Winter Garden Single Family Homes For Rent - 112 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: Move-in ready 4-bedroom, 2.5-bath home located in a desirable Winter Garden/Oakland community. This spacious two-story residence features a functional floor plan with generous living areas, large bedrooms, and ample closet space throughout. Brand-new luxury vinyl flooring was installed on the entire second floor this month, while the main level offers easy-maintenance flooring and no carpet upstairs. The oversized bedrooms provide plenty of comfort and flexibility for families, guests, or a home office. Ideally situated in a well-maintained community, this home offers convenient access to shopping, dining, schools, major highways, and the many attractions of Winter Garden and Oakland. Clean, well-kept, and ready for occupancy, this is a wonderful opportunity to enjoy comfortable living in a great location.

Listing is courtesy of: POINTON REALTY INC (407-395-2860)

Listing Agent: Andrea Pointon (407-446-4414)

Remarks: Virtually Staged. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom, 2500 sq ft ranch-style home, ideally located within a 5-minute walk to historic downtown Winter Garden in the heart of the Golf Cart District. Situated on a spacious corner lot, this home blends classic charm, thoughtful upgrades, and everyday functionality—perfect for families, snowbirds, or anyone seeking a relaxed yet connected lifestyle. Step inside to an open and airy floor plan featuring wood flooring in the main living areas and tile in the kitchen and bathrooms. The generously sized kitchen serves as the heart of the home, offering abundant counter space, ample storage, and natural light—ideal for cooking, entertaining, or casual dining. The fully fenced backyard provides privacy and space for outdoor living, pets, or play. A rare find, the 2-car garage includes a pass-through rear door that opens to an additional parking pad—perfect for a trailer, golf cart, or extra vehicle. You’ll also find a small air-conditioned room inside the garage, ideal for a home office, workout space, hobby room, or climate-controlled storage. Located in one of Winter Garden’s most desirable areas, you’re just a quick walk from local shops, yoga studios, restaurants, the farmers market, and community events. With no HOA and a layout built for both comfort and convenience, this home offers a unique opportunity to enjoy both peace and a vibrant, walkable lifestyle. Flexible Lease Term. Perfect if you are Building a home in Winter Garden. Yard care included.

Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)

Listing Agent: Lisa Pownall (407-927-1698)

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: Charming and Immaculate, Updated 5/3 in Winter Garden's Alexander Ridge This immaculate, meticulously maintained, spacious 5/3 home in Winter Garden’s sought-after Alexander Ridge is as easy to care for as it is charming. Updated tile flooring and louvered wood shutters throughout impart ease and elegance along with many updated, upgraded details. The gourmet kitchen with stainless appliances, convenient granite island, and tall cabinets leading into the large gathering area make cooking and entertaining a breeze. A private guest room/office with adjoining bathroom is on the first floor. The second floor is home to a large theater room, full-size laundry room, the remaining four bedrooms with walk-in closets. The primary bedroom has twin walk in closets, a cozy sitting area, and remodeled ensuite bathroom boasting a luxurious double shower. You’ll make good use of the 3-car garage with EV charging station, screened patio, and large fenced in backyard. Lawn care and pest control are included in the rent. The lovely neighborhood features a community pool, playground, fountain, gazebo, and fields of green. You’ll be close to the charming downtown, theme parks, restaurants, etc., with easy access to SR 50 and 420, Florida’s Turnpike, and connectors to I-4 and SR 408 and 528. You’ll be able to see yourself living life to the fullest in this beautiful home. Schedule your tour today!

Listing is courtesy of: CITRUS PROPERTY MGMT LLC (407-443-5850)

Listing Agent: Cathy Allain (407-341-4456)

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: Available for September move in! 4 Bedrooms, 3.5 Bathrooms plus an Office on ONE FLOOR with the most amazing view available in Horizon West, minutes away from the Hamlin Center! The gourmet Kitchen features Cooktop, Double Ovens, Custom Panel Refrigerator, Under Cabinet Lighting, and large walk-in pantry with Custom Built-Ins. Split floor plan with Primary Suite & Office overlooking the water. Guest Suite in front of the home with large walk-in closet, and 2 other additional decent sized bedrooms share the 3rd Bathroom. 3-Car tandem garage with epoxy floors. Oversized fully screened lanai with fully fenced backyard with gorgeous view and privacy! Waterleigh features resort style pools, mini-golf, fitness center, beach volleyball, nature walking trail, fishing, observation pier, dog Park and multiple playgrounds throughout the community. Call to schedule your showing TODAY.

