Winter Garden/Oakland Homes with Outdoor Kitchen Exterior Features

Winter Garden/Oakland Homes with Outdoor Kitchen Exterior Features

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where the charm of small-town living meets the vibrancy of modern amenities. Nestled just a stone’s throw from the bustling city of Orlando, this picturesque area boasts lush landscapes, scenic lakes, and an inviting community atmosphere that makes it a desirable place to call home.

Winter Garden, known for its historic downtown district, offers a delightful blend of quaint boutiques, delightful eateries, and a rich cultural scene. The nearby Oakland area complements this with its serene parks and scenic trails, perfect for outdoor enthusiasts and families alike. Residents enjoy a wealth of recreational activities, from hiking and biking to boating on Lake Apopka, making it an ideal location for those who appreciate nature.

One of the standout features of homes in this region is the inclusion of outdoor kitchens, which elevate outdoor living to a new level. Imagine hosting summer barbecues or cozy family gatherings under the stars, all while enjoying the beautiful Florida weather. Homes with outdoor kitchen exterior features are designed for both functionality and entertainment, often featuring built-in grills, spacious countertops, and ample seating areas that invite friends and family to gather.

Whether you’re a culinary enthusiast eager to whip up gourmet meals al fresco or someone who simply enjoys the art of entertaining, these outdoor spaces offer a perfect blend of comfort and style. In Winter Garden and Oakland, your dream home awaits—complete with the outdoor kitchen of your dreams, ready to create lasting memories in a community that feels like home. Explore the possibilities today!

Newest Winter Garden/Oakland Homes with Outdoor Kitchen Exterior Features

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

4 Beds ⋅ 3 Baths ⋅ Black Lake Preserve SubDv. ⋅ 34787 Zip Code

Welcome to 14343 Black Lake Preserve Street in Winter Garden, a beautifully upgraded pool home in the sought-after Black Lake Preserve community. Designed for both everyday living and unforgettable entertaining, this exceptional residence combines luxury finishes, premium technology, and thoughtfully designed living spaces. At the heart of the home is a stunning chef's kitchen featuring an impressive 13-foot center island, a GE Monogram wall oven, Thermador 5-burner cooktop, and a spacious walk-in pantry with custom built-in storage. The kitchen flows seamlessly into the main living areas and is complemented by an elegant formal dining room, providing the perfect setting for holiday gatherings, dinner parties, or everyday meals. Luxury vinyl plank flooring, crown molding, and a cozy fireplace add warmth and sophistication throughout the home. The spacious primary suite offers a private retreat with a custom walk-in closet system, while the dedicated theater room delivers an immersive entertainment experience with a 123-inch screen, 4K projector, and surround sound system. Step outside and enjoy Florida living at its finest. The backyard features a fully equipped outdoor kitchen with grill, griddle, and sink, making it the perfect space for entertaining family and friends. The sparkling pool is equipped with a new heat and cool pump, allowing for year-round enjoyment. Additional upgrades include a Generac whole-home generator, providing security and peace of mind during any season. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and area attractions, this move-in-ready home offers the perfect blend of luxury, comfort, and convenience. This is a rare opportunity to own a highly upgraded home in one of Winter Garden's most desirable communities.

14343 Black Lake Preserve 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

7 Beds ⋅ 8 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code

Exceptional custom estate on approximately 1.61 acres in Downtown Winter Garden's desirable Golf Cart District, just minutes from Historic Plant Street, the West Orange Trail, shopping, dining, and entertainment. This extensively renovated residence offers over 7,700 square feet of living space with 7 bedrooms, 6 full baths, 2 half baths, spacious living and entertaining areas, a chef's kitchen with premium appliances, marble countertops, wine bar, and an open-concept design. The resort-style outdoor living area features a heated saltwater pool, covered lanai, summer kitchen with pizza oven and built-in grill, and an NBA regulation half basketball court. A detached guest house with a full kitchen provides ideal space for guests, multigenerational living, or a private office. Additional features include a gated circular driveway, oversized 3-car garage with workshop, golf cart garage, mature oak trees, and no HOA. Conveniently located near SR-429, Florida's Turnpike, Winter Garden Village, downtown Orlando, area attractions, and Orlando International Airport.

