Apartments for Rent Near West Orange High in Winter Garden - 26 rentals

Remarks: For Lease – Updated 2 Bedroom, 2 Bathroom Condo in Southern Pines, Winter Garden. Welcome home to this beautifully updated 2-bedroom, 2-bathroom condo in the desirable Southern Pines community of Winter Garden. This move-in-ready residence offers a bright, open floor plan with modern finishes and comfortable living spaces designed for easy Florida living. The primary suite includes a private bath and generous closet space, while the second bedroom and bath provide flexibility for guests, a home office, or family members. Enjoy this unit's excellent location and take advantage of the community’s resort-style amenities, including a swimming pool, indoor racquet and basketball courts, fitness center, clubhouse, tennis courts and a kid's playground. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, shopping, dining, and major roadways, this condo offers easy access to Orlando, area attractions, and top employment centers. Call your favorite Real Estate Agent and schedule a private showing today!

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

Listing Agent: Jim Kernohan (407-450-3861)

Remarks: Welcome to 224 Faulkner St, a well-maintained 3-bedroom, 2-bathroom single-story home located within the golf cart district of desirable Winter Garden. As you enter the home, you're welcomed into a spacious living and dining area featuring vaulted ceilings, abundant natural light, and direct access to the backyard. The kitchen includes a breakfast bar, refrigerator, oven, and dishwasher, and flows conveniently into the dining space. The primary suite is privately positioned to the right side of the home and features an ensuite bathroom with dual vanities, a separate shower and toilet area, and a walk-in closet. Two additional bedrooms are generously sized and share a full family bathroom. Additional features include a dedicated laundry room with a washer and dryer, interior access to the two-car garage, and a driveway with ample parking. Outside, the home offers a spacious yard perfect for enjoying Florida living. Conveniently located approximately half a mile from Plant Street, this home offers easy access to downtown Winter Garden's shopping, dining, farmers market, and local events.

Listing is courtesy of: WINTER GARDEN REAL ESTATE (407-910-1066)

Listing Agent: Anthony O'Reilly Brookes (407-910-1066)

Remarks: Welcome home to this 3-bedroom and 2.5 bathroom home in the gated community of Tucker Oaks in the heart of Winter Garden. 15350 Oak Apple Ct, Unit 17B offers a bright, open layout with spacious living and dining areas, a well appointed kitchen, and a private screened patio, perfect for relaxing outdoors. There is a half bath on the first level, convenient for guests. All bedrooms are located on the second floor, and the primary suite includes its own en suite bath. The washer and dryer are offered as a convenience item, but the tenant will maintain. There is a large 2 car garage with ample space for parking, along with two storage closets with shelving. Enjoy the community pool, and easy access to shopping, dining, and major roadways. Located just minutes from downtown Winter Garden. No pets and no smoking. This home delivers comfort and convenience in one of Central Florida’s most desirable areas.

Listing is courtesy of: FLORIDA RENTAL TEAM (407-405-8923)

Listing Agent: Sylvia Young (407-405-8923)

Remarks: Complete application required with copy of applicant's driver's license. Complete credit reports for all adults required, proof of income (last two paystubs, last 2 months bank statements). Only 1 pet permitted. Located in Stoneybrook West community. Water view!

Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)

Listing Agent: Susana Stutsman (321-278-0334)

