Winter Garden/Oakland Homes with Custom Architectural style

Winter Garden/Oakland Homes with Custom Architectural style

Welcome to the enchanting communities of Winter Garden and Oakland, Florida, where charming landscapes meet modern living. Nestled just a stone's throw from the vibrant city of Orlando, this picturesque region is renowned for its lush greenery, scenic lakes, and a delightful blend of historic charm and contemporary flair.

Winter Garden, with its quaint downtown area, is a treasure trove of boutique shops, artisanal cafes, and lively farmers' markets that bring the community together. The West Orange Trail, a 22-mile stretch of paved paths, invites outdoor enthusiasts to explore the beauty of the area on foot or by bike, while the nearby Oakland Nature Preserve offers serene trails and stunning views of the natural surroundings.

One of the standout features of this region is the availability of homes boasting custom architectural styles. Whether you're looking for a modern farmhouse, a Mediterranean villa, or a classic Craftsman, Winter Garden and Oakland offer an impressive array of custom-built residences that reflect your unique taste and lifestyle. These homes are designed with meticulous attention to detail, featuring open floor plans, high ceilings, and luxurious finishes that create inviting spaces for both relaxation and entertainment.

In addition, the community is known for its excellent schools, friendly neighborhoods, and a strong sense of belonging, making it an ideal place for families and individuals alike. With its perfect blend of natural beauty, cultural richness, and architectural diversity, Winter Garden and Oakland are not just places to live; they are places to thrive. Discover your dream home in this vibrant region today!

Newest Winter Garden/Oakland Homes with Custom Architectural style

$878,000
4 Beds ⋅ 3 Baths ⋅ Teacup Spgs Cove SubDv. ⋅ 34787 Zip Code
Location, Lifestyle, and a Backyard Retreat unlike any other! Nestled in desirable North Winter Garden, this Custom-built 4 Bedroom 3 Bath Home with a Bonus Room offers a peaceful setting that feels like a vacation escape. The backyard oasis features a picturesque running creek flowing toward Lake Apopka, creating a truly serene outdoor experience~ Enjoy the view with morning coffee from the large back Screened-in Porch! Lovingly Maintained, this Home showcases high ceilings and warm wood flooring, a thoughtfully designed floor plan, Generously sized bedroom closets, and a stunning Primary Suite tucked among the trees~ The spacious Ensuite Bath includes a Garden tub and separate shower for a private retreat feel. Situated in an intimate cul-de-sac community of only 9 homes, this special property combines privacy with convenience. Enjoy close proximity to Newton Park on the shores of Lake Apopka and a quick golf cart ride to Downtown Winter Garden’s Plant Street, where you’ll find popular restaurants, shopping, the Garden Theatre, splash pad, award-winning Farmers Market, and Plant Street Market. A rare opportunity to enjoy natural beauty and the sought-after Winter Garden lifestyle—welcome home!

519 Teagarden Court, Winter Garden
$900,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Rare opportunity to own a unique corner-lot property featuring two attached residences, each with its own street frontage, private entrance, covered front porch, two-car garage, no HOA, and identical floor plan. Unlike a traditional side-by-side duplex, each residence faces a different street, creating the appearance and feel of two individual homes while offering the convenience of a connected design. Designed for both comfort and flexibility, each home features a spacious living and dining area, a bright kitchen with French doors leading to the backyard, and a convenient first-floor guest powder bath. Upstairs, all bedrooms are thoughtfully positioned for added privacy. The primary suite includes a private ensuite bath, while the secondary bedrooms are generously sized and complemented by abundant storage throughout each residence. The Wilson Street residence has been thoughtfully upgraded with luxury vinyl flooring, an enhanced kitchen with stone counters and gas cooking, beautifully updated bathrooms, and an attractive staircase that adds character and style. The Maple Street residence has been a consistently popular rental and has been exceptionally maintained, offering a spotless interior that reflects pride of ownership. The location offers exceptional convenience with nearby access to Downtown Winter Garden, one of Central Florida’s most sought-after destinations. Enjoy a vibrant mix of locally owned restaurants, cafés, boutiques, specialty shops, the award-winning Winter Garden Farmers Market, seasonal festivals, live entertainment, and the renowned West Orange Trail. The property also provides convenient access to the Florida State Road 429, Florida State Road 408, and Florida’s Turnpike, making travel throughout Central Florida simple. Popular destinations, including Winter Garden Village, Walt Disney World Resort, major employment centers, shopping, dining, entertainment, parks, and everyday conveniences, are all nearby. Whether you’re seeking a property that offers exceptional flexibility for evolving lifestyle needs, the opportunity to generate rental income, or the convenience of two complete residences under one roof, this distinctive property delivers a rare combination of privacy, functionality, and long-term versatility. Opportunities like this are seldom available, especially with a layout that allows each residence to maintain its own identity while remaining connected.

