Luxury homes for sale & real estate in Winter Park, FL

Luxury Home for sale in Winter Park, FL:

HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space. Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail—from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere. The chef-inspired kitchen

Luxury Home for sale in Winter Park, FL:

Welcome home to the Ravenstone by OLO Builders! This home has an open layout and natural light for days! The main family room has large windows and is connected to a spacious kitchen with an island and a huge pantry. The entry from the garage comes with a drop zone (mudroom), a half bath, and a laundry room. The primary suite is located on the main floor and has windows on all sides. The walk-in closet is spacious. Upstairs hosts another family room/loft area, four big bedrooms, laundry room, another full bathroom, and a storage closet. Choose from a Modern Prairie, Craftsman, Farmhouse, or Traditional exterior. As well as a front or side-facing garage. Call today to customize your new home

Luxury Home for sale in Winter Park, FL:

Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of upgrades completed in 2025. The home sits on a 1/3-acre lot with 5 bedrooms and 3 ½ baths plus an office and features a 4-way split plan with privacy for all. Upon entering, you're greeted by an open floor plan with marble foyer and white oak engineered wood flooring. The Owners' Retreat

Luxury Home for sale in Winter Park, FL:

Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Co