Winter Garden/Oakland Homes with Cottage Architectural style

Winter Garden/Oakland Homes with Cottage Architectural style

Welcome to Winter Garden and Oakland, two enchanting gems nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant community spirit, these charming towns offer a delightful blend of small-town charm and modern conveniences, making them an ideal place to call home.

Winter Garden, with its historic downtown area, boasts a variety of boutique shops, delightful cafes, and local eateries, all surrounded by the scenic beauty of lush parks and serene lakes. The West Orange Trail, a favorite among residents, winds through the area, inviting outdoor enthusiasts to explore its natural beauty on foot or by bike. Just a stone's throw away, Oakland enchants with its quaint streets, friendly atmosphere, and a close-knit community.

One of the standout features of homes in this region is the captivating Cottage architectural style. These charming residences often showcase inviting front porches, gabled roofs, and whimsical details that evoke a sense of warmth and nostalgia. Cottages in Winter Garden and Oakland are perfect for those seeking a cozy retreat, often featuring lush gardens and a unique character that reflects the area's rich history.

Whether you're drawn to the vibrant community events, the stunning landscapes, or the alluring charm of Cottage-style homes, Winter Garden and Oakland promise a lifestyle filled with warmth and connection. Explore the possibilities of making this idyllic region your new home, where every day feels like a charming escape.

Newest Winter Garden/Oakland Homes with Cottage Architectural style

$544,900
3 Beds ⋅ 2 Baths ⋅ Ellman Park SubDv. ⋅ 34787 Zip Code
Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

46 W Vining Street, Winter Garden
$845,000
5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. ALMOST COMPLETE AND READY FOR MOVE-IN! Discover the elegance and comfort of the Frost plan, a luxurious new home designed to meet all your needs. This stunning home features 5 bedrooms, 4.5 bathrooms, and a spacious layout that includes both a primary suite and a guest bedroom on the first floor, making it ideal for multi-generational living or hosting visitors. The Frost plan also boasts an oversized covered front patio, 8-foot front and first-floor interior doors, parcel entry and a covered backyard lanai for seamless indoor-outdoor living. The chef-inspired kitchen features a large eat-in island, stainless steel appliances including a cooktop, oven, microwave, vent hood and dishwasher, and an undermount sink with a Delta faucet. The kitchen is further enhanced with a ceramic tile backsplash to ceiling, upgraded 42-inch cabinets, abundant countertop space, and a huge walk-in pantry, offering both style and practicality for meal preparation and storage. The upgraded flooring and lighting package throughout the home complete the modern, elegant aesthetic. The luxurious primary suite is located on the first floor for ultimate convenience and privacy. The home is designed with energy-efficient construction and dual-pane energy-efficient windows, keeping your energy costs down while ensuring comfort throughout the year. Additional features of this new home include a full landscaping package, a full sprinkler system, a garage door opener, full gutters, covered back yard lanai, upgraded flooring throughout, and a new home warranty for added peace of mind. Call today to view!

17406 Honeybell Tangelo Court, Winter Garden
$625,000
4 Beds ⋅ 2 Baths ⋅ Mt Park Orange Grove SubDv. ⋅ 34787 Zip Code
LAKEFRONT • 1.16 ACRES • NO HOA • A-1 ZONING • HORIZON WEST / WINTER GARDEN • CUSTOM HOME OPPORTUNITY! Rare lakefront property with over 1 acre in the highly desirable Horizon West/Winter Garden area. An exceptional opportunity for a custom home buyer, luxury home builder, developer or investor looking for a large waterfront homesite with NO HOA. Bring your custom home builder and create the lakefront home you've been dreaming about. The property offers exciting potential for a new construction luxury home, including the possibility of a multi-story modern home with balconies and a rooftop terrace designed to capture lake views, Florida sunsets, stargazing and Disney fireworks views. Existing home is located on the property. Buyer and builder to independently verify zoning, setbacks, building requirements, rooftop terrace feasibility, lakefront restrictions and intended use with the appropriate governing authorities.

17134 Lake Ingram Road, Winter Garden
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