Winter Garden Single Family Homes For Sale - 697 homes

Remarks: Under contract-accepting backup offers. Welcome to luxury lakefront living on the shores of sought-after Johns Lake. Perfectly positioned with breathtaking west-facing sunset views, this fully upgraded waterfront residence offers the ultimate blend of elegance, comfort, and resort-style outdoor living in one of Winter Garden’s most desirable communities. Featuring nearly 3,500 square feet on 1 floor of thoughtfully designed living space, this exceptional home showcases 4 bedrooms, 3.5 bathrooms, a 3-car garage, premium hardwood flooring, and a gourmet chef’s kitchen with high-end finishes, upgraded cabinetry, and expansive entertaining space. Designed to maximize the waterfront lifestyle, the home seamlessly transitions outdoors to a private backyard retreat complete with a sparkling pool, oversized spa, outdoor kitchen, and stunning panoramic lake views — the perfect setting for sunset entertaining year-round. Additional highlights include a newer roof and HVAC systems (approximately 3 and 5 years old), luxurious updated interiors, spacious living areas. This rare Johns Lake opportunity combines elevated style with effortless move-in-ready convenience. With premium designer furnishings negotiable. Making this a possible true turnkey opportunity. Located within the highly sought-after Johns Lake Pointe community, residents enjoy proximity to historic downtown Winter Garden, top-rated schools, shopping, dining, major highways, and Orlando’s world-class attractions. Experience the best of Central Florida lakefront living in a home where every evening ends with unforgettable sunsets over Johns Lake.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Carlos Facchinat (407-433-8109)

Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Julie Bettosini, Pa (321-689-9594)

Remarks: Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!

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

Listing Agent: Jennifer Dollar (407-252-3762)

Remarks: Welcome to 3208 Sailing Pier Ave, the original model home at The Estates at Lakeview Preserve. Built in 2023, this stunning residence offers 5 bedrooms, 4 bathrooms, and nearly 4,000 square feet of living space. It is being sold fully furnished with designer-selected pieces, representing turnkey luxury at its finest. The first level features an open-concept layout filled with natural light, a chef-style kitchen with quartz countertops and a walk-in pantry, a spacious living and dining area, a private flex room, and a serene and elegant primary suite. Two additional bedrooms are also located on the first floor. The second level offers a second living area, two more bedrooms, and a beautifully furnished family/game room, perfect for entertaining and relaxing. As a former model home, every detail was professionally designed, and all furnishings are included. The expansive backyard provides the perfect space to create your dream outdoor oasis. Located in the gated community of Estates at Lakeview Preserve, residents enjoy resort-style amenities including a pool, clubhouse, fitness center, playground, and scenic lakeside trails. The home is just minutes from SR-429, Disney, Winter Garden Village, and top-rated schools. Move-in ready and meticulously maintained, this home offers exceptional style, convenience, and value. Schedule your private showing today.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Mireille Stewart (786-553-6246)

Remarks: Welcome to this stunning brand-new single-story home, perfectly located in the sought-after Horizon West community in Winter Garden. This 4-bedroom, 3-bath residence with a 2-car garage combines modern design, energy efficiency, and a lifestyle of comfort and elegance. Step inside and be amazed by the bright open-concept floorplan, highlighted by natural light and a fresh, modern color palette. The chef’s kitchen is a true showstopper with 42-inch shaker cabinets in light tones, gorgeous quartz countertops, a large island ideal for gatherings, and premium stainless steel appliances—including refrigerator, range, dishwasher, microwave, washer, and dryer. The home’s efficient construction ensures comfort and savings, while the spacious lanai invites you to relax and enjoy serene views of the Star Lake and lush conservation area—your private piece of paradise, right in your backyard. Opportunities like this don’t last long in Horizon West! Don’t miss your chance to own this extraordinary single-story lakeside retreat. Schedule your private showing today and make this dream home yours!

