Winter Garden Single Family Homes For Sale - 607 homes

Remarks: There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.

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

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

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PRICE TO SELL!! Situated on a PREMIUM CORNER LOT, this home features approximately $35,000 in upgrades and is located in the desirable SilverLeaf Reserve community within Horizon West, one of Central Florida’s most sought-after master-planned areas. This elegant 4-bedroom, 2.5-bathroom residence offers a thoughtfully designed open-concept layout with beautiful ceramic tile throughout the first floor, creating a refined and functional living environment. The kitchen and bathrooms feature beautiful cabinetry and modern finishes, while the primary suite showcases a tray ceiling and a spacious, well-appointed layout. A versatile loft provides flexible space for a home office, media room, or additional lounge area. The 2-car garage includes epoxy flooring, offering a clean, polished finish. Residents enjoy access to a community pool, playground, green spaces, and walking trails, along with exceptional proximity to Hamlin Town Center—an expansive lakeside destination with dining, shopping, entertainment, a movie theater, and everyday services, all within the thriving Horizon West corridor. Located just two blocks from highly desirable schools, Hamlin Elementary and Hamlin Middle, and minutes from Winter Garden, Windermere, and Disney, this property offers a convenient and lifestyle-focused setting in one of Orlando’s fastest-growing residential areas. Schedule your showing today.

Listing is courtesy of: BAHIA INTERNATIONAL REALTY (407-608-5308)

Listing Agent: Tatiana Alencar (561-234-9972)

Remarks: Under contract-accepting backup offers. Exquisitely appointed 4-bedroom, 3-bath residence located in the highly desirable Wincey Groves in Hamlin community. Designed for both elegant entertaining and everyday comfort, this home offers an open-concept layout anchored by a light-filled great room and a beautifully upgraded kitchen featuring premium KitchenAid appliances, generous counter space, and an exceptionally large center island perfect for gatherings, casual dining, and hosting. The primary suite serves as a private retreat, highlighted by two expansive walk-in closets and a well-appointed en-suite bath. The home features a built-in sound system with two large speakers in the living room and two additional speakers installed in the lanai ceiling—perfect for entertaining indoors and out. As you step outdoors to a serene backyard oasis with no rear neighbors, offering exceptional privacy. The upgraded, heated saltwater pool is enhanced with a custom fountain and waterfall, creating a resort-style setting ideal for relaxation or hosting guests. Nestled in a quiet, established neighborhood with convenient access to top-rated schools, shopping, dining, and recreational amenities, this exceptional home delivers luxury, privacy, and lifestyle in one refined package. Carpets may need to be replaced or stretched in some areas, and minor paint touch-ups are recommended throughout the property.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Kelley Nolan (407-319-6045)

Remarks: Under contract-accepting backup offers. Welcome to this well maintained home in the highly sought after community of Summerlake in Horizon West, known for its convenient access to shopping, dining, parks, and major roadways. This property offers a thoughtful layout with an open concept design connecting the kitchen, living, and dining areas, creating a comfortable space for everyday living and entertaining. The interior has been freshly painted and features 18 inch tile flooring throughout, providing a clean and cohesive look with easy maintenance. The kitchen is equipped with granite countertops, tall cabinetry, and ample storage, while both bathrooms also feature Corian surfaces and double vanities for added convenience. The primary suite includes a tray ceiling, a spacious bathroom with both a garden tub and separate shower, and a private water closet. Additional interior features include custom blinds throughout, cabinetry in the laundry area, and an upgraded front door with a stained glass insert that adds character and curb appeal. Outdoor living is enhanced by a full side patio with both covered and open areas, offering flexibility for relaxing or entertaining. The side patio has a natural gas line for your future grill outs. The side yard is partially fenced with a railing design that complements the front porch, and the property includes a two car carriage style garage along with a third parking pad accessed from the rear alleyway. The home is fully guttered and features newly installed landscaping, adding to its overall appeal.

