Winter Park Homes with Cottage 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. Known for its rich history and small-town feel, Winter Park offers an idyllic lifestyle that perfectly blends urban convenience with natural beauty. With its delightful boutiques, award-winning restaurants, and lush parks, it’s no wonder that this enchanting city is a sought-after destination for families, retirees, and everyone in between.

One of the standout features of Winter Park is its unique architectural landscape, particularly the delightful homes that showcase the Cottage architectural style. These charming residences, often adorned with whimsical details and cozy interiors, exude warmth and character. With their inviting porches, gabled roofs, and meticulously landscaped gardens, Cottage-style homes create a sense of nostalgia and comfort that resonates with residents and visitors alike.

In Winter Park, you’ll find a variety of Cottage homes that cater to different tastes and preferences, from quaint bungalows to more expansive dwellings. Many of these homes are located within walking distance to the city’s vibrant downtown area, offering easy access to shopping, dining, and cultural experiences. Additionally, the proximity to beautiful lakes and parks makes it an ideal setting for outdoor enthusiasts and families seeking a peaceful retreat.

Discover the charm of Winter Park and experience the allure of Cottage-style living. Whether you’re looking for your first home or a serene getaway, this enchanting city promises a lifestyle filled with beauty, community, and endless opportunities for exploration. Welcome home!

$799,000

4 Beds ⋅ 3 Baths ⋅ Fairbanks Park SubDv. ⋅ 32789 Zip Code

Rare Winter Park Opportunity | City-Approved 4,338 SF Buildable Area | R-2 Zoning | Detached Guest House Just a very short walk to Park Avenue, with restaurants, cafés, wine bars and boutiques within steps in virtually every direction, 950 S. Kentucky Avenue offers an exceptional combination of location, land, flexibility and future potential. Set on a 7,875-square-foot R-2 lot overlooking little Lake Midget and Park, the property allows for 4,338 square feet of buildable area, as approved by the City of Winter Park. The existing property is a charming mid-century residence on a brick-paved, tree-lined street. The block is distinguished by a mix of mature homes and beautiful new custom residences, including several striking modern homes that complement the neighborhood’s established character. The existing 2,155-square-foot home offers four bedrooms and three baths, including a detached one-bedroom, one-bath guest house with cabinetry already in place to complete a kitchenette. The detached guest house adds an unusual degree of versatility, whether used for guests, extended family, a private office or potential rental income. The current home can be enjoyed with some updating and improvements, allowing a new owner to take the time needed to create their ultimate vision. It features hardwood floors and distinctive historic crown molding salvaged from a Winter Park renovation. The kitchen overlooks the backyard and features a granite island and newer stainless appliances. A side entry from the tandem two-car carport leads into a practical mudroom with a tucked-away laundry closet. The spacious yard offers room for gardens, recreation, outdoor living and potentially a future pool. Recent improvements include a new roof in 2024, updated A/C in 2018, newer appliances and a transferable termite bond. Natural gas is available on-site. The location is truly special. Park Avenue and Central Park are a quick stroll away, while favorites including Croissant Gourmet, Ravenous Pig, Sushi Saint, Fiddler’s Green and Winter Park Playhouse are all within an easy walk. Rollins College, the Saturday Farmers Market, Hannibal Square and the many shops and restaurants of downtown Winter Park are also nearby. Families will also appreciate access to highly regarded Winter Park schools, including Audubon Park School (K–8) and Winter Park High School. Whether you choose to update and enjoy the existing home, use the guest house for additional flexibility or income, or ultimately create a new custom residence, 950 S. Kentucky Avenue offers a wonderful opportunity to live in the heart of Winter Park.

950 S Kentucky Avenue, Winter Park

Winter Park Homes with Cottage Architectural style

Newest Winter Park Homes with Cottage Architectural style