Winter Park Homes with Bungalow Architectural style

Welcome to Winter Park, Florida, a picturesque gem nestled in Orange County that seamlessly blends small-town charm with vibrant city life. Known for its stunning tree-lined streets and a rich tapestry of cultural experiences, Winter Park is a haven for those seeking both relaxation and adventure. This delightful city boasts an array of parks, lakes, and scenic walking trails, making it the perfect backdrop for outdoor enthusiasts and families alike. With its historic downtown area filled with boutique shops, art galleries, and gourmet dining options, Winter Park offers an inviting atmosphere that encourages exploration and community connection.

One of the standout features of Winter Park is its enchanting collection of homes, particularly those showcasing the timeless Bungalow architectural style. Characterized by their cozy, inviting interiors and charming front porches, Bungalows are a testament to early 20th-century craftsmanship. These homes often feature open floor plans, built-in cabinetry, and warm wooden accents, creating a sense of comfort and nostalgia. The Bungalow style is not just a home; it’s a lifestyle that emphasizes simplicity and connection to nature, perfectly complementing Winter Park's serene environment.

Living in a Bungalow in Winter Park means being part of a vibrant community that values art, culture, and the great outdoors. With easy access to the scenic lakes, lush parks, and a calendar full of local events, residents enjoy a lifestyle rich in experiences. Whether you’re sipping coffee on your front porch or taking a leisurely stroll through the nearby gardens, Winter Park and its charming Bungalows offer a unique blend of comfort and community that truly feels like home.

Newest Winter Park Homes with Bungalow Architectural style

$299,000

2 Beds ⋅ 1 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Winter Park 32789 - Affordable single-family home across from beautiful Mead Botanical Gardens – or a great parcel to build your new abode. Lot size 60’ x 125’ (.17 acre) on sewer. Perhaps a rental investment property – Rollins College campus is less than 1 mile away. This charming and solid 2 bed, 1 bath block home with carport offers a NEW ROOF (2026) and fresh paint inside and out with original hardwood parquet floors. It even has double pane windows to help keep the heat out and the cool in (AC 2018). The front living room leads to the kitchen (freshly painted wood cabinets), which opens to a bright and sunny eating area (an additional 140 sq ft not accounted for in property records) with a handy inside laundry closet (washer/dryer included). The two bedrooms have ceiling fans and a shared hall bathroom (tub/shower combo) which completes the inside spaces. Out back you’ll find a covered patio and the spacious and grassy fenced-in backyard. This fantastic location in sought after 32789 is just a block away from the entrance to Winter Park’s 55-acre Mead Botanical Gardens, 2 blocks from the Winter Park Tennis Center, the new Seven Oaks Park, and a short bike ride to Foxtail Coffee, Rollins College, and famed Park Ave shops and restaurants (1 mile away). Come call this your new home, rental investment, or buildable parcel for your new construction abode.

1333 S Denning Drive, 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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