Homes for Sale in Winter Park

Casa del Mondo, known as House of the World on Park Avenue in Winter Park, is a gated estate situated on Winter Park Chain of Lakes in the the most exclusive location in Twelve Oaks on a private road. Built in 2003, this gated estate enjoys approximately 16,608 square feet of total living space which seamlessly spreads across 4.08 in total acreage enjoying an abundance of privacy. Spectacular views from the lakeshore of Lake Maitland and the Winter Park Chain of Lakes. The original owners Edyth and Archibald Bush, executive vice-president of 3M (Minnesota Mining and Manufacturing) Company, fell in love with the area at first glance and owned the entire peninsula at one time. Originally designed with architectural features from around the world with amenities and features in the house that are unlike anything seen before. The birdcage elevator is a duplication of the one built by Otis Elevator Company and installed in 1896 at the Biltmore Estate in Asheville, North Carolina. The award-winning media room was featured on ABC’s Good Morning America. The award-winning kitchen was designed with your private chef in mind; a professionally equipped with commercial appliances, imported Japanese wood for custom cabinetry and seamless views to waterfalls and koi ponds. The outside of the two-story, 7-bedroom home looks like a Mediterranean villa set in a Hawaiian rain forest on the shores of a Tahitian lagoon. Behind the wrought-iron gates reveal a stone-paved driveway meandering through a landscape lush with palms, bamboo and multiple live oak trees. The back lawn was created with four waterfalls; one is a two-story waterfall from the master bath, designed and installed by artisans from Disney. The boathouse includes docking for a boat and two jet skis. Separating the house and cabana is a stone bridge over the tiered koi pond. The heated pool hosts a series of water fountains with LED lighting for the lap pool lanes and jacuzzi. Adjacent is an air-conditioned open cabana with an outdoor kitchen and wood-burning pizza oven. The summer grille is surrounded by hand-painted tiles by Cuban artist Jose Fuster that the owners hand-carried out of Havana. The estate includes a guesthouse that is fully equipped with a separate entrance from the gated service drive and integrated into the home. The back of the house service driveway features additional motor court parking service providers. The front of the house includes a dedicated gated guest entrance and paver circle drive for ease of entertaining. This home is extremely well-planned with spectacular appointments & views. Enjoy all the restaurants and shops that Park Avenue offers. This special location provides the quintessential Winter Park lifestyle like no other. All proceeds from the sale of the home owned by sellers, in excess of $12,000,000, will be donated to the University of Central Florida.

Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… This spectacular residence is located on the Isle of Sicily with dramatic water views on both sides of the property to enjoy sunrises and sunsets across Lake Maitland (largest lake on the 6-lake chain of lakes). This property is a one owner custom built home resting on approximately 3/4 acre upland (1.41 total acres per tax records) of property secluded on a private island off the Via’s neighborhood inclusive of the Winter Park Racquet Club walking/boating distance away… This custom-built residence was completed only 9 years ago with wonderful bright-open floor plan and flooded with light from extensive walls of glass… The interiors are not only light, but sleek, modern, and tastefully decorated with gorgeous lighting, extensive moldings and top-quality craftsmanship that will captivate you from the moment you enter the grand foyer looking straight through the 2-story living room to breathtaking views of the pool, grounds & lake... Additionally, downstairs you will enjoy a private library, formal (but open) dining room, fabulous chef’s island kitchen with Sub-Zero, Thermador Italian ILVE appliances including a casual dining area open to the lakeside gathering room with masonry fireplace, plus wine room along with the lavish primary owner’s quarters including a “Four Seasons” spa-like bath & his/her dressing areas, bar with refrigerator, fireplace & steam room… Upstairs commences with a stunning winding stairwell of glass panels taking you up to an expansive, open lounge area with curved corner bar and separate billiards are all open to the lakefront terrace… Plus, 3 flexible rooms: currently utilized as a media room, massage room, and exercise room… As well as a junior oversized guest suite and three more bedrooms all with private en-suite baths… The outdoor lakefront living includes majestic Cypress trees, expansive covered lanai, summer kitchen, tropical heated salt pool and spa with beach entry, fiberoptic lighting, fire bowls & fountain, a dedicated fire pit seating area, complete boathouse & more… Other notable features include an elevator, 5 masonry fireplaces, 2 separate laundry rooms up/down, 2 dishwashers, butler’s pantry, wine room, Control4 home automation, 4 zoned AC systems, termite bond, lake irrigation, dedicated outdoor pool bath, “oversized 4-car garage”, automatic gated circular drive entry, & more…

