Fabulous contemporary lakefront estate on apprx 2 acres walking distance to downtown Winter Park… A contemporary paradise with panoramic views of Lake Maitland on the 6-lake Winter Park chain of lakes. Designed by NBA star Horace Grant, expanded by current owner, and featured in the Wall Street Journal, this iconic estate is just a short walk to famed Park Avenue restaurants, bistros, wine bars and designer shops. Expansive walls of glass span the rear of the home overlooking the pool’s waterfall and panoramic elevated views across Lake Maitland, sitting on ~140-feet of lake frontage. A grand 2-story entrance greets you with a marble foyer w/ a gorgeous Chihuly chandelier and curved suspended staircase. Designed for the ultimate in entertaining, the 1st floor includes a gourmet kitchen, game room with bar, theater, gym, detached guest suite, gathering room with fireplace, bar and sliding glass walls opening to a screened lanai, summer kitchen and bath. A newly added expansive ballroom accommodates 200+ guests with wet bar and a service kitchen. An elevator showcasing original Chihuly glass grants access to the 2nd level with 5 bedroom suites & lavish master retreat w/ private balcony & ultimate privacy. The outdoor living was designed for large gatherings and features terraced gardens, spa, heated infinity-edge pool, boathouse and expansive grounds. This magnificent estate was built in 2000 and maintained to perfection by full-time house and maintenance managers available to transfer to new owners!...
MLS # O5511735 Price 7995000 Bedrooms 7 Bathrooms (Full) 7 Square Footage 17649 Square Footage Source Public Records Status Active
For the first time in almost 20 years, this one of a kind private estate on "chain of lakes" located in the prestigious Twelve Oaks peninsula and walking distance to downtown Park Avenue is becoming available... This unprecedented property is on a spacious ~1.25 acre double lot with 2 boathouses and apprx. 250' of frontage on Lake Maitland, this unique property is the ultimate private retreat... exquisite attention to detail throughout, stunning architectural design with gracious floor to ceiling windows that provide plenty of natural light and amazing lakefront vistas... Elegant 1st level Master retreat & 3 additional bedroom suites in Main residence, plus detached 2 bedroom suite guest house, 8 garages (6 at main house & 2 at guest house), resort style 72' long negative edge swimming/lap pool with separate heated spa, luxurious outdoor living with magnificent landscaping and lighting, plus unique "grandfathered" lake side exercise & billiards studio... Primary residence address is 1202 N Park Avenue & guest house property is 1204 N Park Avenue (separate deeds & both properties are included in listed price) The primary residence is apprx 6564sf, detached lakeside building 1000sf and the guest house apprx. 1202sf - totaling 8766sf under air, plus porches, extensive terraces and 6 garages for main house and 2 additional garages for guest house...
MLS # O5494384 Price 7495000 Bedrooms 6 Bathrooms (Full) 8 Square Footage 8766 Square Footage Source Public Records Status Active
This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park’s most prestigious estate lots. Situated high above expansive Lake Osceola and only a short walk from famed Park Avenue, this lot, with its prevailing breezes, towering cypress trees and breathtaking lake view will inspire visions of the most elegant of estate homes. Located down a long oak lined private driveway, just off of quite brick paved Seminole Drive, this lot provides the ultimate in secluded privacy in the heart of Old Winter Park. There is simply nothing else like it.
MLS # O5439246 Price 6900000 Bedrooms 0 Bathrooms (Full) 0 Status Active
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!
MLS # O5496008 Price 6795000 Bedrooms 6 Bathrooms (Full) 7 Square Footage 10314 Square Footage Source Builder Status Active
For the first time in almost 20 years, this one of a kind private estate on "chain of lakes" located in the prestigious Twelve Oaks peninsula and walking distance to downtown Park Avenue is becoming available... This unprecedented property is on a spacious lot with frontage on Lake Maitland, this unique property is the ultimate private retreat... exquisite attention to detail throughout, stunning architectural design with gracious floor to ceiling windows that provide plenty of natural light and amazing lakefront vistas... Elegant 1st level Master retreat & 3 additional bedroom suites, 6 garages, resort style 72' long negative edge swimming/lap pool with separate heated spa, luxurious outdoor living with magnificent landscaping and lighting, plus unique "grandfathered" lake side exercise & billiards studio...
