Winter Garden Homes For Sale & Real Estate - 987 homes

Remarks: This stunning 4-bedroom, 3.5-bath residence offers an impressive 3,909 sq ft of thoughtfully designed living space, making it one of the best family floorplans available in Winter Garden. The open and airy layout features high ceilings and spacious rooms that create a welcoming, light-filled atmosphere perfect for everyday living and entertaining. The primary bedroom is conveniently located downstairs for privacy and ease, while the remaining bedrooms are upstairs—each boasting a generous walk-in closet for ample storage. Throughout the home, you'll enjoy durable and stylish tile and laminate flooring, providing a clean, low-maintenance look that flows seamlessly from room to room. Step outside to the spacious fenced backyard—ideal for safe play, gardening, pets, or relaxing in your own private outdoor oasis. The yard also has plenty of space for a custom pool. Additional standout features include a dedicated office (ideal for remote work or study), a fun playroom, and a versatile media room—perfect for movie nights, gaming, or family gatherings. These bonus spaces enhance the home's appeal for growing families. Nestled in a family-friendly neighborhood that's centrally located in Winter Garden, this home offers easy access to top-rated schools, shopping, dining, and major roadways. Families love the convenience of a beautiful community pool just steps away from the home. Kids can safely ride their bikes to nearby schools (only .2 miles away), fostering independence and community connections. The community amenities provide plenty of opportunities for recreation and relaxation, including parks, playgrounds, and green spaces that encourage outdoor play and neighborly gatherings. Don't miss this exceptional opportunity to own a move-in-ready gem in one of Winter Garden's most desirable family-oriented areas. Schedule your private showing today!

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

Listing Agent: Paulo Silva (407-790-1649)

Remarks: Under contract-accepting backup offers. Tucked away on 2.5 private lakefront acres in the heart of Winter Garden, this exceptional 4-bedroom, 4 full + 2 half bath estate offers privacy, space, and the ultimate retreat lifestyle. In this beautiful home, you can start your day drinking morning coffee on your screened-in lanai overlooking Lake Tilden, enjoy a mid-afternoon swim in the saltwater, heated pool, and end your evening with Disney fireworks lighting up the sky from your backyard. Inside, the home features fresh interior paint, a dedicated home office, a spacious great room, and formal living and dining areas perfect for both entertaining and quiet relaxation. Custom built-ins throughout the home provide charm, function, and plenty of storage. Three newly remodeled bathrooms include a spa-like master bath with a soaking tub, multi-head shower, and finished walk-in closet, bringing luxury and comfort to daily living. Updated interior and exterior lighting enhances the home while honoring its timeless character. A new electrical panel ensures modern reliability. A versatile ADU adds endless possibilities as a home gym, private office, guest suite, creative studio, or man cave, giving flexibility for multigenerational living or working from home. Recent upgrades include a new well pump, whole-home water filtration system, new septic drain field, two new HVAC units, brand-new pool equipment with iAquaLink automation, and a newly epoxied garage floor. Outdoors, fresh exterior paint, updated landscaping, and a newly fenced backyard with puppy picket fencing create an inviting environment for kids, pets, and entertaining. This rare lakefront property combines acreage, character, and thoughtful updates just minutes from downtown Winter Garden, top-rated schools, dining, and shopping. With space to spread out, enjoy the outdoors, and live a lifestyle others only dream about, this home is meant to be lived in, loved, and enjoyed for years to come.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Lisa Kirsch (678-373-8917)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this single-story home in the highly sought-after Covington Chase community, perfectly positioned on a quiet cul-de-sac hilltop with peaceful lake views. The fully fenced .25-acre yard offers space, privacy, and room for a future pool or patio expansion, while the large covered lanai and expansive outdoor back patio seating areas create the ideal setting for entertaining, relaxing, or enjoying Florida sunsets. Step inside to discover an open and functional floor plan featuring four bedrooms plus a versatile den or office with glass French doors and a built-in Murphy bed, perfect for a home office, guest room, or additional living space. Natural light floods the interior through triple sliding glass doors in the family room and additional sliders in the primary suite, highlighting the bright, airy design. Elevated ceiling heights enhance the spacious feel throughout the main living areas. Premium features include hurricane-proof glass front doors, tile flooring throughout main living areas, and laminate in the dining room. The oversized three-car garage (approx. 32 x 26) provides abundant space for vehicles, storage, a workshop, or a golf cart. The exterior was freshly painted just five years ago, adding to the home’s curb appeal. Covington Chase offers a community pool, park, and low HOA. The West Orange Trail runs directly through the neighborhood, ideal for walking, jogging, biking, or simply enjoying the outdoors. Living in Downtown Winter Garden means embracing a vibrant, walkable lifestyle with award-winning farmers markets, annual festivals, Plant Street Market, Crooked Can Brewery, boutique shopping, eclectic dining, and lively entertainment all within golf cart distance. Convenient access to Winter Garden Village, Highway 429, and the surrounding Orange County attractions puts everything you need right at your doorstep. This home perfectly combines lake views, elevated outdoor living spaces, and an active Downtown Winter Garden lifestyle, making it a true gem in one of Central Florida’s most desirable neighborhoods.