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acres of prime property on Lake Maitland on the Winter Park Chain of Lakes and walking distance to all the shops and restaurants on Park Avenue. As you drive up to the estate, you will be impressed by the entry gate that leads to the huge circular paved driveway complete with a fountain. For the car enthusiast, there are 2 separate garages totaling 7 spaces. There is plenty of additional parking as this house was built for luxury living and entertaining! The home spans 19,304 square feet under air and 25,124 square feet under the roof. There are two separate grand foyers to welcome you, with high ceilings, gorgeous staircases, and magnificent lake views. This home was built to showcase the stunning lake views from almost every room. There are multiple patios and balconies to offer the perfect spots to take in the incredible views. With a total of 8 bedrooms, 3 of which are master suites with ensuite bathrooms and massive walk-in closets there is no shortage of space in this home. In total, there are 9 full baths and 5 half baths making sure everyone has plenty of space in this Park Avenue Estate. Plus, there is a caregiver’s suite with private entries for live-in help. This home is equipped with 3 kitchens making any large gathering a breeze to accommodate! As well as 3 elevators so everyone can move about the estate with ease. The expansive estate is perfect for a multi-generational family, with plenty of bedrooms and bathrooms for everyone to comfortably live together. The grounds are simply beautiful, with mature landscaping and expansive lake views there is truly nothing like it. The possibilities are endless with this home! If you are looking for a one-of-a-kind property, this is it! The grandeur of this estate and its prime location makes it a truly unique find. Don’t miss your chance to own a piece of Winter Park history!

Casa Bianca, the extraordinary Winter Park estate, has entered the market for the first time available in over 40 years. Perfectly positioned on the corner of Via Tuscany and Alabama Drive in the distinguished Vias of Olde Winter Park is one of the area's finest and most notable properties. Resting on an expanse of premier, elevated acreage and surrounded by lush landscaping with gorgeous palms and majestic oaks, this elegant lakefront estate showcases breathtaking sunset scenes over Lake Maitland, the largest lake on the Winter Park Chain of Lakes. Blending sophistication and grandeur, this exceptional, six-bedroom, eight-bath, one-of-a-kind residence boasts an array of spectacular living spaces, with approx. 11,000 square feet of living areas and over 13,000 square feet of under roof, including a separate full two-bedroom guest apartment and separate home caretaker's quarters with its own entrance — hosting countless lavish social and political events through the years, featuring past presidents, governors, actors, international artists, musicians and other dignitaries. There is a stunning 2,500 square-foot ballroom with a 40-foot ceiling — along with a separate catering kitchen, full bar and lavish guest bath that provides the ultimate venue for memorable entertaining. Multiple walls of glass highlight a private outdoor retreat complete with a pool, outdoor living area and boathouse offering a deck and balcony primed to enjoy the best of Central Florida's lakefront lifestyle. Other features include natural gas whole-house generator, hurricane shutters, elaborate security, fireplace, elevator, walk-in basement, boathouse and more. This remarkable lakefront estate property presents a rare, once-in-a-lifetime opportunity to own a landmark property in Winter Park.

