Displaying: For Rent
Location: Winter Garden
Property Type(s): Single Family
Living Area Square Feet: 2500 to 2999
Do Not Show Listings
Winter Garden - 16 properties found
709 GARDEN WEST TER, WINTER GARDEN, FL 34787
$5,5002 Days on yellowkey MLS ID: O6404301
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2591 Built: 2026Community: Garden WestSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Luxury Living Meets Historic Charm: Brand New Custom Home Steps from Downtown Winter GardenExperience the perfect blend of modern luxury and small-town enchantment in this brand-new, custom-built masterpiece. Located just a half-mile stroll from the vibrant heart of historic downtown Winter Garden, this 3-bedroom, 3.5-bathroom home offers an unparalleled lifestyle in one of Florida’s most sought-after neighborhoods.The Space:Every inch of this home features a meticulously thought-out floor plan designed for both high-end entertaining and quiet relaxation.Chef’s Dream Kitchen: Unleash your inner culinary artist in a kitchen equipped with premium finishes, custom cabinetry, and professional-grade appliances.Spa-Inspired Retreats: Each of the 3.5 bathrooms is a sanctuary of its own, featuring luxury tile work and high-end fixtures that evoke the feeling of a world-class resort.Storybook Curb Appeal: Start your mornings or wind down your evenings on the expansive, wrap-around front porch—the perfect spot to enjoy the friendly atmosphere of Winter Garden.The Location:Nature and adventure are literally at your doorstep. This property sits directly adjacent to the West Orange Trail, allowing you to hop on your bike or take a scenic jog at a moment’s notice. When you aren't on the trail, you’re just minutes away from the award-winning Saturday Farmers Market, boutique shopping, and the celebrated dining scene of Plant Street.Key Features:3 Spacious Bedrooms / 3.5 Designer BathroomsBrand new, custom constructionOpen-concept living with abundant natural lightDirect access to the West Orange TrailWalking distance to downtown shops and restaurantsLive the lifestyle you’ve been dreaming of. Schedule your private tour today! Minimum Requirements: 650+ Credit Score No Evictions No Bankruptcies Pass of background check Verifiable Income of at least 3 times the amount of monthly rent per month. All ERA Grizzard Real Estate residents are enrolled in the Resident Benefits Package (RBP) which includes renters insurance, HVAC air filter delivery (for applicable properties), credit building to help boost your credit score with timely rent payments, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. $59.00/month.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-787-6966)
Listing Agent: Jessica Stahlman (407-276-2594)
12626 CLEAR SAPPHIRE DR, WINTER GARDEN, FL 34787
$3,5003 Days on yellowkey MLS ID: O6404139
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2500 Built: 2025Community: Osprey Ranch Ph 1Single Family
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Welcome to Osprey Ranch where modern style meets everyday convenience! Built in 2025, this like-new two-story home in a community zoned for top-rated schools. Inside, you’ll find wood-look tile flooring, upgraded finishes, and a bright open-concept layout. The kitchen features stainless steel appliances, a large island with seating, walk-in pantry, and stylish backsplash—perfect for both daily living and entertaining. Triple sliding glass doors lead to a private, fenced paver patio ideal for relaxing. A first-floor bedroom and full bath provide flexible living options, along with a separate den/office. Upstairs, enjoy a spacious LOFT, a primary suite with walk-in closet and en-suite bath, plus two additional bedrooms with a shared full bath. LAWN CARE INCLUDED! **All Remi Emerson Residential tenants are enrolled in the Resident Benefits Package (RBP) for an additional $50 a month which includes your $100,000 tenant liability insurance, quarterly HVAC air filter delivery, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, plus on-demand pest control!**Security deposit is due upon lease signing. The first full month's rent is due 1 week prior to move in date. The 2nd month of rent is prorated. Every person 18 yrs or older must fill out an application. Please upload your last 2 months of paystubs in your application. If you have an animal/pet you must click on the Pet Screening link in the application. Only complete applications will be considered. A one time admin fee of $250 due upon approval. A lease renewal fee of $125 after 1 year.**
Listing is courtesy of: REMI EMERSON RESIDENTIAL (407-490-1848)
Listing Agent: Shelley Davis (407-625-3489)
1226 PORTMOOR WAY, WINTER GARDEN, FL 34787
$3,70038 Days on yellowkey MLS ID: O6393825
0 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2856 Built: 2003Community: Stoneybrook West 44/134Single Family
