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Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's most exclusive addresses. Situated directly along the coveted brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication, and walkable convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park, and the year-round events that have made Winter Park one of Central Florida's most sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for both comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower, and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private ensuite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security, and an unmatched Park Avenue lifestyle in the heart of Winter Park.
| DAYS ON MARKET | 1 | LAST UPDATED | 6/17/2026 |
|---|---|---|---|
| TRACT | LANDMARK WINTER PARK CONDO | YEAR BUILT | 2008 |
| COMMUNITY | 32789 - Winter Park | GARAGE SPACES | 2.0 |
| COUNTY | Orange | STATUS | Active |
| PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Audubon Park K8 |
|---|---|
| Jr. High School | Audubon Park K-8 |
| High School | Winter Park High |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Gas, Maintenance Grounds, Maintenance Structure, Trash, Water |
| APPLIANCES | Bar Fridge, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Refrigerator |
| AREA | 32789 - Winter Park |
| CONSTRUCTION | Block, Stucco |
| EXTERIOR | Balcony, Courtyard, Lighting |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central |
| INTERIOR | Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, Elevator, High Ceilings, Stone Counters, Walk-In Closet(s) |
| PARKING | Assigned, Deeded, Basement, Attached |
| SEWER | Public Sewer |
| STORIES | 1 |
| SUBDIVISION | LANDMARK WINTER PARK CONDO |
| TAXES | 18654.81 |
| UTILITIES | Natural Gas Available, Natural Gas Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | City |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Mick Night, PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 6/18/26 2:24 AM PDT.
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