Winter Garden Homes with Contemporary Architectural style

Winter Garden Homes with Contemporary Architectural style

Welcome to Winter Garden, Florida – a charming city nestled in Orange County, where the allure of small-town living meets the vibrancy of contemporary architecture. Known for its picturesque landscapes and rich history, Winter Garden is a delightful community that has become a sought-after destination for families, retirees, and professionals alike.

As you stroll through the tree-lined streets of downtown Winter Garden, you’ll discover a delightful blend of historic buildings and modern amenities. The city boasts an array of parks, scenic trails, and a vibrant farmers market, making it an ideal place for outdoor enthusiasts. With its close proximity to Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping while relishing the tranquility of suburban life.

One of the most appealing aspects of Winter Garden is its contemporary architectural style homes. These stunning residences are designed with modern aesthetics in mind, featuring open floor plans, sleek lines, and an abundance of natural light. Many homes are equipped with energy-efficient technologies, ensuring that comfort and sustainability go hand in hand. Whether you’re looking for a chic townhome or a spacious single-family residence, Winter Garden’s contemporary homes offer something for everyone.

The community spirit in Winter Garden is palpable, with numerous events and festivals that bring neighbors together. From art walks to seasonal celebrations, there’s always something happening in this vibrant city. Discover the beauty of Winter Garden and find your dream home in a place where modern living meets a warm, welcoming atmosphere. Your new chapter awaits!

Newest Winter Garden Homes with Contemporary Architectural style

9849 Lost Creek Drive, Winter Garden
$949,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to 9849 Lost Creek Drive, a beautifully appointed 5-bedroom, 4-bathroom home in Winter Garden’s sought-after Waterleigh community. Built in 2021, this impressive residence offers 3,910 square feet of living space, a 3-car garage, and a thoughtful blend of timeless architectural details and modern functionality—all complemented by peaceful lake views. From the meticulously maintained landscaping to the welcoming front porch, the home makes a wonderful first impression. Inside, arched doorways and thoughtfully designed living spaces create a warm, inviting atmosphere. The foyer opens to a formal living room, while the separate formal dining room features sliding doors leading directly to the covered lanai, making entertaining effortless. At the heart of the home, the spacious kitchen overlooks the family room, creating a natural gathering place for everyday living and special occasions. White quartz countertops, 42-inch cabinetry, built-in ovens, a cooktop, stainless steel appliances, and an oversized island are paired with an abundance of cabinetry and generous countertop workspace. There’s room for everything, whether preparing weeknight meals or hosting a crowd. The first-floor primary suite offers a peaceful retreat with tranquil lake views and elegant coffered ceilings. The oversized walk-in closet features custom organization, while the ensuite bath delivers a spa-inspired experience with dual vanities and a spacious walk-in shower featuring shower fixtures on both walls. Upstairs, a generous loft provides flexible space for a media room, game room, or additional gathering area, while the well-proportioned secondary bedrooms offer room for family and guests. A convenient upstairs storage closet, thoughtfully lined with shelving, adds even more practical storage. The large laundry room is equally well designed, with a utility sink, abundant cabinetry, and an expansive work surface to keep household tasks organized. Step outside to the spacious pavered lanai, complete with retractable screens that let you enjoy Florida’s beautiful weather in comfort. Overlooking the lake, this inviting outdoor space is perfect for morning coffee, weekend gatherings, or relaxing at the end of the day while watching the sunset—and, on the right evenings, catching Disney fireworks in the distance. Life in Waterleigh extends beyond your front door, with resort-style amenities that include community pools, fitness facilities, walking trails, a clubhouse, playgrounds, and more. Conveniently located in the Horizon West area of Winter Garden, the community offers access to nearby shopping, dining, parks, and everyday essentials, with Walt Disney World and other Central Florida attractions within easy reach. Beautifully maintained, thoughtfully designed, and ideally situated to enjoy the best of Central Florida living, this home offers the space, comfort, and setting to make every day feel a little more special. Schedule your private showing and discover all that this exceptional Waterleigh home has to offer!

