Displaying: For Sale
Location: Winter Garden
Property Type(s): Townhomes
Price: $400,000 to $499,000
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Winter Garden - 75 properties found
16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787
$490,000248 Days on yellowkey MLS ID: O6353551
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2070 Built: 2021Monthly Fee: $284 Tax: $5,869 (2024)Community: Hawksmoor Ph 3Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,869
Elementary School: None
High School: Horizon High School
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: Welcome to this stunning corner-unit townhome in the heart of Winter Garden, where natural light, extra space, and thoughtful design come together to create the perfect place to call home! As you step inside, you'll be greeted by a welcoming foyer that leads into an open-concept layout. From there, you’ll approach the beautifully designed modern kitchen and spacious dining area that flows seamlessly into the gathering room, ideal for entertaining or everyday living. On the first floor, you’ll find a versatile fourth bedroom with a closet, offering flexibility for guests, a home office, or a playroom. You’ll also love the spacious breezeway that adds both elegance and function to the layout, while upstairs, bedrooms 2 and 3 are connected by a convenient Jack-and-Jill bathroom. The end-unit location provides added privacy and extra green space; plus, knowing this home has been beautifully maintained with a roof (2021), water heater (2021), and AC unit (2021)—all in excellent condition, gives peace of mind. Beyond the home itself, the community offers an incredible lifestyle with resort-style amenities such as a pool, splash pad, clubhouse, gym, pet-friendly parks, soccer field, playground, scenic walking trails, a covered picnic area, regular social events, and more. Located just minutes from Hamlin Town Center, top-rated schools, shopping, dining, and parks within the vibrant Horizon West community—one of Central Florida’s fastest-growing and most desirable areas—this home truly has it all. Don’t miss your opportunity to own this beautifully maintained, move-in-ready corner-unit townhome. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Erica Jefferson (414-248-9118)
18167 CIDER MILL LN, WINTER GARDEN, FL 34787
$469,990117 Days on yellowkey MLS ID: O6386278
1 Days Off yellowkey (back on 5/14/2026)
REDUCED by $5,000 (1.1%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1817 Built: 2025Monthly Fee: $205 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Taxes:$1,424
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under Construction. Welcome to a charming Sandhill townhome in Waterleigh, offering comfort and modern convenience. Features include 1,816 sq ft, 3 bedrooms, 2.5 baths, a garage, loft space, and smart home technology. The open layout includes a bright living area, gourmet kitchen, and dining space. Upstairs, find spacious bedrooms and a versatile loft. Also includes smart home features that enhance comfort and convenience in this desirable community. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
8156 WOOD SAGE DRIVE, WINTER GARDEN, FL 34787
$449,000104 Days on yellowkey MLS ID: V4947783
REDUCED by $10,000 (2.2%) on 04/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1853 Built: 2018Monthly Fee: $315 Tax: $3,792 (2025)Community: SummerlakeTownhouse
Taxes:$3,792
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Winter Garden – Rare, immaculate end-unit townhome in highly sought-after Summerlake, fully updated and truly MOVE-IN READY. Step onto the charming front porch—perfect for morning coffee as the neighborhood comes to life—and then into a bright, open interior with soaring ceilings, a freshly painted interior, and an inviting floor plan. The chef’s kitchen features abundant real wood cabinetry, upgraded granite countertops, and a cozy eat-in area, all overlooking a spacious family room ideal for gatherings. Large windows fill the space with natural light and frame your private rear courtyard—an outdoor area with serious potential. Think Italian courtyard villa vibes: brick pavers, twinkling lights, lush greenery, and maybe that pizza oven you’ve been dreaming about. The courtyard serves as a true extension of your living space, whether you envision a gardener’s paradise, a peaceful retreat, or a stylish entertaining area. Beyond the courtyard, you’ll find a generous 2-car garage, perfect for vehicles and extra storage. Upstairs, the home offers 3 bedrooms and 2.5 baths, all meticulously maintained, including NEW carpet upstairs and tasteful updates throughout. Living in Summerlake means more than owning a home—it’s a lifestyle. With top-tier amenities, nearby shopping, dining, and everything Winter Garden has to offer, this is the perfect place to call home.
Listing is courtesy of: APARO-GRIFFIN PROPERTIES INC (386-738-2845)
Listing Agent: Kathy Aparo-Griffin (386-748-0173)
17736 PORTER RD, WINTER GARDEN, FL 34787
$451,54249 Days on yellowkey MLS ID: G5112009
0 Days Off yellowkey (back on 5/6/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1715 Built: 2026Monthly Fee: $230Community: Serenade At OvationTownhouse
Taxes:$0
Elementary School: Water Spring Elementary
Remarks: One or more photo(s) has been virtually staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. PORTER Townhome offers 3 Bedrooms, 3 Baths with a large open first floor. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or exploring local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, bask in the sun-drenched community clubhouse, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
17025 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$456,55449 Days on yellowkey MLS ID: G5112007
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1697 Built: 2026Monthly Fee: $225Community: Hamlin MeadowsTownhouse
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality.