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 1226 Portmoor Road in the highly sought-after, manned-gated Golf community of Stoneybrook West! This stunning 5-bedroom, 3-bath golf-view home offers over 2,800 square feet of beautifully updated living space. No Carpets!!! Designed for both comfort and entertaining, the home features formal living and dining rooms, a spacious family room, and a desirable first-floor guest bedroom with a full bath. The chef’s kitchen shines with granite countertops, stainless steel appliances, and an extra refrigerator in the garage. Upstairs, enjoy new laminate flooring, generously sized bedrooms, and a luxurious primary suite with tray ceilings and a private balcony overlooking the course. Step outside to your upgraded screened lanai and low-maintenance turf backyard—perfect for relaxing or hosting gatherings. Residents enjoy a Jr. Olympic pool, fitness center, clubhouse, dock, tennis, basketball, playground, high-speed internet, cable, and discounted golf—all minutes from Winter Garden Village, major highways, hospitals, theme parks, and Orlando International Airport. Schedule your showing today!
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Shirley Botansky (407-704-0874)
15532 SWEET ORANGE AVE, WINTER GARDEN, FL 34787
$3,700101 Days on yellowkey MLS ID: O6376556
REDUCED by $250 (6.3%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 2017Community: Highlands/Summerlake Grvs Ph 1Single Family
Remarks: Come view this recently renovated, modern 3 bedroom home in the beautiful Horizon West area. This fully furnished home not only has conservation lake views, but also includes lawn care! Upon entering the foyer, you will immediately notice the high ceilings, custom furnishings, open floorplan, two living rooms, and the spacious kitchen. The chef's kitchen features double ovens, a natural gas cooktop with a chrome vented hood, side by side fridge and wine rack. The dry bar is encased with quartz countertops, and the large island provides a great backdrop to the custom artwork displayed throughout the home. The community offers a swimming pool, playground, dog park and is located next to Orange County National, which is ranked as the #1 public golf facility in Florida. Washer/Dryer included. Lawn, security, and high-speed internet services are included. Available now! $95 non-refundable application fee per applicant. Pets OK with $350 deposit ($150 refundable). Qualifications: Income 3X rent, credit score of 600 plus, and background checks. Equal Opportunity Housing.
Listing is courtesy of: BEST ORLANDO PROPERTY MANAGEMENT LLC (407-955-4158)
Listing Agent: Chris Bright (407-675-3098)
12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$3,3506 Days on yellowkey MLS ID: O6403110
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2781 Built: 2021Community: Encore At OvationSpa: NoSingle Family
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Gorgeous newer home 5 years old. 4-bedroom 3.5 bath home across the street from the pool and fitness center, Off Western Way on the west side of Disney. This home has a covered and paved front porch with direct views across the street to the community clubhouse, fitness center, pool and open park. When you want a little more privacy, you can sneak off to the small side covered patio. this home has some nice touch upgrades. Ceiling fans and decorative wall designs on select walls. As you enter into the home, you are greeted by a wide foyer which opens to the main Great room, the stairs, and the first-floor spare 4th bedroom with full private bath. Walk past the partially open staircase with beautiful iron Rail, into the main Great room featuring Family, dining and kitchen. The family room is very large, over 18x16 feet and has a great storage closet under the stairs. The dining room has a window and large slider to the side covered patio and is completely open to the kitchen. The amazing Kitchen has tons of cabinets, counter space, huge pantry, Large flat island with Stone counter bar top, cabinet crowns, all SS appliances and Gas stove. Just past the kitchen is the half bath powder room and drop zone from when you enter into from the rear facing garage. First floor is tile throughout except for bedroom. Upstairs has carpet in all bedrooms and open loft. The Master Bedroom has 2 very large walk-in closets, and nice large bath with two separate vanities with extra cabinet space, a walk-in shower, and private toilet. The Master has more privacy split away from the other bedrooms by the laundry room. Laundry room has extra space for an ironing board, and laundry sink next to the provided washer and dryer. Bedrooms 2, 3 are separated by a full bath with double sinks and shower/tub. Tankless water heater saves in efficiency and constant hot water. This home is in a great and quite community just a few miles off the 429 west of Disney. While this home sits across from the clubhouse and pool area, the community offers other areas of interest to explore and enjoy. A short block away has a fenced dog park and a walking trail around a long pond with Activities such as Corn hole, Bocce Ball courts, and picnic tables. Further inside the community has more open park areas with trails by scenic ponds currently under construction along with the back park which the playground should soon be built. Just a few miles off the major interchange of 429 and Western, just outside Disney West provides fast and easy access anywhere. Hospitals, restaurants and shopping are all close and many more are being built nearby. The builder states; Water Spring Elementary, Bridgewater Middle, and Windermere Highschool. All information here is deemed reliable but not guaranteed. Please email for more information or to get started in making this incredible home, YOUR home. Rent includes lawn care and all amenities access!