9849 Lost Creek Drive, Winter Garden
1349 Castleport Road, Winter Garden
$749,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

1349 Castleport Road, Winter Garden
17922 Hither Hills Circle, Winter Garden
$699,900
4 Beds ⋅ 4 Baths ⋅ Lake Apopka Sound Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to 17922 Hither Hills Cir. Built in 2022, this beautiful 4-bedroom, 3.5-bath, single-story home offers a highly desirable multi-generational floor plan with approximately 2,800 square feet of living space and beautiful Lake Apopka views. The attached private in-law suite features its own private exterior entrance, living area, kitchen, bedroom with walk-in closet, full bathroom, and convenient access to the garage—providing exceptional flexibility for extended family, guests, or private accommodations. The open-concept main living area features soaring ceilings, elegant tray ceilings, granite countertops, 42-inch cabinetry, stainless steel appliances, tiled backsplash, breakfast bar, prep island, and spacious dining and great room areas. Sliding glass doors open to the covered and screened lanai, creating an inviting indoor-outdoor living space. The spacious primary suite features a tray ceiling, generous walk-in closet, and ensuite bathroom with dual granite vanities, private water closet, and separate soaking tub and shower. Two additional bedrooms share a conveniently located bathroom with dual vanities. An oversized laundry room provides abundant storage and workspace. Enjoy the Florida lifestyle in the fully fenced backyard with gates on both sides, featuring fruit trees, a 3-person stand-alone hot tub, and a covered screened patio perfect for relaxing or entertaining. The attached 3-car garage provides plenty of room for vehicles and storage. Additional features include smart-home technology with app-controlled garage doors, lights, and door locks, as well as a smart security system with sensors on windows and doors. Ceramic tile flooring throughout. Located in the desirable Lake Apopka Sound community, this home is conveniently located near Downtown Winter Garden, Plant Street Market, restaurants, shopping, parks, the West Orange Trail, Highway 50, the Florida Turnpike, and SR-429. A wonderful opportunity to own a nearly new home offering versatility, modern upgrades, beautiful lake views, and convenient Winter Garden living. Low Yearly HOA and no CDD fees.

17922 Hither Hills Circle, Winter Garden
17839 Gourd Neck Loop, Winter Garden
$925,000
7 Beds ⋅ 4 Baths ⋅ Verde Park Ph 2 SubDv. ⋅ 34787 Zip Code
Elegant pool residence in Winter Garden’s Verde Park, minutes from the Turnpike. This impeccably maintained 7-bedroom, 4-bath home offers 4,704 square feet of refined living space, a 3-car tandem garage, and a 0.24-acre lot with no community homes behind it. Multiple living and entertaining areas and a versatile floor plan offer exceptional flexibility for everyday living and hosting in a sought-after location. Step inside to a formal living room on one side of the entry and a formal dining room on the other. The living room is a flexible space that easily serves as a home office, library, sitting room, or whatever suits your lifestyle. At the heart of the home, the gourmet kitchen showcases quartz countertops, a tile backsplash, stainless steel appliances including a cooktop and double wall oven, crown-molded cabinetry with under-cabinet lighting, and a pantry. It opens to the family room, creating an inviting setting for daily living and entertaining. Tile flooring extends throughout the first floor, and a separate breakfast nook overlooks the pool. The downstairs primary suite is a private retreat with its own French doors to the pool area. The en suite bath features dual vanities, a soaking tub, a walk-in shower, and a generous walk-in closet with custom built-in organizers. An additional first-floor bedroom and adjacent full bath offer a comfortable option for guests, and the bath doubles as a convenient pool bath with direct access to the outdoors. Quartz countertops grace all four bathrooms. Upstairs, an expansive loft provides room for a second family room, game area, or gathering space. A separate media room with double doors is a dedicated space for movie nights, complete with a projection screen and projector that convey. Five additional bedrooms and two full bathrooms complete the second floor, with laminate flooring throughout the loft and bedrooms. Outside, your private backyard retreat features a sparkling 35x12 saltwater pool and a covered paver patio, designed to make the most of Florida living, whether you’re enjoying a quiet afternoon poolside or entertaining friends and family. The location is hard to beat. Just 5 minutes to Florida’s Turnpike, within walking or biking distance of the West Orange Trail, and minutes from shopping including Costco, dining, and Montverde Academy. With its thoughtfully designed floor plan, multiple entertaining areas, and convenient location, this exceptional home is ready to welcome its next owners. Schedule your private showing today.