5755 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$455,00052 Days on yellowkey MLS ID: O6404161
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1797 Built: 2019Monthly Fee: $338 Tax: $4,506 (2025)Community: Orchard Hills Ph 4Townhouse
Taxes:$4,506
Elementary School: Keene Crossing Elementary
Remarks: Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills community of Winter Garden, offering 3 bedrooms, 2.5 baths, a 2-car garage, and abundant natural light throughout. As you enter the home, you are welcomed into the dining area which then flows seamlessly into the spacious living room and kitchen, creating an inviting layout perfect for everyday living and entertaining. Tile flooring extends throughout the downstairs living areas, kitchen, and wet areas for style and easy maintenance. The kitchen features stunning granite countertops that contrast beautifully with the white cabinetry, along with stainless steel appliances all included. Upstairs, you’ll find all three bedrooms with comfortable carpet flooring, as well as a convenient laundry room complete with washer and dryer. The primary bedroom offers private access to a balcony where you can enjoy peaceful water views and relax in a serene outdoor setting. Residents of Orchard Hills enjoy exceptional amenities including a clubhouse, fitness center, picnic area with grills, dog park, playground, and a vibrant community atmosphere with events and social clubs designed to build lasting relationships.
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
15038 WINDFLOWER ALY, WINTER GARDEN, FL 34787
$441,00050 Days on yellowkey MLS ID: O6405201
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 2024 Tax: $5,956 (2025)Community: Osprey Ranch Ph 1Spa: NoTownhouse
Taxes:$5,956
Remarks: Welcome to this beautiful and well-maintained home located in the highly desirable community of Winter Garden. This charming property offers a perfect blend of comfort, functionality, and modern living. Featuring a spacious layout, the home provides ample natural light throughout, creating a warm and inviting atmosphere. The kitchen is designed for both convenience and style, with plenty of cabinet space and room to entertain. The living and dining areas flow seamlessly, ideal for gatherings and everyday living. The bedrooms are generously sized, offering comfort and privacy, while the bathrooms are well-appointed. The property also includes a private outdoor space, perfect for relaxing or enjoying Florida’s year-round sunshine. Conveniently located near major highways, shopping centers, restaurants, and top-rated schools, this home offers both tranquility and accessibility. Don’t miss this opportunity to own a home in one of Winter Garden’s most sought-after areas!
Listing is courtesy of: DTB FLORIDA REALTY, INC. (786-543-8296)
Listing Agent: Pedro Henriq Stuart Lima (813-943-7731)
12780 SUNSET WALK DR, WINTER GARDEN, FL 34787
$465,00074 Days on yellowkey MLS ID: O6398355
1 Days Off yellowkey (back on 5/5/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1760 Built: 2026Monthly Fee: $150 Tax: $400 (2025)Community: Westhaven At OvationTownhouse
Taxes:$400
Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion Fall 2026. Our Kellogg Townhome features a covered entry that leads to an open and expansive living space, L shape cabinet kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities and separate shower.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Dayene Grubert (863-521-4474)
15140 WINDFLOWER ALY, WINTER GARDEN, FL 34787
$410,00051 Days on yellowkey MLS ID: S5149180
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1536 Built: 2024Monthly Fee: $200 Tax: $5,304 (2025)Community: Osprey Ranch Ph ITownhouse
Taxes:$5,304
Remarks: Stunning 3-bedroom, 2.5-bath townhome in the highly desirable Winter Garden area! This home offers a bright and inviting atmosphere with a sought-after south-facing exposure, filling the space with natural light all day long. Featuring a modern open layout, spacious living areas, and all bedrooms privately located upstairs, it’s designed for both comfort and functionality. Perfectly located just minutes from shopping, dining, and major highways, this property is ideal for homeowners and investors alike. Don’t miss the opportunity to own a beautiful home in one of Central Florida’s fastest-growing communities!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Jenny Caso (407-694-9682)
5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787
$488,00084 Days on yellowkey MLS ID: S5146601
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2131 Built: 2012Monthly Fee: $264 Tax: $5,449 (2025)Community: Signature Lakes Ph 02 A B H I JTownhouse
Taxes:$5,449
Remarks: Beautiful 4-bedroom, 2.5-bathroom townhouse located in the desirable Winter Garden area. The primary bedroom is conveniently located downstairs, offering comfort and privacy, while upstairs you’ll find additional spacious bedrooms. This home features a modern layout perfect for everyday living and entertaining, along with a cozy patio, a 2-car garage, and ample natural light throughout. The community also offers great amenities including a pool and clubhouse, tennis court and more ...Located in a quiet community, close to everything you need. Perfect for living or investing.Ideally located near Publix, Walmart, major expressways, and just minutes from Winter Garden Village, Walt Disney World Resort, cinemas, restaurants, and more. All appliances and the pergola on the patio are included.