402 E Maple Street, 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
$372,500
4 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and modern living come together, and you keep more of what's yours with no HOA fees. Built in 2023, this beautifully designed 4-bedroom, 2-bath home with a 1-car garage offers the perfect blend of contemporary comfort and timeless neighborhood character. Start your mornings on the inviting front porch, the ideal spot for coffee, fresh air, and easy neighborhood conversations. Step inside to an open-concept layout that feels bright, spacious, and instantly welcoming, whether you're hosting friends or enjoying a quiet evening in. The modern kitchen impresses with granite countertops, sleek cabinetry, and a generous workspace that flows seamlessly into the main living areas. Laminate flooring throughout the main living spaces adds a clean, low-maintenance finish. Beyond your front door, downtown Winter Garden is just minutes away, a historic district one of Central Florida's most beloved. Spend your weekends at the popular Saturday Farmers Market, dining at local restaurants ranging from cozy cafés to fine-dining establishments, or soaking up the seasonal festivals and community events that give this area its unmistakable energy. Newer construction. Modern finishes. A welcoming, active community. And no HOA. This Winter Garden gem checks every box, so don't miss your chance to make it yours.

884 Klondike Street, Winter Garden
$539,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to the highly desirable Oakland Trails, where this 2019 Meritage Home combines modern style, energy efficiency, and a thoughtfully designed layout for everyday comfort. Ideally situated approximately 30 minutes from Walt Disney World, Universal Orlando, and Downtown Orlando, the home provides convenient access to Central Florida's most popular destinations while preserving the peaceful atmosphere of an established neighborhood. Designed with functionality and flexibility in mind, this residence offers 3 bedrooms, 2.5 bathrooms, a two-car garage, and over 3,200 square feet of total living space. The open floor plan connects the living area, dining space, and gourmet kitchen, creating an inviting setting for daily living and entertaining. A spacious first-floor flex room offers endless possibilities as a home office, media room, formal living room, playroom, fitness space, guest room, or potential fourth bedroom. The gourmet kitchen features KitchenAid stainless steel appliances, quartz countertops, a custom tiled island, abundant cabinetry, and generous workspace while overlooking the main living and dining areas. High ceilings and oversized interior doors enhance the bright, open feel throughout the home. Upstairs, the primary suite includes a custom walk-in closet system and an ensuite bathroom. Additional bedrooms are generously sized, with ample storage throughout. Built with Meritage Homes' renowned energy-efficient construction, the home includes spray foam insulation, an advanced HVAC system with fresh-air intake and enhanced air purification, a combination metal and shingle roof, and a full gutter system. Enjoy the private courtyard, perfect for relaxing or entertaining. Oakland Trails offers scenic walking and biking trails, a community pool, clubhouse, dog park, beautifully maintained common areas, and top-rated schools. Historic Downtown Winter Garden, with its restaurants, breweries, boutiques, farmers market, and year-round events, is just minutes away. The property is well suited for long-term rental investment. For buyers with pet-related allergies or sensitivities, it may be helpful to know that no pets have lived in the home during the current ownership. A detailed list of builder upgrades and owner improvements will be provided to prospective buyers. Quality construction, flexible living, and an exceptional location make this move-in-ready home an outstanding opportunity in one of Winter Garden's most sought-after communities.

2065 White Feather Loop, Oakland
$1,200,000
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
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