Winter Garden/Oakland Homes with Three+ Story Property Description

Winter Garden/Oakland Homes with Three+ Story Property Description

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where the charm of small-town living meets the vibrant pulse of modern amenities. Nestled just a short drive from Orlando, this picturesque area boasts a rich history, scenic landscapes, and a tight-knit community atmosphere that makes it a coveted destination for families and professionals alike.

Winter Garden is renowned for its historic downtown district, brimming with delightful shops, eclectic eateries, and a lively farmers market that draws locals and visitors every Saturday. The area is adorned with beautiful parks and scenic trails, perfect for outdoor enthusiasts who enjoy biking, hiking, or simply soaking in Florida's sunshine. Oakland, with its serene lakes and lush greenery, adds to the region's appeal, offering a tranquil escape while still being conveniently close to urban conveniences.

For those seeking spacious living, Winter Garden and Oakland offer an impressive selection of homes with three or more stories. These stunning properties provide ample room for families to grow, entertain, and create lasting memories. With expansive floor plans, modern designs, and luxurious finishes, these homes are perfect for those who value both comfort and style. Many of these residences feature breathtaking views, private balconies, and outdoor spaces that invite you to unwind after a long day.

Whether you’re drawn to the vibrant community events, the beautiful natural surroundings, or the diverse housing options, Winter Garden and Oakland promise a lifestyle that is both fulfilling and enjoyable. Discover your dream home in this charming corner of Florida today!

Newest Winter Garden/Oakland Homes with Three+ Story Property Description

$675,000
4 Beds ⋅ 2 Baths ⋅ Covington Chase Ph 2b SubDv. ⋅ 34787 Zip Code
Virtually Staged. This is not your typical "fully upgraded" listing - this home has been thoughtfully and extensively renovated throughout. Featuring 4 bedrooms, 2 bathrooms, a dedicated office and an additional flex/formal space, it offers exceptional versatility for modern living. The completely remodeled kitchen showcases custom oversized upper cabinetry, upgraded finishes, as a wine/beverage fridge and a rare oversized walk-in pantry not found in the original Ryan Homes floor plan. Both bathrooms have been fully transformed into spa-inspired retreats with luxury bidet features and a full-body shower system, delivering a true at-home spa experience. Even the light switches have been updated, reflecting the level of detail throughout the home. The main living area includes a custom built-in entertainment center, creating a refined focal point ideal for entertaining or everyday relaxation. Step outside to an oversized, fully fenced back yard offering endless potential for a future pool, outdoor kitchen, firepit, garden or custom outdoor living space. Ideally located just minutes from historic Downtown Winter Garden and Plant Street, residents enjoy easy access to dining, shopping, breweries, farmers markets and community events. The West Orange Trail funs through the neighborhood providing direct access to walking, biking, and outdoor recreation. Convenient proximity to major highways ensures quick access to Orlando and surrounding Central Florida destinations. A truly move-in-ready Winter Garden home combining extensive upgrades, flexible living spaces and an unbeatable location, this is a home designed to be lived in, not just listed.

527 Copperdale Avenue, Winter Garden
$480,085
3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in December 2026! 3 Level Townhome with 3 Bedrooms! 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 1,846 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.

15213 Groveside Road, Winter Garden
$505,435
4 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 4 bedrooms, 3 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your 4th bed with ensuite bathroom. 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. Your inner gourmet will be 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.

15153 Groveside Road, Winter Garden
$494,890
3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in November 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, a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex space. 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. Your inner gourmet will be 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.

15159 Groveside Road, Winter Garden
$915,000
3 Beds ⋅ 4 Baths ⋅ Park Place At Winter Garden SubDv. ⋅ 34787 Zip Code
Experience luxury living in the heart of historic downtown Winter Garden! This beautifully designed corner-unit brownstone offers 3 bedrooms, 3.5 bathrooms, 2,242 square feet of thoughtfully crafted living space, and an unbeatable location just steps from everything that makes downtown so special. Situated right next to Plant Street Market and Crooked Can Brewing Company, you'll enjoy effortless access to the award-winning Saturday Farmers Market, local festivals, live entertainment, boutique shopping, and an incredible selection of restaurants and cafés, all just outside your front door. Step inside to discover a the first-floor layout featuring a private bedroom with its own en suite bathroom, creating the perfect retreat for overnight guests, extended family, or even a private home office. The second floor is the heart of the home, where an open-concept living, dining, and kitchen area creates an inviting atmosphere for both entertaining and everyday living. As a coveted corner unit, oversized windows fill the space with natural light, while crown molding adds an elegant finishing touch throughout. The gourmet kitchen is designed to impress, showcasing an oversized center island, stainless steel appliances, stylish finishes, generous counter space, and abundant cabinetry. A dedicated bar area nearby makes hosting gatherings even more effortless, while the adjoining living room features access to the covered balcony and large sliding doors, giving you the perfect place to enjoy fresh air or unwind after a day exploring downtown. Occupying the third floor, the spacious primary suite offers a peaceful escape with a large walk-in closet and a luxurious en suite bathroom complete with dual vanities and a stunning freestanding soaking tub. An additional upstairs bedroom provides generous closet space, abundant natural light, and comfortable accommodations for your loved ones. Additional highlights include a two-car garage and a location within Winter Garden's highly desirable golf cart district, making it easy to explore downtown's vibrant shops, restaurants, parks, and community events without ever needing your car. Convenient access to major highways places the rest of Central Florida within easy reach, while your everyday lifestyle is centered around one of the region's most sought-after downtown destinations. If you've been searching for luxurious low-maintenance living with unmatched walkability, this exceptional townhome is the opportunity you've been waiting for. Schedule your private showing TODAY!!!

