Homes for Sale in Winter Park

NEW PRICE! Stunning Mediterranean Lakefront Estate. Across from the secret gardens of Kraft Azalea Park sits this palatial 1-acre compound with over 10,000 SF of luxurious living space, private tennis court, resort-style pool, and more! Offering formal living areas, gourmet chef’s kitchen, open great room, his and her home offices, elevator, 12-person home theater, billiard room, and six guest suites, each with a private en suite, and a separate guest apartment with kitchen, this home leaves nothing to be desired. Detailed with high-end finishes throughout, the home is exquisite in every way. Polished travertine and hardwood flooring, trim moldings, wrought-iron railings, 27’ ceilings, and a whole-house entertainment system are just a few of the custom details that have been installed throughout the home. Walkout balconies off the front and rear of the home take full advantage of the home’s picturesque surroundings. The nearly 1,000 SF second floor lanai overlooks the pool and tennis courts and the attached 4-car garage, a rare and highly desirable find, along with the front circular drive provide a sophisticated entry for visiting guests. Private boathouse on Lake Maitland faces westward and offers gorgeous sunset views and convenient access to Winter Park’s main attraction the Chain of Lakes. Located on one of the most prestigious drives in town, this extraordinary trophy home is like no other and is just a short walking distance from the award-winning restaurants and boutique shops along Park Avenue.

Incredible 2-acre Modern Mediterranean lakefront estate on hidden peninsula between Lake Mizell & Virginia on the 6-lake chain of lakes… Enjoy both picturesque sunrises & sunsets with Rollins College chapel and downtown Orlando illuminated in the evening. This property is on a private street with only 2 other lakefront homes and the only gated lakefront street in all of Winter Park! This award-winning home was designed by Bernie Johnson and Master Custom Builder, Rial Jones with exceptional attention to detail… Over 10,000 sf of living area & apprx 15,000 sf under roof, this home offers every amenity, masterfully designed open floor plan, 6 bedroom suites, media rm, library, loft & other flexible spaces… Features include ceilings artfully designed, wood beams, coquina baseboards, Venetian plaster, custom millwork, travertine & distressed wood floors & exquisite detail… Gourmet island kitchen has commercial grade natural gas appliances, unique wood burning grill, adjacent butler's pantry plus a wine room. Downstairs master retreat overlooks lake with gas fireplace, sitting room, spacious dressing area, plus his/her baths. Four themed bedroom suites upstairs with offices for each. The lakefront lifestyle includes elegant pool with water features, 1260sf covered lanai with gas fireplace, pizza oven and summer kitchen, sport court, 4 garages in motor court all encompassed by lushly landscaped grounds with surrounding lakes... Truly one of the finest homes in Winter Park and Central Florida!

Stunning lakefront estate in premier location close to Park Ave… Situated on 1.5 acres with 280' of lake frontage on Lake Maitland – 6 lake chain of lakes. Enjoy lake views from almost every room including the grand master suite, formal living room with wood burning fireplace, elegant entry and kitchen that leads to sunroom. The spacious backyard with pristine landscaping features resort style pool, outdoor shower, multiple lanai areas & private boat house.

Featured in the Orlando Museum of Art Antiques Magazine and selected for the Winter Park Garden Tour. This spectacular Tudor-style residence boasts serene Lake Sue views. Offering a kitchen and family room combo, gorgeous views can be enjoyed from the dining, formal living and downstairs master bedroom. The home has a spacious kitchen and 4 bedrooms with en-suites and sitting rooms. Crafted with meticulous attention to detail, there are hand-hewn antique wood floor beams in the master and pecky cypress ceiling in the basement, wine room, front and back porch. This home has hardwood floors throughout and includes natural gas grill, kitchen stove, fireplace and outside lamps, five-inch copper gutters and a gorgeous slate roof. A travertine tile basement provides a media room and wine cellar. Outside, you will find a lavish courtyard with pool. Watch beautiful sunsets from your boat dock and private beach on Lake Sue. There is a full guest apartment with kitchen and separate utilities above the garage. This is a once in a lifetime home, it has its own distinctive, elegant personality. A must see!

