Winter Garden/Oakland Homes with Contemporary Architectural style

Winter Garden/Oakland Homes with Contemporary Architectural style

Welcome to the picturesque region of Winter Garden and Oakland, Florida, where charming small-town vibes meet modern-day conveniences. Nestled just west of Orlando, this enchanting area is celebrated for its vibrant community, lush landscapes, and a rich history that dates back to the citrus boom of the 1800s. Residents enjoy a perfect blend of outdoor activities, cultural experiences, and family-friendly amenities, making it an ideal place to call home.

The heart of Winter Garden is its historic downtown, where you can stroll along brick-paved streets lined with quaint shops, delightful eateries, and the famous Winter Garden Farmers Market. Meanwhile, the nearby Oakland area offers serene natural beauty, with scenic parks and trails that invite outdoor enthusiasts to explore the stunning surroundings.

For those seeking a modern lifestyle, the homes in Winter Garden and Oakland boast contemporary architectural styles that cater to today's discerning buyers. These residences are designed with open floor plans, abundant natural light, and sleek finishes that create a harmonious blend of comfort and sophistication. From stylish single-family homes to chic townhouses, the contemporary designs reflect a commitment to quality and innovation, appealing to families, professionals, and retirees alike.

Living in Winter Garden and Oakland means enjoying a vibrant community spirit, with numerous events and festivals throughout the year, fostering connections among neighbors. With excellent schools, convenient access to major highways, and proximity to Orlando's attractions, this region is not just a place to live; it’s a lifestyle choice. Discover your dream home in Winter Garden and Oakland, where contemporary living meets timeless charm!

Newest Winter Garden/Oakland Homes with Contemporary Architectural style

$450,000
3 Beds ⋅ 2 Baths ⋅ Corsino Place SubDv. ⋅ 34787 Zip Code
Set on a quiet cul-de-sac near the heart of Winter Garden, this updated single-story home pairs an easy, open layout with an unusually spacious backyard. Inside, 3 bedrooms and 2 bathrooms are arranged across 1,307 square feet, with vaulted ceilings and ceramic tile connecting the kitchen, dining area, and living room. The refreshed kitchen features white cabinetry, quartz countertops, a glossy subway-style backsplash, a deep undermount sink with a pull-down faucet, modern lighting, and a peninsula with breakfast-bar seating. Sliding glass doors extend the living space directly to the backyard. The primary suite offers tile flooring, a feature wall, private patio access, an en-suite bath, and a true walk-in closet. Two additional bedrooms and a second full bath provide flexible space for guests, an office, or everyday living. Fresh interior paint, updated light fixtures, ceiling fans, and a functional split-bedroom design complete the interior. Outside, the fully fenced 0.23-acre lot is a standout. A roofed pergola creates a generous shaded patio and room for outdoor dining and lounging. Beyond it, the broad lawn leads to a defined circular firepit area and a 10-by-20 storage shed, with ample open space for recreation, gardening, and outdoor hobbies. Aerial views highlight the depth and usability of the yard, while the attached two-car garage adds everyday storage and convenience. With no HOA and no CDD, the property offers flexibility in an established neighborhood close to the West Orange Trail, local parks, Lake Apopka, and the shops, dining, Plant Street Market, and brewery district of downtown Winter Garden. Enjoy an evening downtown, a weekend bike ride, or a relaxed night around the backyard firepit, all from a well-located home with room to make it your own.

1312 Corsino St, Winter Garden
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$859,500
5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to your dream home in the highly desirable community of Wincey Groves! This stunning 5-bedroom, 3.5-bath single-family residence, built in 2021, boasts contemporary design and upscale finishes throughout. Enjoy soaring 10-foot ceilings with elegant fascia, and a chef-inspired modern kitchen featuring luxurious quartz countertops and top-of-the-line stainless steel appliances. Experience custom-built cabinetry and exquisite upgraded millwork that add character and style to every room. The spacious primary suite offers generous walk-in closets, a versatile bonus fifth bedroom, perfect for guests or a home office. Step outside to an upgraded back patio and balcony, where you'll find a fully equipped outdoor kitchen with a wine fridge, refrigerator, built-in grill, and a cozy fire pit—ideal for entertaining or relaxing under the stars. Ideally situated just one mile from Hamlin Town Center, you'll have easy access to premier shopping, dining, and entertainment options.