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

Listing Agent: Vanessa Scotland, Pa (407-217-4580)

Remarks: Welcome to one of Winter Garden's most coveted addresses — nestled in the heart of the Golf Cart District, this beautifully appointed Oakland Park home delivers the Florida lifestyle you've been waiting for. With 4 bedrooms, 3.5 bathrooms, and 3,012 square feet of thoughtfully designed living space, this 2013-built corner lot residence blends everyday comfort with elevated finishes at every turn. Step inside to soaring vaulted ceilings in the family room that create an immediate sense of volume and light. Rich wood flooring flows through the downstairs living areas, complemented by clean ceramic tile and plush carpet in the bedrooms — a seamless combination of warmth and function. The open layout is designed for real living, whether it's a quiet evening in or hosting the people you love most. Outside, brick pavers set the tone for an outdoor living experience that's genuinely special. A large covered back patio creates the perfect setting for morning coffee or evening entertaining, while a classic breezeway connects the home to the garage with both style and practicality. But it's the location that truly sets this home apart. Oakland Park is one of Central Florida's most sought-after communities — complete with two resort-style pools, a beautifully appointed clubhouse, and a dedicated dog park. Step outside your door and hop on your golf cart to access the iconic West Orange Trail, or cruise just minutes into the heart of Downtown Winter Garden, where Plant Street Market, award-winning restaurants, rooftop bars, and a thriving local food scene await. This is the rare home where community, convenience, and character all converge.

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

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

Remarks: Exquisite! Enjoy the experience of living in the finest of MODERN LUXURY in this "architecturally" designed estate. Situated in one of the Top Rated communities in Winter Garden, at Encore Ovation, on a 0.38-acre premium lot. Boasting over $200,000 in QUALITY UPGRADES, this residence features, 5 bedrooms and 4 bathrooms. Step onto the elegant 48 X 48 ceramic tiling that flows throughout the main level, transitioning to rich engineered hardwood on the second floor. A striking custom wood and TEMPERED glass staircase serves as a focal point, leading to a spectacular second floor entertainment gallery enclosed in TEMPERED glass with private balcony. A GOURMET DREAM KITCHEN , featuring custom wood cabinetry, Exotic Quartzite countertops, and a custom-fitted pantry. Equipped for the foodie enthusiast, with a SUB -ZERO refrigerator for peak freshness, a Wolf precision oven, a Thermador hub, and a dual-zone wine chiller, for years of gatherings and conversations. Retreat to the oversized travertine-floored lanai, overlooking a sprawling backyard already prepped with plumbing for a summer kitchen-the perfect. The perfect canvas for a custom infinity pool. Other features include;motorized designer blinds, custom lighting installations, and high-efficiency ceiling fans. A spacious garage with built-in overhead storage racks. HOA INCLUDES LAWN CARE AND BASIC LANDSCAPING, for true low-maintenance living.Enjoy resort-style community amenities just steps from your home.These include a clubhouse, fitness center, community pool and steps from a dog park and walking trails. End your day on your private Master Suite balcony, embracing breathtaking sunsets over Lake Mac. Welcome to paradise!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Renee Rodriguez (407-927-2055)

Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom home offering comfort, space, and versatility for modern living. With a thoughtfully designed floor plan, this home is perfect for families, multigenerational living, or anyone needing extra space for a home office or guest rooms. The open living areas are filled with natural light and provide a welcoming atmosphere for both everyday living and entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly into the dining and living areas, ideal for gatherings and family meals. The primary suite features a private bathroom and generous closet space, creating a relaxing retreat. Additional bedrooms are well-sized and flexible, perfect for children, guests, or work-from-home needs. Three full bathrooms ensure comfort and convenience for everyone. Outside, enjoy a private backyard with plenty of room for outdoor entertaining, play, or relaxation. Whether you envision weekend barbecues, a garden, or a peaceful outdoor escape, this space delivers. Conveniently located near schools, shopping, dining, and major roadways, this home combines space, comfort, and location, ready for its next owner to make it their own. Serious buyers welcome. Schedule a showing today!

Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)

Listing Agent: Matt Buttner (352-385-7636)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2.5-bath single-family home built in 2023, offering 2,048 sq ft of modern living in the highly desirable city of Winter Garden. This thoughtfully designed home features a stylish kitchen with stainless steel appliances and granite countertops, seamlessly connecting to the main living and dining areas—perfect for everyday living and entertaining. With its open layout and contemporary finishes, this home offers both comfort and functionality. Upstairs, spacious bedrooms provide privacy and relaxation, including a well-appointed primary suite. The additional half bath on the main level adds convenience for guests. Located in a great community, you’ll enjoy easy access to local highlights such as the Downtown Winter Garden Historic District, known for its charming shops, dining, and events. Outdoor recreation is just minutes away along the scenic West Orange Trail, perfect for biking and walking. You can also enjoy the vibrant atmosphere of Plant Street Market for local food and entertainment. Modern, move-in ready, and ideally located—this home offers the perfect blend of lifestyle, convenience, and community living.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Keegan Siegfried (813-670-7226)

Remarks: Under Construction. This stunning Plant II single-family home is located in the desirable Northlake at Ovation community. This popular one-story, open-concept layout features 4 bedrooms and 3 bathrooms, ideal for modern living. With finishes from the AW Collection Sapphire vibrant blues meet bright whites for a bold look. Enjoy a chef-inspired kitchen with 42" cabinets, quartz countertops, and large island overlooking the living and dining areas, perfect for entertaining. The home also includes luxury vinyl flooring, a private primary suite with walk-in closet, a covered lanai for outdoor living, and a spacious 2-car garage. Conveniently located in Winter Garden near shopping, dining, major roadways, and top-rated schools. Community amenities include pool, clubhouse, playground areas and dog park.

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

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

Remarks: Welcome Home! Step inside this gorgeous 2024-built bungalow-style home featuring a fully detached STUDIO apartment with its own entrance, perfect for guests, in-laws, or potential rental income. This 4-bedroom, 4.5-bathroom home offers the perfect blend of space, style, and flexibility. Inside the main home, you’re welcomed by tall ceilings, an open layout, and a convenient downstairs bedroom and full bathroom. The modern kitchen is beautifully designed with a gas range, quartz countertops, shaker cabinets, and an open-concept flow overlooking the main living spaces. Upstairs, you’ll find two additional guest bedrooms, a shared full bathroom, and a conveniently located laundry room. The grand primary suite is a true retreat, featuring a spacious layout with soaring ceilings and a stunning en-suite bathroom complete with a walk-in shower, generous counter space, and an oversized walk-in closet. The studio apartment is privately accessed just outside of the garage and is fully equipped with its own full bathroom, kitchenette, and closet—making it ideal for guests or income-producing potential. Located in one of Horizon West’s most desirable communities, this home offers unbeatable convenience just minutes from Flamingo Crossings, Walt Disney World, and Hamlin Town Center.

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

Listing Agent: Elliott Hunt (770-355-9149)

Remarks: One or more photo(s) has been virtually staged. Stunning brand-new, energy-efficient home in the desirable Hamlin community of Winter Garden. This spacious 5-bed + Bonus Room, 4-bath, 3,700+ sq ft property sits on a cul-de-sac corner lot and features an open layout with 10-ft ceilings, Ceramic flooring, a built-in electric fireplace, and upgraded 3-panel sliding doors that fully open to the covered lanai. The chef's kitchen includes an oversized quartz island, extended L-shaped cabinetry, quartz countertops, stainless steel canopy hood (vented outside), 30" ceramic cooktop, and all new stainless appliances. The first floor offers the primary suite plus three additional bedrooms, including one with a private bath-ideal for guests or an office. Upstairs features two more bedrooms, a full bath, and a 16' x 20' bonus room with two walk-in closets and wet-bar pre-plumbing. The 2.5-car garage includes a hobby area, epoxy floors, extra outlets, water softener loop, and sink plumbing. Laundry room includes new washer/dryer and cabinets. Enjoy a private backyard with no rear neighbors, vinyl fencing, lanai pre-plumbed for a sink, and pool pre-wire (60A) already installed. HOA includes fiber-optic internet (750-900 Mbps). Minutes from Orlando Health, Publix, dining, and more.