17839 Gourd Neck Loop, Winter Garden
14807 Winter Stay Drive, Winter Garden
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14807 Winter Stay Drive, a beautifully upgraded luxury residence located in the heart of Horizon West in Winter Garden. Spanning 3,856 square feet of refined living space on an oversized lot, this 5-bedroom, 4-bathroom home combines upscale comfort, privacy, and resort-style living. The outdoor sanctuary is custom-built for the Florida lifestyle, featuring a fully fenced backyard, a heated saltwater pool and spa, a spacious covered lanai with retractable awnings, and scenic sunset views overlooking the prestigious Orange County National Golf Course. Inside, the open-concept layout flows effortlessly for everyday living and grand entertaining. The gourmet kitchen boasts premium appliances, upgraded finishes, and an expansive quartz center island. The primary suite offers a private retreat with a spa-inspired bathroom, complemented by custom closets and a dedicated drop zone for extra organization. Upstairs, a large bonus room provides flexible space for a home theater, media room, or executive office, while an oversized 3-car garage offers generous vehicle and storage space. Value-adding upgrades include an owned solar panel system to significantly reduce energy costs. Situated just 0.5 miles from The Mark Plaza and minutes from Horizon West Hospital, top-rated dining, and shopping, this home offers fast access to SR 429, Florida’s Turnpike, and Walt Disney World. Schedule your private tour today.

14807 Winter Stay Drive, Winter Garden
13541 Parkfield Way, Winter Garden
$1,049,000
5 Beds ⋅ 4 Baths ⋅ Encore/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
Extensive custom upgrades, thoughtfully designed living spaces, and panoramic conservation views distinguish this 5-bedroom, 4-bath home in Encore at Ovation. Built by M/I Homes, this ENERGY STAR Certified, 3,688-square-foot home combines open gathering spaces, a flexible first-floor bedroom, customized storage, and outdoor living with a heated pool and spa. The east-facing backyard offers beautiful sunrise views across the pond and conservation landscape. The main level features high ceilings and wood-look ceramic tile flooring. Open to the living room, the kitchen features quartz countertops, solid wood cabinetry, GE Profile and LG stainless steel appliances, under-cabinet lighting, and a stainless steel farmhouse sink. A breakfast nook offers casual dining, while the separate formal dining room connects to the kitchen through a butler's pantry with built-in wine rack. The spacious walk-in pantry has a glass door and custom shelving. Custom built-in cabinetry and shelving with integrated lighting highlight the living room. A first-floor bedroom offers flexibility as a guest room or office, with an adjacent full pool bath providing direct access to the lanai and pool. Upstairs, maple hardwood flooring extends across the second floor and staircase, complemented by metal spindle railings. Double doors open to the primary suite, featuring a tray ceiling with recessed lighting and a private balcony overlooking the pond and conservation views. The ensuite bath offers dual sinks, a dedicated vanity area, glass-enclosed rainfall shower, and separate water closet. The custom walk-in closet includes drawers, shelving, shoe storage, and linen storage. Another bedroom features a private ensuite bathroom and custom closet, making it an ideal option for guests or a potential in-law suite. Two additional bedrooms offer walk-in closets, with a fourth full bathroom accessible from the hallway. The upstairs laundry room includes a sink, cabinetry, and attic access. Outside, the custom heated pool features an integrated spa, sun shelf, and lighting. An expansive screened enclosure, paver deck, and covered lanai provide room for outdoor dining and entertaining against a backdrop of conservation and pond views. Extras include a gas grill hookup, outdoor TV pre-wiring, and a motorized sliding-door shade with remote and app controls. Additional upgrades include modern lighting and ceiling fans, Nest thermostats, a tankless water heater, water softener and purification system, UV air-handler purification, security cameras, Wi-Fi-enabled irrigation, custom window blinds, and custom metal shelving in the garage. Beyond the property itself, Encore at Ovation offers a clubhouse, fitness center, resort-style community pool, playground, bocce ball court, dog park, walking trails with outdoor fitness equipment, and covered picnic areas overlooking ponds. Within the master-planned Horizon West area, residents have access to shopping, dining, entertainment, medical facilities, and nearby A-rated schools. Flamingo Crossings and Hamlin Town Center offer retail and dining options, while Walt Disney World Resort and access to SR 429 add to the location's appeal. With so much to enjoy both at home and throughout the surrounding community, this property offers a lifestyle that extends well beyond its front door. *Aerial photo property lines are an estimate and to be verified by buyer.

