Winter Park Homes with Bungalow Architectural style

Welcome to Winter Park, Florida, a picturesque city nestled in the heart of Orange County. Known for its stunning tree-lined boulevards, vibrant arts scene, and charming historic districts, Winter Park offers an idyllic blend of small-town charm and modern amenities. With its proximity to the bustling city of Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping, all while relishing the tranquil lifestyle that Winter Park provides.

One of the most enchanting aspects of Winter Park is its diverse architectural landscape, particularly the delightful bungalow-style homes that dot the neighborhoods. These charming residences, characterized by their low-pitched roofs, wide front porches, and cozy interiors, exude warmth and character. Often adorned with intricate woodwork and inviting gardens, bungalow homes in Winter Park capture the essence of a bygone era while offering modern comforts for today’s homeowners.

Living in a bungalow in Winter Park means embracing a lifestyle that celebrates community and connection. The welcoming neighborhoods encourage strolls along the scenic streets, where neighbors become friends and local cafés beckon with the aroma of freshly brewed coffee. With parks, lakes, and cultural venues like the Charles Hosmer Morse Museum of American Art and the Winter Park Playhouse nearby, residents can enjoy a plethora of recreational and cultural activities.

Whether you’re a first-time homebuyer or looking to downsize, Winter Park’s charming bungalow homes provide the perfect backdrop for creating lasting memories. Discover the allure of this enchanting city and find your dream bungalow today in Winter Park, where every day feels like a vacation.

Newest Winter Park Homes with Bungalow Architectural style

$479,000

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

$449,000

3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and flexibility. The true standout is the detached 1-bedroom, 1-bath guest house, a rare feature that's ideal for visitors, a private home office, fitness studio, creative space, or even an income-producing opportunity. The main home features two spacious bedrooms and a beautifully renovated bathroom, while timeless charm is showcased throughout with original hardwood floors, crown molding, custom built-ins, and an open-concept living space. The thoughtfully designed kitchen combines butcher block and custom concrete countertops with quality appliances, while the adjacent laundry and utility room adds extra functionality. Step outside to a backyard designed for year-round Florida living. The covered patio, complete with café lighting and ceiling fans, overlooks a fully equipped outdoor kitchen with custom concrete countertops, creating the perfect setting for entertaining. Lush tropical landscaping, an outdoor shower, and abundant storage complete the private outdoor oasis. Beyond its charm, this home is packed with practical upgrades including a metal roof, whole-house natural gas generator, and an exterior security camera system, providing comfort and peace of mind through every season.

2007 Cornell Avenue, Winter Park

Start Your Search