Winter Park Homes with Bungalow Architectural style

Winter Park Homes with Bungalow Architectural style

Welcome to Winter Park, Florida – a picturesque city nestled in the heart of Orange County, renowned for its charming tree-lined streets, vibrant cultural scene, and stunning lakes. Just a stone's throw from downtown Orlando, Winter Park offers a perfect blend of small-town charm and modern conveniences, making it an ideal place to call home.

One of the most alluring features of Winter Park is its diverse array of architectural styles, particularly the enchanting bungalows that dot the neighborhood. These homes, often characterized by their cozy, one-story layouts, wide porches, and inviting front yards, exude warmth and character. Bungalow-style homes in Winter Park are not just residences; they are a testament to the city's rich history and commitment to preserving its unique architectural heritage.

Imagine waking up in a charming bungalow, where the morning sun filters through the trees, casting playful shadows on your front porch. These homes often feature original hardwood floors, built-in cabinetry, and vintage details that create a sense of nostalgia and charm. Many bungalows also boast spacious gardens, perfect for outdoor gatherings or quiet evenings spent under the stars.

Living in Winter Park means enjoying a vibrant lifestyle, with an array of boutique shops, art galleries, and gourmet restaurants just around the corner. The city is also home to beautiful parks and scenic lakes, providing endless opportunities for outdoor recreation. Whether you’re strolling through the enchanting Park Avenue or exploring the lush landscapes of Mead Botanical Garden, Winter Park is a place where community and beauty thrive. Discover your dream bungalow in this idyllic city today!

Newest Winter Park Homes with Bungalow Architectural style

4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code

Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.

2215 Woodcrest Drive, Winter Park

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

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