13541 Parkfield Way, Winter Garden
2020 Portcastle Circle, Winter Garden
$455,000
3 Beds ⋅ 3 Baths ⋅ Stone Crk A-1 & A-2 SubDv. ⋅ 34787 Zip Code
MOVE-IN READY | 2025 ROOF & NEW GUTTERS | NEW FLOORING & FRESH PAINT | NEW STAINLESS REFRIGERATOR & RANGE | SPACIOUS UPSTAIRS LOFT | LOW HOA -- Move-in ready and beautifully updated, this Winter Garden home sits in the Stone Creek community. Updates include a 2025 roof, new gutters, fresh interior and exterior paint, new carpet, and new LVP flooring in the main living areas. The main floor features an open, connected layout. The dining and family rooms flow into the breakfast nook and a bright kitchen equipped with a breakfast bar, an upgraded pantry, and a brand-new stainless refrigerator, range, and range hood. A sliding glass door leads to the patio and a spacious backyard that adapts to how you use it: perfect for entertaining, gardening, or relaxing outdoors. Upstairs, the spacious loft adapts to however you live: a home office, media room, or lounge. The primary suite offers a walk-in closet and an ensuite bath with dual sinks, a vanity, a garden tub, and a private water closet. The secondary bedrooms feature new carpet and ceiling fans, including one with an extended layout for added space. The location offers everyday convenience, in close proximity to Publix and minutes from Winter Garden Village and SR-429. Low HOA. Zoned for Whispering Oak Elementary, SunRidge Middle, and West Orange High School.

2020 Portcastle Circle, Winter Garden
16513 Silver Brook Way, Winter Garden
$879,000
4 Beds ⋅ 4 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Nearly new and ready for you in Horizon West! Built in 2025, this two-story Thoreau floor plan by Meritage Homes in Silverleaf Reserve at Hamlin offers 4 bedrooms, 3.5 bathrooms and 3,424 sq ft of living space. Curb appeal starts at the street with a craftsman-style elevation, tropical landscaping, a paver driveway and a two-car garage. A covered front porch welcomes you in, and a second-floor covered balcony above it gives you a private spot to catch the Florida breeze. Inside, wood-look plank tile runs throughout the entire first floor, with a tray ceiling and column accents framing the entry. To the front, a formal dining room and a flex space work beautifully as a home office, sitting room or playroom. The floor plan then opens up to a bright great room and a bay-window café nook overlooking the backyard, with French doors leading out to the screened patio. The kitchen is the heart of it all, with quartz counters, shaker cabinetry, a subway tile backsplash, glass-front uppers, a stainless vent hood, built-in double oven, walk-in pantry, coffee bar, an oversized island with seating and a single-basin sink. All appliances stay with the home, so there's nothing left to buy before move-in. A powder bath and a built-in drop zone with cabinets and counter space round out the main level. Upstairs you'll find all four bedrooms in plush carpet, the laundry room right where you need it, and a large media/flex room, space most homes this size simply don't have. Make it a theater room, game room, home gym or second living area, and change your mind later without giving up a bedroom. Out back, the oversized lot is nearly 1/4 acre with a huge backyard and open green space beyond the fence, leaving room for a pool, a play set, a garden or big get-togethers. The home also has a whole-house water softener and a reverse osmosis drinking water system on each floor. The location is hard to beat. Hamlin Town Center is right next door with shopping, dining and entertainment. Hamlin Elementary and Hamlin Middle are nearby. SR 429 is minutes away, and so is Orlando Health Horizon West Hospital. The Walt Disney World area, Winter Garden's historic downtown and the West Orange Trail are all a short drive. Schedule your showing today!

16513 Silver Brook Way, Winter Garden
13557 Parkfield Way, Winter Garden
$650,000
4 Beds ⋅ 3 Baths ⋅ Encore At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location!  Minutes from Walt Disney World and all that Winter Garden has to offer with the new hospitals, stores, restaurants, downtown Winter Garden, Horizon West and the list goes on! Single stories are hard to come by and this MI Home is waiting for you!  It sits on a gorgeous conservation lot with no neighbors on one side. Sit on the front porch or the back patio and enjoy the good life!  Walk to the pool, fitness center and dog park. The perfect community to walk or bike.  This 4 bedroom 3 bath rare find single story is move in ready-well maintained, built in 2021, quartz countertops, NEW AC, huge walk-in closet in the primary bedroom, a popular 3 way split floor plan, and ample room for entertaining with the dining room and large family room.  The home is stunning with its gorgeous wooded and pond view. Lawn Care is included in the HOA leaving you time to enjoy all Central Florida has to offer!  Schedule your showing today!

13557 Parkfield Way, Winter Garden
13211 Lakeshore Grove Drive, Winter Garden
$715,000
4 Beds ⋅ 4 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code
Amazing Floorplan!! Three way split floorpan with 4 bedrooms and an office located on the first floor. Formal dining and living rooms. Corian kitchen counters with wood cabinets. Large spacious bonus room on the second level with half bath. Screen enclosed pool with large lanai. Large vinyl fenced in backyard. ROOF 2023. Gated Community with basketball court, playground and dock to Lake Luntz. Located just a few minutes from Winter Garden Villages and access to the 408 near Stoneybrook Parkway. All furniture is available for purchase.