One of Winter Park’s most prestigious lakefront estates that allows horses. Enter into the grand two-story foyer with the grand double staircase, you are immediately greeted by the picturesque lake views. This spacious lakefront home has soaring ceilings, den/office and formal living and dining rooms and a three-car garage. The newly updated chef’s kitchen has solid wood white cabinets and quartz countertops and is equipped with top-of-the-line Thermador appliances and Sub-Zero refrigeration in the oversized walk-in pantry. The large family room is perfect for entertaining guests and offers breathtaking views of Lake Howell. The first level's fabulous master suite has a spa-like bath with a soaking tub and large custom his-and-her closets and a separate sitting area which can be used as an exercise room or nursery. The second level has four large bedroom suites connected by a sitting area. Enjoy all that a lakefront lifestyle has to offer from the expansive open porch that overlooks the pool and lake.

Under Construction... Park Hill, an ultra-luxury 10 townhome project by Hill Gray Seven LLC (only 5 remaining), is a once-in-a-lifetime opportunity to own the most exclusive and luxurious townhome ever built in Winter Park. Designed by award winning Slocum Platts architects, Park Hill's classically styled architecture will likely be the only remaining new residential construction along the famed stretch of Park Avenue that encompasses downtown and its many charms. Unmatched quality construction with slate & copper roofs & gutters, precast siding and handmade brick. Interior features include magnificent detailing and unsurpassed craftsmanship with three bedrooms in each townhome, approximately 3,300 - 4,300 sq. ft. of living area under roof, private elevators, two-car garages + additional parking, private first-floor courtyards with lush elegant landscaping, covered rooftop terraces with summer kitchens and fireplaces, plus literally walls of glass providing natural light into every floor. Energy efficient construction and state-of-the-art smart home technology throughout. Exterior maintenance handled by the association makes Park Hill an ideal lock and leave primary residence... note: interiors may be custom designed... Reserve your new residence now as there are only a handful of homes remaining for this soon to be award winning downtown Winter Park lifestyle!

Under Construction... Park Hill, an ultra-luxury 10 townhome project by Hill Gray Seven LLC (only 5 remaining), is a once-in-a-lifetime opportunity to own the most exclusive and luxurious townhome ever built in Winter Park. Designed by award winning Slocum Platts architects, Park Hill's classically styled architecture will likely be the only remaining new residential construction along the famed stretch of Park Avenue that encompasses downtown and its many charms. Unmatched quality construction with slate & copper roofs & gutters, precast siding and handmade brick. Interior features include magnificent detailing and unsurpassed craftsmanship with three bedrooms in each townhome, approximately 3,300 - 4,300 sq. ft. of living area under roof, private elevators, two-car garages + additional parking, private first-floor courtyards with lush elegant landscaping, covered rooftop terraces with summer kitchens and fireplaces, plus literally walls of glass providing natural light into every floor. Energy efficient construction and state-of-the-art smart home technology throughout. Exterior maintenance handled by the association makes Park Hill an ideal lock and leave primary residence... note: interiors may be custom designed... Reserve your new residence now as there are only a handful of homes remaining for this soon to be award winning downtown Winter Park lifestyle!

Casa Fiera Vista ~ Rare opportunity to own an Elegant Custom Lakefront Estate located on the Winter Park Chain of Lakes. This home is an Aurora and Parade of Homes Grand Winner! The attention to detail, workmanship and quality is unapparelled. Designed by Architects-Lucia Kassik & Monday, Grant Gribble Interiors, Landscape Architect- Frank Joseph Brooks and built by Victor Farina. 130 feet of lakefront on Lake Virginia -Sunrise and Sunsets overlooking Rollins and the tranquil Knowles Chapel. The boat dock with covered electronic lift, Majestic Cypress trees, rolling green lawn, Chicago brick herringbone pavers, covered patio, grill, gas fireplace, and spa outdoor shower complete the backyard oasis. The top of the line home interiors will impress any discriminating buyer. Wood floors, custom built-ins, Anderson doors and windows, exquisite walk-in pantry, Wolf, Viking appliances, Copper hood range and more. Enormous open family room has wood beams and coffered ceilings with plenty of room to entertain. The sophisticated bar/wine room is tucked under the stairs off the great room. The master suite is a welcoming retreat with a spa bathroom, custom closets & endless storage. Well-appointed double office with beautiful wood built-ins. Spanish tile stairs welcome you to the second floor -entertaining area, bonus room, bar, kitchenette and additional bedroom with ensuite bath. This gorgeous estate is located on a quiet cul-de-sac in the highly sought after neighborhood of Timberlane Shores.