MLS # O5509097 Price 5495000 Bedrooms 4 Bathrooms (Full) 6 Square Footage 6564 Square Footage Source Public Records Status Active
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…..
MLS # O5493376 Price 4995000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 7800 Square Footage Source Owner Provided Status Active
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!!!
MLS # O5484879 Price 4995000 Bedrooms 6 Bathrooms (Full) 7 Square Footage 10493 Square Footage Source Public Records Status Active
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.
MLS # O5486486 Price 4600000 Bedrooms 6 Bathrooms (Full) 7 Square Footage 7677 Square Footage Source Public Records Status Active
Winter Park Chain of Lakes estate site with opportunity to build new or restore. 5.06 acres per tax rolls with riparian rights. Buildable acreage of 1.82 acres. City says can put up to 26,162 square feet of structure on site or can restore old home and add on. Magnificent Property!
MLS # O5498770 Price 4250000 Bedrooms 0 Bathrooms (Full) 0 Status Active
LUXURIOUS LAKEFRONT ESTATE! This Winter Park Chain of Lakes Custom 3 car garage home has panoramic views of Lake Minnehaha w/ 110' of water frontage. The beautifully built mediterranean home was designed by Bernie Johnson of Johnson Estate Designs and built by Charles Clayton Construction. The living & entertaining areas are spacious & elegant, w/ sweeping views of the lake from almost every room. High end finishes throughout the home and extensive detailed millwork and ceiling details. Downstairs encompassing 5000 SQFT you'll find the master suite with sitting area and views of the lake, his and hers walk-in closets a spacious master bath with his and hers private toilets, Jacuzzi tub and large walk-in shower.
Downstairs you’ll also find breath taking lake views from the formal living room with a fireplace, dining room with limestone hand carved columns, Game / Billiard room with a large walk-in 1500 bottle thermostatically controlled wine cellar and full bar. Downstairs baths include 2 full Baths, Pool bath with steam sauna, and formal Powder bath. A huge family room with a wood burning fireplace and beam ceilings opens into the kitchen and large eating area a large guest bedroom with private bath and custom built in cabinets in study complete this home. This house was built for entertaining guests both inside and out. Don't miss the opportunity.
MLS # O5497898 Price 3950000 Bedrooms 5 Bathrooms (Full) 6 Square Footage 8310 Square Footage Source Appraisal Status Active
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.
MLS # O5509686 Price 3950000 Bedrooms 5 Bathrooms (Full) 4 Square Footage 4810 Square Footage Source Public Records Status Active
36+ acre site located right next to the planned Apopka Village Center. This property is perfect for possible residential development. The Apopka Village Center is going to be a 3,900 acre commercial and high density residential project, modeled similarly to Baldwin Park and the Winter Garden Village. There are several housing developments being built around this property making this land more and more valuable. Less than 2 miles from the new Wekiva Parkway Interchange which completes the outer beltway around metro Orlando. The zoning for this acreage has recently changed to "City" mixed use. Call today for more details!
MLS # O5346165 Price 3900000 Bedrooms 0 Bathrooms (Full) 0 Status Active
Magnificent Mid-Century Modern estate in downtown Winter Park setting walking distance to Park Ave, Winter Park Village & new Whole Foods… A resort style extremely private retreat you will never want to leave... Enjoy the clean lines and simple elegance of perfection with glass porcelain floors and dramatic floor to ceiling picture windows surrounding the tremendous “park like” setting courtyard from every room… Entertaining options are endless with multiple generous size living areas with wonderful high ceilings and light flooding in every room… Impressive entry with immediate paradise surrounding you bringing the outside in along with spacious seating area, designer lighting, tongue & grove ceiling, and wonderful dining area… Magazine quality sleek - sophisticated interiors, spacious multi-island commercial grade kitchen open to additional dining & casual gathering area… Display your own private art collection in gallery walls thru-out with lighting to enjoy for all… 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. Perfect home for the collection enthusiast with space for up to 20 cars or custom motor coach, boat(s), motorcycles & more in the over-sized air-conditioned garages with over 20 ft. of ceiling height & commercial rolling doors. This one-of-a-kind contemporary masterpiece in the heart of Winter Park and the ultimate in design, privacy, luxury, and security…
MLS # O5487045 Price 3750000 Bedrooms 5 Bathrooms (Full) 7 Square Footage 8900 Square Footage Source Owner Provided Status Active
Come see this extraordinary Lakefront Estate in premier neighborhood of Windsong Preserve Point. This stunning home features 100' frontage on Lake Berry. It was completely remodeled with the finest of materials. The gourmet kitchen features top of line built in appliances and oversized granite island. Wine lovers can rejoice with the built in wine cellar below the stairs. Beautiful travertine floors with solid wood accents can be seen throughout the living area. This home features 5 oversized bedrooms, movie theater, library, and five and half bathrooms. The back yard is simply breath taking, take a dip in your private pool and spa, while looking over the gorgeous Lake Berry, with a majestic Oak tree swaying in the background. Entertain friends in the game room upstairs, at the built in wet bar, in the formal dining room, or with your summer kitchen in the back. This home has it all, and it is centrally located in the heart of Orlando.