13211 Lakeshore Grove Drive, Winter Garden
261 Zachary Wade Street, Winter Garden
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Few homes make an entrance like this one: renovated, lakefront and minutes from downtown! Welcome to this exquisitely updated 4-bedroom, 3.5-bath pool home with 90 feet of frontage on Lake Apopka, the fourth-largest lake in Florida, in the gated, golf-cart-friendly community of Lakeview Reserve. Expansive open-water views, streaming natural light and a beautifully reimagined interior create an unforgettable first impression. LOCATION: Just 2 miles to historic Downtown Winter Garden, reachable by golf cart, with Plant Street's restaurants, boutiques, events and the famous Saturday Farmers Market. The West Orange Trail is right outside the community gate, six highly rated golf clubs are within a 5-mile radius, and top-rated elementary and middle schools are less than a mile away. Enjoy easy access to shopping, Florida's Turnpike, downtown Orlando and the theme parks. RENOVATION: An extensive whole-home renovation brings a polished contemporary feel, with large-format porcelain tile, fresh paint and striking new lighting. The living room's panoramic water views anchor an open-concept layout that flows into the oversized dining room and kitchen. The completely renovated kitchen features high-gloss white flat-panel cabinetry, frosted glass accents, quartz countertops, a full-height quartz backsplash, an oversized waterfall island, stainless steel appliances, abundant storage and a built-in bar with wine storage. Every bathroom is beautifully remodeled, and each has a window and exhaust fan. The first floor hosts the primary suite plus two additional bedrooms, all with 11-ft ceilings, and every bedroom in the home enjoys a lake view. The primary suite offers real hardwood floors, two walk-in closets and a private screened porch overlooking the lake. Its spa-inspired bathroom includes dual vessel sinks, a makeup area, jetted soaking tub and glass-enclosed shower with rainfall and body spray fixtures. A first-floor office or den adds a quiet place to work. Upstairs, real hardwood continues to an oversized loft/flex space with full bath, walk-in closet and separate HVAC, ideal for guests or entertainment. Two Florida rooms, one on each floor, each with its own mini-split system, offer year-round panoramic lake views. OUTDOORS: A fenced, private backyard opens to sweeping open-water views. The recently resurfaced saltwater pool (new pump and filter 2026) and freshly repainted pool deck lead to a private covered dock with a 5,000-lb electric boat lift, electricity and water. Spend afternoons swimming, boating or fishing, then watch brilliant Florida sunsets from the dock. An extensive driveway and freshly painted two-car garage with built-in storage add everyday convenience. ENERGY EFFICIENT: This solar-powered home also features all new windows (2024), a new main first-floor AC (2026) and mini-split systems in both Florida rooms. The seller currently pays only an approximately $30 monthly grid fee, compared to a previous $500-$600 monthly electric bill. The seller will pay off the solar loan at closing, OR the purchase price may be reduced if the buyer assumes the existing low-interest solar panel loan. Mornings of sunlight on the lake, afternoons by the pool or on the boat, evenings on the dock beneath a painted Florida sky, with downtown Winter Garden just a golf cart ride away. This is the feeling of being on vacation every day, without ever leaving home.

261 Zachary Wade Street, Winter Garden
15223 Evergreen Oak Loop, Winter Garden
$500,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 3b-4 3b-5 & 3 SubDv. ⋅ 34787 Zip Code
Welcome to the highly sought-after Independence community in Winter Garden! This spacious 4-bedroom, 3.5-bath home offers 2,502 square feet with a versatile layout that includes two primary suites—one conveniently located downstairs and a second upstairs. The open main living area features tile flooring and brings together the living room, dining area, and kitchen, creating plenty of space for everyday living and entertaining. The kitchen is equipped with granite countertops, stainless steel appliances, a center island, and pantry for additional storage. The downstairs primary suite offers the convenience of first-floor living, with an en suite bath featuring a double vanity, walk-in shower, and soaking tub. A separate half bath is also located downstairs for guests. Upstairs, you'll find a versatile loft, the second primary suite plus two additional bedrooms connected by a Jack-and-Jill bathroom. A 2-car rear-entry garage completes the home. Independence offers an impressive lineup of community amenities, including two clubhouses, two community pools, fitness centers, parks, and miles of walking and biking trails. Enjoy a prime Winter Garden location near A-rated schools, shopping, dining, entertainment, medical facilities, and major roadways. Don’t miss your chance to make this spacious Winter Garden home your own! *Aerial photo property lines are an estimate and to be verified by buyer.

15223 Evergreen Oak Loop, Winter Garden
Start Your Search