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Bryce Rysewyk (407-340-1754)
455 WINTER GROVE BLVD, WINTER GARDEN, FL 34787
$5,09027 Days on yellowkey MLS ID: O6397196
REDUCED by $100 (1.9%) on 04/28/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2631 Built: 2026Single Family
Remarks: Welcome to this stunning new construction home (2026) located in the desirable city of Winter Garden. This beautifully designed residence offers 5 bedrooms, 3 full bathrooms, and 1 half bath, providing ample space for comfortable living and entertaining. The home features a spacious open floor plan, modern finishes, and abundant natural light throughout. The kitchen flows seamlessly into the living and dining areas, creating the perfect setting for gatherings. Situated within a gated community, residents enjoy added privacy and a peaceful environment. Conveniently located near shopping, dining, top-rated schools, and major roadways, this property combines style, functionality, and an excellent location. A must-see opportunity!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Paloma Eduar Andrade Froldi (407-360-5466)
9131 CUT SHOT DR, WINTER GARDEN, FL 34787
$3,1509 Days on yellowkey MLS ID: O6402316
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2638 Built: 2019Community: Panther ViewSingle Family
Remarks: Freshly Painted!!! Now available for lease is this gorgeous 5-bedroom, 3-bathroom residence situated in one of Central Florida's most coveted neighborhoods! This exceptional home boasts an attached rear load 2-car garage and a charming front porch. Inside, you'll find an inviting open-concept layout with tile flooring adorning the living spaces. The airy kitchen features 42" cabinets, stone countertops, stainless steel appliances, a closet pantry, and an island sink with a delightful breakfast bar. The expansive master bedroom showcases a tray ceiling, a generous walk-in closet, and a master bath with dual sinks, a garden tub, and a separate shower. Innovation at Panther is enveloped by natural beauty and offers convenient access to highways, with Disney World and other popular theme parks, shopping centers, dining options, golf courses, and hospitals just minutes away! With top-rated schools and an unbeatable location, this opportunity is not to be missed! ***All Blue Chip Property Managers residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application.
Listing is courtesy of: BLUE CHIP INTERNATIONAL REALTY LLC (407-988-6543)
Listing Agent: Zane Place (407-663-9129)
17834 ADRIFT RD, WINTER GARDEN, FL 34787
$4,30085 Days on yellowkey MLS ID: O6380850
0 Days Off yellowkey (back on 4/25/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2674 Built: 2024Community: Waterleigh Ph 4B & 4CSingle Family
Remarks: Impressive residence with 3,821 square feet, designed to comfort, functionality, and practicality. The house features 4 spacious bedrooms, 3 full bathrooms, and an office ideal for a home office or study space. The highlight is the beautiful lake view in the back, offering tranquility and a perfect setting for relaxing or entertaining guests. Two-car garage with excellent storage space. A unique opportunity for those seeking quality of life, privacy, and a environment.
