Homes for Sale in Winter Park

Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue's shopping and restaurants. This iconic and historic property boasts the rarity of 1.57+ acres elevated above Lake Maitland, with 138 feet of waterfrontage and breathtaking views from sunrise to sunset. Built in 1919 in the Georgian Revival style, the home captures the essence and elegance of a bygone era but is resplendent in every aspect to withstand the test of time. Spectacular curb appeal with stunning mature landscaping, a park-like backyard with a gazebo and sweeping lawn to the lake, a boat dock, an outdoor fireplace, and an impressive screened indoor pool provide endless enjoyment and entertaining possibilities. The grand entry foyer welcomes with a balance of informal and formal rooms on the first floor, ideal for large-scale entertaining, both inside and out. The first floor features an oversized living room, a formal dining room, a den, a study, a kitchen, a breakfast room, a Butler's pantry, and two sunporches. Two sets of staircases lead to 5 bedrooms and 4 full baths, plus numerous flex spaces. The upstairs owners' suite is luxurious with a fireplace, a sitting area, oversized walk-in closets, a small bar area, a closet with a second washer/dryer, elevator access, a private porch, and a rooftop terrace. There is also a guest cottage with a bedroom, a bathroom, a living room, and a kitchen. The enormous attic and basement offer large amounts of storage. Features include soaring ceilings (12-14'), heart pine floors, plantation shutters, an elevator, intricate millwork and crown molding, and a 4-car garage. The total of 8,353 heated square feet includes 7,367 sq ft in the main house and 986 sq ft in the guest cottage. The property has been meticulously maintained and enormously loved. Prime location and unrivaled lot quality.

Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… Extremely RARE opportunity to purchase a spectacular residence located on the Isle of Sicily (only 11 homes on this exclusive island) 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…

Exquisite Winter Park estate designed by award winning architect Larry Boerder. Located just steps from Park Avenue’s upscale boutique shopping and restaurants, this architectural masterpiece is the epitome of luxury Winter Park Living. From the Restoration Hardware lighting, to the Thassos marble floors, nero marquina marble fireplace, laser cut stainless steel art panels, and designer finishes throughout, no expense was spared during the construction of this stunning residence. As you step through the custom glass front doors, you’re immediately greeted by the soaring 18-foot ceilings of the great room. The expansive kitchen is a chef’s dream, featuring imported custom cabinetry, marble countertops, Wolf & Subzero appliances, and the crown jewel, a French La Cornue gas range. Owners can choose from two primary bedroom suites, both with top-of-the-line custom closets, rich wood floors, and spacious spa baths. On the second floor there are three additional ensuite bedrooms, two of which have access to a 25 ft long balcony overlooking the pool and impeccably maintained grounds. At the end of the 90 ft grand hallway, you will find a magnificent, curved staircase with a striking chandelier, and the entrance to the lower level which is an entertainers dream, featuring a bar, theater, fitness room, and a full bathroom. Additional features include a home office, lounge, wine cellar, and multiple laundry rooms. Exterior amenities include a travertine driveway, dual 2 car garages with room for car lifts if you’re a car enthusiast, a resort style back yard with a summer kitchen, 50 ft covered lanai for entertaining, a massive pool and spa, and a private putting green to practice your short game. Don’t miss your opportunity to own one of Winter Parks most remarkable residences.