Remarks: Beautiful Fully Furnished, French Country model Home. This gorgeous pool home features 5 Bedrooms (2 Master Suites 1st and 2nd floor) plus an office/study with 4.5 baths, Cinema (with top of the line equipment and sound system, over $30K) with 3 car garage on a prime location in Winter Garden, nearby shopping, highway, hospital and Disney Parks. Canopy Oaks is a gated community, home of 49 beautiful Estates just between the Winter Garden Village and the quaint historic downtown Winter Garden, Orlando's most popular suburb! Location is a privilege. The Mediterranean style property features a pavered driveway, tropical taylored landscape, iron banister railings, arched wooden entry door, soffit and coach lights, plenty of tall windows with beautiful plantation shutters throughout, lots of natural light, This open floor plan offers a huge great room for gathering with family and friends flows easily into the kitchen, dining area, and out to the amazing pool area to a beautiful and fully equiped Summer Kitchen through the 3-panel stackable sliding doors onto a covered lanai equiped with an automated screen, creating a bigger indoor-outdoor space. Kitchen features the large granite island which can easily seat 5 guests, stainless steel appliances, custom cabinetry, and pendant lights. The luxurious second floor features a large family room which opens through stackable sliding glass doors overlooking a lovely porch overlooking the pool area. Master suite is gorgeous with tray ceiling, wet bar with a kitchenAid Wine Cooler/coffee station, an expansive master closet, and an impressive curved dual walk-in shower and a free-standing soaking tub, Master also have a private entrance to the upstairs balcony. This community has a park and walking trail around a small pond. Easy access to 429, 408, Highway 50, turnpike, Disney World, and Universal. Schedule a showing quick, you don't want to miss this one!

Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE (407-217-7573)

Listing Agent: Oscar Rodriguez (321-297-7264)

Remarks: Move in Ready! Come check out this Maintenance Free house! Rent includes Lawn care, Pest control and Solar Fee! This beautiful 4 bed/3 bath, two-story SOLAR energy-saving home is located in Winter Garden and the desirable Waterside community. The house has 1 guest suite downstairs, 1 Master suite, and two bedrooms upstairs with a built-in study nook. The kitchen includes quartz countertops and stainless steel appliances, and it opens up to the spacious living room. Upgraded wood plank tile throughout the first floor. The community offers a Club House with Pool, Gym Fitness, Party Hall, Playground, Lake, trails, BBQ/Picnic, etc. Located just a few minutes from Winter Garden Village, Publix, shopping, A-rated schools, restaurants, hospital, and Disney World!

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: An amazing opportunity has become available for you to become a resident of the guard-gated Stoneybrook West Golf Community. This pool home is located on a less travelled road to enjoy minimal traffic and peace and quiet. Get ready for the magic to begin with an amazing formal living room and dining room. The home then opens into the gourmet kitchen which will impress the chef of the family. A nice family room completes this area that leads to the pool. The backyard is a true highlight, featuring a spacious area, and screened private pool. Lush landscaping surrounds a generous green space, perfect for your enjoyment. An extended patio providing ample outdoor living space. When you’re ready to retire for the evening, this large, 4-bedroom split place allows everyone to have their privacy. Living in the Stoneybrook West community means enjoying resort-style amenities, including a community swimming pool, golf courses, a clubhouse with a fitness center, tennis courts, a pickle ball court, an inline skating rink, and basketball courts. Basic cable and internet are included in the HOA package. In addition to these amenities, the neighborhood is home to highly rated schools, with Whispering Oaks Elementary conveniently located just across the street from the main entry gate. Winter Garden offers excellent shopping and dining options at the Winter Garden Village Mall and nearby areas, with the trendy historic downtown Winter Garden and the West Orange bike trail just a short drive away. Make your private appointment today, while the opportunity still exists.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Sharon O'Malley (407-291-4665)