Desirable Location in the Horse Capital of the world! This exquisite income producing Equine estate is located only 17 minutes from the World Equestrian Center set to be the largest in the nation! Just 5 minutes from HITS, and 25 minutes from Ocala Breeders Sales, this sprawling 220 acres boasts a custom built executive home perfect for entertaining with a pool/spa cabana, and outdoor stone fireplace over looking beautiful barns and lush paddocks. If you like to play golf or just want to sharpen up your game no worries, your own golf simulator room is included with this fabulous home. 1 Double wide mobile home, 7 barns totaling 105 stalls, including an office and apartment for quests, 32 paddocks, 2 round pens, 1 eurosizer and a machanics shop with shed for shavings and hay.

Under Construction. Today’s Florida living at its finest in this premier 2023 new construction residence nearing completion in the heart of the Vias by Z Properties Inc. This custom-designed California contemporary boasts walls of glass (Windsor & Euro-Wall with a pivoting front entry door), painted brick and Japanese burnt Nakamoto wood siding. The property is resting on elevated lot at top of hill with a sprawling 1/2 acre lot. This home has it all with an incredibly flexible, modern open floor plan including an expansive owner’s retreat with exercise/flex room, cedar sauna and outdoor shower garden and a dedicated guest suite or library, along with incredible massive island kitchen, gathering room, dining area, sun room, gallery and mud room on the main level. Upstairs includes 3 more spacious en-suite bedrooms as well as 2 huge flex rooms that could be utilized as a game room, lounge area, theater, etc. Additionally, there is approximately 1,000 square feet more of outdoor living spaces including expansive covered porches, full cabana with summer kitchen, fireplace and 1/2 bath. Almost 9,000 square feet under roof! The grounds are sprawling with multiple landscaped areas (to be completed by Signature Landscape Contractors) and a secluded motor court with 3 oversized garages (2-car garage and separate 1-car garage). There are still opportunities for the buyers to be involved in selecting some of the finishes as well as pool/spa, landscaping, details, etc.! Estimated turnkey project finished date to be in MARCH of 2023.

WELCOME HOME to this Amazing Lake House situated just minutes away from the Charming and Historic Winter Park Avenue. This Wonderful Estate is set on 1.70 ACRES of land and has nearly 200 feet of frontage on beautiful and highly sought after Lake Mizell. This uniquely rare property features a lovely long and windy driveway lined with pavers. As you begin approaching The Estate you will feel swept away by its Mediterranean Charm. A gorgeous solid Oak door sits right below the Juliet Balcony that comes off of the Primary Bedroom Suite. The backyard is in an ultra private setting boasting breathtaking mature Oak Trees, lush landscaping, a fabulous pool area. This backyard is truly immense and perfect serene setting for entertaining friends and family, hosting parties, ceremonies, events, holidays and more. 4 Bedrooms, 5 Full bathrooms, an office AND bonus living room area. This property has it all, and is in one of the most desirable areas in all of Central Florida. More photography and description to come soon of this home's interior, however do not wait, get ahead of the crowd and SCHEDULE YOUR SHOWING TODAY!

Enjoy the finest that Winter Park, Florida has to offer in this refined lakefront property on Winter Park Chain of Lakes, Lake Mizell. Situated in the elegant neighborhood of Windsong, this well-maintained 5 bedroom, 7 bath home is ready for waterfront living, sunset entertaining, and convenient access to Winter Park’s renowned shopping and dining. Its new owners will appreciate space for 4 cars between the two garages, an expansive master suite complete with a wet bar and a private covered balcony, elevator access to the second floor, central vacuum system, and gourmet kitchen with walk-in pantry and prep space. Notable updates to this spacious property include plumbing fixtures and light fixtures, resurfaced pavers, fresh landscaping, and more. Come fall in love with the picturesque views, the 7500+ ft of luxury living, and the tree-lined street where you’re likely to encounter Windsong's resident peacocks!

