Winter Garden/Oakland Homes with Fire Pit Exterior Features

Winter Garden/Oakland Homes with Fire Pit Exterior Features

Nestled in the heart of Orange County, Florida, the charming communities of Winter Garden and Oakland offer a delightful blend of small-town charm and modern conveniences. Just a stone's throw from the vibrant city of Orlando, this picturesque region boasts lush landscapes, historic downtown areas, and a warm, welcoming atmosphere that draws residents and visitors alike.

Winter Garden, with its quaint brick-lined streets, is known for its vibrant farmers' market, unique boutiques, and delightful eateries that serve everything from fresh farm-to-table meals to artisanal coffee. The nearby Oakland area complements this charm with its scenic parks and stunning views of Lake Apopka, making it a haven for nature enthusiasts and outdoor lovers.

One of the standout features of homes in this region is the inclusion of fire pits in their outdoor spaces. Imagine cozy evenings spent under the stars, gathered around a crackling fire with family and friends. These fire pits create the perfect ambiance for storytelling, roasting marshmallows, or simply enjoying the serene Florida evenings. Many homes in Winter Garden and Oakland are designed with outdoor living in mind, allowing residents to fully embrace the beautiful weather and stunning surroundings.

Whether you’re looking for a modern family home or a quaint cottage, Winter Garden and Oakland offer a variety of options that cater to all lifestyles. With their rich community spirit, beautiful landscapes, and inviting homes complete with fire pits, this region is not just a place to live, but a place to thrive. Discover your perfect home in this enchanting corner of Florida today!

Newest Winter Garden/Oakland Homes with Fire Pit 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 ⋅ 2 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to Wintermere—where comfort, privacy, and location come together in one exceptional home. Nestled on a quiet cul-de-sac within the desirable gated Wintermere community, this beautifully maintained 4-bedroom, 2-bath residence offers an ideal blend of indoor and outdoor Florida living. The open split-bedroom floor plan is filled with natural light and features soaring ceilings, spacious living areas, and an updated kitchen complete with a large center island, stainless steel appliances, generous cabinetry, and abundant counter space overlooking the main living area—perfect for everyday living and entertaining. The private primary suite offers a relaxing retreat with dual vanities, a spacious walk-in closet, a garden tub, and a separate shower. Step outside to your own backyard oasis featuring a saltwater pool, expansive lanai, and oversized fenced backyard situated on a generous 0.31-acre lot. Whether you’re hosting family gatherings, enjoying quiet evenings by the pool, or simply taking advantage of Florida’s year-round sunshine, this outdoor space was designed to be enjoyed. Additional highlights include an indoor laundry room, two-car garage, extended driveway, mature landscaping, and the security of a gated neighborhood with sidewalks throughout. Ideally located just minutes from Winter Garden Village, Hamlin Town Center, Walt Disney World, SR-429, Florida’s Turnpike, shopping, dining, hospitals, major employers, and highly regarded schools, this home offers exceptional convenience while maintaining a peaceful residential setting. If you’ve been searching for a move-in ready pool home in one of Winter Garden’s most sought-after gated communities, this property is one you won’t want to miss. Saltwater pool! Screened lanai! Cul-de-sac! Gated community Split floor plan Open concept! Stainless steel appliances! Center island! Fenced backyard! No rear neighbors! Move-in ready! Winter Garden Close to Disney Near Winter Garden Village Near Hamlin Easy access to SR-429 & Florida’s Turnpike Ask about the Incentives that you may QUALIFY FOR!!!

2031 Wintermere Pointe Drive, 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 ⋅ 4 Baths ⋅ Hillcrest SubDv. ⋅ 34787 Zip Code

A truly rare find in beautiful Downtown Winter Garden's highly coveted Golf Cart District, with NO HOA this exceptional 5-bedroom, 3.5-bath residence offers a once-in-a-lifetime opportunity to own a home where luxury, character, and location come together beautifully. Thoughtfully renovated from top to bottom, this one-of-a kind property combines timeless craftsmanship with modern elegance and resort-style outdoor living. Every inch of this home has been meticulously updated with high-end finished , including a stunning chef's kitchen featuring quartz countertops, a large center island, custom cabinetry with panel-ready appliances, double ovens, a wine refrigerator, a walk-in pantry, and gorgeous copper accents including a double farmhouse sink, matching range hood, pot filler, and faucet. The inviting living spaces showcase custom craftsman trim, elegant wainscoting, oversized baseboards, shiplap ceilings, a beautiful fireplace with a custom stone entertainment wall, a built-in library, designer lighting, and travertine flooring in the kitchen and bathrooms. Step outside into your own private backyard oasis where you'll find a heated, newly resurfaced pool and above-ground spa, a spacious paver pool deck, screened lanai, pergola with a fire pit, raised garden beds, and professionally designed landscaping surrounded by mature hedges, picket fencing, majestic oak trees, crepe myrtles, gardenias, and rose bushes, creating exceptional beauty and privacy. The expansive property also features a detached workshop, and an extra-long spacious driveway with abundant parking for all your toys!!This home offers peace of mind with countless recent upgrades, including a NEW ROOF with metal porch roofing, two NEW HVAC systems a NEW HOTWATER HEATER, NEW POOL PUMP, Ecobee smart thermostats, digital entry, a new pool bath, Centricon termite protection, and in-wall pest control tubing. Perfectly located just a short golf cart ride from Winter Garden's award-winning restaurants, charming boutiques, the famous Farmers Market, and the West Orange Trail, this is more than just a home—it's a lifestyle. Homes of this caliber, with this level of craftsmanship, outdoor amenities, and an unbeatable Downtown Winter Garden location, and NO HOA rarely come to market. Schedule your private showing today to experience everything this extraordinary property offers. If you are lucky enought to purchase this home you are not just getting a home, you're getting a rare opportunity in one of Central Florida's most desirable communities.