Distinctive, inspirational, timeless & harmonious. This newly constructed contemporary estate located in the heart of Winter Park and only steps from Park Avenue was designed by internationally respected architect, Kamal Rizk. The unique fusion of innovative design, superior craftsmanship & luxury finishes shaped this almost 9,000 SF, 5 bedroom, 7.5 bathroom residence w/ guest suite into the resort style, sanctuary in the city, that it is today. Upon entry the retreat-like elegance of the great room is remarkable. This commodious space incorporates the foyer, formal living, dining, bar & family rooms. It seamlessly opens to the outside via a Pella made “wall of sliding glass.” Italian wood flooring & elaborate millwork are appreciated features as well as modern lighting, custom window treatments & sound operated w/ ease via Lutron. Beyond the family room is the kitchen & hidden scullery where livable luxury resides. Poliform cabinetry, Cambria countertops & top of the line appliances complete these exceptionally versatile spaces. The showcase glass enclosed floor to ceiling wine refrigeration anchors the kitchen & artfully displays up to 975 bottles. The outdoor living is a natural extension of the interior spaces & features a courtyard style pool complete w/ a hand carved, granite rear wall & 16’ linear in-pool fire feature. The kitchen terrace offers a DCS grill, motorized screens, cooling misters & more. A private office, lounge & 1.5 bathrooms complete the downstairs. Bathrooms on both levels showcase elevated selections from Boffi, Zucchetti, Poliform, Inbani, Paffoni & other iconic brands that enforce the refined, contemporary style & quality throughout. Notable Lighting in the office, lounge & throughout include artistic fixtures by FLOS, Moooi, Serge Mouille & more. Access to the 2nd floor is possible via the elevator or stairwell. The upper floor is composed of the primary suite, 2 alternate bedroom suites, a 2nd office/flex room w/ en-suite bath, laundry room, gym & flex use guest apartment. Through a soft entry, discretely located at the rear of the property, the dreamy primary bedroom was designed with a private terrace & hidden closet entry. The closets are part luxury boutique, part meticulously organized space w/ Poliform customization, motion activated light & windows w/ motorized shades made w/ UV protection to shield the interior spaces. The elegant approach to the primary bath includes floating vanities secured to stone covered walls, glass enclosed shower, standalone tub, custom-made dressing table & private water closet. Set apart from the primary, the remaining spaces are finished w/ consistent quality & design. With flawless connection the guest apartment may be used as an extension of the main home or it can be securely separated at a point just beyond the gym. The current owners use one of the bedroom suites as a craft room which opens to the guest apartment’s main living spaces; the family room, full kitchen w/ island seating, laundry & a final bedroom suite. Above is a magical roof top terrace with fireplace & bar. The resident’s entry is at the rear of the property, via a concealed driveway where guest parking is also available. Resident access is via the 4-car garage & a hidden door which opens directly into the kitchen. In this haven of opulent serenity, you may live the life you want, where you want it. The ultimate in luxury and location.

Under contract-accepting backup offers. Under Construction. *** UNDER CONSTRUCTION *** Welcome to an unparalleled expression of sophistication, situated in the heart of Winter Park and just a short walk from the acclaimed Park Avenue, renowned for its exclusive shopping and dining establishments. Your locale is further elevated by a tranquil park, featuring an enchanting fountain, located directly across the street. Designed by Johnson Estate Designs and crafted by Maroon Fine Homes, this home seamlessly blends style and comfort across two levels. Inside, five expansive bedrooms and 5 full and one-half baths await, including a primary suite and an inviting guest suite on the first floor. Each room is adorned with Andersen windows, flooding the interior with an abundance of natural light. The grand foyer, distinguished by its exceptional maple paneling, welcomes you to an interior of unrivaled elegance. The gourmet kitchen features state-of-the-art Wolf & SubZero appliances, complemented by a pantry housing a SubZero wine cooler, offering an enviable backdrop for the discerning host. Modern technology is seamlessly integrated within the residence. A cutting-edge Lutron lighting system, an external surveillance camera system, and high-efficiency Carrier electric heat pumps equipped with smart Ecobee thermostats offer optimal comfort and security. Outdoors, the large saltwater pool, complete with a heated spa and water feature, becomes the centerpiece for alfresco entertainment. A summer kitchen, equipped with a 36” stainless steel DCS grill and undercounter refrigerator, caters to open-air gatherings. The striking glass garage doors reveal a spacious, epoxy-floored 3-car garage, presenting an admirable blend of practicality and aesthetic appeal. The interior architectural detailing and material specifications were created by Niemann Interiors. From a harmonious blend of hardwood, stone, porcelain, and carpet flooring to the convenience of an elevator, this home exudes an air of luxury. It encapsulates the Winter Park lifestyle — where convenience is meets refined style. We invite you to experience this magnificent residence, destined to captivate the most discerning of buyers.