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

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

Remarks: Under contract-accepting backup offers. Tucked away at the end of a quiet cul-de-sac in the highly sought-after Tuscany community of Winter Garden, this pool home offers the rare combination of privacy, space, and lifestyle that buyers are searching for. Set on an oversized pie-shaped lot shaded by mature oak trees, the property welcomes you with beautiful curb appeal and lush landscaping before opening to a backyard retreat designed for everyday enjoyment and effortless entertaining. A screened pool with a natural rock waterfall and expansive lanai creates the ultimate outdoor living space, while the fully fenced yard extends well beyond the enclosure, offering abundant green space for pets, play, gardening, or future possibilities. Inside, the thoughtfully designed split-bedroom floor plan blends comfort with functionality. Upon entry, you’ll find a flex space enclosed with elegant French doors, currently used as a private home office—perfect for today’s work-from-home lifestyle. Across the foyer sits a formal dining room ready for gatherings and celebrations. The heart of the home flows seamlessly between the family room with a cozy wood-burning fireplace, the breakfast area, and the well-appointed kitchen featuring granite countertops, generous cabinetry, pantry storage, breakfast bar seating, and newer appliances. Sliding glass doors frame beautiful pool views and bring in natural light, creating a warm and inviting atmosphere. The owner’s suite is a peaceful retreat with room for a sitting area and direct access to the pool and lanai. The spa-inspired primary bath features dual vanities, a soaking tub, separate shower, and walk-in closet. Three additional bedrooms and an updated guest/pool bath are thoughtfully positioned on the opposite side of the home for privacy. Beyond the home itself, the location delivers the best of the Winter Garden lifestyle. Tuscany is a beloved neighborhood with limited turnover, situated just moments from the West Orange Trail and the vibrant shops, dining, and charm of Historic Downtown Winter Garden. With its oversized lot, cul-de-sac setting, private pool oasis, and prime location, this property offers a rare opportunity to own a home where space, serenity, and community come together.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Silvia Kinkela, Pa (407-284-9254)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

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. ARLINGTON bonus 6 bedrooms. Discover the newest community by Dream Finders Homes in the highly sought-after Hamlin, Winter Garden. Welcome to the Arlington, an award-winning single-story open-concept home designed for modern living and effortless entertaining. The layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, wrap-around cabinetry, and ample counter space, connecting directly to the living areas—perfect for everyday living and entertaining. The owner’s suite and additional main-floor bedrooms are thoughtfully placed to maximize privacy and comfort, making this home ideal for families or multi-generational living. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from schools, Hamlin Town Center, Hwy 429, and Disney. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

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. Opportunity in Avalon Woods! Discover the newest community in highly sought-after Hamlin, Winter Garden. Welcome to the Carter, a thoughtfully designed bungalow that combines style, comfort, and modern functionality. This brand-new home offers 4 bedrooms, 3.5 bathrooms, and 2,520 sq. ft. of living space. The inviting front porch creates charming curb appeal, while inside, abundant natural light enhances the open-concept layout. The first floor features a bedroom with private bath, perfect for guests or multi-generational living, while the upstairs showcases spacious secondary bedrooms and a well-appointed primary suite. Outdoor living shines with a covered breezeway and private courtyard, ideal for gatherings, dining, or quiet relaxation. Located in Avalon Woods, residents will enjoy proximity to top-rated schools, Hamlin Town Center, Hwy 429, and Disney, all just minutes away.