Never before on the market this is a rare opportunity to own a piece of Winter Park History! Gorgeous 1955 Gamble Rogers home with double waterfrontage (155’ on Lake Osceola, 235’ on the Venetian Canal). Amazing architecture, both inside and out. Grand foyer with spiral staircase. Formal living areas with panoramic views of the majestic oaks and lake. Double master suites, one upstairs and one down. Room for an expansive, gourmet kitchen. Oversized bedrooms, each with full bath. Walk out balconies off the front and back of the home featuring detailed iron work. Home is impeccable and is representative of timeless elegance and class. Stunning property offers over 1 acre of land and is set quietly back from Winter Park’s prestigious Palmer Avenue. Surrounded by both historic and brand new multi-million dollar homes, this one-of-a-kind property is walking distance to Park Avenue, and minutes from the Interlachen Golf & Country Club and Winter Park Racquet Club. Properties this special hardly ever come on the market, so don’t wait. If you’ve been looking for the perfect place to renovate or build your lakefront estate, this is it.

Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the glass porcelain floors and dramatic windows, as you overlook the spectacular courtyard from every room. Entertain large parties simply with the spacious and commercial grade kitchen, grand family and living rooms, and resort-like courtyard. Display art, cars, or RVs in the oversized heated and air-conditioned garage space with over 20 ft. of ceiling height (with space for 19 cars). And, with the push of one button, activate the external shades to cover all exterior windows, doors, and garage doors, providing the ultimate in security and privacy. This one-of-a-kind contemporary masterpiece in the heart of Winter Park is the ultimate in design, privacy, luxury, and security.

JUST REDUCED by $455,000! Priced to sell – it’s the lowest $/SF on the Winter Park Chain of Lakes!!! Come see this unbelievably gorgeous lakefront estate home in Winter Park. Located on the quiet side of Lake Maitland, this 5 bedroom, 7,600 SF home features formal living areas, a home office, downstairs master and guest suite, upstairs bonus room, a game room with a temperature controlled wine chateau, heated pool, a private boathouse, and 4-car garage. Beautiful travertine and wood floors flow throughout the home, complimented by extensive millwork and crown moldings, 4 gas fireplaces, high ceilings, and French doors that seamless blend indoor and outdoor living together. The gourmet kitchen offers high-end appliances, including gas range, double ovens, built-in expresso machine, and a large walk-in pantry. The luxurious master retreat has a spa bath fit for a king, an attached sitting room, and access to the resort-style pool and spa. Each of the 4 guest suites are oversized and have a full, private bath, as well as spacious walk-in closets. Upstairs, in addition to the game room is an expansive bonus room, 2nd laundry room, and covered balcony with panoramic views. Completely fenced, the backyard has a large green space ideal for entertainment and the 4-car garage and motor court are located behind an electronic gate. Just minutes from the Racquet Club, Interlachen Golf & Country Club, and Park Avenue this home is sure to impress with all its amenities.

Under Construction. Completion is scheduled for September 2018. Only two residences remain. Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park Avenue, across the street from the Alfond Inn and just a stone’s throw from the Winter Park Chain of Lakes. Comprised of six exquisitely appointed townhouses, South Interlachen Place is being built with premium level specifications; a standard of luxury usually only found in world-class destinations. The project was designed by award-winning architect Randall Slocum of Slocum Platts. Privacy is the top priority: every fee-simple residence includes a private two-car garage, private elevator to all levels and lush, mature landscaping defining the entrances. A truly unique aspect of the design is the extraordinarily large and private rooftop terrace for each individual residence, providing both covered and open areas for outdoor dining and entertaining. Each private rooftop terrace comes with a fireplace and powder bath. The residences are designed with age in place features throughout, allowing for the adaptation of changing lifestyles. Each townhouse embraces smart technology for entertainment, lighting, energy management and security. Live in one of the most extraordinary residences in a truly exceptional Winter Park location at South Interlachen Place.