Remarks: One or more photo(s) has been virtually staged. Available June 1st. 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: One or more photo(s) has been virtually staged. Welcome to this beautifully renovated 2-bedroom, 2-bath condo in the sought-after Southern Pines community of Winter Garden, where modern upgrades and comfortable living come together effortlessly. Thoughtfully updated with stylish finishes and a bright open floor plan, this home offers an inviting atmosphere perfect for both relaxing evenings and entertaining guests. Natural light fills the spacious living and dining areas, while ceiling fans throughout add comfort and energy efficiency year-round. The upgraded interior features a flexible seating area ideal for a home office, reading nook, or cozy lounge space. Beneath the staircase, you’ll find convenient additional storage—perfect for keeping everyday essentials neatly organized. The desirable split-bedroom layout provides enhanced privacy, with both generously sized bedrooms offering large walk-in closets and easy access to their own full bathrooms. Located within a gated community, residents of Southern Pines enjoy access to resort-style amenities including a sparkling swimming pool, fitness center, indoor movie theatre, clubhouse, business center, playground, tennis courts, indoor basketball court and beautifully maintained green spaces. The community’s prime Winter Garden location places you just minutes from Historic Downtown Winter Garden, Winter Garden Village, and the popular West Orange Trail. This exceptional condo is also within close proximity to Walt Disney World Resort, Universal Orlando Resort, and Disney Springs, along with countless shopping, dining, entertainment, and recreation options nearby. For added convenience, cable and internet service are included in the rent, along with water, sewer, trash, and lawn care, providing a more simplified and low-maintenance living experience. Association approval is required prior to move-in. Prospective tenants must complete the Southern Pines Occupancy Application as part of the community approval process. Married couples: $100 total / Unmarried applicants: $100 per person With its recent renovations, spacious design, included utilities, and prime location, this condo is ready to offer comfortable Florida living at its best. This property offers an option of a security deposit-free lease using Obligos billing authorization technology for qualified tenants. Non-refundable application fee of $80 per person above the age of 18 years of age. One time admin fee of $295 for approved application.

Listing is courtesy of: CANI PROPERTY MANAGEMENT (321-280-9065)

Listing Agent: Jeremy Porter (321-280-9065)

Remarks: Enjoy this Gorgeous home in the beautiful Waterside Community. This home features 3 Bedrooms, 3 Full bathrooms, a Den, a second floor loft, a Screened Patio and Two-car Garage. High Ceiling, upgraded tile flooring throughout the first level. BRAND NEW CARPETS! Spacious, modern kitchen with large center island over looking the living room. Master bedroom and the 2nd bedroom downstairs with 2 full baths. Upstairs you will find a loft area with the 3rd bedroom and it's own full bath. Large laundry room with cabinets, plenty of room for storage. The Waterside Clubhouse offer a Resort-style swimming pool, a Fully-equipped fitness center includes state-of-the-art cardio and weight equipment. Natural lakes, ponds and walking trails throughout the community, perfect for outdoor activities. Location is excellent. Just minutes from Publix, shops, restaurants, Winter Garden Villages and major highways. A rated schools! All of this and only about 15-20 minutes to Disney World. Tenant is responsible for utilities, internet, lawn care and pest control. Text Listing Agent today for a showing today!

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Come enjoy a carefree lifestyle in this beautifully designed home offering nearly 3,000 square feet under roof, a versatile three-way split floor plan, sparkling pool, and spacious three-car garage. Ground care and pool maintenance services are included. There are high ceilings throughout the home. The kitchen boasts 42 inch wooden cabinets with plenty of counter space. A spacious closet is strategically located to store big items. There is a very generous loft space with plenty of windows upstairs. All bedrooms are very spacious too. The primary bedroom features a coffered ceiling and has direct access to the enclosed pool/jacuzzi area with two exits. The property is located in a desirable subdivision with two boat docks and tenis courts. It is just across the street from West Orange High School and minutes away from restaurants and shopping plazas. There is convenient access to 429 which connects this area to Orlando and Disney.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jordan Heidrich (407-223-3495)

Remarks: Welcome to the spectacular neighborhood of Regency Oaks in Winter Garden! This home has just been renovated with a quartz countertop, new stainless steel appliances, and beautiful laminate flooring. It is zoned for all A-rated schools and is close to the Groves Shopping Center, great restaurants, and has easy access to the 429. As you enter, the home opens up to a long formal dining room and sitting room combo, with the informal family room to the rear, both separated by the spacious kitchen. The Master Suite is situated on the right side of the home, making this a great split floor plan. The Master Bath includes a Roman tub, standalone shower, double vanity, and walk-in closet Well planned 4 bedroom 2 Bath, . Kitchen opens to the family room. Pets allowed. Close to Winter Garden Village and Historical Downtown Winter Garden, Restaurants and shopping

