Winter Park Homes with Craftsman Architectural style

Winter Park Homes with Craftsman Architectural style

Welcome to Winter Park, Florida – a charming city nestled in the heart of Orange County, renowned for its picturesque landscapes, vibrant arts scene, and rich history. With its tree-lined avenues, stunning lakes, and a delightful mix of boutique shops and fine dining, Winter Park offers a unique blend of small-town charm and urban sophistication. The city is also home to the prestigious Rollins College, adding to its vibrant cultural tapestry.

One of the standout features of Winter Park is its stunning collection of Craftsman-style homes. These architectural gems are characterized by their intricate woodwork, wide porches, and low-pitched roofs, exuding a warm and inviting atmosphere. The Craftsman style emphasizes craftsmanship and natural materials, making each home a unique reflection of artistry and attention to detail. Many of these residences are nestled among the lush landscapes of Winter Park, providing a seamless connection between indoor living and the beautiful outdoors.

Owning a Craftsman home in Winter Park means embracing a lifestyle steeped in character and charm. Imagine sipping your morning coffee on a spacious front porch, surrounded by blooming gardens and the gentle rustle of oak trees. The community spirit here is palpable, with local events, farmers' markets, and art festivals bringing neighbors together. Whether you’re exploring the scenic shores of Lake Osceola or enjoying a leisurely stroll down Park Avenue, Winter Park offers a lifestyle that is both enriching and fulfilling.

If you’re seeking a home that embodies timeless elegance and a strong sense of community, Winter Park’s Craftsman-style homes are waiting to welcome you. Discover your dream home in this enchanting city today!

Newest Winter Park Homes with Craftsman Architectural style

$1,725,000
6 Beds ⋅ 6 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code
Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

2914 Reef Knot Place, Winter Park
$1,780,000
4 Beds ⋅ 4 Baths ⋅ Green Terrace V/140 Lot 3 Blk B SubDv. ⋅ 32789 Zip Code
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

1750 Carollee Lane, Winter Park
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