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

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

Remarks: Under Construction. What's Special: Close to Park | Dedicated Study | Covered Patio | No Stairs | No Rear Neighbors. New Construction - August Completion! Built by Taylor Morrison, America's Most Trusted Home Builder. Welcome to the Caicos at 11287 Silver Trumpet Loop in Esplanade at McKinnon Groves! This unique new twin villa home welcomes you with a side entry that opens into the heart of this charming home. The kitchen, dining area, and great room flow effortlessly together, creating an easygoing space perfect for everyday living. Sliding doors lead to the extended covered lanai, giving you a bright spot to enjoy the outdoors. The primary suite sits quietly at the back of the home with an en-suite bath and a spacious walk-in closet for a peaceful retreat. At the front of the home, a secondary bedroom with a nearby bathroom, the laundry room, and a dedicated study create a thoughtful and convenient layout. Additional Highlights Include: Study with French doors in place of flex, extended covered lanai, 8' interior doors, and garden fence. Photos are for representative purposes only. MLS#O6388502 Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)

Listing Agent: Michelle Campbell (407-756-5025)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Amelia floor plan offers the ease of one-story living with a smart and stylish layout featuring three bedrooms, two bathrooms, and a two-car garage. A spacious great room flows effortlessly into the dining and kitchen areas, making entertaining and everyday living a breeze. The private primary suite is tucked away with a large walk-in closet and a well-appointed bath. Two additional bedrooms and a full bath provide flexibility for guests, kids, or a home office. With thoughtful touches like a lanai, a dedicated laundry room, and a roomy garage, the Amelia delivers comfort and convenience in one beautifully designed space.

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. The Anna Maria with Bonus floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage,

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 Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and two and a half bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality in a layout that fits most lifestyles.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after community of Highlands at Summerlake Groves in Winter Garden offering comfort, functionality, and serene lake views. The open concept kitchen is the heart of the home, featuring a large center island, perfect for entertaining and casual dining. The kitchen flows seamlessly into the spacious great room – perfect for everyday living and entertaining. The private home office features elegant double French doors, creating the ideal space for working from home or a quiet retreat. The luxurious primary suite is a true retreat boasting an oversized walk-in closet, spa-like bathroom with a jacuzzi style tub, walk in shower and private toilet room. The inside laundry room includes a washer and dryer for added convenience, and a water softener system is already in place. Relax on the inviting front porch, perfect for morning coffee or evening conversations. Step out to the screened lanai and unwind while taking in peaceful lake views with no rear neighbors—offering exceptional privacy and a serene backdrop. Completing the home is a 2-car garage and thoughtful details throughout. Ideally located just minutes from the world-famous Walt Disney World Resort theme parks, as well as premier shopping, dining, movie theaters, and entertainment venues, this home offers the perfect blend of everyday convenience and resort-style living. Community amenities include a resort-style pool, playground, tennis courts, dog park, soccer field, and expansive green spaces perfect for relaxation and recreation. This move-in-ready home combines style, comfort, and a desirable setting—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)

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)

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

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: Pre-Construction. To be built. This is a pre-construction opportunity in partnership with Vazquez Family Builders. Final floor plan, square footage, and sales price will be determined by the buyer based on selected model and upgrades. Positioned on a desirable corner lot in the heart of Winter Garden, this pre-construction ranch-style home presents an exceptional opportunity to create your ideal living space. This home is planned for 1713 square feet of meticulously designed living space, featuring 4 spacious bedrooms, two full bathrooms, and an attached two-car garage. The open-concept layout will seamlessly connect the main living areas, creating an inviting environment for everyday life and entertaining. The absence of stairs makes this home highly accessible and a perfect "forever home or vacation property."

