Drew Henner

Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique

Welcome to Villa Valencia, a gated community offering convenience, comfort and top-tier amenities. This charming ground-floor two-bedroom, two-bath condominium offers 962 square feet of well-designed living space with an open floor plan ideal for entertaining or relaxing. The spacious living room flows into a functional kitchen, complete with modern appliances. Both primary suites feature walk-in

Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental

Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this

Located near Orlando’s vibrant Packing District and the historic College Park neighborhood, this updated residence blends modern design with enduring appeal. A screened-in front porch provides a peaceful space for morning coffee or evening relaxation. Inside, the open-concept great room features rich hardwood flooring and abundant natural light, offering a versatile setting for both entertaining

Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the

A rare offering on the shores of Lake Virginia, this prime lakefront parcel presents a distinguished opportunity within Winter Park’s most coveted waterfront corridor. Encompassing a significant Lake Virginia homesite on the Winter Park Chain of Lakes, the site currently includes a 1926 structure that may be preserved, redesigned or removed to accommodate a custom waterfront residence. Positioned

Under contract-accepting backup offers. Located on the second floor of Villa Siena, this two-bedroom, two-bath residence offers 1,511 square feet of elegantly appointed living space with two balconies overlooking New England Avenue’s tree-lined brick streets in the heart of Winter Park. A split-bedroom layout ensures privacy, with wood flooring and tray ceilings defining the open-concept living

Under contract-accepting backup offers. A unique opportunity in unincorporated Orange County, these three contiguous residential lots, each approximately 0.15 acres, totaling 0.45 acres or 20,244 square feet, are offered together as a prime redevelopment site. Zoned R-2, this assemblage is positioned adjacent to some of Winter Park’s most vibrant retail and restaurant corridors, including