Winter Garden/Oakland Homes with Cottage Architectural style

Winter Garden/Oakland Homes with Cottage Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is a delightful blend of small-town charm and modern conveniences, making it an ideal place to call home. With its picturesque landscapes, lush parks, and a rich history that dates back to the citrus boom, Winter Garden offers a unique lifestyle that captures the essence of Florida living.

One of the standout features of this region is its stunning homes, particularly those designed in the charming cottage architectural style. These quaint residences exude warmth and character, often adorned with cozy porches, gabled roofs, and inviting gardens. The cottage style is perfect for those who appreciate the beauty of craftsmanship and the allure of a bygone era. Many of these homes are nestled in friendly neighborhoods, where community spirit thrives and neighbors become friends.

Living in Winter Garden and Oakland means enjoying a wealth of amenities, from the vibrant downtown area filled with boutique shops and delightful eateries to the scenic West Orange Trail, perfect for walking, biking, or simply soaking in the natural beauty. The area also hosts a variety of festivals and events throughout the year, fostering a strong sense of community.

With its blend of historical charm and modern-day conveniences, Winter Garden and Oakland are not just places to live; they are places to thrive. Discover your dream cottage home in this beautiful region and experience the magic of Florida living at its finest!

Newest Winter Garden/Oakland Homes with Cottage Architectural style

3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code

Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! This Farm-House townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Trenton Burlap cabinetry, a decorative tile backsplash, Lagoon quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, gathering room, bathrooms, and laundry room, is finished with elegant tile for both style and easy maintenance. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Orchid townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6258 Sunny Time Avenue, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code

Welcome to 217 W. Story Road, a beautifully located home in Downtown Winter Garden, Florida, offering the walkable, golf cart friendly lifestyle that has made Winter Garden real estate some of the most sought after in Central Florida. Situated just a few blocks from the iconic Plant Street Market, this home places you in the center of everything that makes historic Downtown Winter Garden one of the area's premier destinations. Enjoy convenient access to local restaurants, boutique shopping, coffee shops, breweries, and the award winning West Orange Trail. Spend your weekends at the popular Winter Garden Farmers Market, live entertainment events, and seasonal festivals, all just minutes from your front door. Located in the highly desirable golf cart district, residents can easily access Downtown Winter Garden's newest restaurants and exciting developments that continue to enhance the area's charm and long term appeal. With close proximity to Winter Garden Village, major highways, Walt Disney World, and all that Central Florida has to offer, this location combines small town character with modern convenience. Whether you're searching for a home near Plant Street Market, a property in the golf cart district, or a home in historic Downtown Winter Garden, 217 W. Story Road offers a rare opportunity to experience one of the most desirable lifestyles in Winter Garden, FL.

217 W Story Road, Winter Garden

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

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

Under Construction. 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

4 Beds ⋅ 2 Baths ⋅ Mt Park Orange Grove SubDv. ⋅ 34787 Zip Code

Welcome to 17134 Lake Ingram Rd, which offers LAKEFRONT living with NO HOA on Lake Ingram, The property is 1.16-acres and has 118 feet of waterfront. WALT DISNEY WORLD is approximately 15 minutes away, while Orlando College of Osteopathic Medicine is just minutes away. Opportunity awaits for the current home and pool to be updated to suit the buyer’s personal style and taste. Zoned A-1, the parcel may appeal to buyers seeking space for a custom home or long-term investment. Property sold as-is. Due diligence recommended regarding zoning and development options. Call today to see this unique property in the desirable area of Horizon West.

17134 Lake Ingram Road, Winter Garden

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