Winter Garden Single Family Homes For Sale - 709 homes

Remarks: PRICE IMPROVEMENT! Exceptional opportunity in Winter Garden. This 2024 home offers 5 bedrooms, 4.5 bathrooms, and a private suite with a separate entrance, bedroom, bathroom, and kitchenette. With over $60,000 in upgrades already completed, this property delivers value from day one. Ideally located just minutes from Disney, Flamingo Crossings, Hamlin Town Center, shopping, dining, entertainment, hospitals, and top-rated schools. The open-concept floor plan features high ceilings, a remodeled kitchen, porcelain tile flooring on the first floor, upgraded second-floor flooring, wood stairs, upgraded paint, paver driveway and patio, epoxy garage flooring, and numerous additional improvements throughout the home. The private suite provides excellent flexibility for multigenerational living, guests, or additional private living space. A rare opportunity to purchase a nearly new home in a prime Winter Garden location with major upgrades already completed. Buyer and buyer’s agent to verify all information, including room sizes, HOA, school zoning, rental restrictions, lease details, and all property information. Proof of funds or pre-approval required prior to showing.

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Keyla Chirinos Sivira (786-380-5541)

Remarks: Nestled within one of Central Florida's most exclusive neighborhoods this stunning home offers the perfect blend of luxury, comfort, and effortless entertaining. Located on a quiet cul-de-sac street boasting 5 bedrooms, 4.5 baths, a large loft and open floor plan this home is designed for everyday living and seamless hosting! Step outside to your private resort style salt water pool and enjoy nightly views of the Disney fireworks lighting up the sky! The upgraded "picture frame" pool screen design offers an uninterrupted view of the serene pond and the diverse wildlife that visits it! On the main level you will find the PRIMARY SUITE COMPLETE WITH A LUXURIOUS SPA LIKE BATH AND HUGE walk-in closet, a guest bedroom with its own full bath, the glass enclosed wine room and a convenient half bath for guests. The GOURNET KITCHEN flows to the expansive great room where 4 large sliders can open to the covered patio for the "outside inside" living!! Upstairs, in addition to the large loft are 2 bedrooms that share a full bath and another private en-suite bedroom. Recent upgrades include beams on the main level ceiling, beautiful built-in wall unit in the loft, outdoor kitchen and outdoor lighting. Located just minutes from Walt Disney World, premier shopping, dining, and everyday conveniences, and approximately 30 minutes to Orlando International Airport, this beautiful home is perfect for that unbeatable central Florida lifestyle!

Listing is courtesy of: HAMMOND REALTY GROUP LLC (407-468-0074)

Listing Agent: Lesa Dolan (407-925-5786)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2.5-bath home located in the highly desirable Watermark community in Winter Garden! This home features a bright open-concept floor plan where the kitchen, dining, and living areas seamlessly flow together — perfect for entertaining and everyday living. Upstairs, you’ll find all three bedrooms, two full bathrooms, a convenient upstairs laundry room, and an additional flex space ideal for a playroom, office space, media room, or second family room. The spacious primary suite offers privacy, while the two secondary bedrooms share access to a charming private balcony overlooking the neighborhood. A downstairs half bath adds convenience for guests. Additional features include a 2-car garage, energy-efficient solar panels, and thoughtfully designed living spaces throughout. Enjoy an unbeatable location with Starbucks, Walgreens, restaurants, shopping, and everyday conveniences all in close proximity. For Disney lovers, Magic Kingdom is approximately 9 miles away and Disney Springs is about 12 miles away, making this an ideal primary residence, vacation home, or investment opportunity. Residents of Watermark enjoy resort-style amenities including a community pool, tennis courts, clubhouse, playground, fitness center, and scenic walking trails. This home offers the perfect combination of location, lifestyle, and modern Florida living!