5128 Breezy Acres Street, Winter Garden
$1,100,000
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Luxurious Fully Furnished 5-Bedroom Home in Winter Garden Experience the perfect blend of elegance, comfort, and convenience in this stunning fully furnished two-story home located in the highly desirable Winter Garden area. Designed with both style and functionality in mind, this exceptional residence offers 5 spacious bedrooms, 4 full bathrooms, and 1 half bathroom, providing plenty of room for families of all sizes. The thoughtfully designed open-concept floor plan creates a seamless flow between the expansive living and dining areas, making it ideal for everyday living and entertaining. At the heart of the home is a beautifully appointed kitchen featuring solid wood cabinetry, stone countertops, and a full suite of included appliances, offering both timeless style and modern convenience. The luxurious primary suite serves as a private retreat with a generous walk-in closet and an elegant en-suite bathroom. The additional bedrooms are equally well-designed and include built-in closets, providing excellent storage and comfort for family members or guests. Upstairs, you'll also find a spacious loft that offers endless possibilities as a second living area, media room, home office, or playroom. Step outside to enjoy the convenience of a 2-car attached garage and the peace of mind that comes with owning a meticulously maintained, move-in-ready home. Being fully furnished, this property is perfect for buyers seeking a seamless transition without the hassle of furnishing an entire home. Ideally situated in Winter Garden, this home offers easy access to major highways, shopping, dining, entertainment, and highly rated schools, making it an outstanding choice for those seeking both convenience and an exceptional lifestyle. Don't miss this incredible opportunity to own a beautifully furnished home in one of Central Florida's most desirable communities. Schedule your private showing today and discover everything this remarkable property has to provide.

16091 Silver Brook Way, Winter Garden
$660,000
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers new construction. The Autumn townhome offers 2,593 square feet of thoughtfully designed living space with 4 bedrooms and 4 bathrooms. An inviting foyer leads to a first-floor bedroom, ideal for guests, a home office, or flexible living. The open-concept floor plan seamlessly connects the kitchen, casual dining area, and great room, creating an ideal space for everyday living and entertaining. The kitchen features designer cabinetry, upgraded countertops, and a decorative tile backsplash. Upstairs, the private primary suite includes a spacious walk-in closet and en-suite bath, while two secondary bedrooms share a full bathroom. Additional highlights include a private rear courtyard, a detached 2-car garage with a versatile loft above that provides additional flexible living space for a home office, media room, fitness area, or playroom, and professionally selected finishes throughout. Residents enjoy access to resort-style community amenities.

12776 Sunset Walk Drive, Winter Garden
$605,000
3 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Crowley townhome by Toll Brothers, located in the desirable Winter Garden/Horizon West area. This thoughtfully designed new construction home features a covered front entry that opens to a spacious, open-concept living area, seamlessly connecting the great room, kitchen, and dining space. Enjoy outdoor living in the private courtyard with convenient access to the detached 2-car garage. Above the garage, a finished loft with a full bathroom adds approximately 550 square feet of flexible living space, perfect for a guest suite, home office, fitness room, media room, or hobby space. The spacious primary suite offers a large walk-in closet and a well-appointed bath featuring dual vanities and a separate shower. Experience low-maintenance living with exceptional design in one of Central Florida's most sought-after communities.

12800 Sunset Walk Drive, Winter Garden
$890,000
5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code
Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden
$400,000
3 Beds ⋅ 3 Baths ⋅ Hamilton Gardens SubDv. ⋅ 34787 Zip Code
You found it! Amazing LOCATION and priced to sell! You will love the open floorplan and PRIVATE COURTYARD that is perfect for outdoor gatherings. REAR-ENTRY TWO-CAR GARAGE in the highly desirable Hamilton Gardens community! The bright kitchen features granite countertops, a spacious pantry, and overlooks the dining area and great room, creating a seamless layout. Enjoy peaceful views of mature trees with NO REAR NEIGHBORS. Hamilton Gardens offers RESORT-STYLE POOL, cabana, dog park, and playground. Residents even enjoy NIGHTLY DISNEY FIREWORK VIEWS right from the community! Located in the HEART OF HAMLIN in sought-after HORIZON WEST just minutes from Hamlin Town Center with dining, cafés, entertainment, and a weekly farmers market. Convenient to SR 429, TOP-RATED SCHOOLS, major medical facilities, Winter Garden Village, Historic Downtown Winter Garden, Windermere, and ALL DISNEY ATTRACTIONS. Don't miss this one!

6208 Aralia Ivy Lane, Winter Garden
$739,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home in the highly sought-after Winter Garden area! Perfectly positioned on a premium homesite, this home offers breathtaking water and conservation views with NO REAR NEIGHBORS, providing exceptional privacy and a peaceful backdrop. Designed for both comfort and functionality, the open floor plan features a private first-floor guest suite with a full bathroom, ideal for multigenerational living, overnight guests, or a home office. The spacious kitchen flows seamlessly into the dining and family room, creating the perfect setting for entertaining and everyday living. Upstairs, you’ll find a versatile loft that can serve as a media room, playroom, or second living area, along with the remaining bedrooms, including the spacious primary suite. Step outside to relax and unwind while enjoying the tranquil pond and conservation views from your backyard. Best of all, the HOA MAINTAINS the LAWN, allowing you to enjoy a low-maintenance lifestyle. Residents enjoy outstanding community amenities, including multiple resort-style swimming pools, a fully equipped fitness center with a play area, tennis courts, and more. Conveniently located near top-rated schools, shopping, dining, major highways, and Orlando’s world-famous attractions, this home offers the perfect blend of luxury, comfort, and convenience. Don’t miss this rare opportunity to own a home with stunning water and conservation views in one of Winter Garden’s most desirable communities!

