luxury real estate for sale Winter Garden, United States

Executive-style townhome in Hamlin Reserve featuring four bedrooms — including a convenient first-floor bedroom — three full bathrooms, and over 2,000 square feet of thoughtfully designed living space, plus a two-car garage and private patio. Ideally situated directly across from the community pool and playground, this home offers both comfort and convenience. Location truly sets this property apart — just a short walk or five-minute drive to Hamlin Town Center for premier shopping, dining, entertainment, and everyday essentials.The main level showcases an open-concept floor plan featuring a spacious guest bedroom and full bath — ideal for a home office, guest suite, or flexible living space. The well-appointed kitchen is designed for both everyday living and entertaining, complete with a large granite island, stainless steel appliances, abundant cabinetry, and a generous walk-in pantry. A private, partially covered courtyard offers a comfortable outdoor space and leads to an oversized rear-entry two-car garage. The second level features a split floor plan with three bedrooms, two full baths and a laundry room. Relax and unwind in the serene primary suite, complete with a private balcony offering picturesque views of the pool and playground, an ideal vantage point for nightly views of Walt Disney World fireworks. The primary suite also includes an en-suite bath with dual vanities, a glass-enclosed shower and a generously sized walk-in closet. Residents enjoy a maintenance-free lifestyle with HOA-covered exterior care, landscaping, roofing and access to resort-style amenities including a pool, clubhouse, playground, dog park and scenic green spaces, all just near your front door. Positioned near Hamlin Town Center, you'll experience a vibrant, accessible community with boutique shopping, dining and entertainment, including Cinépolis Luxury Cinemas. With proximity to Orlando Health Horizon West Hospital, Orange County National Golf Center and Horizon West Regional Park, plus easy access to major highways, this home offers a balance of luxury, convenience and lifestyle in one of Central Florida's sought-after communities. A 2016 roof (HOA maintains), 2016 air conditioner and 2026 water heater.

A rare opportunity in a desired luxury neighborhood. A home designed for the way you live today, where walls of glass open completely, blending indoor and outdoor spaces into one seamless experience. In the gated community of Canopy Oaks, this A.R. Bailey Homes LLC Delray model offers elevated design, flexibility and everyday convenience. Well-maintained and only eight years young, this residence is set within an intimate enclave of just 49 homesites, offering a rare sense of privacy while remaining ideally positioned on Roper Road between Winter Garden's historic downtown district and the Winter Garden Village shopping complex. From moment you arrive, the home makes a lasting impression with high-end driveway pavers, a durable concrete tile roof, woodgrain garage doors, stone facade accents and grand 8-foot solid wood arched double entry doors. Inside, the layout unfolds with intention, balancing elegant design and functional living. At the center of the home, the kitchen is designed to bring people together, featuring a natural gas cooktop with exterior venting, a built-in oven, upgraded appliances, a pot filler, 42-inch cabinetry with crown molding, a tile backsplash, under-cabinet lighting, a walk-in pantry and a large island that opens to the great room with coffered ceilings. Just beyond, a wine cellar with an iron gate adds a distinctive focal point for entertaining. The first-floor primary suite offers a peaceful retreat with a soaking tub, an oversized walk-in shower with dual heads and a bench, dual granite vanities and a custom closet system. A secondary first-floor, en-suite bedroom or office provides flexibility, while upstairs features a second primary suite, two additional en-suite bedrooms, a loft, a guest half bath and a covered rear balcony for added privacy and comfort. The standout is the home's seamless indoor-outdoor connection. A full corner-opening glass wall, along with three-panel stackable sliding doors, extends the dining and great rooms to a covered lanai with a motorized retractable screen, creating a natural flow for entertaining or everyday living. The spacious backyard, framed by a concrete stucco privacy wall, offers a blank canvas for a future pool or custom outdoor retreat. Thoughtful upgrades continue throughout, including motorized custom light filtering roller shades in the dining and great rooms, dual tankless water heaters, two air-conditioning units with zoned climate control, mudroom, a reading nook and elegant iron stair railings. Residents of Canopy Oaks also enjoy a nature trail and a children's play park. With proximity to downtown Winter Garden, Winter Garden Village, area hospitals, shopping, dining and major roadways including Florida Turnpike, state roads 429 and 408, and Interstate 4, this home presents a compelling opportunity to experience a lifestyle where design, comfort and location come together effortlessly.

Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you with elegant, durable ceramic tile in a natural wood-grain finish. This flooring flows seamlessly through the main living areas, which are accented by striking arched doorways and a beautifully crafted staircase. The heart of the home is the stylish chef's kitchen, which shines with pristine shaker-style cabinetry, expansive granite countertops, a classic tiled backsplash and a generous center island with an undermount double sink and an extended breakfast bar perfect for casual dining. Fully equipped with sleek stainless-steel appliances and a dedicated built-in beverage cooler station, this culinary space overlooks a main living zone flooded with natural Florida sunshine through large windows with custom blinds. The primary bedroom ensuite features dual vanity sinks, stone countertops and a massive walk-in closet. Upstairs, the second-floor balcony is the place to unwind after a long day or start your morning with sun salutations. A brick-paved backyard patio and a rear-entry garage offer ultimate privacy for your new sanctuary. Living in Waterleigh means enjoying a vacation-style lifestyle every day. With HOA-included lawn and ground maintenance, you have nothing left to do but relax and enjoy the community's premier amenities, including multiple resort-style pools, fitness centers and tennis and pickleball courts. Plus, you are just minutes from Disney's Magic Kingdom, upscale shopping at Winter Garden Village, historic downtown Winter Garden and Orlando International Airport.

This is the one you've been waiting for! Tucked away on a peaceful cul-de-sac and situated on an expansive half-acre corner lot, this stunning Horizon West home, in the highly sought-after community of Independence, offers exceptional curb appeal, privacy and luxury living at every turn. Inside, experience soaring, double-height ceilings and an abundance of natural light that fills the spacious, open-concept living area. The thoughtfully designed floor plan features a private office, a formal dining room and an oversized main living space with incredible two-story ceilings and breathtaking views of the resort-style pool and outdoor entertaining areas. At the heart of the home is the chef's kitchen, complete with extensive cabinetry and storage, a large center island and top-of-the-line stainless steel appliances, perfectly designed for both everyday living and entertaining. The spacious owner's suite is a true retreat, featuring custom walk-in closets and a spa-inspired bath designed for relaxation. An additional main-level living space offers incredible flexibility and can easily serve as a private guest retreat or multigenerational living suite. Upstairs, entertainment takes center stage with a spacious bonus and playroom, an included pool table and an impressive, dedicated private home theater, featuring luxury powered seating for eight with a built-in projector and amazing quality in-wall surround sound for the ultimate movie-night experience. Outside, enjoy your private backyard oasis. The inviting and refreshing oversized pool showcases a stone wall spillover water feature and Baja sun shelf, all surrounded by lush landscaping for added privacy. The expansive lanai offers two separate seating areas, plus a natural gas fire pit and outdoor kitchen, creating the perfect setting for family fun and entertaining. Beyond the pool area, you'll find more than 2,000 square feet of private, fenced backyard space with lush grass, shaded by mature trees, ideal for play, pets or relaxing outdoors. Additional upgrades include an oversized, three-car garage plus workspace, a dependable, powerful 20-kilowatt-hour Kohler whole-house generator, two tankless water heaters, a newly-upgraded HVAC and pool equipment and newer pool solar panels, all offering added efficiency and peace of mind. In a community known for its beautiful lake views, incredible scenery and abundant natural wildlife, this home also offers nightly views of Disney fireworks, spectacular sunsets over Lake Hancock and unforgettable rocket launches, all from inside and around this beautiful home. Experience this incredible home in the ideal location for yourself, and discover luxury living at its finest.

Gorgeous, pristine and clean, four-bedroom, three-bath, like-new townhome, is approximately 20 minutes to the Disney area and approximately 35 minutes to Universal and on a prime corner lot in the desirable West Haven Ovation community of Winter Garden. Built by Toll Brothers, this nearly new townhome offers an opportunity to move in now so why wait to build! This two-story townhome features an open-concept floor plan filled with abundant natural light. The kitchen is a showstopper, boasting quartz countertops, wood cabinetry, stainless steel appliances, ample lighting, an extended island with a breakfast bar, a large walk-in pantry and a separate dining area. The spacious family room flows seamlessly from the kitchen and dining areas, making it ideal for entertaining. The first floor includes a guest bedroom with a large closet and a full bath with tub/shower, offering flexibility for a home office, playroom or workout space. Upstairs, you'll find three additional bedrooms, including the oversized primary suite, complete with a spacious walk-in closet and a private en-suite bath featuring dual vanities. The second floor also includes a large walk-in laundry room, with washer and dryer included. Enjoy the convenience of a rear-facing two-car garage with opener and a private courtyard, ideal for relaxing in the sun. There is an enclosed walkway from the garage to the home. Residents of West Haven Ovation enjoy resort-style amenities, including a community clubhouse and pool, playground, and sidewalks for recreation, biking or jogging. Near Horizon West Town Center, with easy access to Interstate 4 and the 429 Expressway, and close to shopping, dining, highly rated schools and an easy commute to Disney area theme parks. Call today to schedule your private tour. This beautiful home could be yours!

