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 arts scene, and stunning lakes. Just a stone’s throw from the bustling city of Orlando, Winter Park offers a delightful blend of small-town charm and modern conveniences. With its historic architecture, lush parks, and a plethora of boutiques and cafes, this city is an idyllic place to call home.

One of the standout features of Winter Park's real estate market is its collection of beautiful bungalows. These homes, often characterized by their low-pitched roofs, wide porches, and open floor plans, exude a cozy and inviting atmosphere. The bungalow architectural style, which gained popularity in the early 20th century, is perfect for those seeking a blend of comfort and character. Many of these charming homes are nestled within mature neighborhoods, allowing residents to enjoy the tranquility of tree-shaded streets while being just minutes away from the vibrant downtown area.

Living in a bungalow in Winter Park means embracing a lifestyle that celebrates community and connection. Whether it’s sipping coffee on your porch, hosting gatherings in your spacious backyard, or enjoying the scenic beauty of nearby parks, these homes offer a unique opportunity to experience Florida living at its finest. With a strong sense of community, access to top-rated schools, and a rich tapestry of cultural events, Winter Park is not just a place to live; it’s a place to thrive. Come discover the warmth and charm of bungalow living in this enchanting city!

Newest Winter Park Homes with Bungalow Architectural style

$549,900

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

This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment. 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

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