900 W Plant Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Winding Bay Ph 3 SubDv. ⋅ 34787 Zip Code

Beautifully upgraded home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home over 2,100 square feet of comfortable living space with modern finishes and an open floor plan filled with natural light. The spacious kitchen is truly the heart of the home, featuring a large quartz island, built-in oven and microwave, gas cooktop, stainless steel appliances, plenty of cabinet space, and a walk-in pantry. Master Bedroom Suite offers a spa-like bathroom with dual vanities, a large walk-in shower, and a custom walk-in closet. The dedicated office with built-in cabinetry provides an ideal work-from-home space. The backyard offers your own private retreat with a heated saltwater pool, covered lanai, outdoor kitchen, pergola, and a fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. Additional features include solar panels, luxury laminate flooring throughout the main living areas, a custom wood panel for the TV, a spacious laundry room with built-in cabinets and utility sink, an irrigation system, and a two-car garage with storage racks and an EV charger. Winding Bay enjoy resort-style amenities including a community pool, playground, dog park, and scenic walking paths, all conveniently located near Disney, Horizon West, shopping, dining, and top-rated schools.

15009 Lebeau Loop, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to 9225 Holliston Creek Place, an exceptional pool home nestled on a premium corner lot in one of Winter Garden's most sought-after communities. From the moment you arrive, the lush landscaping, side-entry garage, and beautifully maintained exterior set the tone for everything this home has to offer. Step inside and you are immediately greeted by soaring ceilings, an abundance of natural light, and a thoughtfully designed open floor plan that flows seamlessly from the formal living and dining areas into the heart of the home. The spacious kitchen is a true entertainer's dream, featuring generous counter space, ample cabinetry, and a layout that opens directly to the main living area — perfect for gatherings of any size. The dedicated home office is one of the standout features of this property — large, well-appointed, and completely separate from the living spaces, giving you the ideal work-from-home setup or the flexibility to use as a fifth bedroom, playroom, or media room. The primary suite is a private retreat, offering a generous layout, spa-like en suite bathroom with dual vanities, soaking tub, and walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned for privacy. Step outside and discover your own backyard oasis. The screened pool and lanai area is designed for true Florida living — whether you are taking a morning swim, hosting a weekend cookout, or simply unwinding at the end of the day. The summer kitchen is fully equipped and perfectly positioned to make outdoor entertaining effortless, with everything you need just steps from the pool deck. Being on a corner lot provides additional yard space, extra privacy, and enhanced curb appeal that interior lots simply cannot match. Located in a vibrant, well-established Winter Garden community with easy access to top-rated schools, SR-429, the 408, shopping, dining, and all of Central Florida's best attractions — this one truly checks every box.

9225 Holliston Creek Place, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code

Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code

Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Perfectly positioned on a quiet cul-de-sac in the sought-after Oakland Hills community near historic downtown Winter Garden. This FULLY FURNISHED and thoughtfully designed custom home on a single level, combines timeless modern farmhouse architecture with today's finest technology and craftsmanship. Curb appeal abounds with a classic mix of Hardie board siding and brick, anchored by a large, shaded front porch glowing with authentic gas lanterns from New Orleans — a true farmhouse welcome. When evening arrives, intentional landscape lighting accentuates the lush grounds and craftsmanship evident in every corner. Inside, the statement grand great room makes an unforgettable first impression with soaring 22+ foot ceilings, exposed beams, and dormer windows that fill the room with natural sunlight from morning to evening. Throughout the home, ten-foot ceilings, custom moldings and baseboards, LBU lighting with LED bulbs, and natural hardwood floors (in all but the media room) keep the ambiance light and welcoming. The heart of this custom residence is a true chef's kitchen: Monogram appliances, two oversized islands, a 36" gas range, paired with Moen and Kohler fixtures, all wrapped in custom Wellborn cabinetry with soft-close doors and drawers. A back second kitchen — the ultimate working pantry — adds double ovens, a microwave, a commercial Keurig, and abundant storage for effortless entertaining. Just off the main living space, a warm and welcoming library/office with custom-built bookcases and Zoom room offers a quiet retreat. The generous primary suite is a luxurious escape, complete with a spa-inspired bathroom centered around an oversized Kohler clawfoot tub. Two additional guest suites offer king beds and ensuite baths with double vanities, while a thoughfully designed bunk room with its own private bath means every guest feels right at home. Movie nights reach a new level in the dedicated media room with a 4K projector and Atmos surround sound. Outdoor living takes center stage on the expansive covered lanai, where a fully equipped summer kitchen with 36" Coyote natural gas grill, exhaust vent, steel doors, and retractable screen — makes alfresco entertaining effortless. Beyond, a private backyard with a heated pool and natural gas fire pit invites year-round gatherings that won't be forgotten. Enjoy smart home living at it's best with a Crestron home automation system, WattBox® UPS battery, Uniview Turret security cameras monitored by Future Home Integration, plus whole-home Wi-Fi with service options from Spectrum or Quantum. Custom closets, two laundry rooms, and an oversized three-car garage with an incredible amount of extra storage. Oakland Hills is an exclusive enclave of just 17 custom homes, minutes from the West Orange Trail, downtown Winter Garden, and Winter Garden Village. Perfectly positioned with easy access to the Turnpike, SR 429, and SR 408, it makes commuting, theme park visits, and airport runs a breeze. Schedule your private tour today and experience everything this meticulous one-of-a-kind home has to offer!