Listing Agent: Jean Dadam (407-961-2182)
17877 PHIL C PETERS RD, WINTER GARDEN, FL 34787
$4,29910 Days on yellowkey MLS ID: O6402176
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2501 Built: 1982Single Family
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Location, Location, Location! Exceptional opportunity in Winter Garden, just 4 minutes from Hamlin Town Center, in one of the fastest-growing areas in Central Florida. This unique property features approximately 2.5 acres of land, delivering something increasingly rare in today’s market: space, privacy, and flexibility of use. The home includes 3 bedrooms, 2 bathrooms, and a bonus room, with a functional layout and spacious living areas ideal for comfort and versatility. The standout feature is the expansive lot—perfect for hosting family and friends, enjoying gatherings, and making the most of group living without the usual limitations of close neighbors. The property provides ample parking and vehicle circulation space, easily accommodating multiple guests. In addition, this is truly a “country-style setting within the city”—you get the benefits of a rural feel with space, tranquility, and privacy, while remaining just minutes from urban conveniences, including shopping, dining, and everyday services. Located in the Horizon West area, the property is near highly regarded schools such as Hamlin Elementary School, Hamlin Middle School, and West Orange High School, and is surrounded by modern infrastructure and ongoing growth. Whether for personal use, long-term value, or a lifestyle centered on space and freedom, this property stands out in a high-demand, appreciating area. Contact us for more information and to schedule a private showing.
Listing is courtesy of: REIS E SILVA REALTY GROUP LLC (407-274-8510)
Listing Agent: Mara Brasil (407-970-9935)
15030 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$3,80012 Days on yellowkey MLS ID: O6400523
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2861 Built: 2024Community: Harvest At Ovation 112/64 Lot 142Single Family
Remarks: Nestled in the sought-after Harvest at Ovation community in Horizon West/Winter Garden, this beautifully appointed single-family home offers the perfect combination of comfort, style, and location. Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, the home includes a desirable first-floor suite—ideal for guests or multi-generational living. Enjoy the convenience of being just minutes from Walt Disney World, top-rated schools, shopping, dining, and everyday essentials. With easy access to FL-429 and US-192, as well as close proximity to Horizon West, Winter Garden Village, and Orlando, this home is perfectly positioned in one of Central Florida’s most rapidly growing and desirable areas. Please be aware that the garage apartment is currently rented until August 2026. it will become available after for additional rent. Easy to show on lock box.
Listing is courtesy of: KICANTO REALTY (305-744-2297)
Listing Agent: Cristiane Leon (305-744-2297)
WINTER GARDEN, FL 34787
$3,40022 Days on yellowkey MLS ID: O6398448
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2570 Built: 2015Community: Signature LakesSingle Family
Elementary School: Independence Elementary
Remarks: Winter Garden area, mintues to the Horizon West Shopping Center. Closing to Disney Parks, Community amenities including 2 Pools, Green spaces & Park areas, Boat Ramp, Fishing Docks, Tennis & Basketball courts, 2 Clubhouse with Fitness, Billiards & arcade, Dog Park, Bike & walking paths. Excellent Shool District. The 429 entrance/exit for an easy commute, Hamlin Shopping Center, Supermarket, and Winter Garden Grove is also nearby. Open Floor Plan. Tenants responsible for Power, Water and Lawn Mowing, Phone, renter insurance. The application Fee is $75 per adult 18 years and older. The application fee is Non-refundable.