1324 Vic Kay Court, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code

Some homes are simply updated. This one has a personality all its own. Welcome to this one-of-a-kind 4-bedroom, 4-bath home in the gated community of Carriage Pointe, where artistic design, modern renovations, and exceptional indoor-outdoor living come together to create a truly unforgettable home. This oversized 0.34-acre corner lot sits on a quiet dead-end street with no neighbors to the left or rear. Mature privacy hedges surround the fenced backyard, creating a peaceful retreat, while two gated community entrances provide convenient access to shopping, dining, and major roadways. From the moment you arrive, the home impresses with its stacked stone façade, paver driveway, oversized 3-car garage, and professionally landscaped grounds featuring majestic oak trees, palms, agave, and decorative rock landscape beds. Inside, every detail has been thoughtfully designed. Updated flooring, beautifully renovated bathrooms, plantation shutters, and brand-new Reece impact-rated windows provide modern comfort, while artistic finishes add a distinctive character rarely found in residential homes. The welcoming foyer and formal living and dining spaces feature custom faux brick and textured wall finishes created by an artist who contributed to the Wizarding World attractions at Universal Orlando. The beautifully renovated kitchen is designed for everyday living and entertaining with dramatic black-and-white quartz countertops, a full-height matching backsplash, a stunning waterfall-edge island, abundant cabinetry, breakfast bar seating, and a sunny breakfast nook overlooking the spacious family room. The spacious primary suite offers a private retreat with a custom designer accent wall, dual walk-in closets, and a luxurious bath featuring dual vanities, a soaking tub, and a large frameless glass shower. Two secondary bedrooms share a convenient Jack-and-Jill bath, while the fourth bedroom and additional full bath provide flexibility for family, guests, or a home office. A standout feature is the private upstairs bonus room with its own full bath. Professionally soundproofed and currently used as a DJ studio, this versatile space can easily become a recording studio, podcast room, theater, gaming lounge, fitness space, office, or private guest suite. Enjoy Florida living year-round in the enclosed sunroom with insulated ceiling, creating a comfortable extension of the home's living space. Beyond awaits an incredible backyard retreat featuring a beautifully designed raised paver gathering space anchored by a grand wood-burning fireplace, creating the perfect outdoor setting for entertaining, relaxing, and enjoying evenings under the stars. Professional landscape lighting and mature privacy landscaping complete this special outdoor escape, with plenty of room to play, garden, or add a future pool. If you've been searching for a home that feels anything but ordinary, you've found it. With its creative design, thoughtful updates, versatile spaces, and unforgettable backyard, this is more than a home - it’s a place where memories are made.

15604 Granlund Street, Winter Garden

5 Beds ⋅ 7 Baths ⋅ Grove/Oakland SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless craftsmanship, thoughtful design, and elevated luxury living. Spanning 4,210 square feet of livable space (5,914 total sq ft) across a thoughtfully designed floor plan, The Wildflower offers 5 bedrooms, 5 full baths, and 2 half baths, providing ample room for families who prioritize space and style. From the moment you arrive, every detail speaks to the quality and care poured into this home. Inside, a versatile loft and flex room provides endless possibilities — a home office, media room, playroom, or private retreat. The open, flowing layout is designed for both everyday living and effortless entertaining. Step outside to your own private resort. A custom pool and spa take center stage in the backyard oasis, a covered rear lanai with roll down screens, a fireplace complemented by a summer kitchen and cabana — perfect for hosting under the Florida sun. Enjoy evenings at home with a built in fire pit and beautiful landscape lighting. A 3-car garage rounds out the thoughtful features that make this home as functional as it is beautiful. Located just minutes from downtown Winter Garden's vibrant dining and shopping scene, top-rated schools, and easy access to the Florida Turnpike, The Grove offers the rare combination of peaceful small-town living with big-city convenience. Estimated completion Spring 2027. Secure your lot today and experience the Justice & Wood difference — where every home is built with excellence, without cutting corners.

1155 Prado Lane, Oakland

5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve SubDv. ⋅ 34787 Zip Code

An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.