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

Listing Agent: Daniel Pavel (407-747-3408)

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions

Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)

Listing Agent: Sylvester Harding (407-557-3119)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE Welcome to the Arlington with Bonus and 6 Bedrooms! This stunning 4,236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE Welcome to the Arlington with Bonus and 6 Bedrooms! This stunning 4,236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Move-in ready and ideal for first-time homebuyers, downsizers, or empty nesters seeking low-maintenance living, this beautiful single-family home offers the perfect blend of comfort, convenience, and style. From the moment you arrive, you'll appreciate the welcoming covered front porch overlooking a peaceful pond—an ideal spot to enjoy morning coffee or relax at the end of the day. Inside, soaring ceilings, durable laminate and porcelain tile flooring, and an open-concept layout create a bright and inviting atmosphere. The spacious living room features a decorative fireplace and flows seamlessly into the heart of the home: a well-appointed kitchen with a large island, pendant lighting, walk-in pantry, and plenty of space for casual dining, entertaining guests, or everyday living. Designed for easy living, the open floor plan provides comfortable gathering spaces without the upkeep of a larger home. Best of all, yard maintenance is included through the HOA, allowing you to spend more time enjoying life and less time working outdoors. Whether you're purchasing your first home, looking to simplify your lifestyle, or searching for a move-in-ready retreat, this home offers the convenience and carefree living you've been looking for. Conveniently located near shopping, dining, healthcare, and major roadways, this charming property is ready for its next owner. Don't miss your opportunity to enjoy comfortable, low-maintenance living in a beautiful setting.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Cindy Brads (407-625-7443)

Remarks: Beautiful 5-Bedroom Home in Independence – Winter Garden, FL Located in the highly desirable Independence community in Winter Garden! This exceptionally maintained 5-bedroom, 2.5-bath home sits on an oversized 0.27-acre lot with beautiful water and conservation views in both the front and back, offering privacy, tranquility, and plenty of space for family living. This spacious home features approximately 2,639 sq. ft. of living space with an open floor plan, granite countertops, stainless steel appliances, crown molding, and abundant natural light throughout. The covered patio overlooks a large fenced backyard with no rear neighbors and peaceful wooded reserve views outdoors. Located on one of the most desirable streets in Independence, the home is within walking distance to top-rated schools, parks, pools, fitness center, trails, playgrounds, and community amenities. HOA includes cable and high-speed internet. Highlights: • 5 Bedrooms | 2.5 Bathrooms • 2,639 Sq. Ft. • Large 0.27-acre lot • Water views front and back • Granite countertops • New AC •Big Bedrooms

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026 The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large walk-in closet and a private bath with a free-standing tub, a separate shower with a seat, and a private toilet area. The second floor features a spacious loft, and large secondary bedrooms. The Griffin is well planned for a comfortable, luxurious lifestyle. Model home available for walkthrough.

Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)

Listing Agent: Dayene Grubert (863-521-4474)