Luxury lakeview living with private apartment above the garage. Welcome to your dream home, where luxury, comfort and thoughtful design come together in one of Hamlin's sought-after communities. This exceptional residence features four spacious bedrooms, each with its own en-suite bath on the second floor, including one bedroom with en-suite bath conveniently on the first floor, plus an additional half bath for guest convenience. A standout feature is the desirable private Next Gen suite above the garage, offering incredible flexibility for multigenerational living, extended guests, a home office or potential rental income. Enjoy peaceful water views that create the perfect backdrop for both relaxing mornings and beautiful Florida sunsets. In a top-rated A-rated school district, this home offers not only luxury living but also outstanding educational opportunities. Enjoy a walkable lifestyle with direct access to dining, cafés, boutique shopping, fitness studios, parks and entertainment all nearby. This vibrant, growing community offers unmatched convenience and everyday enjoyment right outside your doorstep. More than just a home, this is a place where neighbors become friends and lasting memories are made in one of Central Florida's desirable areas. Schedule your private showing today and experience it for yourself!

Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

Income producing opportunity! This home includes a private one-bedroom garage apartment with separate entrance and kitchenette. Welcome to the Enclave at Hamlin, one of Winter Garden's desirable communities, featuring the popular Taylor Morrison Ashwood floor plan that blends style, space and versatility. This beautifully designed two-story home offers two bedrooms, 2.5 baths, a spacious loft that can be converted into a third bedroom and a private one-bedroom with kitchenette garage apartment, providing exceptional flexibility for multi-generational living, guests or potential rental income. Upon entry, you are greeted by a welcoming foyer that opens into an expansive great room, ideal for entertaining and everyday living. Overlooking the space is the gourmet kitchen, complete with a large island, quartz countertops, stainless steel appliances and ample cabinetry. The kitchen flows seamlessly to the covered lanai, creating an ideal indoor-outdoor living experience. Also on the first floor is versatile flex space that can be used as a home office, formal dining room or additional bedroom. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with dual quartz vanities, a walk-in shower, private water closet and a generous walk-in closet. The second floor also includes a secondary bedroom, a full bath with tub/shower combination, a private laundry room and a loft with built-in features, ideal for a playroom, craft room, media space or easily converted bedroom. Adding tremendous value is the one-bedroom, one-bath garage apartment with kitchenette, walk-in closet and private entrance, offering an excellent income opportunity or private accommodations for guests or family. The HOA maintains the lawn, including areas inside the fenced yard, providing a low-maintenance lifestyle. Community amenities include a resort-style pool with cabana overlooking Lake Hartley, a tot lot and peaceful open recreation areas with benches positioned to capture scenic lake views. The location is exceptional, with a quick half-mile experience, bike ride or visit to Hamlin, a vibrant 900-acre destination featuring a luxury theater, shopping, dining, salons, waterfront restaurants and entertainment. Convenient access to SR 429, theme parks, and major roadways makes commuting easy. Residents will also enjoy being within distance of the anticipated Horizon West Regional Park, a 215-acre destination park under development. Once complete, the park will offer miles of scenic trails, playgrounds, picnic pavilions, open green spaces, a splash pad, lake access for kayaking and community event areas, delivering an outstanding outdoor lifestyle right outside your door. This home offers a combination of comfort, convenience and future-forward living in one of Winter Garden's fastest-growing areas.