Listing is courtesy of: ORLANDO SUNSHINE REALTY (407-666-7448)
Listing Agent: Annie Kwan (321-948-0882)
15045 LEBEAU LOOP, WINTER GARDEN, FL 34787
$3,55035 Days on yellowkey MLS ID: O6395013
0 Days Off yellowkey (back on 4/21/2026)
REDUCED by $200 (5.3%) on 04/14/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2832 Built: 2021Community: Winding Bay Ph 3Spa: NoSingle Family
Remarks: Welcome to this stunning 5-bedroom, 4 bath home offering modern comfort with stylish flair. Open floor plan with gorgeous Gourmet Kitchen. Nice upgrades, and versatile living spaces with a loft and separated large office with closet in one of the most desirable areas of Winter Garden. The dedicated home office and 5th bedroom with full bath are on the main floor with the large Chefs kitchen that offers a huge walk in pantry, breakfast bar island, built in microwave and over with separate gas cooktop and larger side eating area with a slider that looks out over the large covered lanai 10x14 and partially fenced yard. At the top of the stairs is a oversized loft 13-6 x 18 which connects the primary bedroom and suite, along with bedrooms 2, 3 which share bath 3, and bedroom 4 has a private bath. This amazing home is in the highly desirable community Winding Bay. The community offers a cute parks, dog parks, playground, picnic pavilion, resort style pool and cabana, and serene pond views. The community is off Avalon Road between Seidel and Western Way near the 429 and Disney just minutes from brand new shopping and restaurant centers. Email to book a viewing. Rent includes lawn care and all amenities access! Photos will be updated 4-2
17329 BEACHGRASS ALY, WINTER GARDEN, FL 34787
$3,70038 Days on yellowkey MLS ID: O6394144
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2510 Built: 2025Community: Lakestar At OvationSingle Family
Remarks: Be the first to live in this brand new home in Lakestar at Ovation, just 15 minutes from Disney. This spacious 4 bedroom, 3 bath property features an open layout with modern finishes and quartz countertops, an upstairs loft, a covered lanai, and a two car garage. Bright natural light and thoughtful design make this home perfect for comfortable everyday living. Residents enjoy resort style amenities including a community pool, fitness center, and clubhouse. Conveniently located near schools, and less than 5 miles to SR 429 for easy commuting. Schedule your tour today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Maite Martinez (407-446-1280)
8025 NAVEL ORANGE LN, WINTER GARDEN, FL 34787
$3,47534 Days on yellowkey MLS ID: O6395339
0 Days Off yellowkey (back on 4/7/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2722 Built: 2015Community: Summerlake GrvsSingle Family
Elementary School: Summerlake Elementary
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)
16021 TOLLINGTON ALY, WINTER GARDEN, FL 34787
$3,50041 Days on yellowkey MLS ID: O6393427
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2689 Built: 2025Community: Encore/Ovation Ph 1Single Family
Remarks: Beautiful home with a stunning contemporary design, premium upgrades, and an unbeatable location just minutes from Disney Parks, top-rated schools, and premier shopping destinations. Property is featured with 4 bedrooms and 3 bathrooms - In law suite on first floor is , modern open floorplan with high ceilings and abundant natural light. Laundry room fully equipped with washer and dryer and a stand alone sink. The community is a resort-style living, families can enjoy top-tier community amenities including pool, fitness center, playground, and a dog park. The house is currently tenant occupied until April 3rd 2026. The house will be ready to show as of April 4th 2026. Be aware there's road constructions around the area.
12763 CHARMED DR, WINTER GARDEN, FL 34787
$4,10072 Days on yellowkey MLS ID: O6384328
0 Days Off yellowkey (back on 3/21/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2587 Built: 2024Community: Waterleigh Ph 4B & 4CSingle Family
Remarks: Welcome to your SEMI-FURNISHED home in one of Winter Garden's most desirable communities! This property offers a perfect blend of comfort and convenience. Enjoy the benefit of A-rated schools right within the community—both the elementary and middle schools—with no need for additional transportation. Plus, the high school, just a short distance away, is also highly rated, making this an ideal location for families seeking exceptional education at every level. The community offers a wealth of amenities, including a pool, fitness center, tennis courts, playgrounds, mini golf, and year-round events for all ages. Here, you're not just getting a home—you're embracing a lifestyle. This spacious home features 5 bedrooms and 4 bathrooms, with an open kitchen and living area perfect for family gatherings. The semi-furnished setup makes it move-in ready. The large backyard provides plenty of space for outdoor activities or relaxation. With easy access to major roads, shopping, dining, and parks, everything you need is right at your door. Don’t miss this unique opportunity to live in a community where convenience, comfort, and top-tier education come together. Schedule your showing today!
Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)
Listing Agent: Bruna Canesin Motta (407-580-1367)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.