Listing is courtesy of: CROSS KEYS REALTY, INC. (352-505-5049)

Listing Agent: Morgan Coleman (352-222-9093)

Remarks: Welcome to 9107 Grand Island Way, a beautiful Corner Lot Home in the heart of Horizon West’s Watermark community! This home is the perfectly balance of comfort, style, and convenience, designed for both everyday living and entertaining. Upon entering the front door, you will see your updated, modern kitchen with granite countertops, modern 42" cabinets and modern pendant lights overlooking your spacious living room. You will space for a nice dining room table to entertain as well as a half bathroom and the entrance to the 2 car garage! Upon walking up the modern staircase, you will find a very nice spaced loft/entertainment room, to where you can have your private second living room, office or movie theater room! The primary bedroom provides a relaxing and spacious space with a nice sized primary bathroom and walk in closet, while the additional bedrooms offer flexibility for family, guests, or a home office. As this is a corner lot, there home is filled with natural light. flowing seamlessly into the kitchen and dining space. One of the most unique aspects of this property is its prime corner location directly across from the vibrant Horizon West Retail Center, placing you just steps from such stores like Starbucks, New York Beer Project, 7-11 and Walgreens and more! Enjoy the rare ability to walk or bike to dining, entertainment, and local hotspots while still enjoying the privacy of a residential neighborhood. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse, fitness center, dog parks, playgrounds and more! With easy access to Interstate 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center and Walt Disney World just minutes away, this home offers the perfect balance of lifestyle and location in one of Winter Garden’s most sought-after communities conveniently located in the middle of everything!

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Jeff Inman (407-505-7600)

Remarks: Under contract-accepting backup offers. Under Construction. .

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

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

Remarks: Prime corner lot home in the highly sought-after Horizon West community of Watermark in Winter Garden with no front neighbors and peaceful water views. Ideally located just a short walk to the community amenity center and The Mark shopping center featuring Starbucks, New York Beer Project, 7-Eleven, Walgreens, dining, entertainment, and more. Enjoy nightly Disney fireworks views right from the front porch, living room or loft sofa. Conveniently located near State Road 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center, and Walt Disney World. This home offers the perfect blend of lifestyle, convenience, and location in the heart of Horizon West.

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

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

Remarks: Virtually staged. Welcome to Chapin Station! On an almost quarter-acre lot, this four-bedroom, three-bath home offers a light and spacious split-bedroom open floor plan designed for comfort and functionality. Go inside to find soaring ceilings and an open layout featuring a formal dining room, a large family room and a bright breakfast nook overlooking the kitchen. Double-pane windows provide added energy efficiency throughout the home. The living areas seamlessly connect to the expansive covered rear patio and private backyard, creating the ideal setting for everyday living and entertaining. The thoughtfully designed split floor plan provides privacy for all. The primary suite features vaulted ceilings, dual walk-in closets and an en-suite bath with double vanities, a garden tub and a separate shower. On the opposite side of the home, two secondary bedrooms share a full bath, while a separate guest suite and additional bath offer ideal accommodations for visitors or multigenerational living. The oversized backyard provides ample space to create your dream outdoor oasis, whether you envision a pool, play area, garden or outdoor entertainment space. The large covered patio is ideal for grilling, relaxing, and gathering with family and friends. In the sought-after Chapin Station community, this well-maintained home offers easy access to the West Orange Trail, historic downtown Winter Garden, major highways, hospitals, shopping, dining and Central Florida's world-famous theme parks.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Naresh Mistry (321-356-7882)

