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$4,750,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park
$4,900,000
5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible 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 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 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 en-suite 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.

140 E Morse Boulevard Unit J, Winter Park
$989,500
1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park
$1,295,000
4 Beds ⋅ 4 Baths ⋅ Hamilton Place SubDv. ⋅ 32789 Zip Code
Now offered out an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest – seller is actively moving. This remarkable home represents one of the best opportunities in today’s Winter Park luxury market, featuring exquisite finishes, modern design, and an unmatched lifestyle just moments from Park Avenue. Built in 2018, this custom-designed 4-bedroom, 3.5-bath residence offers 2,843 square feet of thoughtfully crafted living space, just a short walk from Park Avenue and the historic Winter Park Golf Course. Distinctive architectural details—including shiplap ceilings in the living room and kitchen, decorative ceiling treatments, and a dramatic tile staircase feature illuminated by natural light—create a home that is both elegant and inviting. At the heart of the home is a chef-inspired kitchen featuring Wolf and Sub-Zero appliances, custom cabinetry, Kohler fixtures, and an open-concept layout that flows effortlessly into the living and dining spaces, making it ideal for everyday living and entertaining alike. The primary suite serves as a peaceful retreat with a spa-inspired marble bathroom, while the upstairs bonus room offers flexible space for a media room, home office, or playroom. Outside, enjoy your own backyard oasis complete with a sparkling pool and spa combo—perfect for relaxing or hosting family and friends. Located just minutes from Park Avenue’s renowned restaurants, boutiques, and year-round events, this home delivers one of Central Florida’s most sought-after lifestyles. Schedule your private showing today.

802 Hamilton Place Court, Winter Park
$1,995,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

1398 Grove Terrace, Winter Park
$3,275,000
4 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code
This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

1581 Forest Avenue, Winter Park
$6,900,000
6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park
$8,950,000
7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park