Listing is courtesy of: MD3 HOMES LLC (407-557-8810)
Listing Agent: Monica Duran (407-702-5796)
15659 JUNGLE ALY, WINTER GARDEN, FL 34787
$435,00095 Days on yellowkey MLS ID: S5143684
INCREASED by $75,000 (20.8%) on 04/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1732 Built: 2021Monthly Fee: $203 Tax: $6,265 (2024)Community: Winding Bay Ph 2Townhouse
Taxes:$6,265
Remarks: Seller motivated. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs offers generously sized bedrooms, including a private primary suite with walk-in closet and an-suite bath. Enjoy low-maintenance outdoor living with a private patio and rear-entry garage. Conveniently located near top-rated schools, shopping, dining, and major roadways. A fantastic opportunity to own in one of Central Florida’s most sought-after communities! Offers may be entered ONLINE through Tuesday, April 14, 2026 at 3:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Dinorah Navarro (407-625-7522)
12036 HOLYSTONE ST, WINTER GARDEN, FL 34787
$455,000202 Days on yellowkey MLS ID: S5139531
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1817 Built: 2022Monthly Fee: $256 Tax: $6,116 (2024)Community: Waterleigh Ph 4ATownhouse
Taxes:$6,116
Remarks: This townhome stands out with its bright, open layout and an exceptionally versatile design. As you step inside, you’re welcomed by a spacious first floor with a seamless flow between the living room, dining area, and kitchen—perfect for everyday living and entertaining. The kitchen features granite countertops, a breakfast bar, and a convenient pantry closet. A half bath is also located on the main level for added ease.Upstairs, you’ll find all three well-appointed bedrooms along with a generous flex space enclosed with sliding doors, ideal for a home office, media room, playroom, or guest area—whatever your lifestyle needs. The primary suite includes a walk-in closet and a private bathroom with a granite dual-sink vanity and a tiled shower. The split layout provides separation from the additional two bedrooms, enhancing privacy and comfort. Nestled in a thoughtfully designed community, residents enjoy access to multiple clubhouses, fitness centers, resort-style pools, splash zones, playgrounds, dog parks, sports courts, scenic walking paths, lakeside pavilions, mini-golf, sand volleyball, and peaceful spots to enjoy the sunset.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Santiago Actis (689-248-5695)
16209 ADMIRALS COVE LN, WINTER GARDEN, FL 34787
$414,99590 Days on yellowkey MLS ID: S5145675
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1568 Built: 2020Monthly Fee: $275 Tax: $6,070 (2025)Community: WaterleighTownhouse
Taxes:$6,070
Remarks: Rare opportunity to own one of the largest townhome lots in the highly sought-after Waterleigh community in Horizon West. This beautifully maintained 3-bedroom, 2.5-bath IBIS model townhome, built in 2020, offers 1,568 sq ft of thoughtfully designed living space and sits on an oversized lot of approximately 4,100 sq ft — nearly double the lot size of many newer townhomes in the community. One of the most exceptional features of this property is the extended driveway with space for up to 6 vehicles, in addition to the 1-car garage — a rare and highly desirable feature among townhomes in Waterleigh, perfect for families and guests. Inside, the home features a bright open-concept layout with a modern kitchen, spacious living and dining areas, and abundant natural light throughout. Upstairs, you’ll find well-sized bedrooms, including a comfortable primary suite with walk-in closet and private bath. Step outside and enjoy the added outdoor space that truly sets this property apart — ideal for relaxing, entertaining, or simply enjoying extra privacy. Waterleigh offers resort-style amenities including multiple pools, clubhouse, fitness areas, parks, walking trails, and top-rated schools nearby, all within one of the fastest-growing areas of Horizon West.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Carlo Ovalles Caicedo (407-692-3706)
5706 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$460,000 MLS ID: O6386620
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1712 Built: 2018Community: Orchard Hills Ph 4Townhouse
Taxes:
Tax Year:
Remarks: Welcome to 5706 Cypress Hill Rd, a 3-bedroom, 2.5-bath townhome located in the Orchard Hills community of Winter Garden. With 1,886 sq ft of living space, this home offers an open layout that flows comfortably between the kitchen, dining, and living areas, making it practical for everyday living. Orchard Hills features amenities including a community pool, fitness center, playgrounds, dog park, and green spaces. The location provides convenient access to major roadways, shopping, dining, and area attractions. Excellent investment opportunity
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Mariana Nossa (407-455-9565)
13278 SERENE GLADE RD, WINTER GARDEN, FL 34787
$434,990 MLS ID: G5105229
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1715 Built: 2025Community: Serenade At OvationTownhouse
Remarks: One or more photo(s) has been virtually staged. Under Construction. Sample ImagesPorter Town Home – Stylish Living Beautiful townhome offering 1,715 sq. ft. of thoughtfully designed living space, featuring three bedrooms, two and a half baths, and a spacious two-car garage with a charming paver driveway. Step inside to impressive tall ceilings, enhancing the natural light and creating a bright, open, and airy atmosphere throughout. Elegant linen cabinets and sleek quartz countertops, perfectly paired with durable, designer-inspired RevWood laminate flooring that flows seamlessly across the first floor. A perfect blend of style, functionality, and modern comfort—ideal for everyday living and effortless entertaining.
Listing Agent: Cindy Sapp (352-516-2843)
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