Remarks: Welcome to 1610 Beulah Road, a custom built home in one of Winter Garden's most convenient locations. Situated directly across from West Orange High School, this exceptional property offers the perfect blend of privacy, tranquility, and accessibility. Just five minutes from Historic Downtown Winter Garden and Plant Street Market, you'll enjoy easy access to award winning dining, boutique shopping, the popular Farmers Market, Crooked Can Brewing Company, and countless community events throughout the year. Designed with comfort and quality in mind, this custom residence is nestled against protected wooded wetlands, creating a peaceful backdrop rarely found so close to town. Relax and unwind from the screened rear patio while taking in the serene views and natural beauty of the private backyard setting. With no rear neighbors and lush conservation views, this home offers a quiet retreat that feels worlds away. Commuters will appreciate the easy access to State Road 429 and the Florida Turnpike, providing convenient connections to Downtown Orlando, Lake County, and major employment centers throughout Central Florida. Whether you're searching for a home near Downtown Winter Garden, top rated schools, or a property with privacy and scenic views, 1610 Beulah Road delivers an unbeatable combination of location, craftsmanship, and lifestyle. Experience the best of Winter Garden living with the perfect balance of convenience and natural beauty.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Welcome to 15121 Evergreen Oak Loop, a stunning 6-bedroom, 4-bathroom home offering over 4,200 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities. Situated on an oversized homesite with no rear neighbors, this exceptional property combines space, comfort, and privacy with beautiful conservation views and breathtaking Florida sunsets. The heart of the home is the expansive gourmet kitchen featuring stainless steel appliances, a large center island, abundant cabinetry, and an open-concept design that flows seamlessly into the main living areas—perfect for entertaining family and friends. Flexible living spaces include a first-floor bedroom and full bath, ideal for guests, a home office, or multigenerational living. Upstairs, you'll find a spacious theater room complete with reclining theater seating, projector, screen, and surround sound system—all included with the home—creating the ultimate space for movie nights, sporting events, and gaming. The luxurious primary suite serves as a private retreat with a spa-inspired bath, dual vanities, soaking tub, separate shower, and oversized walk-in closet. Step outside to enjoy peaceful conservation views from multiple outdoor living spaces, offering a level of privacy rarely found in Horizon West. Whether you're enjoying your morning coffee or winding down in the evening, this home provides the perfect backdrop for Florida living. Location is everything, and this home delivers. Just minutes away is the newly opened Horizon West Regional Park, a 215-acre recreational destination featuring an inclusive playground, walking and biking trails, picnic pavilions, athletic fields, open green space, and recreational facilities. Future phases are planned to bring additional trails, expanded recreational amenities, and nature-focused areas, adding even more value to this already exceptional location. Residents enjoy convenient access to top-rated schools, shopping, dining, major highways, Disney attractions, and everything that makes Horizon West one of Central Florida's most sought-after places to live. Offering an ideal combination of size, functionality, entertainment, and location, this is a rare opportunity to own a truly special home in the heart of Winter Garden.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Adam Jackson (407-572-6252)

Remarks: Virtually Staged. Under Construction. Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out the Brantley today and imagine your life in the beautifully designed home!

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

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

Remarks: Welcome to what may be the most impeccably maintained and beautifully upgraded home in Oakland Park! This stunning 4-bedroom, 3.5-bath residence showcases designer-inspired finishes throughout, featuring soaring ceilings, modern color palettes, and countless custom enhancements that make it truly one of a kind. Built just four years ago and nestled on a quiet street directly across from green space, this exceptional David Weekley Seaside model offers the perfect blend of elegance, comfort, and convenience. The thoughtfully designed floor plan features a luxurious first-floor owner's retreat complete with a spacious spa-like bath, while the additional bedrooms, study, dining area, and generous living spaces provide room for everyone to spread out and enjoy. No detail has been overlooked. The current owners have invested extensively in premium upgrades, including custom wood trim and accent walls, designer wallpaper, upgraded lighting throughout, custom Zebra window shades, professionally designed closets in the owner's suite, secondary bedroom, and laundry room, plus a water softener, gutters, epoxy-coated garage floors, updated landscaping, and an inviting paver patio. Both the interior and exterior have been freshly painted, creating a truly move-in-ready experience. Step outside to the screened rear porch, where you'll enjoy peaceful mornings, evening breezes, and endless opportunities for birdwatching and outdoor dining. The spacious 3-car garage provides ample storage and functionality for today's lifestyle. Beyond the home itself, Oakland Park offers an award-winning lifestyle unlike any other. This celebrated Parade of Homes community is known for its charming streetscapes, abundant green spaces, waterfront gathering areas, parks, and strong sense of community. Golf-cart-friendly and ideally located just minutes from the West Orange Trail, you'll also enjoy the convenience of walking or riding into vibrant downtown Winter Garden for exceptional dining, shopping, entertainment, and year-round events. This is more than a home—it's a lifestyle defined by luxury, connection, recreation, and the timeless charm of Winter Garden Living.

Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)

Listing Agent: Lynette Piontek (407-222-4310)

Remarks: PRICE IMPROVEMENT! PRICED TO SELL, SELLER WILLING TO CONTRIBUTE UP TO $7,500.00 TOWARDS CLOSING COSTS OR BUYER RATE BUY-DOWN! Welcome to 12566 Westhaven Oak Drive in the desireable Osprey Ranch community of Winter Garden. This beautifully designed 4-bedroom, 3-bath home offers the perfect blend of modern comfort and luxury finishes, featuring an open-concept layout ideal for everyday living and entertaining. The gourmet kitchen shines with quartz countertops, a spacious island and stylish cabinetry, flowing seamlessly into the main living and dining areas. The downstairs guest suite offers flexability for visitors or a home office, while the upstairs primary retreat provides a relaxing escape with a spa-like bathroom and generous walk-in closets. This home reflects over $10,000 in uprgrades including an extended fenced in lanai, frameless shower doors and more! Residents of Osprey Ranch enjoy a welcoming community athomsphere with a scenic walking paths, beautiful community pool and convenient access to Horizon West's shopping, dining, top-rated schools and world class attractions. Experience luxury, comfort and the best of the Winter Garden lifestyle in this exceptional home. Call to schedule a private tour today!

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Kendra Wallace (407-457-7069)

Remarks: Virtually Staged. Under Construction. 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.

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

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

Remarks: Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES The Amelia is a beautifully designed one-story offering three bedrooms and two baths, thoughtfully arranged for comfortable everyday living. The open concept layout features a spacious great room, dining room combo with no wasted space. 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: BUY THIS HOME WITH 100% FINANCING! LOCATION, LOCATION, LOCATION! Welcome to Your Trailside Oasis in Historic Oakland/Winter Garden! Nestled directly along the scenic West Orange Trail, this meticulously maintained, lightly lived-in bungalow offers the ultimate Florida lifestyle. Cycle straight into vibrant, historic downtown Winter Garden, or retreat to your own peaceful haven under the towering Live Oaks of Oakland Trails. Sophisticated Design Meets Modern Comfort...From the moment you arrive, the extended paver driveway and charming, shaded front porch welcome you home. Step inside to an airy, open-concept living area adorned with gleaming ceramic tile floors, quartz countertops, and upgraded builder finishes. Thoughtful, highly functional details elevate the main floor, including a stylish drop zone by the two-car garage, an under-stair coat closet, and a convenient powder room. High-end custom shades, luxury ceiling fans, and designer light fixtures make this residence completely turn-key and move-in ready. The second level opens into a versatile loft perfect for a media room, home office, or play space. The primary suite serves as a true sanctuary, boasting a grand double-door entrance, two spacious walk-in closets, and an ensuite bath with elegant quarts countertops. Two additional bright bedrooms and a dedicated upstairs laundry room complete this flawlessly designed upper level. Equipped with modern exterior lighting and a security camera system, this home offers total peace of mind. Outside your door, the vibrant Oakland Trails community features a resort-style pool, playground, dog park, and endless walking trails. Abundant dedicated street parking makes hosting family and friends effortless. Positioned perfectly between Clermont and Orlando, you will enjoy rapid access to the Florida Turnpike, 429, 408, and Highway 50. With Killarney Station right outside the neighborhood and the breathtaking Oakland Nature Preserve on the shores of Lake Apopka less than five minutes away, this is a dream destination for outdoor enthusiasts. Don't miss the chance to own this pristine, upgraded gem in one of Central Florida's most desirable trailside communities! Offering a lender credit towards costs or interest rate buy-down, when the client uses the preferred lender ACE Lending Group, ASK HOW.

