Winter Garden/Oakland Homes with Contemporary Architectural style

Winter Garden/Oakland Homes with Contemporary Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, Florida—where charm meets contemporary living! Nestled just west of Orlando, this thriving area boasts a rich history, vibrant community, and an abundance of outdoor activities, making it a perfect place to call home.

Winter Garden is renowned for its picturesque historic downtown, complete with quaint shops, delightful eateries, and a lively farmers market. The area is surrounded by lush parks and scenic lakes, making it an ideal spot for families and outdoor enthusiasts. Meanwhile, the neighboring town of Oakland offers a serene, small-town atmosphere, with tree-lined streets and a close-knit community feel.

In this beautiful region, contemporary architectural homes are making waves. These modern residences are characterized by clean lines, open floor plans, and an abundance of natural light. With an emphasis on functionality and style, contemporary homes in Winter Garden and Oakland often feature sleek finishes, innovative designs, and eco-friendly elements. Whether you’re drawn to a minimalist aesthetic or a more eclectic vibe, you’ll find a diverse selection of homes that cater to your unique taste.

Living in Winter Garden and Oakland means enjoying a perfect blend of suburban tranquility and urban convenience. With easy access to major highways, residents can quickly reach the excitement of Orlando’s theme parks, shopping centers, and cultural attractions. Plus, the area is known for its excellent schools, making it a fantastic choice for families.

Discover the charm of Winter Garden and Oakland, where contemporary living meets a vibrant community, and find your dream home today!

Newest Winter Garden/Oakland Homes with Contemporary Architectural style

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

5 Beds ⋅ 5 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code

LOCATION, LOCATION, LOCATION! Discover a rare gated lakefront retreat in the heart of Winter Garden, tucked away on a quiet, tree-lined cul-de-sac and conveniently located just minutes from local schools, grocery stores, dining, and Downtown Winter Garden. Enjoy grandfathered boat access on Lake Luntz, breathtaking sunset views, a screened pool with grotto seating and waterfall, a fully equipped Florida Grill/Bar room, and a private boathouse with a covered dock, boat lift, pontoon slip, and jet ski slips. Additional highlights include a guest suite, loft, media room, air-conditioned garage with gym/rec space, and two new AC systems installed in 2025—an exceptional combination of privacy, recreation, and waterfront living.

2450 Dahlgren Way, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code

Welcome to this exceptional 5-bedroom, 3 full bathroom and 1 half bathroom two-story home located in the highly desirable Signature Lakes at Independence community of Winter Garden. Offering approximately 3,438 square feet of thoughtfully designed living space, this residence showcases a perfect blend of modern upgrades, elegant finishes, and exceptional indoor and outdoor living. The home was fully renovated and modernized in 2024 with high-quality materials carefully selected for the owners’ personal enjoyment and long-term use. The inviting open-concept floor plan features beautiful flooring, custom lighting throughout, upgraded details, a spacious family room, formal dining area, and flexible spaces ideal for a home office, media room, or additional entertainment area. The modern kitchen offers beautiful cabinetry, ample storage, and a functional layout designed for everyday living and entertaining. Additional features include customized closets, a complete laundry room, and a whole-house water filtration system. The washer and dryer will convey with the sale. Enjoy the ultimate Florida lifestyle with a large private screened-in pool area featuring a pool approximately 30x14 and a separate spa approximately 8x8, creating the perfect setting for relaxing, entertaining, and enjoying year-round outdoor living. The home also features a covered outdoor living area and outdoor kitchen space. Major improvements include two air conditioning systems replaced in 2023 and 2024, a Tesla electric vehicle charger, and an additional EV charger compatible with other electric vehicles. The custom lighting throughout the home will remain, including the one-of-a-kind natural stone chandelier at the staircase, a truly unique statement piece designed specifically for the residence. The spacious primary suite offers a private retreat with an upgraded spa-inspired bathroom and elegant finishes, while additional bedrooms provide comfort and flexibility for family members and guests. Located in Signature Lakes at Independence, residents enjoy resort-style amenities including a clubhouse, community pools, fitness center, parks, playgrounds, sports courts, and scenic walking trails. Conveniently located near Hamlin Town Center, shopping, dining, entertainment, major highways, and Walt Disney World attractions, this beautifully upgraded Winter Garden residence offers the perfect combination of luxury, comfort, and community lifestyle. Please note: curtains do not convey with the sale. Buyer and buyer’s agent are encouraged to verify all measurements, HOA information, restrictions, fees, and community requirements.

14418 Avenue Of The Rushes, Winter Garden

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

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

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

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

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

3 Beds ⋅ 3 Baths ⋅ Winding Bay Phase 1b SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully upgraded 2020-built home in Horizon West offering 3 spacious bedrooms, 2.5 bathrooms, and a thoughtfully designed floor plan that blends style, comfort, and functionality. From the elegant formal living room to the expansive great room that seamlessly connects the kitchen, dining, and family areas, this home is perfect for both everyday living and entertaining.The heart of the home is the stunning chef's kitchen, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, and abundant workspace for cooking and gathering. Luxury tile flooring, upgraded in 2025, flows throughout the entire home, while crown molding, oversized baseboards, and decorative hallway columns add timeless architectural detail throughout the home.The spacious owner's suite offers a beautifully renovated spa-inspired bathroom, fully upgraded in 2026, creating a private retreat you'll love. A convenient Jack-and-Jill bathroom serves the secondary bedrooms, providing both functionality and privacy for family or guests.Outside, enjoy the screened lanai complete with sun shades, overlooking a fully fenced backyard with elegant iron fencing. Additional exterior features include an extended driveway, whole-home security camera system, and solar panels installed in 2022 for enhanced energy efficiency.Additional upgrades include a whole-home water softener system with reverse osmosis filtration in the kitchen, a dedicated garage outlet for an additional refrigerator or freezer, and numerous custom finishes that make this home truly move-in ready.With modern upgrades, exceptional attention to detail, and an ideal layout, this home offers the perfect combination of luxury, efficiency, and everyday comfort. Don't miss the opportunity to make this exceptional property your next home!

10750 Petrillo Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code

Under Construction. 3 Level Townhome with 3 Bedrooms! Ready August 2026! This stunning new construction townhome, The Lantana End Unit, features a popular farmhouse exterior and offers 1,846 square feet of thoughtfully designed living space. With 3 bedrooms, 2 full bathrooms, and a powder room, this home combines style and functionality throughout. As you enter through the charming front porch and impressive 8-foot entry door, you're welcomed by a spacious flex room, perfect for a home office, gym, or additional living area. Upstairs, luxury vinyl plank flooring leads you into the open-concept main living area, where the living room, dining room, and kitchen flow seamlessly together. The gourmet kitchen is designed to impress with a large eat-in island, 42-inch cabinets with crown molding, quartz countertops, and soft-close drawers. A wall of windows fills the dining area and kitchen with an abundance of natural light, creating a bright and inviting atmosphere. On the third level, the generously sized primary suite features a spacious walk-in closet and a private ensuite bathroom with dual vanities and a glass-enclosed shower. Two secondary bedrooms, a full guest bathroom, and a conveniently located laundry room complete the upper floor.

15081 Groveside Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code

Under Construction. Ready in September 2026! 3 Level Townhome with 3 Bedrooms! Ready in August 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms with a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by a Study room. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15075 Groveside Road, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lake Ph 2a SubDv. ⋅ 34787 Zip Code

Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!

17059 Harbor Oak Parkway, Winter Garden

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