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)

Remarks: Within the gated community of Southern Pines you will enjoy the FLORIDA LIFESTYLE everyday! Soak up the sun by the resort-style pool and spa. What's your pleasure? Enjoy the tennis courts, a volleyball court, or indoor racquetball, basketball courts and full fitness center with a kiddie playroom. The clubhouse feature a media room, theatre room, computer terminals with free internet and then there's the playground, barbecue areas and even a car wash. This is the LARGEST one-bedroom unit available with a BONUS/ SUNROOM. It is a two-story condo with your own private entrance. NEWLY REMODELED with NO CARPET. Tile floors in the kitchen & in the FULLY REDESIGNED LUXURY BATH. Large TILE WALK-IN SHOWER w/GLASS ENCLOSURE & NEW STONE counters. The main living/dining areas, stairs and the bedroom feature the NEW HYBRID Plank Flooring (better than Luxury Vinyl or laminate). Crown moldings throughout. Close to everything...Winter Garden Village shopping and restaurants, hospitals, easy access to downtown, Disney, or almost anywhere via SR 429, FL. Turnpike, I-4. Must see! All rentals include the Claire Schwartz & Associates Resident Benefits Package (RBP) which delivers savings and convenient, professional services that make taking care of your home second nature. All as a part of your cost of $35/month, payable with Rent. APPLY FOR THIS HOME ON OUR WEBSITE. LOOK FOR THE LINK TO "OUR RENTAL LISTINGS/APPLY HERE" & OPEN YOUR HOME BY CLICKING ON IT AND "APPLY HERE" OR CALL YOUR REALTOR TO VIEW.

Listing is courtesy of: CLAIRE SCHWARTZ & ASSOCIATES (407-352-5244)

Listing Agent: Claire Schwartz (321-439-6995)

Remarks: Beautiful 2-bedroom, 2-bath condo in the desirable Southern Pines community of Winter Garden. This second-floor unit features a bright open floor plan with a spacious living area that flows into a light-filled solarium—ideal for a home office, reading nook, or additional sitting area. The kitchen is centrally located with ample cabinet and counter space, adjacent to a dedicated dining area. The split-bedroom layout offers privacy, with the primary suite featuring a walk-in closet and private bath, while the second bedroom is generously sized with easy access to a full bathroom. Enjoy low-maintenance living with access to community amenities including pool, fitness center, playground, and tennis courts. Conveniently located near shopping, dining, major highways, and top-rated schools. Unassigned common parking available with a maximum of 2 vehicles per unit. Unit currently tenant-occupied through 5/30. Carpets will be steam cleaned and interior paint will be professionally touched up prior to move-in.

Listing is courtesy of: AFT PROPERTY LLC (407-900-0056)

Listing Agent: Seyed Azimi (407-900-0056)

Remarks: One or more photo(s) has been virtually staged. AMAZING LOCATION - GREAT PRICE - VERY NICELY UPDATED UNIT! SCREENED IN BALCONY PATIO! 2 Bedroom + 2 Bath condo just 3 minutes from Plant Street in Winter Garden. Kitchen has been beautifully updated and unit has stylish flooring throughout (no carpet). Wonderful split floor plan: the 2 bedrooms are separated by open concept kitchen/ living room combo and each has their own bathroom. Community has private pool area, basketball courts, and plenty of green space for outdoor activities. Application process and fees apply. Call today for your private showing.