279 Zachary Wade Street, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to 15554 Panther Lake Dr, a beautifully maintained residence located in the highly desirable Winter Garden community of Lakeshore Preserve. This spacious two-story 4345 sq ft home offers 5 bedrooms and 4.5 bathrooms with a thoughtfully designed layout that combines comfort, functionality, and style. One of the home’s standout features is the presence of two primary suites; one conveniently located on the first floor and another upstairs, providing exceptional flexibility for multigenerational living, guests, or private retreats.This exceptional home is being offered fully furnished, providing a truly move-in-ready opportunity. The open-concept living spaces are filled with natural light and designed for both everyday living and entertaining. With the kitchen connecting seamlessly to the dining and great room areas, this charming layout is perfect for hosting friends and family. After dinner, step outside to your own private backyard retreat, where the pool, fountains, fire pit, and outdoor entertaining areas create the perfect setting to enjoy Florida living year-round. Adding to the home’s appeal, it is equipped with a radiant barrier designed to help improve energy efficiency and reduce cooling costs, a valuable feature for enhanced comfort and long-term savings in the Florida climate. The home also brandishes spacious secondary bedrooms, abundant storage, a 2-car garage, and a meticulously maintained interior that reflects true pride of ownership throughout. One of this home's greatest features is its unbeatable location for families. Panther Lake Elementary School, a highly rated A school, is just behind the home, while Horizon High School is directly across the street. It's a rare opportunity to enjoy the convenience of top-rated schools just steps from your front door. Ideally situated just minutes from shopping and dining at Hamlin Town Center, major highways, and Walt Disney World Resort, this home offers both convenience and an exceptional lifestyle. Residents of Lakeshore Preserve enjoy resort-style amenities including a community pool, clubhouse, fitness center, playground, and scenic access to Panther Lake. A rare opportunity to own a spacious pool home with a flexible floor plan in one of Winter Garden’s most sought-after communities.

15554 Panther Lake Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. EXPERIENCE ELEVATED LAKEFRONT LIVING IN THE HEART OF HORIZON WEST!!! Welcome to 15594 Shorebird Lane, an exceptional Toll Brothers lakefront residence located in the Lakeshore Preserve community of Winter Garden. Perfectly positioned on a premium oversized 0.34-acre homesite overlooking beautiful Panther Lake, this stunning 4-bedroom, 3.5-bath home offers over 3,000 square feet of thoughtfully designed living space, breathtaking water views, and nightly Disney fireworks from your own backyard. From the moment you enter the grand two-story foyer, you'll be captivated by the home's elegant design, abundant natural light, and seamless connection between indoor and outdoor living. The open-concept floor plan showcases a spacious great room, gourmet chef's kitchen with oversized island, and expansive windows framing panoramic lake views throughout the main living areas. The luxurious first-floor owner's retreat serves as a private sanctuary featuring tranquil water views, custom closet systems, and a spa-inspired bathroom. Upstairs, a spacious loft provides endless possibilities as a media room, game room, home office, or secondary living space. Step outside and discover one of the most impressive outdoor living spaces in the community. The enormous 1,250-square-foot screened lanai creates the perfect setting for entertaining, relaxing in the hot tub, enjoying the peaceful fountain, or gathering around the fire pit while watching spectacular sunsets and Disney fireworks illuminate the night sky. Designed with comfort and efficiency in mind, the home features Fully paid solar panel system for substantial energy savings, Tankless water heater, Advanced foam insulation, Plantation shutters throughout, Built-in pest control system, Upgraded irrigation system, and Custom storage and closet solutions. Move-in ready condition! This beautiful gem includes RESORT-STYLE AMENITIES, Residents of Lakeshore Preserve enjoy an unmatched lifestyle with access to Resort-style swimming pool, State-of-the-art fitness center, Yoga and wellness studio, Clubhouse and gathering spaces, Sand volleyball courts, Playground and dog park, Community canoes and lake access, and walking, and biking trails. One of the greatest advantages of this home is its unbeatable prime location in the highly desirable Horizon West area: Minutes to Walt Disney World Resort, Approximately 15 minutes to Winter Garden Village's premier shopping, dining, and entertainment, Convenient access to Flamingo Crossings Town Center, Close to Hamlin Town Center featuring restaurants, retail, movie theater, and waterfront events, Near Orange County National Golf Center and Lodge, one of Florida's premier golf destinations, Easy access to SR-429, Florida's Turnpike, and I-4, Approximately 30 minutes to Orlando International Airport, Close to Downtown Winter Garden, known for its award-winning farmers market, boutique shopping, breweries, and dining. Whether you're seeking a luxury primary residence, a relocation destination, or simply a home that delivers unforgettable lakefront sunsets and resort-style amenities every day, this extraordinary property offers a lifestyle few homes can match. Wake up to sparkling lake views. Spend your evenings watching Disney fireworks. Live where every day feels like a vacation. It won't last. Schedule your showing today!

15594 Shorebird Lane, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code

PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

205 Surprise Drive, Winter Garden

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

Seller Motivated , Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!

10067 Austrina Oak Loop, Winter Garden

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