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

Listing Agent: Jorge Barcelo (407-267-8415)

Remarks: ***Beautiful and spacious fully-furnished fifth floor 2-bedroom condo located in The Grove Resort and Water Park! This condo easily sleeps six, with a screened in balcony for enjoying those evening sunsets! A full washer and dryer is located off the fully equipped kitchen, and overlooks the family room with dining area. Every unit has a sleeper sofa for extra sleeping also! The primary bedroom has a king bed, and a large en-suite bathroom with separate tub and shower! The second bedroom has two double beds, with a door directly into the second full bathroom, giving you the choice of also making this room an en-suite! The condo is located in The Grove Resort, with its fantastic amenities, including the Surfari Water Park, with large pool, lazy river, water slides, splash area, and the Flowrider surf simulator! Enjoy delicious food and drinks from the Longboard Bar and Grill, with optional poolside service! In addition, there are three more pools and a hot tub located near beautiful Lake Austin, at the Springs Pools! The tropical landscaping around truly makes you feel on vacation! The 24/7 gym is located next to the Springs Pools, along with the Valencia full service restaurant, where you can eat indoors, or outdoors!! The Grove Resort provides free daily transportation to and from Disney, although it is only a short car ride away! Call now for more information!!***

Listing is courtesy of: FLARE PROPERTIES LLC (407-729-3930)

Listing Agent: Lesley O'Neal (407-729-3930)

Remarks: ***Beautiful 2-bedroom Palm model condo located on the fifth floor at The Grove Resort and Water Park. This fully-furnished condo is professionally managed by the onsite property rental team, and owners can use it themselves for up to 179 nights per year! This spacious condo offers a full kitchen, with separate room with full washer and dryer, and is open to the large living room with screened-in balcony where you can enjoy the sunsets every night! The large primary bedroom has a king bed, and an en-suite with dual sinks, and separate tub and shower. The second bedroom has two double beds, and has direct access to the second full bathroom. Owners can enjoy the many amenities at The Grove, including the Surfari Water Park, with large pool, lazy river, water slides, splash area, and the Flowrider Surf Simulator! If you are hungry or thirsty there is the Longboard Bar and Grill ready to serve up your favorites! In addition, there are three more pools and a hot tub located near Lake Austin at The Springs Pools! Also next to the pools are the 24/7 gym, and Valencia restaurant, where you can enjoy eating indoors, or outdoors! The Grove Resort provides a free daily shuttle to and from Disney, which is also just a short car ride away. Have the best of both worlds, and make an income, while enjoying the property that you own with friends and family! Call now for more details!!***

Listing is courtesy of: FLARE PROPERTIES LLC (407-729-3930)

Listing Agent: Lesley O'Neal (407-729-3930)

Remarks: HUGE PRICE REDUCTION! Welcome to your fully furnished, turn-key 2-bedroom, 2-bath retreat at the Grove Resort & Water Park—just minutes from Disney! Whether you’re searching for the perfect vacation getaway or a smart investment property, this unit has it all. From your private balcony, enjoy peaceful conservation views while knowing your condo is working for you when you’re away. With a strong rental history and enrollment in the resort’s professionally managed short-term rental program, generating income couldn’t be easier. Enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—everything you and your guests need for a memorable stay. Don’t wait—units like this move quickly! Showings are by appointment only, as this condo is a guest favorite and often booked.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Arturo Delfierro Pa (786-273-5715)

Remarks: HUGE PRICE REDUCTION! Don’t miss this rare opportunity to own a fully furnished, turn-key 3-bedroom, 2-bath resort condo at the world-famous Grove Resort & Water Park, just minutes from Disney. Located in Building 2, Unit #2129 offers tranquil conservation views from your private balcony and quick access to the resort’s incredible amenities. Whether you’re seeking a personal vacation retreat or a hands-free income-producing property, this condo delivers both. With a proven rental history and participation in the professionally managed short-term rental program, you can generate income seamlessly when you’re not here. Guests can enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—completely worry-free. Act quickly—this unit is a guest favorite, showings are limited, and opportunities like this don’t last.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Arturo Delfierro Pa (786-273-5715)

Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus and 5th Bedroom, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, ample counter space, and an open layout that connects directly to the living areas, making it perfect for everyday living and entertaining. The owner’s suite and additional bedrooms are thoughtfully placed to maximize privacy and comfort. Upstairs, a spacious loft provides versatile space for a media room, play area, or home office. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

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

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