Pre-Construction. To be built. This Incredible Modern Transitional Home will be Breaking Ground Soon! It will be built on an Oversized Lot and is just Minutes to Park Avenue with Wonderful Shops and Restaurants. The Winter Park 9 Golf Course is also just a 6 Minute Walk. Designed by Renowned Architect, Dan Delong of Origins Residential Design and to be built by Custom Builder Sean Wulff of Native Homes, this Luxury Home will “Wow” the most Distinctive Buyer. The Floor Plan is Amazing Featuring 5 Bedrooms, 5 Full Bathrooms, 3 Half Baths, Great Room, Family Room, Study, Additional Downstairs Guest Suite & Upstairs Game Room. As you enter you will be greeted with an Open Great Room Showcasing Floor to Ceiling Windows Overlooking the Pool & Patio. The Gourmet Kitchen which opens to the Family Room, will be Designed with Custom Handmade Stacked European Modern Style Cabinets, Wolf Appliances including Dual Ovens & Dishwashers, Wine Cooler, Beverage Center, Quartz Countertops, Island with Bar & a Walk in Pantry. The Spacious Laundry and Mud Rooms are just off of the kitchen. The luxury Primary Suite, Guest Suite & Study are all Located on the first floor. Upstairs you will find a Spacious Game Room and 3 Additional En Suite Bedrooms. The Outdoor Living will be a True Oasis and an Entertainers Dream with Two Separate Covered Lanai’s Showcasing Remote Screens, Summer Kitchen, Built in Fireplace, Free Standing Fire Pit & Luxurious Landscaping. The Salt Water Pool will feature a Sun Shelf and Heated Gas Spa. Enjoy the convenience of a Circular Driveway as you enter your 3 Car Garage (one bay on opposite side). Additional Features Include. Wood Floors Throughout, 12’ Ceilings on First Level and 10’ on Second, Anderson Windows, Flat Concrete Tile Roof, Tongue & Groove Ceilings on all Lanai’s, Electric Fireplace with LED Flame in Family Room, Floor to Ceiling Windows in the Great Room and Family Room Bringing the Outdoors in and so Much More. Now is the time to get in on the ground floor to choose your colors and finishes. See all attachments with Rendering of Home, Floor Plan and Specifications.

Pending - Open house cancelled April 2022 construction! This newly constructed home is move-in ready and available for a quick closing! Do not miss the once-in-a-lifetime opportunity to own this rare, single-family home located in the heart of Winter Park, STEPS from Park Avenue. This luxurious Modern English Cottage designed home was built by the distinguished FG Schaub Custom homes, known for grand open spaces and superior craftsmanship. As you enter the grand foyer, you will be awed by the marble floors, modern chandeliers, and impressive elevator doors. Walk through to the large open great room with an electric fireplace and huge, eloquently appointed kitchen with Sub Zero/Wolf appliances, a catering kitchen or bar with a second dishwasher for those who like to entertain, a wine refrigerator, a pot filler, and gorgeous countertops. Many more features that are a must-see. The island is large enough to seat six comfortably. Take a short walk around the corner to the incredible master suite with a chandelier, oversized ensuite bath with towel warmers, a soaking tub, and a water closet with motion-sensored seating. The master closet has a second private laundry, accent lighting, and storage space. Open the folding doors to a large outdoor area with retractable screens, fans, and an outdoor kitchen. The pool with integrated heated spa and sun deck is sure to please family and friends or enjoy the ambient outdoor lighting in the evening while entertaining for a party. Step into the luxurious elevator to the second floor, or if you choose, take the beautiful staircase with ambient and deck lighting that overlooks the grand foyer through glass panels. The second floor offers a home gym with rubber flooring, a second laundry with plenty of storage, and a flex room for a fifth bedroom, den or home office. Enjoy the second great room with built ins and refrigerator - perfect for a family or a separate entertaining area. Winter Park offers