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

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

Remarks: Under Construction. Waterleigh presents the Bellmore This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Home is Connected 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: Under Construction. Waterleigh presents the Clearden. This two-story 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 a bedroom and downstairs powder room. 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 all 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 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. Like all homes in Waterleigh, the Clearden includes a Home is Connected 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: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Rick Evans, Ii (407-538-9295)

Remarks: Luxury lake view living at its finest in the heart of Horizon West Ovation. Welcome to one of the most impressive and exclusive homes in the area. This stunning nearly brand new residence offers the largest and most prestigious floor plan built by the builder, featuring 5 spacious bedrooms, 5 full bathrooms, 1 powder bath, and nearly 5,000 sqft of refined living space designed with elegance, comfort, and functionality in every detail. Situated on an oversized premium homesite with exceptional spacing between neighboring homes, this property delivers a rare sense of privacy, tranquility, and open luxury that is almost impossible to find in Central Florida. The home is positioned with breathtaking rear lake and conservation views, creating an incredible atmosphere of peace and exclusivity. There is also potential to build a private deck and further enhance the outdoor lake lifestyle experience. Built with top tier finishes and upgrades identical to the builder’s model home, every space in this residence was carefully designed to impress. The home features an incredible open concept layout, expansive living spaces, soaring ceilings, premium flooring, designer finishes, and a spectacular gourmet kitchen perfect for entertaining and everyday luxury living. The bedrooms are exceptionally spacious, while the oversized laundry room is filled with cabinetry and includes a utility sink for convenience and organization. The owner’s suite is a true masterpiece and private retreat, surrounded by an extended balcony overlooking the lake and conservation views, creating the perfect setting to relax while enjoying breathtaking sunsets and even Disney fireworks at night. This home offers the perfect combination of luxury, space, privacy, nature, and location. Positioned in one of the fastest growing and most desirable communities in Central Florida, Horizon West at Ovation, the property is located only about 10 minutes from Disney, with easy access to shopping, restaurants, entertainment, major highways, and top rated schools. Opportunities like this are extremely rare. Do not miss the chance to own one of the finest luxury lake view homes in Horizon West.

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

Listing Agent: Francisco Tatagiba Junior (386-517-3488)

Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Stunning four-bedroom, three-bathroom home in the highly sought-after Wintermere Pointe community, complete with a spacious three-car garage. Upon entry, you are welcomed by a bright, open-concept floor plan. The formal dining room at the front of the home flows seamlessly into the main living area, which features direct access to a large covered back porch—perfect for indoor-outdoor living. The chef-inspired kitchen is a true standout, offering granite countertops and an abundance of cabinet and counter space for prep and storage. The primary suite serves as a private retreat, featuring an ensuite bathroom with dual sinks, a garden tub, and a separate standing shower. This property is ideally situated just minutes from local schools, parks, and major highway access, putting daily conveniences and entertainment options right at your fingertips. Schedule your showings today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under Construction. .

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

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

Remarks: Some properties check a box. This one opens a door. This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It's a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one. At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You're minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County's strongest markets. House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense. ROOF is 2020, WATER HEATER 2021 and HVAC 2016

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Phat Nguyen (407-452-8751)

Remarks: LUXURY RENOVATED 4-BED HOME WITH NEW ROOF + AC — OVERSIZED 3-CAR GARAGE — MOVE-IN READY This beautifully renovated 4-bed, 2.5-bath single-family home in the heart of Winter Garden (34787) is truly move-in ready — offering a luxury 2025 redesign from top to bottom. Located in the highly desirable Golf Cart District, this home sits on a quiet cul-de-sac just minutes from Downtown Winter Garden, Plant Street Market, and the West Orange Trail. The interior features a bright open floor plan with dramatic double-height ceilings, brand-new tile flooring downstairs and durable LVP upstairs, all-new baseboards and trim, and a fully updated 2025 kitchen with stone countertops and modern cabinetry. The spa-style primary suite includes two walk-in closets, a glass walk-in shower, and a soaking tub. Major upgrades include a new roof, new AC, updated electrical and plumbing, and fresh exterior paint — making this home feel like new construction. The oversized 3-car garage provides rare extra storage and golf cart space. Only 4 minutes to Newton Park with a public boat ramp — perfect for lake access, sunsets, and outdoor recreation. Schedule your private showing today!

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)