484 W Plant Street, Winter Garden
$489,890
4 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in October 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 4 bedrooms, 3 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your 4th bed with ensuite bathroom. 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. Your inner gourmet will be 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.

15165 Groveside Road, Winter Garden
$491,080
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
$889,000
3 Beds ⋅ 4 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
Fully furnished, turnkey Urban retreat in Downtown Winter Garden — perfect for snowbirds, recent life-chapters, or anyone craving an active, walkable Florida lifestyle. This immaculate three-story townhome at Park Place offers 2,030 sq ft of stylish, move-in ready living with 3 beds, 3.5 baths and a custom elevator for easy access to every level. Why you’ll love it? Move-in ready: thoughtfully curated furnishings and decor — unpack, relax, entertain. Ideal for flexible living: private first-floor guest suite with full en-suite bath — perfect for in-laws, guests, or a live-work setup. Entertainer’s kitchen: chef-inspired with oversized island, breakfast bar, stainless appliances and gas range. Private primary level: spa bath with dual vanities, soaking tub and large walk-in shower. Comfortable modern features: natural gas, ceramic floors, plantation shutters, tankless water heater and rear-entry 2-car garage. Accessibility: custom elevator makes all three levels effortless. Location: You can live steps away from Winter Garden’s Plant Street scene — Plant Street Market, Crooked Can Brewing, Award winning Restaurants, Boutique shops, and the 22 mile long West Orange Trail. Enjoy year round festivals, dining, weekly farmers’ markets and nightlife within easy walking distance, plus quick access to major highways and all Orlando’s Theme Parks and attractions. Perfect fit for: Northern snowbirds seeking low-maintenance seasonal living, those starting fresh after a divorce who want an elegant, turnkey sanctuary, or anyone who values design-forward, walkable downtown life. Schedule a tour and see how effortlessly this home fits your next chapter.

129 S Park Avenue Unit 8E, Winter Garden
$424,900
3 Beds ⋅ 3 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained END-UNIT townhome featuring one of Lakeview Pointe's most versatile floor plans in one of Horizon West's most desirable communities. Offering nearly 1,900 square feet of thoughtfully designed living space, 3 bedrooms, 2.5 bathrooms, and a RARE THIRD-FLOOR BONUS ROOM, this move-in ready home delivers the flexible living space today's buyers are searching for. Whether you're working from home, creating a media room, fitness studio, playroom, or simply need extra space, this home adapts to your lifestyle. Recent improvements include REFRESHED INTERIOR PAINT (2026) and EXTERIOR PAINT (2024), making this home truly move-in ready. Built in 2016, the OPEN-CONCEPT floor plan is enhanced by ADDITIONAL WINDOWS EXCLUSIVE TO ITS END-UNIT LOCATION, filling the home with abundant natural light while creating a bright, open, and inviting atmosphere. From the moment you enter, you'll appreciate the stacked stone accents, extended tile flooring, and tasteful designer finishes that add warmth and character throughout. The beautifully appointed kitchen is the heart of the home, featuring GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, DESIGNER TILE BACKSPLASH, PANTRY, and a LARGE CENTER ISLAND overlooking the dining and family rooms—perfect for both everyday living and entertaining. The first floor area also includes a FULL LAUNDRY ROOM, WALK-IN STORAGE CLOSET, and convenient HALF BATH. Upstairs, the Owner's Suite offers a WALK-IN CLOSET and an en-suite bathroom featuring DUAL VANITIES, a WALK-IN SHOWER, and PRIVATE WATER CLOSET. Two additional bedrooms and a full bathroom are thoughtfully positioned on the opposite side of the home, providing privacy and flexibility for family or guests. The RARE THIRD-FLOOR BONUS ROOM is truly one of this home's standout features and sets it apart from many townhomes in Horizon West. Whether you envision a HOME OFFICE, MEDIA ROOM, PLAYROOM, FITNESS STUDIO, GAME ROOM, or hobby space, this versatile room provides valuable additional living space that adapts to your needs. Step outside to your PRIVATE PAVER COURTYARD, perfect for grilling, relaxing, or entertaining friends and family. A COVERED BREEZEWAY provides sheltered access to the DETACHED TWO-CAR GARAGE, while the welcoming front porch offers the perfect place to enjoy your morning coffee. In the evening, stroll to the community dock on Lake Huckleberry to enjoy breathtaking sunsets and Disney's nightly FIREWORKS.. Lakeview Pointe residents enjoy resort-style including a community pool, fitness center, splash pad, playground, lakefront dock, fireworks viewing area, and lawn maintenance, creating an exceptional low-maintenance lifestyle. Ideally located near the NEW RETAIL & DINING PLAZA and just minutes from Hamlin Town Center, Orange County National Golf Center, Publix, Starbucks, shopping, dining, entertainment, Walt Disney World, Highway 429, and top-rated schools, this home offers exceptional convenience in one of Central Florida's fastest-growing communities. If you've been searching for a bright END-UNIT townhome with a RARE THIRD-FLOOR BONUS ROOM, nearly 1,900 square feet of flexible living space, abundant natural light, and exceptional community amenities, this is the one you've been waiting for. Schedule your private showing today!

