Homes for Sale in Winter Park

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!

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! 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!!!

One of Winter Park’s most premier and timeless traditional lakefront estates elevated on apprx. 1.5 acres and 200’ of lake frontage on Lake Virginia walking distance to Rollins College and famed Park Avenue... The home was originally built in 1925, but the current owners completely renovated and expanded the home in 2010. There are spacious living spaces & high ceilings in the main home includes 4 bedrooms/5 baths, library, formal living and dining rooms, and family room. There is a detached guest suite over the main 2-car garage and separate private 1 bed/1 bath guest house on the back of the property over an add’l 2-car garage. Interior features include gorgeous chef’s island kitchen with professional grade appliances and picturesque views of the lake, 2 fireplaces, extensive custom moldings and millwork throughout, and stunning original hardwood floors. Fabulous master retreat with spa-like bathroom, soaking tub, large custom closet, and separate exercise room. The outdoor living spaces take full advantage of lakefront lifestyle with expansive open porch, screened lanai, and trellis covered patio perfect for al fresco dining, all capturing the panoramic elevated views across the expansive manicured yard and lake at Rollins College and downtown Winter Park. Boat dock with power lift, storage room, and sun deck. Other features include 2 private automatic gated entrances, 4 garages, motor court, circular drive, basement, mature landscape with magnificent Live Oaks and Palms, and much more…..

Elegant Mediterranean Lakefront with over an acre of land in the “heart of Winter Park” With 227ft. of lakefront, the view is one of the most breathtaking on the Winter Park Chain. This 6 bedroom/7 ½ bath, pool home was designed by Slocum Platts Architects and built by Maroon Fine Homes. Lake views from almost every room in the home. All of the ceilings in the main living areas are coffered and uniquely designed using Ipe and Pecky Cypress wood in the family and billiard rooms. The kitchen is gourmet featuring double ovens, warming drawer, two dishwashers, gas cooktop, granite countertops, custom cabinetry, butler’s pantry and a hidden pantry, opening up to the cozy family room and breakfast nook. Beautiful Brazilian Walnut hardwood floors and travertine in main living areas. The downstairs features a secondary master bedroom, billiard room with bar, theatre and a laundry room. Upstairs you will find the master bedroom with an expansive balcony overlooking the lake, an office, 3 bedrooms that are all en suite and a secondary laundry room. There is a 1 bedroom/1 bath guest suite located over the 5 car garage. The backyard is truly an oasis featuring a 12 x 77ft covered patio, with a summer kitchen and gas fire pit. Beyond the 50ft. swimming pool and Jacuzzi is a beautiful backyard with plenty of room for the kids and dogs. The boathouse is equipped with boat lift and storage. Other great features include crown molding, surround sound throughout. Walking distance to WP Racquet Club & A rated schools.

Extraordinary Winter Park Chain of Lakes opportunity with 1.8 buildable acres! Incredibly large 79,409 square feet tract of direct lakefront property on Lake Osceola with 231.4 ft of shoreline and spectacular views of Rollins College across the lake. This magnificent property boasts a stately two story five bedroom French Provincial style 4,259 sf home circa 1914 and a two bedroom 1,260 sf carriage house circa 1935, a tennis court and a boat dock. The home is in need of restoration and has lovely architectural details such as leaded glass transoms, beautiful wrought iron stair rail, arches, high ceilings and wood floors throughout all main areas. This size acreage with direct southern lakefront exposure on the exclusive Winter Park Chain of Lakes is a rare and remarkable opportunity to restore or build new. Please call for an appointment to see this exclusive lakefront property close to downtown Park Avenue and all its wonderful amenities. Sold in As-Is condition.

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.

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. Request your private showing to tour this exquisite home today.

