Winter Garden/Oakland Homes with Other Architectural style

Winter Garden/Oakland Homes with Other Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant community is a delightful blend of small-town charm and modern convenience, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle without sacrificing access to urban amenities.

Winter Garden, known for its picturesque downtown area, boasts a rich history that dates back to the early 1900s. Stroll along Plant Street and discover an array of charming boutiques, delightful cafes, and local eateries that reflect the town's warm, welcoming spirit. The vibrant farmers’ market held every Saturday is a must-visit, offering fresh produce, artisanal goods, and a chance to mingle with friendly locals.

Just a stone's throw away lies Oakland, a quaint town that exudes a peaceful vibe with its historic homes and lush landscapes. The scenic West Orange Trail, perfect for biking, walking, or jogging, runs through both Winter Garden and Oakland, providing residents with a beautiful outdoor space to enjoy nature.

When it comes to housing, the region offers a diverse array of architectural styles, from classic Craftsman bungalows to contemporary masterpieces. Whether you’re looking for a cozy cottage or a spacious family home, Winter Garden and Oakland present an impressive selection of properties that cater to various tastes and budgets. With their unique charm and character, these homes are not just places to live; they are spaces where memories are made.

Experience the best of Florida living in Winter Garden and Oakland, where community spirit meets architectural diversity in a stunning natural setting. Your dream home awaits!

Newest Winter Garden/Oakland Homes with Other Architectural style

$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
$880,000
5 Beds ⋅ 4 Baths ⋅ Lake Forest Sec 10a SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed 5-bedroom, 4-bath home located in a gated Winter Garden community, offering an exceptional blend of elegant finishes, functional living spaces, and resort-style outdoor living. With soaring ceilings and an inviting open entry, this home is filled with architectural details including crown molding, coffered and tray ceilings that add character throughout. Designed for both everyday living and entertaining, the thoughtfully crafted floor plan offers formal living and dining areas while maintaining an open flow between the kitchen and family room. Tile flooring extends through the main living areas and luxury vinyl in the primary suite and entire upstairs, providing both style and durability. The spacious kitchen serves as the heart of the home with granite countertops, abundant cabinetry, generous counter space, bar seating, a separate dinette, and seamless views into the family room. Expansive pocket sliding glass doors create a true indoor-outdoor living experience, opening the family room to the covered lanai and pool area—perfect for entertaining family and friends. The first-floor primary suite is a private retreat featuring abundant natural light, direct access to the lanai, dual walk-in closets, separate vanities, a walk-in shower, and a relaxing soaking tub. A dedicated office with built-in shelving and closet space provides an ideal work-from-home setup. Two additional bedrooms and bathrooms are also located downstairs, including a private en-suite with direct access to the pool. Upstairs offers exceptional flexibility with a spacious loft that can serve as a second living area, game room, or playroom, along with a fourth bedroom and full bath. A fifth bedroom is currently configured as a media room with surround sound and projector hookups, making it ready for movie nights or easily converted back to a bedroom. Step outside to your own backyard retreat featuring a sparkling pool with a natural rock waterfall, a unique swim-up table, and a spacious covered lanai. The fully fenced backyard provides both privacy and room to relax, play, or entertain. Additional highlights include a three-car garage and an ideal location just minutes from Winter Garden Village, offering shopping, grocery stores, restaurants, and healthcare. With convenient access to SR-429 and Historic Downtown Winter Garden, this home combines the comfort of a gated community with easy access to everything Central Florida has to offer.