Welcome to this sophisticated, modern and spacious, elegant two-story home in the beautiful neighborhood of Independence in the Horizon West area. Across the pond, this 2,524-square-foot home offers an open concept living space. As you enter through the front door, you are greeted with gorgeous tile floors. The kitchen features beautiful modern espresso cabinetry, a large pantry, stainless steel appliances, and an oversized island overlooking the family room and dining area. This open floor plan provides a great space for entertaining and includes dual primary bedrooms on the main and second levels. The expansive primary suite features a walk-in closet, separate sinks with beautiful cabinetry, a soaking tub and a luxurious walk-in shower. Other features completing this exquisite home include three bedrooms and an upstairs loft on the second level, plus a two-car garage. Capturing some of the best living in Florida, the Independence neighborhood provides a resort-style swimming pool, walking trails, basketball courts, tennis courts, fitness center and a private community boat ramp. Conveniently minutes from Disney World, Orange County National Golf Course, restaurants, shopping, hospitals and zoned for top-rated schools. Schedule your private showing and start enjoying the Florida lifestyle!

Welcome to Watermark in Winter Garden. Built by Meritage Homes in 2016, this two-story detached single-family home offers three bedrooms, two full baths, one half bath, 1,904 square feet and an upstairs loft for added flexibility. The main level features ceramic tile flooring, while the second floor includes carpeting, and all bedrooms offer walk-in closets. The kitchen is equipped with dark cabinetry, quartz countertops, a large island, stainless steel appliances, electric cooktop and double ovens. The primary suite includes a tray ceiling, custom walk-in closet system and en-suite bath with dual sinks and a standalone shower. Additional features include owned solar panels, clay tile roof, rear-entry two-car garage with alley access and a cozy covered front porch with stacked stone detail. Plantation shutters are featured on the French doors leading to the porch and in the downstairs half bath. Set on a low-maintenance homesite, this home also offers access to Watermark amenities including a pool, fitness center, clubhouse and tennis courts. Ideally positioned near shopping, dining, Starbucks and everyday conveniences, and zoned for Panther Lake Elementary, Hamlin Middle and Horizon High School.

Experience elevated living in the heart of Winter Garden, in the desirable Horizon West community. This beautifully appointed home offers three bedrooms (Total of 3 beds - being 2 in the main house and the other one in the in law apartment), 3.5 baths, a dedicated office/flex space, and a rare multi-generation home (studio apartment) above the detached two-car garage, ideal for guests, a private office or additional income potential. The open-concept layout features a modern kitchen with gas range, stainless steel appliances, walk-in pantry and generous seating. Soaring ceilings and abundant natural light enhance the spacious living area. Upstairs, the serene primary suite and guest bedroom provide comfort and privacy. A charming private courtyard connects the main home to the garage and studio, creating a setting for relaxing or entertaining. Just a short distance to shops, dining and entertainment, this home offers luxury, flexibility and unbeatable convenience.

One-story three-bedroom, two-bath home in desirable Summerlake featuring a fenced yard with paved patio. Recent upgrades include new landscaping, laminate tile flooring in the primary bedroom, updated kitchen and primary bath countertops, and new stainless appliances including refrigerator, microwave and gas range. Backyard highlights a fully functioning hot tub (included) and enhanced pergola with lighting, drainage system, adjustable top and reinforced concrete base. Lawn care included in HOA with access to resort-style amenities. Convenient to Disney, Winter Garden, shopping, dining and top-rated schools.

Discover unparalleled elegance in this stunning 5-bedroom, 5.5-bathroom lakefront estate, nestled in the highly sought-after Signature Lakes community. Designed by Davila Homes, this Lexington Floorplan, Luxury Collection residence offers a seamless blend of sophistication, comfort, and breathtaking water views. Spanning 5,098 sq. ft. of living space and an impressive 6,544 sq. ft. total, this two-story masterpiece is a sanctuary of modern design and timeless charm. The open-concept layout boasts soaring ceilings, expansive windows framing picturesque lake views, and elegant finishes throughout. The chef's kitchen is a culinary dream, featuring top-of-the-line appliances, custom cabinetry, and a generous island perfect for entertaining. The primary suite is a private retreat with a spa-inspired ensuite and serene lake vistas, while the additional four bedrooms each offer en-suite bathrooms for ultimate convenience. Step outside to your private waterfront oasis, where you can enjoy lake access, stunning sunset views, and endless outdoor possibilities. The 3-car garage provides ample storage, completing this extraordinary lakeside retreat. Experience luxury living at its finest in this exquisite Signature Lakes estate, where every detail is designed to impress!

