Winter Garden/Oakland Homes with 3 Car Garage Garage Description

Winter Garden/Oakland Homes with 3 Car Garage Garage Description

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a vibrant community that beautifully blends small-town charm with modern conveniences. Nestled just a short drive from the bustling city of Orlando, this area is renowned for its picturesque landscapes, rich history, and a warm sense of community. With its lush parks, scenic lakes, and a charming downtown filled with boutique shops and delightful eateries, Winter Garden and Oakland offer a lifestyle that is both relaxed and engaging.

One of the standout features of homes in this region is the availability of properties with three-car garages. These spacious garages provide ample room for your vehicles, tools, and recreational equipment, making them perfect for families or individuals who value both convenience and space. Imagine the ease of coming home to a dedicated area for your cars, storage solutions for your hobbies, or even a workshop for your creative pursuits.

The homes in Winter Garden and Oakland are designed for modern living, often featuring open floor plans, gourmet kitchens, and outdoor spaces perfect for entertaining. Living here means enjoying the best of both worlds—easy access to the vibrant attractions of Orlando while being able to retreat to a peaceful, family-friendly neighborhood at the end of the day.

Whether you’re a first-time homebuyer or looking to upgrade, consider the charm and practicality of homes with three-car garages in Winter Garden and Oakland. This is more than just a place to live; it’s a place to thrive. Discover your dream home in this delightful region today!

Newest Winter Garden/Oakland Homes with 3 Car Garage Garage Description

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

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

4 Beds ⋅ 4 Baths ⋅ Lake Apopka Sound SubDv. ⋅ 34787 Zip Code

Built in December 2023 and situated on one of the largest homesites in sought-after Lake Apopka Sound, this exceptional 4-bedroom, 3.5-bath single-story multi-generational home offers over half an acre (0.61 acres) with stunning views of Lake Apopka and a rare private attached in-law suite! Designed for true multi-generational living, the in-law suite features its own private entrance, living room, kitchenette, bedroom, full bathroom, and convenient access to the garage—perfect for extended family, guests, long-term flexibility, or private accommodations. Inside, you'll find soaring ceilings, an open-concept floor plan, elegant tray ceilings, granite countertops throughout, ceramic tile with professionally sealed grout, and an oversized laundry room offering exceptional storage and everyday convenience. The screened lanai overlooks the expansive fully fenced backyard with premium cream vinyl fencing, while additional upgrades include a whole-home water softener, smart security system with app-controlled sensors on every window and door, insulated garage, and a polyaspartic-coated garage floor for superior durability over traditional epoxy finishes. Located in the highly desirable Lake Apopka Sound community in Winter Garden, residents enjoy quick access to Downtown Winter Garden, Plant Street Market, award-winning restaurants, shopping, parks, the Florida Turnpike, SR-429, and Orlando International Airport, making commuting and travel exceptionally convenient. This is a rare opportunity to own a nearly new home with premium upgrades, an oversized homesite, breathtaking lake views, and one of the most versatile floor plans in the community.

17954 Hither Hills Circle, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code

Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Discover elevated living in this thoughtfully designed home at Northlake at Ovation, offering flexible spaces and curated finishes to fit your everyday lifestyle. From the inviting covered lanai to the spacious loft and soaring ceilings, this floor plan provides room to relax, work, and entertain with ease. Inside, you’ll find a balance of bold and neutral finishes from the AW Collection Rosemary. Design upgrades include 8' interior doors, quartz countertops, tiled backsplash, stainless steel appliances and more. Whether you’re hosting gatherings or enjoying quiet evenings at home, the open layout and versatile rooms adapt to your needs. Perfectly located in Winter Garden near some of Central Florida’s most beloved destinations, this home is just 35 minutes from Orlando International Airport, 15 minutes from world-famous Disney theme parks, and 30minutes from charming Celebration. Residents can also enjoy the charm and rich local history of nearby downtown Winter Garden, known for its vibrant shops, and eateries. Paired with great local schools and a peaceful community setting, this home delivers the ideal blend of comfort, convenience, and Central Florida living. Residents also enjoy a clubhouse, community pool, playground areas and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17625 Lake Star Road, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Highlands/Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

Timeless elegance meets modern luxury in this exceptional 5 bedroom, 4.5 bath estate in the sought after Highlands at Summerlake Grove community. From the moment you enter, soaring ceilings and an abundance of natural light set the tone for a home designed to impress. At the heart of the residence, a chef inspired kitchen showcases stunning granite countertops, an oversized island, stainless steel appliances including a built in double oven and gas cooktop, a space made for both effortless entertaining and everyday living. The open concept living areas flow seamlessly, framed by wide plank wood look flooring and walls of sliding glass doors that draw in serene views of the private backyard. A sophisticated, neutral palette throughout offers a polished canvas ready for any design aesthetic. With 5 spacious bedrooms and 4.5 beautifully appointed baths, this home offers room to grow, work, and unwind. Ideally located just minutes from Orange County National Golf Center, and within easy reach of The Mark, a walkable retail center just minutes away as well as easy reach of Winter Garden’s charming downtown, top-rated schools, and major highways for effortless commuting throughout Central Florida. This is refined Winter Garden living!

