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$1,200,000
3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
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 shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef’s kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park’s sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.

106 S Interlachen Avenue Unit 118, Winter Park
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Perfectly positioned just one street from iconic Park Avenue, this exceptional Winter Park residence is a masterclass in refined luxury and bespoke design. With unobstructed views often lush landscape and lake views from coveted fourth-floor vantage point, this one-of-a-kind pied-'a-terre has been completely transformed by W DESIGNS LTD. into a sophisticated sanctuary with an old-world Ritz Carlton vibe. Every detail has been curated to the highest standard-from the dramatic CALCUTTA GOLD and Harlequin Marble Flooring to the rich Quartzite surfaces and fully customized solid wood cabinetry throughout. The kitchen and baths are adorned with SOLID BRASS hardware and fixtures, including a custom Phylrich faucet, while both bathrooms are enveloped entirely in Marble, creating a true spa-like experience. GOLD LEAF LIGHTING, Exquisite Millwork, Custom paneling, Crown Molding, Solid Wood Beams, Lacquered Doors, and a flawless LEVEL 5 Finish elevate this home to a level rarely seen. No expense has been spared. Set along the coveted Winter Park Chain of Lakes and just a block away from the boutiques and restaurants of exclusive Park Avenue, is this rare offering for the most discerning buyer seeking timeless elegance, location, and exclusivity. This type of real estate does not come on the market often.

100 S Interlachen Avenue Unit 404, Winter Park
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
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 two-bedroom, two-bath residence now reflects a highly customized living experience. Every surface, system and layout choice has been elevated, beginning with level 5 smooth drywall, Emtek polished nickel hardware, custom millwork, full-height solid-core doors and Panaget engineered hardwood flooring. Lutron lighting systems control dimmable LED lighting throughout. Bedrooms, as well as the family room, include prewiring for additional fixtures, and the primary suite features dedicated pendants over each nightstand, independently controlled bedside. The kitchen is anchored by a full suite of smart Thermador appliances, including an induction range, range hood and a full-height refrigerator with a convertible Flex drawer for additional refrigeration or freezer storage, an internal water dispenser, built-in compartment cameras and Thermador’s signature Diamond ice maker. Calacatta Laza quartz surfaces and full-height backsplash accentuate custom oak cabinetry featuring soft-close drawers, an integrated appliance station with interior outlets, and an oversized pantry for seamless storage. A breakfast bar opens to the dining and living areas, which comfortably accommodate full-size furnishings and create defined spaces for formal dining, casual living and media use. The primary suite offers two built-in closets and a spa-inspired bath with Fantasy Brown quartz countertops on a wall-to-wall vanity. A lighted medicine cabinet mirror with integrated speakers sits above the vanity, with interior power outlets for charging accessories. A fully tiled frameless shower features a lighted accent wall, overhead rain shower and wall-mounted handheld options. Additional built-in cabinetry provides deep storage for linens and supplies, as well as a dedicated laundry storage closet. The second bedroom functions as a guest suite, supported by a beautifully appointed bath in matching design. Additional highlights include custom-trimmed window casings throughout, ready for shades or shutters, and an entry closet that can double as storage or pantry overflow. The residence includes assigned covered parking and private storage. Residents of The Cloisters enjoy an amenity-rich lifestyle with on-site management, access to a heated pool, two fitness rooms with saunas, a clubhouse and manicured lakefront park space. This turnkey optional offering places you at the heart of Winter Park’s cultural, dining and retail corridor, where enduring architectural character meets elevated, modern living.

100 S Interlachen Avenue Unit 415, Winter Park
$840,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
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 community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

100 S Interlachen Avenue Unit 503, Winter Park
$750,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Experience refined Winter Park living in this stunning 2-bedroom, 2-bath pied-a-terre in the Cloisters condominium. Perfectly situated in the heart of town, this residence offers serene lake and pool views, a deeded parking space, and effortless access to the upscale boutiques and renowned dining of Park Avenue. Thoughtfully designed interiors feature luxe furnishings and accessories curated by SMRS Design, blending timeless elegance with modern comfort. Whether enjoying your morning coffee by the water or entertaining in style, this home captures the best of Winter Park’s coveted lifestyle.

100 S Interlachen Avenue Unit 203D, Winter Park
$535,000
2 Beds ⋅ 1 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience. Upon entering this residence, you are greeted with a bright and open living area accentuated by abundant wide-plank oak hardwood flooring and complete with features such as crown molding, a Nest thermostat, recessed lighting, and plantation shutters. The primary bedroom provides ample space and natural lighting, while the updated kitchen boasts modern finishes, including new quartz countertops & backsplash, stainless steel appliances, and an induction oven. The bathroom has been upgraded with Kohler fixtures and porcelain tile. For added convenience, the home includes an in-unit washer and dryer, as well as a balcony providing access to the scenic views and spacious grounds. The electrical panel box has been updated, along with new electrical outlets throughout. Residents can enjoy the community's numerous amenities, including a heated pool, hosting events in the renovated social room with a full kitchen, boat dock, and putting green, all set against the tranquil backdrop of Lake Osceola. The association dues include cable TV, building insurance, internet, maintenance (grounds, exterior, pool), on-site management, sewer, trash collection and water, providing a maintenance-free lifestyle. Additional highlights include an assigned covered parking space, storage room and a lakefront seating area. This sophisticated condominium creates a welcoming and refined atmosphere, making this an ideal residence. The location is conveniently located within walking distance to the vibrant Park Avenue, offering access to boutique shopping, dining, Rollins College and the renowned Morse Museum.

100 S Interlachen Avenue Unit 410F, Winter Park