Premier downtown Winter Park condominium. It doesn’t get any better than this. Unit #601 has been artfully remodeled with top quality finishes and amenities located in The Residences. It is a 2-story penthouse covering the entire west end of the top two floors and offering the most spectacular views of any residential unit in Winter Park. To the south, you look down and across the Rollins College campus with its traditional Mediterranean roof lines and the blue waters of tree-lined Lake Virginia. To the southwest, view the unimpeded downtown Orlando skyline, dramatically lit at night with seasonal fireworks displays. To the north is The Alfond Inn hotel & Lake Osceola, and to the direct west is Park Avenue and the downtown shopping district. The unit is wrapped with large entertainment balconies and features key interior rooms. The effect is like floating in the air. The building offers 24/7 security and concierge service with staff on duty at all times. There is an awe-inspiring rooftop pool and entertaining deck area, a spacious card room, parlor, art-work lined promenade and secured underground parking. Unit #601 has its own private oversized 2-car garage within the main parking garage. Coded elevators bring you safely to your special entrance lobby and double door foyer with fabulous 2-story great room and wall of glass beyond with adjacent piano/sitting area. Additional rooms on the main floor are the dining area, magnificent chef's kitchen with top-of-the-line appliances, exquisite cabinetry & butler's pantry. Office/library, secluded bedroom suite, laundry room and powder bath. A sweeping staircase (or private elevator) takes you to the 2nd floor containing the luxurious expansive master suite with sumptuous bath, morning kitchen, and spacious walk-in closet, plus 3rd and 4th separate and private bedroom suites including one with its own lounge area. This is truly a one-of-a-kind and special opportunity to own the best of the best in lock-n-leave in downtown Winter Park.

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June’s “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded section in the Via’s of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms, 1 half bathroom, 3 car garage, pool, patio, outdoor shower and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with lacquered walls and 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted white custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include new slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine new iron French doors, new ebony-stained white oak hardwood floors, lacquered walls, newly renovated master bath and two ensuite baths. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for A-rated Dommerich Elementary, Maitland Middle School, and Winter Park High School.

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.

Welcome to 1391 Richmond Road. A true work of art and surreal living experience is now on the market for the first time. The most discerning buyer will fall in love with the optimal location within Winter Park, which is a short stroll to Park Avenue along the stunning shores of Lake Virginia. This truly handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. As you arrive, you are greeted by an enticing mix of traditional and old Florida plantings, highlighted by Bevolo exterior lighting and gas lanterns leading the way to your custom mahogany/iron work front entry door. The grand foyer with soaring ceilings, stunning black and white marble flooring, and grand staircase which was built in place, with hand molded railing providing a welcoming signature. Flanked by separate formal living and dining areas on either side, the formal dining room features custom hand painted Gracie brand wallpaper and leads to the butler’s pantry with wine refrigerator. The gourmet kitchen boasts Busby cabinetry, new six burner Decor gas range, Subzero refrigerator, large island with prep sink, built-in oven, and naturally lit breakfast area overlooking the backyard oasis. The kitchen opens to the spacious family room with extensive venetian painted millwork, gas/wood burning fireplace with custom Italian made marble surround, 11’4” ceilings, and French doors leading to the terrace and backyard retreat. The formal living room complete with venetian plaster, gas fireplace with custom marble is connected to the family room with a stunning barreled ceiling hallway conveniently located to a chic powder bath. The main floor also includes a full pool bath with access to one of the two garages with air conditioned work room, and a 2nd back staircase. The upstairs primary suite is a sanctuary, graced with an antiqued mirror entry, gas fireplace, double French doors leading to the serene balcony overlooking the statement backyard, and two custom closets with vast cabinetry and lighting. The spa-like bath features Walker Zanger flooring, generous walk-in shower, soaking tub and dual vanities with make-up area. Two additional ensuite bedrooms are also upstairs along with an office/flex room, full bath and laundry room. The second detached garage features a bonus room/convenient home gym. No expense was spared when building this home which displays antique and unique lighting fixtures throughout, custom millwork, surround sound, central vacuum, reverse osmosis water filtration, and extensive storage throughout. Notable window treatments from the finest textile manufacturers worldwide (Clarence House, Elitis, Nancy Corzine, Carragio), as well as wallcoverings (Fornasetti, Gracie, Schalamandre), lighting (Aerin, Niermann Weeks), fixtures (Kohler, Toto, Newport Brass). This bespoke home is an entertainer’s dream with multiple outdoor areas to relax amongst the secret garden of terraced landscaping and four thoughtfully placed fountains. Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High.