15778 Sweet Limetta Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, three full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior cool. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lake Apopka Sound Ph 1 SubDv. ⋅ 34787 Zip Code

Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, and calming bird watching right from the backyard. Highlights of this home from outside to inside are wide paver driveway with parking pad, spacious 3 car garage, covered front and rear porches, fully fenced in backyard, extended rear concrete patio, large flex room, mother in law suite with private entrance and kitchenette, and incredible kitchen to love at the center of an open floorplan. Floorplan: Triple split layout puts the primary suite, the secondary bedrooms, and the mother in law suite each in their own private area of the home. The mother in law suite has its own private exterior entrance, kitchenette, bedroom, and full bath. Large flex room for a home gym, office, studio, gaming room, or playroom. Kitchen: Cabinets to the ceiling, stone counters, beveled subway tile, farmhouse sink, island with seating for four, built-in wall oven and microwave, stainless vented hood, pot filler above the cooktop, spacious pantry, open to the living and dining space. Interior: Tray ceilings in the dining room, living room, and primary suite, wood slat accent wall, crown molding, upgraded lighting, ceiling fans, window treatments installed. Primary suite with walk in closet, corner tub, double sinks, and glass shower. Ceramic tile in main living areas, carpet in secondary bedrooms, inside laundry room. Exterior: Wide paver driveway with large paved parking pad, spacious three car garage, covered front porch, covered rear porch, extended full width concrete patio, fully fenced backyard with gates on both sides, sprinkler system throughout, tile roof. Recreation: Killarney Station trailhead five minutes out with bike rentals, repairs, and supplies center. West Orange Trail runs 20 plus miles into historic downtown Winter Garden. Lake Apopka Wildlife Drive and Lake Louisa State Park both an easy drive. Convenience: Downtown Wintergarden 25 minutes, Costco 8 minutes, Disney 25 minutes, Downtown Orlando 30 minutes, MCO Airport 35 minutes.

17854 Hither Hills Circle, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Covington Chase Ph 2b SubDv. ⋅ 34787 Zip Code

Virtually Staged. Beautiful five-bedroom, three-bath pool home located in the highly sought-after Golf Cart District of Downtown Winter Garden. Situated on a spacious, fully fenced corner lot, this home offers a versatile floor plan with room to live, work, and entertain. Upon entry, a flex room is located to the right and may be used as an office, playroom, sitting room, or study. A formal dining room is located to the left. The main living area features an open-concept kitchen, living room, and dinette area. A downstairs bedroom and full bath provide a convenient option for guests or multigenerational living. Upstairs, the primary suite includes two walk-in closets. Three additional bedrooms, a full bath, and the laundry room are also located upstairs. The large media room offers flexible use as a theater room, home office, game room, or bonus space. Enjoy the private outdoor area with a covered porch, fully fenced yard, and saltwater pool and spa. Upgrades include freshly painted interior and exterior, and new carpet installed on 7/23/26. The AC unit is one year old. The seller will pay off the solar system at closing, providing added energy-efficiency benefits for the next owner. Conveniently located near the West Orange Trail, Plant Street Market, local shopping, dining, parks, and Downtown Winter Garden. Golf cart is available for purchase separately and is not included in the sale of the home.

637 Grassy Stone Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Dedicated Study | Close to Amenities | Covered Lanai. New Construction - December Completion! Welcome to the Cresta at 17742 Sedona Street in Esplanade at McKinnon Groves! Welcome home to a thoughtfully designed floorplan that balances open-concept living with comfortable private spaces. The spacious great room serves as the heart of the home and flows seamlessly into the dining area and gourmet kitchen, complete with upgraded appliances, abundant cabinetry, and a large center island that is perfect for entertaining. Extended vinyl flooring runs throughout the main living areas, while elegant tray ceilings and 8' interior doors add the perfect touch. Just off the foyer, the study features beautiful French doors, creating an ideal space for a home office. The private primary suite is tucked away at the rear of the home and offers a spacious bedroom, luxurious bath, and generous walk-in closet. Two additional bedrooms, one with an en-suite, and an additional full bathroom provide comfortable accommodations for family or guests. Enjoy indoor-outdoor living with sliding glass doors leading to the covered lanai, perfect for relaxing or gathering with friends. Completing the home is a spacious three-car garage, dedicated laundry room, and a charming courtyard entry that enhances the home's curb appeal. Additional Highlights Include: 42" cabinetry in kitchen and laundry room, and whole house blinds. Photos are for representative purposes only. MLS#O6427570 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

17742 Sedona Street, Winter Garden

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