Positioned on a premium homesite with an expansive manicured common area along one side, this property offers added privacy and open space, along with sweeping views of John's Lake from the front of the home. Inside, the home opens to a formal dining area accented by wood beam ceilings, while custom wall details in the foyer and along the staircase add a refined, designer touch. The main living area features soaring ceilings, abundant natural light, wood beam ceiling accents, and a striking floor-to-ceiling accent wall, creating a dramatic yet inviting focal point that flows seamlessly into the dinette and open kitchen. Designed for both everyday living and entertaining, the kitchen includes a large island with seating, sleek cabinetry, stainless steel appliances, a gas cooktop, built-in oven, and generous pantry space. Just off the pantry, a connecting space between the kitchen and dining room offers the perfect opportunity for a coffee station or butler's pantry. The main level also offers a spacious primary suite with a well-appointed bath and a custom walk-in closet featuring built-in drawers, cabinetry, and shelving, along with a secondary bedroom and full bath, ideal for guests or multigenerational living. Upstairs, you will find three additional bedrooms, including one with a private bath, while the remaining two share a full bath, plus a generous loft overlooking the living area that provides flexible space for a secondary living area, home office, or play space. The outdoor living space is designed for true Florida living, featuring a saltwater pool and spa added in 2021 with full automation, expansive Travertine tile decking, and a lanai with a motorized screen that extends your living space year-round. The patio is also pre-plumbed for a future outdoor kitchen, offering even more potential for entertaining. Additional highlights include a split three car garage configuration with a separate side entry one car bay and a 2 car garage equipped with an EV charging outlet. Waterside on John's Landing offers a clubhouse, fitness center, resort-style pool, playground, covered dock, and pavilion on John's Lake, all conveniently located near Horizon West, Hamlin, shopping, dining, and major roadways.

One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

Sunset Lake Views , Cul-de-Sac Lot , Renovated Interior , Positioned on a 0.3-acre homesite with unobstructed views of Lake Avalon, this six-bedroom residence offers a functional two-level layout. Built in 2024 and extensively upgraded by the current owner, the main floor supports single-level living with a primary suite, guest bedroom, study, and an extensively upgraded kitchen and butler's pantry featuring a 10' x 7' island, quartz countertops, stacked cabinetry, dual Bosch dishwashers, a Thermador drawer microwave, and Samsung appliances. New luxury vinyl flooring extends throughout the first level, complemented by 12-foot ceilings. The primary suite features tray ceilings, automatic blinds, a large walk-in closet, and a remodeled bath with floor-to-ceiling tile and a seamless glass shower. Upstairs includes a 33x22 loft, media room, four additional bedrooms, climate-controlled storage, and a balcony with elevated lake views. Other recent updates include interior paint, lighting, and gutters. Community amenities include a recreation area and walking trails, with convenient access to the 429, downtown Orlando, Walt Disney World, and top-rated schools.

LUXURY LAKEFRONT ESTATE – Minutes from Historic Downtown Winter Garden! Experience elevated waterfront living in this beautiful 4-bedroom, 4.5-bath lakefront pool residence on just under 1 acre, ideally located just minutes from the heart of Winter Garden and the charm of Plant Street. Built in 2020 and situated within the coveted GOLF CART DISTRICT near Historic Downtown, this property offers the rare combination of private lakefront serenity and walkable convenience. RECENT CUSTOM UPGRADES with designer millworker throughout, new wide plank oak wood floors, entire property custom fenced and designer hardscape and landscape with lakefront hot tub and lakefront sauna house! Inside, gorgeous hardwood floors flow throughout the thoughtfully designed single-story layout. The open-concept living spaces are warm yet modern, highlighted by a cozy electric fireplace and seamless indoor-outdoor connection. A distinctive wine and bourbon room adds a refined touch—perfect for entertaining or curating your private collection. The primary suite is positioned to capture sweeping lake views and features a spa-inspired bath and generous walk-in closet. Each additional bedroom includes ensuite bath access, while a private guest cottage provides flexible space for visitors, extended family, or a studio retreat. Step outdoors to your personal resort-style setting. Enjoy the screened salt water heated pool and spa, summer kitchen, and private dock for boating and sunset cruises. A detached private sauna house offers a true at-home wellness experience, while the outdoor fire pit overlooking the lake creates an unforgettable gathering space framed by panoramic water views. OWNED and FULLY PAID SOLAR PANELS with extremely low utilities cost. With upscale finishes, distinctive amenities, and an unbeatable lakefront location just moments from dining, shopping, and the vibrant downtown district, this exceptional property delivers the ultimate Florida lifestyle—where luxury meets laid-back lakeside living.Schedule your private showing and discover one of Winter Garden’s most compelling lakefront opportunities.