9152 Sonoma Coast Drive, Winter Garden
$720,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Designed for comfortable everyday living and easy gatherings, this inviting Waterleigh home pairs a flexible two-story layout with fresh interior finishes and thoughtfully connected living spaces. Brand-new interior paint creates a bright, polished backdrop throughout, while decorative wainscoting and chair rail added in 2021 bring character to the main living areas. Just off the foyer, a versatile flex room can serve as a home office, formal dining room, playroom, hobby space, or additional sitting area based on your needs. Wood-look tile extends across the first floor, where wide archways create an easy flow between the kitchen, casual dining area, and family room. The kitchen is anchored by a large island with seating and features white cabinetry, stainless steel appliances, a blue glass-tile backsplash, generous counter space, a walk-in pantry, and a cabinet-lined serving area. The refrigerator was replaced in July 2024, and the microwave was replaced in November 2023. The first-floor primary suite offers a comfortable retreat with a tray ceiling, multiple windows, and an en suite bath featuring dual vanities, a soaking tub, separate shower, and an exceptionally large walk-in closet. Upstairs, one secondary bedroom includes its own full bath, while two additional bedrooms share another full bathroom with dual sinks. The oversized loft provides adaptable space for media, recreation, work, or hobbies. A dedicated laundry room, powder bath, built-in drop zone cabinetry, and attached two-car garage add everyday convenience. Wi-Fi-enabled features include the refrigerator, washer, dryer, microwave, thermostat, garage door openers, Ring device, and two smoke detectors. The exterior was painted in August 2025, and the covered front porch, covered rear lanai, and grassy backyard provide additional space to relax outdoors. Waterleigh residents have access to amenities throughout every phase of the community, including four resort-style pools, three fitness centers, tennis courts, sand volleyball, mini-golf, multiple playgrounds, pavilions, and walking paths. Lawn maintenance is included with the HOA, allowing more time to enjoy the neighborhood and its convenient Horizon West location near SR-429, shopping, dining, and Central Florida attractions.

9561 Waterway Passage Drive, Winter Garden
$230,000
3 Beds ⋅ 2 Baths ⋅ The Grove Resort SubDv. ⋅ 34787 Zip Code
The Jasmine model is the MOST SPACIOUS condo in the sought after Grove Resort & Water Park. The condo 2233 is FULLY FURNISHED, DECORATED and equipped with everything you need and is located in NEWEST STERLING TOWER-II. Featuring an open concept living & dining area with a screened balcony overlooking lush gardens. The modern kitchen has quartz countertops, stainless steel appliances, and attached laundry room with full size washer and dryer. YOUR PERFECT VACATION HOME IS AT THE GROVE RESORT where you will enjoy privacy and convenience, including a concierge, multiple bars, restaurant, convenience store, spa, elaborate game room, stunning water park oasis, breathtaking 22-acre activity lake all professionally managed with turnkey hotel rental programs to help offset costs. The property is JUST 6 MILES FROM WALT DISNEY WORLD and close to all Central Florida’s attractions, shops, restaurants and major highways.

14501 Grove Resort Avenue Unit 2233, Winter Garden
$619,000
4 Beds ⋅ 3 Baths ⋅ Grove Pk/Stone Crest A-E SubDv. ⋅ 34787 Zip Code
A home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 square feet. A full 2022 refresh. New roof, new water heater, new softener, new stainless appliances, EV charger in the garage. Inside, warm wood flooring runs uninterrupted through the main floor, from the foyer and dedicated office space into the kitchen and living area that anchors the back of the home. Fresh white cabinets, durable granite counters, stainless appliances, custom tile backsplash. A kitchen you'll love to use and to look at. The bay window pulls in the morning light over the breakfast nook, and the living space is big enough for the family gatherings you'll actually host. Then the rarity, a massive fully screened lanai on brick pavers that stretches the width of the home with ample space to entertain a party of two or twenty, along with a long serving counter ready for a grill setup, drinks station, or whatever the party calls for. Past the screen, the yard is vinyl and stone fenced, artificial turf underfoot so you're not wasting Saturdays mowing. Upstairs, the primary suite carries real volume with a tray ceiling, plus a separate flex space that reads as a sitting area, office, or nursery, really whatever you need it to be. Two walk-in closets built out with custom shelving, and a bath with dual vanities, garden tub, and separate shower. The other three bedrooms are generously sized, all fitted with custom built-ins in the closets. You'd be pleased to know the beauty extends beyond the home itself and into where it sits. You're two minutes from Winter Garden Village. Target runs, AdventHealth, restaurants, shopping for the retail-therapy days, all of it. Ten minutes north drops you onto Plant Street: Crooked Can, the Saturday farmers market, the West Orange Trail running twenty-two miles through the middle of it. Disney sits twenty minutes away so close enough for a Tuesday afternoon, far enough that the tourism doesn't reach here. Not to mention the pool, tennis courts, playground, and clubhouse are all a short walk from the front door, so you don't have to leave the neighborhood to have a good time. If a picture is worth a thousand words, walking through is worth a lifetime. Come see it in person!

932 Lost Grove Circle, Winter Garden
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