Winter Park Homes with Bungalow Architectural style

Welcome to Winter Park, Florida, a picturesque gem nestled in Orange County that beautifully blends small-town charm with modern sophistication. Known for its stunning parks, vibrant cultural scene, and historic architecture, Winter Park is a community that offers a unique lifestyle for residents and visitors alike. With its tree-lined streets, serene lakes, and a delightful array of boutiques and eateries, this enchanting city is a haven for those seeking both relaxation and excitement.

One of the standout features of Winter Park’s real estate landscape is its collection of charming bungalows. These homes, characterized by their cozy, inviting designs, often feature low-pitched roofs, wide front porches, and an abundance of natural light. Bungalow-style homes in Winter Park exude warmth and character, making them ideal for families, young professionals, and retirees alike. Many of these properties are nestled in quiet neighborhoods, just a short stroll from the city’s vibrant downtown area, where you can enjoy art galleries, fine dining, and the renowned Winter Park Farmers’ Market.

Living in a bungalow in Winter Park means embracing a lifestyle that celebrates both community and nature. With nearby parks such as Central Park and Mead Botanical Garden, outdoor enthusiasts will find plenty of opportunities for recreation and relaxation. Plus, the city’s commitment to the arts is evident in its numerous cultural events, including the annual Winter Park Sidewalk Art Festival.

Discover the charm of Winter Park and the allure of its beautiful bungalows—your dream home awaits in this idyllic Florida city!

Newest Winter Park Homes with Bungalow Architectural style

$549,900

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