Remarks: One or more photo(s) has been virtually staged. Welcome to Covington Chase, one of the most sought-after communities in Winter Garden, just minutes from the charm and energy of historic downtown. Situated on an oversized 0.38-acre lot, this 4-bedroom, 4 full bathroom home offers a rare combination of space, functionality, and flexibility. The fully fenced backyard provides plenty of room to relax, entertain, or create your own outdoor retreat, while the long driveway and 3-car garage give you ample parking and storage, including space for a golf cart so you can fully enjoy this golf cart district lifestyle. The floor plan is thoughtfully designed for both everyday living and long-term versatility. The primary suite is located downstairs, creating a private retreat with two walk-in closets and a large bathroom that offers both space and comfort. Also on the first floor is a dedicated office, perfect for working from home or creating a quiet, separate space for productivity. In addition, the first floor features a Jack and Jill bedroom and bathroom setup, ideal for guests, kids, or multigenerational living. This layout allows for privacy while still maintaining a connected and functional flow throughout the home. Upstairs, you will find a spacious loft that can be used as a second living area, media room, or play space, along with a full bedroom and full bathroom. This upstairs setup is perfect for guests, older children, or anyone who would benefit from having their own private area within the home. The overall layout gives you multiple living zones and flexibility, making it easy to adapt the home to your lifestyle, whether that means working from home, hosting guests, or simply enjoying extra space. The roof was replaced just a few years ago, offering added peace of mind and reducing one of the major future expenses for a new owner. Beyond the home itself, the lifestyle here is what truly stands out. You are just minutes from the Downtown Winter Garden Historic District, known for its brick-lined streets, locally owned restaurants, coffee shops, boutiques, and the popular weekly farmers market. Living in the golf cart district means you can easily head downtown for dinner, events, or a casual night out without needing to get in your car. You are also close to the West Orange Trail, a 22-mile scenic trail perfect for biking, walking, and enjoying the outdoors. Homes with this kind of lot size, a flexible floor plan with a downstairs primary suite, office, additional bedroom, plus an upstairs loft and private guest space, and a 3-car garage are hard to find this close to downtown. This is a unique opportunity to own a home that offers both the space you need and the lifestyle you want.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Under Construction. Waterleigh presents the Clearden. This amazing all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find the first bedroom complete with ensuite bathroom and a powder room across the hall. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and additional three bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity sinks and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor for convenience. This home features a two car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Clearden includes a Smart home technology package which allows you to control your home with your smart device while near or away. *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)

Remarks: Welcome to 8018 Bowery Drive, a spacious 5-bedroom, 3-bathroom home perfectly positioned in Winter Garden right on the edge of Windermere. This layout offers flexibility and comfort for everyday living while also providing the space to entertain. Upstairs, you’ll find the private primary suite, a generous loft, a full bathroom, and three additional bedrooms, two of which offer nightly views of Disney fireworks right from the window. Downstairs features two separate living spaces, plus a conveniently located bedroom and full bathroom ideal for guests or in-laws. Step outside through the telescoping sliding glass door to enjoy a large covered porch and private backyard with no rear or side neighbors. Curb appeal shines with a paver driveway and charming wrap-around front porch. Just minutes from the 429, Disney, and all that Windermere has to offer, this home blends location, privacy, and everyday convenience. Don’t miss the chance to make this beautiful home yours!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath.

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 15' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under Construction. Welcome to Northlake at Ovation! Gorgeous brand new home located in the highly desirable Horizon West area of Winter Garden. This beautiful two story home has an open kitchen with plenty of upgrades from the AW Collection Harmony such as beautiful 42 inch cabinets, all stainless steel appliances including stove, dishwasher, and microwave. Large island with upgraded quartz countertop perfect for gatherings that is open to the family room that has tall two story ceiling with many windows. Main living space features wood look tile flooring and bedrooms with upgraded carpet for comfort. Enjoy the amenities with a swim in the community pool, clubhouse, playground, and dog park. This home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World.

Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)

Listing Agent: Reed Williams (813-918-4491)

Remarks: Stunning single-story home featuring 3 bedrooms and 2.5 bathrooms, situated in the highly sought-after Hawksmoor community. This property boasts modern tile and carpet flooring, complemented by elegant granite countertops and a spacious 2-car garage. Residents can enjoy top-tier community amenities, including a resort-style pool, walking trails, and a playground. Strategically located, you are just minutes away from historic downtown Winter Garden, Disney, and premier theme parks. With an abundance of shopping, dining, and entertainment nearby, plus quick access to SR 429 and Florida’s Turnpike, your daily commute will be a breeze.

Listing is courtesy of: ON ME REALTY (321-370-1474)

Listing Agent: Eduardo Pavone (407-232-1241)

Remarks: Under contract-accepting backup offers. .

Listing is courtesy of: K HOVNANIAN FLORIDA REALTY (321-263-2601)

Listing Agent: Richard Selikoff (201-741-7242)