Elegant Charleston style lakefront residence in secluded setting on premier Lake Osceola overlooking an absolutely gorgeous, tranquil cove! Sophisticated home where the attention to detail, character and quality in craftsmanship with this home is outstanding… Located on a quiet tree-lined dead end street walking distance or a short boat ride across the lake to downtown Winter Park! Flexible open, yet warm traditional interiors with spacious rooms, high ceilings, extensive moldings, gorgeous heart of pine wood flooring, LED lighting, upgraded AC systems & insulation, fireplace, French doors, built-ins & wine room… In 2009 as well as other recent enhancements by current owner, this property has experienced significant renovations to bring it up to current expectations… Grand double-sided entrance/lake view foyer, generous chef’s island kitchen w/ separate breakfast room, open to family/gathering room, stunning solid paneled library, home office, bonus/media rm, separate private guest quarters… oversized 3-car garage, plus motor court for ample guests parking… Lushly landscaped grounds including private courtyard, sandy white beachfront, fabulous grandfathered covered double boathouse with expansive decking and air-conditioned lakeside room with apprx 200' of lake frontage… A truly one of a kind lakefront estate the most discriminating buyer!

Timeless perfection encompasses every room of this stunning Winter Park estate. Custom built by Charles Clayton, this seven bedroom, seven bath home exudes character and charm throughout and includes features so seldom found in today’s homes including brick laid floors, wood beam ceilings, formal living and dining rooms, three brick fireplaces, a gourmet kitchen that opens to the family room, downstairs master retreat, home office, movie theater, upstairs game room, a detached in-law suite, and a bonus room with full bath above the four car garage. Resort style pool and spa pairs perfectly with the outdoor kitchen and gazebo with fireplace, surrounded by a private brick wall. Home sits high on 0.87 acres of land, offering beautiful sunset views over the Via Tuscany pond. Nestled in the heart of the Vias this home is truly a magnificent estate.

Just completed – 2017 new contemporary lakefront masterpiece on Chain of Lakes and convenient walking distance to downtown Winter Park / Park Ave and Alfond Inn…! Approx 5,000sf of air conditioned living area with bright - wide open floor plan, clean lines, neutral designer interiors , 10'8 architectural ceilings, expansive picturesque windows/doors thru-out, 10’ Casablanca folding LaCantina doors, 4 bedroom suites w/ Master down, 2nd level spacious media/flex room w/ private terrace overlooking tranquil Lake Mizell… Fabulous chef’s kitchen with all Sub Zero/Viking appliances… Technologically advanced home automation with ipad docking stations (or use your iphone app) for security, surround sound, media, AC systems, and more… Amazing entertaining home with the indoors seamlessly flowing outdoors with wonderful summer kitchen, pool, spa, expansive terrace, fire pit, gas tiki torches, lavish landscaping, lawn, specimen live oak tree on lakeshore, new boathouse with enclosed storage room, and more… Must see to appreciate… fantastic one of a kind opportunity available for new construction currently on Chain of Lakes!

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!

This is the first time in almost 50 years this amazing Mediterranean lakefront estate has been available for purchase. Located just blocks from Park Avenue on the shores of Lake Virginia you can enjoy panoramic views across the lake at Rollins College. Originally built in 1928, this home has been lovingly maintained, enhanced, and updated over the years all while maintaining the original charm. Nestled on over 3/4 acre with more than 150’ of lakefront, this is one of Winter Park’s premier lakefront properties. Once you enter the home you instantly see the original detail that you cannot reproduce today. Downstairs you will find the expansive family room overlooking the back yard and the lake, formal dining room, living room, Florida room, study, and chef’s island kitchen with professional grade appliances. Off the kitchen is a stairwell down to the +/-3,000 bottle climate controlled wine cellar. Upstairs houses the master bedroom suite and 3 other bedrooms. Interior features include 2 wood burning fireplaces (natural gas starter), gorgeous mouldings, built-ins, and French doors throughout; beautiful oak hardwood and tile floors; and detailed tongue & groove and beamed ceilings. Outside has multiple entertaining areas including poolside and lakeside vistas, a wonderful patio under a majestic Live Oak, huge back yard, and boathouse with power boat lift and rooftop deck, all surrounded by meticulously maintained landscape and grounds. Truly a classic and beautiful Winter Park estate for the ages.