Listing is courtesy of: UNIONE REALTY INC (407-808-9080)

Listing Agent: Kyle Li (407-808-9080)

Remarks: Brand-new 5-bedroom, 4.5-bath home with a private office in one of Winter Garden's most desirable communities! This spacious single-family residence features an open-concept layout, a designer kitchen with premium appliances, two A/C units, a luxurious primary suite, and a 2-car garage. Enjoy a private backyard with no rear neighbors, offering peaceful views and the perfect space to relax or entertain. Conveniently located near top-rated schools, parks, shopping, dining, and major highways. Move-in ready—don't miss this exceptional rental opportunity!

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Silvia Beltran Martinez, Llc (407-773-9991)

Remarks: Beautiful FULLY FURNISHED house in a gated community offers 4 bedrooms, 3 full bathrooms, separate office area and a bonus space! Recent upgrades are new flooring throughout and carpet in the bedrooms. Comes with furniture, rugs, TV's, full appliance package, outdoor furniture and table tennis. Ready to move in and live the Florida life! House has extra tall ceilings making the space seem even more spacious. Large outdoor space is half paved and half grass with some fruit trees (star fruit, peach, pear and more). No rear neighbors and fully fenced backyard is great for family gatherings and BBQ's. House has new windows and sliding doors that will help with energy efficiency. Garage has an additional fridge if needed. Conveniently located 2 mins from highway 429 and Winter Garden Villages with several shops and restaurants. Rent includes HOA fees, lawn care and pest control. Schedule your private showing today!

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

Listing Agent: Sevara Botirova Patel (407-242-9546)

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: Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and modern living come together, and you keep more of what's yours with no HOA fees. Built in 2023, this beautifully designed 4-bedroom, 2-bath home with a 1-car garage offers the perfect blend of contemporary comfort and timeless neighborhood character. Start your mornings on the inviting front porch, the ideal spot for coffee, fresh air, and easy neighborhood conversations. Step inside to an open-concept layout that feels bright, spacious, and instantly welcoming, whether you're hosting friends or enjoying a quiet evening in. The modern kitchen impresses with granite countertops, sleek cabinetry, and a generous workspace that flows seamlessly into the main living areas. Laminate flooring throughout the main living spaces adds a clean, low-maintenance finish. Beyond your front door, downtown Winter Garden is just minutes away, a historic district one of Central Florida's most beloved. Spend your weekends at the popular Saturday Farmers Market, dining at local restaurants ranging from cozy cafés to fine-dining establishments, or soaking up the seasonal festivals and community events that give this area its unmistakable energy. Newer construction. Modern finishes. A welcoming, active community. And no HOA. This Winter Garden gem checks every box, so don't miss your chance to make it yours.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nicole Mickle (407-353-0826)

Remarks: Welcome to this beautiful home located in a highly sought after gated community with 24 hour security. Residents enjoy a wide array of resort style amenities including a community pool, basked all courts, beach volleyball, clubhouse, tennis court, and a scenic golf course. This neighborhood also offers walking trails, playgrounds, and plenty of outdoor recreational spaces. Conveniently situated near shopping, dining, and major highways, this property provides easy access to everything Central Florida has to enjoy. Zoned for top-rated schools, this home is an ideal choice for those looking for comfort, convenience, and an active community lifestyle.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Karina Bencomo (305-926-7690)

Remarks: Be the first to live in this stunning, brand-new home in one of Winter Garden’s most desirable communities! This spacious two-story residence features a modern design, high-end finishes, and a functional floor plan ideal for today’s lifestyle. The gourmet kitchen showcases an oversized quartz island, shaker-style cabinetry, quartz countertops, and premium stainless steel appliances, including a built-in oven, microwave, and gas cooktop. The open-concept design seamlessly connects the kitchen, living, and dining areas, creating the perfect setting for everyday living and effortless entertaining. The luxurious primary suite features a tray ceiling and a spa-inspired bathroom with a double vanity, a large walk-in shower, and a spacious walk-in closet. The additional bedrooms are generously sized and filled with natural light. A spacious laundry room—equipped with a utility sink, washer, and dryer—is conveniently located on the upper floor. Please note that the apartment above the detached garage is not included in this lease. Ideally located just minutes from the Walt Disney World entrance, Flamingo Crossings, Horizon West, Hamlin Town Center, premier shopping, dining, major highways, and top-rated schools. Move-in ready. Schedule your private tour today!