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

Listing Agent: Ariel Vargas (407-558-5161)

Remarks: Imagine coming home to a place where comfort, convenience, and community come together perfectly. Nestled in the highly desirable Deerfield Place neighborhood, this beautiful 4-bedroom, 2-bath home offers the space, style, and location today's buyers are searching for. From the moment you step inside, you'll appreciate the bright, open layout designed for making memories. The heart of the home is the spacious kitchen, featuring upgraded cabinetry, stainless steel appliances, and plenty of room to gather with family and friends. Whether you're hosting holiday celebrations, enjoying a quiet morning coffee, or helping with homework while preparing dinner, this home was designed for the moments that matter most. The private owner's retreat provides a peaceful escape at the end of the day, while the additional bedrooms offer flexibility for family, guests, a home office, or a fitness space. Step outside to your fully fenced backyard, perfect for weekend barbecues, pets, playtime, or simply relaxing under the Florida sunshine. What truly sets this home apart is its incredible Winter Garden location. Just minutes from Historic Downtown Winter Garden, the award-winning West Orange Trail, Winter Garden Village, top-rated schools, dining, shopping, and entertainment, you'll enjoy the best of Central Florida living right outside your door.

Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)

Listing Agent: Rick Coles (321-299-4981)

Remarks: Experience a lifestyle defined by elegance, privacy, and exceptional design in this luxury residence within the gated community of Canopy Oaks in Winter Garden. Built by A.R. Bailey Homes, this sought-after Delray floor plan offers nearly every feature today's discerning buyer desires, blending sophisticated architecture with functional living spaces designed for entertaining, multigenerational living and everyday comfort. Within an intimate enclave of just 49 homesites, this residence enjoys a premier location, minutes from historic downtown Winter Garden, Winter Garden Village, top-rated schools, dining, shopping, recreation and major commuter routes. A striking exterior presentation sets the tone with a paver driveway, concrete tile roof, stone-accented elevation, wood-look garage doors and grand solid wood double-entry doors. Beyond the entry, thoughtfully designed interiors showcase expansive gathering spaces, architectural ceilings, elegant finishes and abundant natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring a natural gas cooktop with exterior venting, built-in oven, upgraded appliances, pot filler, 42-inch cabinetry with crown molding, under-cabinet lighting, tile backsplash, walk-in pantry and oversized island overlooking the spacious great room with coffered ceilings. Adjacent to the living areas, a gated wine cellar creates a memorable entertaining feature rarely found in homes at this price point. The first-floor primary suite offers a private retreat with a spa-like bath featuring dual granite vanities, a soaking tub, oversized walk-in shower with dual shower heads and bench seating, and a custom-designed closet system. A separate first-floor en-suite bedroom provides ideal flexibility for guests, extended family or a dedicated home office. Upstairs, the versatile layout continues with a second primary suite, two additional en-suite bedrooms, a generous loft, guest powder bath and a covered balcony, creating multiple private living spaces throughout the home. Designed to embrace Florida's year-round outdoor lifestyle, the residence seamlessly connects indoor and outdoor living through a dramatic corner-opening glass wall and expansive stackable sliding doors. The covered lanai, enhanced by a motorized retractable screen, creates an ideal setting for entertaining, relaxing or enjoying peaceful evenings outdoors. The oversized backyard, with stucco privacy wall, offers ample space to create a custom pool, outdoor kitchen and private resort-style retreat. Additional features include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, mudroom, reading nook and extensive storage throughout. Residents of Canopy Oaks enjoy access to community nature trails and a playground while remaining conveniently located near downtown Winter Garden, Winter Garden Village, the Roper YMCA, Orlando Health facilities, and major transportation corridors including the Florida Turnpike, SR 429, SR 408 and Interstate 4. Offering luxury, flexibility and an exceptional Winter Garden location, this beautifully maintained home presents a rare opportunity to enjoy elevated Central Florida living in one of the area's desirable gated communities. Also listed for lease MLS #O6416527

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Lisa Rutkowski (407-793-2416)

Remarks: Under Construction. .

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

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

Remarks: Under Construction. .

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

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

Remarks: Under Construction. .

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

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