13624 Larsen Lane, 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
$775,000
5 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Luxury New Home by RockWell Homes near Walt Disney World theme parks. The Faulkner Plan on Homesite #267. Experience the ultimate in modern luxury with this stunning new home minutes to Walt Disney World theme parks. Spacious 5 bedroom, 4-bathroom design offers the perfect combination of style, functionality, and comfort. The home features a 3-car garage, a covered front porch and a covered backyard lanai, ideal for outdoor relaxation or entertaining. The heart of the home is the chef-inspired kitchen, which includes solid surface countertops, an island, and high-end stainless steel gas appliances, such as a cooktop, oven, microwave, and dishwasher. The kitchen also features an undermount sink with a Delta faucet, a beautiful ceramic tile backsplash, upgraded 42-inch cabinets, Delta faucet and a huge walk-in pantry, providing ample storage and making it a dream space for any home chef. The spacious living area is designed with upgraded flooring and enhanced with natural light flowing in through dual-pane energy-efficient windows. These windows offer access to the covered backyard patio, seamlessly blending indoor and outdoor living spaces. The private primary suite is a true retreat, featuring dual sink vanities with Delta faucets, ceramic tile flooring, and a luxurious oversized shower with a glass enclosure. Additional features include a lighting package, towel bars, and a huge walk-in closet, offering plenty of storage and comfort. The secondary bedrooms are generously sized, each with its own walk-in closet and access to separate bathrooms. These bathrooms include ceramic tile flooring, ceramic tile tub/shower surrounds, Delta faucets, lighting packages, and towel bars, ensuring both style and functionality. Additional features of this exceptional new home include a full sprinkler system, a complete landscaping package, energy-efficient construction, a garage door opener, and a utility area with ceramic tile flooring. The home also boasts an 8-foot front door, a private backyard for added privacy, and a new home warranty for peace of mind. Northlake at Ovation is equipped with a clubhouse, community pool, kids' playground, dog park and walking trails. This luxury new home by RockWell Homes offers a perfect combination of upscale living, energy efficiency, and a beautifully designed layout. It’s ideal for those looking for both style and comfort in their next home.

17422 Honeybell Tangelo Court, Winter Garden
$700,669
3 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Park. New Construction – August Completion! Welcome to the Marino at 11235 Carding Mill Lane in Esplanade at McKinnon Groves! The great room flows into the dining and a gourmet kitchen featuring a large island and a walk-in pantry. The private primary suite provides a spacious bath and walk-in closet, direct access to the laundry room. Two secondary bedrooms, one with an en-suite bath, an additional full bath, and a dedicated study create flexible space. Enjoy Florida living with a covered lanai, a courtyard, and 2-car garage. Additional Highlights Include: tray ceiling pkg, 10' ceilings, pavers at lanai, 8' interior doors, pre-plumb water softener loop, and extended tile flooring to primary suite. Photos are for representative purposes only. MLS#O6407112 - Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11235 Carding Mill Lane, Winter Garden
$265,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
High-Occupancy Investment Opportunity at The Grove Resort & Water Park Orlando Welcome to a standout turnkey investment at The Grove Resort & Water Park Orlando—fully furnished and located on the prime first floor with Tall Ceilings and stunning fountain views. This spacious floor plan features 2 bedrooms, 2 full bathrooms, and 1,265 sq. ft. of beautifully upgraded living space. The primary suite offers a comfortable king-size bed, while the guest bedroom includes two full-size beds—ideal for families or group vacations. High-end interior finishes include luxury vinyl plank flooring, granite countertops, stainless steel appliances, large smart TVs in every room, a premium washer and dryer, and a private screened-in patio. The oversized bathrooms are equipped with a walk-in shower, soaking tub, and generous closet space for added convenience. Set across 106 acres of lush Florida landscape, Guests can enjoy Surfari Water Park with a dual FlowRider surf simulator, lazy river, and thrilling water slides; multiple heated pools with private cabanas; a full-service spa; a state-of-the-art fitness center; and Flip Flop’s arcade. Kids will love the splash zones, while outdoor enthusiasts can explore 20-acre Lake Austin with paddle boats, a fishing pier, and nature tours. On-site dining options include Valencia Restaurant, Springs Bar & Grill, Longboard Bar & Grill, Alfresco Market, and even an in-house pizza spot. Daily complimentary shuttle service to Walt Disney World®, Universal Orlando, and SeaWorld makes this an attractive destination for travelers. The resort also hosts a variety of family-friendly activities like karaoke nights, scavenger hunts, and fishing tournaments—ensuring every visit is packed with memorable moments. Owners benefit from a professionally managed rental program, allowing you to earn passive income while enjoying up to 179 days of personal use annually. Best of all, the monthly condo fee includes all utilities—electricity, water, cable, and internet—making ownership completely hassle-free. Whether you're looking for a luxury vacation retreat, a top-performing rental, or both, this opportunity checks all the boxes. (The current owner also has a second unit available for buyers interested in multiple properties) Schedule your private showing today and secure your slice of Central Florida paradise.

14501 Grove Resort Avenue Unit 2103, Winter Garden
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