Homes for Sale in Winter Park

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 within walking distance 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.

LUXURIOUS LAKE MAITLAND ESTATE! This Winter Park Chain of Lakes Custom 5 car garage home has panoramic views of Lk. Maitland w/ 175' of water frontage on 1.09 acres. This magnificient home has it ALL & Below Appraisal!! The living & entertaining areas are spacious & elegant, w/ sweeping views of the lake from almost every room. High end finishes in the main house include French doors, central vacuum, custom built-ins, surround sound, security camera, wine cellar, gas fireplaces, & extensive detailed millwork. The downstairs has formal living room, dining room, media room, game room with a large impressive granite full bar, library, exercise room, en suite bedroom & family room that opens into the kitchen. This kitchen is a Chef's entertaining dream with a 6 burner gas cooktop, convection & double ovens, Thermador S/S freezer & frigerator, 10x5 granite island, triple sink, Butler's pantry w/coffee bar & wine frig. There are 3 more en suites bedrooms upstairs plus the master suite which resembles a 5 star Hotel with sitting room, double walk-in closets, balconies w/ lake views and expansive master bathroom. This property also has a separate bonus/ 6th en suite/ or guest studio apt. in the main interior and a detached 1 bedroom/1 bath full cottage apt. with a full size kitchen. Outdoor living spaces include gazebo w/ fireplace & summer kitchen, salt water pool, heated spa, & double slip boat dock. TRULY AN IMPECCIBLE PIECE OF PROPERTY WITH A RATED SCHOOLS AND ALL WITHIN WALKING DISTANCE TO PARK AVENUE!!!

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.

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.

Huge price reduction!! This amazing 2 story lakefront home is located in Winter Park’s exclusive Windsong Preserve Point neighborhood and features stunning views of Lake Berry. The house was extensively renovated in 2008-2009. Enjoy the Florida luxury lifestyle while relaxing in your private pool and spa or entertain your friends and family with a full outdoor kitchen and huge patio area. The large covered dock has a motorized lift that’s perfect for your boat, jet ski, fishing or you can simply enjoy the nature of the lake while relaxing on the built-in seating. This incredible home has 5 bedrooms, 5.5 bathrooms, gourmet kitchen with top chef quality appliances and an incredible granite topped island, temperature controlled wine room, movie theater, library/study, upstairs game room, built-in wet bar and fireplace. The fabulous master suite is an oasis unto itself with vaulted ceilings, lake and pool views and a stellar master bathroom with his & her walk-in closets, walk-in shower and Jacuzzi bath. The home’s open floor plan features beautiful travertine tile with hand crafted wood beams and custom wrought iron accents throughout. Beautiful inside and out, this fantastic home has A+ rated schools and is only minutes from downtown Winter Park, Park Avenue shopping & dining.

Come enjoy Florida living at its best with this gorgeous Craftsman style home, featuring approximately an acre of land and 200’ on Lake Mizell. Impeccably designed, with attention to every detail, this stunning four bedroom home offers four full baths, three half-baths, a detached one bedroom + living quarters guest house, a home fitness center, boathouse & more! The Chef’s kitchen includes state-of-the-art Viking appliances, a gas range, custom wood cabinetry, a breakfast nook with built-in seating, and a wine bar. The heart of the home is the oversized Greatroom with sliding glass doors that seamlessly bring the indoor/outdoor living rooms together and provide panoramic views of the lake. Downstairs master retreat has access to the covered porch, water views, and a BainUltra spa bath. Upstairs are three very generously sized bedrooms and a home theater with projection screen. Hardwood floors, slate tiles, wood-beam ceilings, extensive crown moldings, iron railings, and exquisite chandelier and lighting fixtures – it’s no wonder this home is an Aurora Award winner. Located on the north shore of Lake Mizell, this home takes advantage of beautiful sunrises and peaceful views of the Genius Preserve. Just a few blocks from Park Avenue, you’re only minutes away to the brand new Winter Park Golf Course and a short walking distance to fabulous restaurants, Rollins College, the Polasek Museum, & Alfond Inn.

Exclusive LAKEFRONT home in Bear Gully Point. This majestic home rests on private Bear Gully Lake. Home was constructed by the original owner who was a private home builder for over 30 years, so this home has every option imaginable. Every option was hand picked and crafted to rest on just over acre with fantastic views and designed to have views lake from practically every room in the house. Features include 4 fire places, 30 foot ceilings, 4 wet bars, over 2000 square feet music/game room with a huge stage for performances for your favorite band or symphony, breath taking lake views from your private 600 plus size lanai and to much to list. A truly affordable Winter Park address minutes from Trinity Prep, 417, Shopping and much much more. Must see to appreciate.

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.