Listing is courtesy of: ROMAN REALTY GROUP, LLC (407-876-1990)

Listing Agent: Brian Lemay (321-314-5412)

Remarks: Welcome to this charming 2-bedroom, 2.5-bath townhome in the gated Daniels Landing community of Winter Garden! Both bedrooms feature private en-suite bathrooms and walk-in closets. Enjoy a private courtyard, attached two car garage, and all major appliances included. Community amenities include a pool, clubhouse, playground, and walking trails. Basic internet and cable are included in the rent! Located minutes from Historic Downtown Winter Garden, Highway 50, SR-429, and the Florida Turnpike, with easy access to top-rated Orange County schools. Shopping, dining, and entertainment are all right at your doorstep. This one will not last — schedule your showing today! All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: One or more photo(s) has been virtually staged. one or more photos have been digitally edited. WHERE MODERN MEETS ELEGANCE. AMAZING TOWNHOUSE in Winter Garden, FL. 3 BEDS, 2.5 BATHS, 2 CAR GARAGE, WITH LOFT. The LARGEST FLOOR PLAN in The Westbrook Community . GRANITE AND STAINLESS STEEL in the kitchen. Gorgeous Farm style sink. Very spacious bedrooms. Oversized master bedroom with 2 walk in closets and the master bath features double sinks and a walk in shower. The unit also features a loft or bonus room on the second floor which can be used as an office or a second living room. LOTS OF STORAGE. COMMUNITY POOL. From your rear porch, you can access the pool just crossing the street. WATCH VIDEO LINK below the pictures

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Maria Ubillus (954-242-7900)

Remarks: Spacious 2-bedroom, 2-bath end-unit duplex located in the well-situated Townhomes of Winter Garden community. This unit offers a practical and comfortable layout with generously sized bedrooms, two full bathrooms, and the added privacy of an end-unit location. Hard-surface flooring runs throughout the home, featuring ceramic tile and laminate for easy maintenance and a clean, modern feel. A washer and dryer are conveniently located inside the unit for everyday convenience. The community is ideally positioned just off Park Avenue and SR 50 (E Colonial Drive), placing residents within close proximity to a wide selection of shopping centers, grocery stores, restaurants, and daily services. With quick access to the Florida Turnpike, SR 429, SR 408, and US 27, this location provides excellent connectivity to Downtown Orlando, Clermont, and surrounding areas, making it a great option for commuters and those looking to stay close to Winter Garden’s growing amenities and attractions.

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

Listing Agent: Melquisedec Martins (407-952-6948)

Remarks: Modern Comfort Meets Effortless Living! BRAND NEW KITCHEN APPLIANCES INCLUDING DISHWASHER!!! Welcome to this beautifully maintained and spacious 2-story townhome featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage—designed for both comfort and functionality. Step inside to an inviting open-concept layout filled with natural light, high ceilings, and seamless flow between the living, dining, and kitchen areas—perfect for entertaining or everyday living. The neutral tones and bright spaces create a warm, modern ambiance you’ll love. House was recently painted (all interior) and brand new carpet. Upstairs, retreat to your private primary suite, complemented by two additional well-sized bedrooms and a full bath—ideal for family, guests, or even a home office setup. Come check it out! Please use the following RentSpree link for application: https://apply.link/_ZzvQXU

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Emilia Rivero (412-944-3471)

Remarks: Prime Location & Resort-Style Living! Welcome home to this beautifully appointed first-floor, 2-bedroom, 2-bath condo in the highly sought-after GATED community of Southern Pines. The desirable open, split floor plan offers both space and privacy, enhanced by wood laminate flooring throughout the living, dining, and kitchen, tile in the baths, and plush carpeted bedrooms. The kitchen features granite countertops, and the home includes an in-unit washer and dryer for added convenience. Relax year-round in the bright solarium just off the living room—perfect for morning coffee or unwinding after a long day. Water, sewage, basic cable, and internet are all included, making this home as practical as it is comfortable. Enjoy resort-style amenities right outside your door, including a community pool, fitness center, indoor basketball court, tennis court, sand volleyball, playground, business center, game room with pool table, gas grilling area, and a private movie theater. Ideally located close to everything, but tucked away from the hustle and bustle. Located just minutes from the Florida Turnpike, SR-408, Winter Garden Village, and historic downtown Winter Garden, this condo offers the perfect blend of convenience, comfort, and community living.

Listing is courtesy of: MARTI PURDY PROPERTIES INC (407-614-6177)

Listing Agent: Marti Purdy (407-761-0848)