7279 Duxbury Lane, Winter Garden
$699,500
4 Beds ⋅ 3 Baths ⋅ Citrus Cove Unit 01 SubDv. ⋅ 34787 Zip Code
Welcome to a rare opportunity in sought-after Winter Garden! This spacious multi-level residence offers 4 bedrooms, 3 bathrooms, a private in-law suite with separate entrance and kitchenette, and an entertainer’s dream backyard with pool, cabana, outdoor kitchen, and oversized driveway. Situated on a generous .35-acre lot with no HOA, this home offers flexibility for multigenerational living, rental potential, boat parking, or work-from-home lifestyle. Impact windows and doors add long-term value and peace of mind. Conveniently located near shopping, dining, major highways, and lake access. A unique Florida lifestyle property you won’t find often.

13332 Suburban Terrace, Winter Garden
$850,000
3 Beds ⋅ 4 Baths ⋅ Park Place At Winter Garden SubDv. ⋅ 34787 Zip Code
DOWNTOWN WINTER GARDEN LIVING-CORNER END UNIT JUST STEPS FROM PLANT STREET! Leave the car in the garage and walk to dinner, the Saturday Farmer's Market, Crooked Can, live music, community events and the West Orange Trail. This beautifully updated 2432 square foot townhome offers the rare combination of a true Downtown Winter Garden lifestyle, generous living space, three ensuite bedrooms and a two car garage. Inside, the home feels practically new, with fresh paint throughout and an exceptionally well-maintained interior that shows beautifully. The END-UNIT DESIGN brings in additional natural light and provides a more open, private feel than an interior townhome. Wood-look tile flooring, crisp white trim, crown molding, recessed lighting, modern door hardware, decorative wall trim, and a cohesive neutral palette create a bright, polished, move-in-ready interior. The open main living level is designed for everyday comfort and entertaining, with the kitchen, dining, and living areas flowing together in one spacious, connected layout. The kitchen features light cabinetry, stone countertops, subway tile backsplash, stainless steel appliances, a NATURAL GAS RANGE, vent hood, pendant lighting, and an oversized island with seating. The adjoining dining and living areas offer generous space, excellent natural light, balcony access, and plenty of room to gather without feeling crowded. The flexible three-level floor plan includes THREE ENSUITE BEDROOMS, giving every bedroom its own private bath and providing exceptional privacy for family and guests. The first-floor ensuite bedroom creates a private retreat for overnight visitors, extended family, work-from-home needs, hobbies, or multigenerational living. Upstairs, the spacious primary suite features a beautifully updated bath with dual vanities, new flooring, and a BRAND-NEW STEAM SHOWER with floor-to-ceiling tile, built-in bench, recessed niche, decorative tile accent, and a spa-inspired design. A third ensuite bedroom, upstairs laundry, generous closets, built-in storage, and additional storage throughout make the home as practical as it is attractive. An ELEVATOR-READY LAYOUT adds long-term flexibility and future convenience. Additional highlights include NATURAL GAS SERVICE, a tankless water heater, updated fixtures, balcony, landscaped courtyard setting, and a TWO-CAR GARAGE with valuable parking and storage in a location where both are especially desirable. Compared with many current Downtown Winter Garden townhome options, this home offers a compelling combination of END-UNIT POSITIONING, generous square footage, updated condition, three private bedroom suites, and a lower price than several smaller competing properties. Schedule your private showing today.

461 Geranium Park Way, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Invest where others vacation. This beautifully furnished 2-bedroom, 2-bathroom condo at The Grove Resort & Water Park Orlando offers the perfect blend of personal enjoyment and income potential. The property participates in the resort’s professionally managed income program, allowing for a seamless, hands-off experience. Enjoy exclusive access to the water park and a prime location just minutes from Disney. Generate revenue while having your own vacation retreat—ideal as both an investment property and for personal use.

14501 Grove Resort Ave Unit 2413, Winter Garden
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