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of November. This custom-built Winter Park home is the epitome of luxury. Located at Morse and Pennsylvania is neighboring 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. The Summer Kitchen is perfect for indoor/outdoor entertaining. 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 an 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 glass-enclosed shower. Outside the owner’s suite is a bright, airy loft that opens to a second-floor balcony. The Game room with a double coffered ceiling, located on the third level, includes 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.

Under contract-accepting backup offers. Welcome to Modern Hacienda, the recipient of the 2022 American Residential Design Award - Best Custom Home by the American Institute of Building Design. A magnificent courtyard and garden masterpiece designed and built by award-winning and renowned architect/builder, Phil Kean Design Group. A perfect blend of indoor and outdoor living located on a lovely, large private oversized lot, walking distance to Park Avenue and Rollins College. With just over 4000 square feet, this one-story sprawling villa includes 14 ft. vaulted ceilings in the main living and gallery room, an oversized state-of-the-art Wolf/Subzero kitchen, a detached guest apartment with private living room, kitchenette, washer/dryer, and patio overlooking the pool and backyard. The very private owner's suite offers a luxury bathroom with two separate walk-in closets. The oversized, side-entry garage accomodates 4 cars, and is accessed by a covered walkway. The custom European-style cocktail pool is a focal point to the professionally landscaped backyard oasis, flanked by gorgeous, resort-style covered lanais.

Pre-Construction. To be built. Homes don’t come along like this very often! Here’s your opportunity to own a Magnificent Estate Elanza on Lake Killarney. Enter through your own gated entrance and into your private enclave almost an acre of land that features 5 Bedrooms, 5 full baths and a 5 CAR GARAGE!! Bring all your toys, there is space for everything! The 5th bay of the garage features a full size overhead door for easy to access to your boat or jet skis. You’ll be blown away by this Casual Contemporary home with gorgeous views and curated finishes. The soaring, 2 story foyer greets you with a custom staircase and magnificent trim details. The first floor has a study with wainscoting and glass doors as well as a secondary master suite with a spacious walk in closet and bath with double vanities. The kitchen is an entertainer’s dream with a Sub Zero/Wolf appliance package, huge island for casual dining and a separate scullery area with an extra refrigerator, dishwasher and sink that makes throwing a big party a snap! The large dining room is designed to accommodate an oversized table and has a beamed ceiling and custom trim. There is also an elevator for convenience and safety. As you ascend the staircase to the second floor, the private master suite features a large wrap around deck that affords views of the lake on bath sides. This master suite has it all with a huge, custom closet, luxurious spa like bath and coffee bar to get your day started. There are 2 other large, ensuite bedrooms upstairs and a self-contained in law suite with a kitchenette and separate entrance. This gorgeous property is located near everything with easy access to all that Winter Park has to offer as well as great proximity to College park, Downtown and the exciting new Packing District. Make an appointment today and let us show you all the wonderful things planned for this special home.