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

Listing Agent: Danilo De Faria Alvim (407-520-2173)

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: Like-new 4-bedroom, 3-bath single-family home in desirable Waterleigh at Horizon West. Bright, open floor plan filled with natural light, featuring a formal dining room that flows into a spacious kitchen and living area—perfect for entertaining. One bedroom and full bath downstairs is an ideal space for guests or multigenerational living. Upstairs includes three additional bedrooms plus a versatile loft, perfect as a second living area, game room, or office. Enjoy a paved driveway, covered lanai, nicely sized backyard, and included washer and dryer. Located in a resort-style community near Hamlin Town Center, FL-429, Winter Garden Village, and just minutes to Disney. Zoned for highly rated schools. Move-in ready and beautifully maintained. The nearby Winter Garden Village provides a more modern shopping experience with over 100 retailers. Community features clubhouses, three pools, fitness center, playgrounds, walking trails, dog parks, and more. Move-in ready and beautifully maintained.

Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE (904-996-9144)

Listing Agent: Nigina Ikromi, Llc (321-370-9696)

Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2.5 bathrooms, 2 car garage and approximately 1,651 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated.

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Laidy Mataushek (844-874-2661)

Remarks: Welcome to 14252 Title Way, a beautifully maintained home in the highly desirable Storey Grove community of Winter Garden. Ideally located in the heart of Horizon West, this home offers quick access to SR-429, Walt Disney World, Hamlin Town Center, shopping, dining, and everyday conveniences. Families will appreciate the zoning for sought-after Water Spring Elementary and Water Spring Middle, with Horizon High School just minutes away. Residents enjoy resort-style community amenities including a sparkling pool, clubhouse, fitness center, playgrounds, parks, and scenic walking trails, making this an exceptional place to live, relax, and enjoy the best of Central Florida living.

Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)

Listing Agent: Emma Yue (626-328-8535)

Remarks: Welcome to 14186 Title Way, a beautifully maintained home in the highly desirable Storey Grove community of Winter Garden. Ideally located in the heart of Horizon West, this home offers quick access to SR-429, Walt Disney World, Hamlin Town Center, shopping, dining, and everyday conveniences. Families will appreciate the zoning for sought-after Water Spring Elementary and Water Spring Middle, with Horizon High School just minutes away. Residents enjoy resort-style community amenities including a sparkling pool, clubhouse, fitness center, playgrounds, parks, and scenic walking trails, making this an exceptional place to live, relax, and enjoy the best of Central Florida living.

Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)

Listing Agent: Emma Yue (626-328-8535)

Remarks: Welcome to this beautiful home located in the highly desirable Horizon West/Hamlin area of Winter Garden. This spacious 4-bedroom, 3.5-bath residence offers an open and functional layout designed for comfortable everyday living and entertaining. The home features a bright living area, a modern kitchen with stainless steel appliances, and a private primary suite with ample space to unwind. Enjoy the lifestyle this location offers. Just minutes from Hamlin Town Center, where you’ll find shopping, dining, a movie theater, fitness studios, and waterfront walking paths. Residents also benefit from top-rated schools, nearby parks, and convenient access to major roads connecting you to Downtown Winter Garden, Disney, and Orlando. A perfect blend of comfort, convenience, and vibrant community living in one of Central Florida’s most sought-after areas.

Listing is courtesy of: TRUVISION REAL ESTATE LLC (407-271-2470)

Listing Agent: Tony Hernandez (407-271-2470)

Remarks: Beautiful 2021 Bungalow-style home featuring 4 bedrooms, 3 bathrooms, and a 2-car garage. Designed with a functional and inviting floor plan, this newer home offers comfortable living spaces and timeless bungalow-inspired architecture. Built in 2021, it combines modern construction with thoughtful design, making it an excellent opportunity in the highly desirable Winter Garden area. Don't miss your chance to own this beautiful home!

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

Listing Agent: Ana Sampaio Pereira Willeman Moura (312-523-7720)