15217 Farm Stand Court, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Estates At Lakeview Preserve SubDv. ⋅ 34787 Zip Code

New Price! Welcome to this beautifully appointed residence in Estates at Lakeview Preserve. Situated on an oversized homesite within this gated Winter Garden community, this exceptional home showcases over $100,000 in owner-added custom upgrades in addition to premium builder selections. Thoughtfully designed and meticulously maintained, it offers an incredible combination of luxury finishes, modern convenience, and resort-style outdoor living that's ready to be enjoyed from day one. Designed with both everyday living and entertaining in mind, the spacious open floor plan features a first-floor owner's suite, generously sized secondary bedrooms, a private flex room ideal for a home office, an oversized upstairs loft with an additional guest suite and full bath, and a three-car garage with included electric vehicle chargers. The heart of the home is the beautifully designed kitchen, complete with quartz countertops, premium cabinetry, abundant workspace, and an open layout that flows seamlessly into the main living area and covered lanai. Throughout the home you'll find custom built-in cabinetry, professionally designed closet systems, and motorized window treatments that add both style and functionality. The backyard was designed to be enjoyed year-round. Relax by the heated pool, entertain from the fully equipped summer kitchen, enjoy your favorite music through the built-in surround sound system, or take advantage of the convenient cabana bath after a day outdoors. Every space was thoughtfully designed to make Florida living as enjoyable as possible. This home is equally impressive behind the walls, featuring an owned solar panel system, whole-home CAT6 networking, enhanced Wi-Fi, smart TV connections, integrated surround sound, security and camera prewiring, and numerous smart-home features that provide modern convenience and energy efficiency. Living in Estates at Lakeview Preserve means enjoying gated access and outstanding community amenities including a resort-style pool, clubhouse, fitness center, playground, scenic walking trails, and beautiful lake views. Conveniently located just minutes from SR-429, Winter Garden Village, Walt Disney World, shopping, dining, and highly rated schools, the location is just as impressive as the home itself. From the extensive custom upgrades to the exceptional attention to detail, this home has been lovingly maintained and thoughtfully improved throughout. Opportunities to own a property finished to this level are few and far between. Schedule your private showing today.

4708 Weatherbell Road, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Johns Lake Pointe SubDv. ⋅ 34787 Zip Code

Tucked inside sought-after Johns Lake Pointe, this impeccably maintained 6-bedroom, 5-bathroom, pool home offers 4,693 square feet of thoughtfully designed living space where style, comfort, and exceptional entertaining come together. With a versatile floor plan that includes a first-floor Primary suite, and additional Primary suite upstairs, expansive gathering spaces, and standout rooms for both relaxation and recreation, this home offers the flexibility and scale today’s buyers are searching for. Soaring ceilings and a bright, open layout create an inviting sense of space from the moment you enter, while the beautifully updated Kitchen serves as the heart of the home with quartz countertops, elegant white cabinetry, stainless double workstation sink, and Samsung Wi-Fi-enabled appliances. Luxury vinyl plank flooring runs throughout, adding warmth, durability, and a cohesive finish. Upstairs, the oversized Bonus/Game room with wet bar and beverage refrigerator offers the perfect place to unwind, while the dedicated Home Theater with projector, screen, surround sound, and reclining seating makes movie night an event of its own. And then there’s the backyard—an absolute showstopper! With tranquil pond and greenspace views, no rear neighbors, and a resort-style setting designed for year-round enjoyment, this outdoor space truly sets the home apart. The saltwater pool and spa feature a sun shelf, fire features, and electric heater, while the fully equipped Outdoor Kitchen with built-in grill, smoker, beverage refrigerator, and bar seating was made for effortless entertaining. Additional highlights include a 4-car garage with air conditioning, insulation, ceiling-mounted storage, and finished floors, along with a Mudroom, upstairs Laundry and updated lighting. Ideally located just minutes from Downtown Winter Garden, Winter Garden Village, the West Orange Trail, local schools, and major roadways, this is more than just a home—it’s a place to gather, celebrate, and enjoy the very best of Florida living.

427 Egret Place Drive, Winter Garden

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