Sitting on over a ½ acre lot on a private lane in the heart of Winter Park, this traditional and elegant estate offers ultimate privacy and is located just minutes from iconic Park Avenue. Featuring 5,534 sf of living space in the main house, and a separate carriage house with an additional 722 sf, this home is perfect for entertaining. As you walk through the front door, you’re greeted by the grand foyer adorned with two gorgeous Schonbek crystal chandeliers, a sophisticated wrought iron staircase and a welcoming sitting area. To the right of the foyer, you will find the formal living room exhibiting custom window treatments, Venetian plaster, and crown molding with spectacular millwork. The library connects to the formal living room and showcases beautiful wood built-ins and coffered ceilings, and is adjacent to the cozy sunroom, where you can read a book or enjoy your coffee with tranquil views of the “Butterfly Sanctuary”. To the left of the foyer, you will find the expansive dining room with a fireplace and a stunning crystal chandelier. Through the built-in display cabinets that light up, the side entry from porte-cochere and the wonderful butler’s pantry, you will find the fully equipped kitchen. Boasting custom WoodMode cabinets, double sinks with touchless faucets, six-burner Wolf gas range, Miele dishwasher, in-drawer microwave, double ovens, Sub Zero refrigerator, wine cooler, and refrigerator drawers, the well-appointed kitchen is a chef’s dream. The breakfast nook is covered in natural light and over-looks the backyard. The family room is next to the kitchen and includes an additional fireplace, wood built-ins, and French doors leading to the staggering outdoor space. As you make your way to the second floor, in the stylish elevator with custom woodwork, you will find two generously sized bedrooms with a Jack-and-Jill bathroom on one side, and the all-embracing master wing on the other. As you enter the master suite, the large bedroom will be on the left and the right side completes the suite with two separate “His & Hers” bathrooms, two walk-in closets, and a large laundry room. The first full bathroom includes a vanity, shower stall and marble finishes, and the hallway ends with another massive full bathroom with additional closets, a free-standing tub, and separate shower stall. As you step outside, the porch features remote controlled screens, a gas fireplace, outdoor kitchen and an additional courtyard, all overlooking the sparkling pool. The guest house sits on the three-car garage, and includes a full kitchen, sitting area, one bedroom, a full bathroom and an adjoining art studio. The perfectly manicured landscape was completed in 2022 to include lighting and irrigation, offering picturesque views from almost every room. Other highlights include 4 gas fireplaces, Brazilian cherrywood and marble floors, and an abundance of natural light and high-end finishes throughout. This home has been meticulously kept and it’s truly upgrades galore. Refer to the attached “Features Sheet” for a detailed list of updates and improvements.

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of May. This custom built Winter Park home is the epitome of luxury. The last unsold home at Morse and Pennsylvania is walking distance to Park Avenue and Hannibal Square for fabulous dining and shopping. This Phil Kean designed home features an open porch entry showcasing a courtyard heated pool/spa with a dramatic waterfall feature. Perfect for indoor/outdoor entertaining the summer kitchen features a 36” Heston grill. This 3-level home, with a walnut finished elevator, offers multiple gathering and entertaining areas, a study or office, and a 3-car garage with electric car charging station. The spacious gourmet kitchen features a Wolf professional range and 54” Dacor column refrigerator and freezer. The kitchen has a huge island, coffered lighted ceilings, beautiful custom wood cabinets that extend to the 10-foot ceilings, storage space, and a walk-in pantry. The adjacent wet bar features a built in Wolf coffee maker, Dacor wine tower, and ice maker. The lower level gathering space showcases a 20-foot ceiling with clerestory Anderson windows for a healthy lifestyle. The private owner’s suite, located on the second level, has separate his and hers closets with custom built ins, a spa like master bath with separate vanities, expansive mirrors, a free-standing soaking tub, and glass enclosed shower. Outside the owner’s suite is a bright and airy loft that opens to a second-floor balcony. The Game room with a double coffered ceiling, located on the third level, includes a golf simulator and wet bar. The massive entertaining balcony has expansive views of Winter Park. Additional exceptional features include; Anderson doors and windows, Smart house wiring, speakers, lighted staircase, elevator, upstairs balcony wired for projector, ensuite secondary bedrooms, water filtration system, tankless hot water, linear AC ventilation, prewires for window shades, ice maker, glass garage doors, and many more fabulous custom features.