both Orange and Lake counties offer an easy commute to all of central Florida’s attractions, downtown Orlando & the international airport. Just a few miles from a local favorites! Enjoy the weekly Farmer’s Market on Saturday morning in Winter Garden and Sunday morning in Clermont! Both have monthly and seasonal celebrations year round! The West Orange Bike Trail runs through the middle of town w/ a splash pad, posh restaurants, specialty boutiques, coffee shoppes & more! Enjoy the historic architecture with brick streets and a true hometown feel! Be sure to visit The City of Winter Garden’s website to find out “Where Good Things Grow”, where you can stay up to date with all the news & events! A great the place to live, work & play for ALL ages!

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Autumn Makin (352-455-0044)

Remarks: AVAILABLE NOW – Beautiful 3-bedroom home with a fenced backyard, located in the sought-after Waterleigh community. Enjoy an open-concept layout featuring a stylish kitchen with Samsung stainless steel appliances, a walk-in pantry, and a large island—perfect for entertaining. The kitchen flows seamlessly into a spacious family room, ideal for modern living. Brick pavers highlight both the driveway and the covered lanai, where you can relax and take in views of the Magic Kingdom fireworks from your own backyard! Waterleigh offers resort-style amenities including two stunning clubhouses, multiple pools, a miniature putting green, three fitness centers, and tennis courts—all just minutes from Disney in Winter Garden/Horizons West. Note: No representations or warranties are made regarding school districts or school assignments. Please verify independently.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Roselyn Diaz Marcano (407-715-1719)