MLS # O5470579 Price 3700000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 6272 Square Footage Source Public Records Status Active
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.
MLS # O5398109 Price 3500000 Bedrooms 7 Bathrooms (Full) 7 Square Footage 7670 Square Footage Source Owner Provided Status Active
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.
MLS # O5500763 Price 3495000 Bedrooms 4 Bathrooms (Full) 3 Square Footage 4908 Square Footage Source Appraisal Status Active
Located in Windsong on a quiet cul-de-sac only 10 minutes from Downtown Orlando. This lot faces west and overlooks Rollins College. The total square footage of the lot is 64,407 sq. ft. (1.48 acres). There are five very beautiful large oak trees, one is about 350 years old and 15 cypress trees on the water. It is by far the best available vacant lot on the Winter Park Chain of Lakes. Plans are available for a gorgeous 9782 sq. ft. home that was designed by Randall Slocum, Architect.
MLS # O5504034 Price 3450000 Bedrooms 0 Bathrooms (Full) 0 Status Active
Phenomenal apprx 3.5-4 acre Lake Maitland estate property with water on 3 sides... Private setting on this one of a kind Chain of Lakes lakefront property with majestic live oaks & cypress trees around perimeter... A picturesque park like setting on a peninsula with panoramic water views of Lake Maitland, Lake Nina and canal frontage. Existing dock and boat lift on property. Build a lifelong dream gated estate -or- possibly split into 2 or 3 properties... inquire for survey, etc...
MLS # O5510323 Price 3450000 Bedrooms 0 Bathrooms (Full) 0 Status Active
Premier Park Avenue lakefront lot situated on just under an acre in the downtown corridor on Lake Maitland. Expansive long and wide elevated views of the lake are enjoyed surrounded by canopy of majestic trees. Walking distance to famed Park Avenue upscale shops, fine dining, sidewalk cafes and the downtown golf course... Unique opportunity whereby lot is cleared, boathouse updated and ready for you to design and build your dream custom lakefront estate... survey available upon request.
MLS # O5510336 Price 3425000 Bedrooms 0 Bathrooms (Full) 0 Status Active
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!
MLS # O5513191 Price 3350000 Bedrooms 3 Bathrooms (Full) 3 Square Footage 4244 Square Footage Source Builder Status Active Living in Winter Park, FL
Winter Park is one of Central Florida’s most desirable places to live. Boutique stores, fine dining and year round events give Park Avenue in downtown Winter Park small town charm in a big city. Winter Park is a wonderful city which offers something for the whole family.
Home to Leu Gardens, Morse Museum, and annual art and craft fairs, fine arts and culture are easy access when in this beautiful city. Easy access to I-4 and two major hospitals, Winter Park Memorial Hospital & Florida Hospital Orlando.
History of Winter Park, FL
Established in 1858 as Lakeview, what became Winter Park in 1881 was chartered just six years later and developed as a winter resort for wealthy Northerners. This tranquil haven for rest and relaxation has evolved into an urban Mecca for travelers and residents alike. Incorporated in 1925, this Orange County community three miles North of Orlando is an epitome of what can happen when everyone works together for the greater good of the community.
Figures from the City of Winter Park show more than 28,486 residents as of 2015.
32789 – Search for homes in
Winter Park Median Income
$62,420, about $18,000 greater than 2015’s national average.
Notable City Ratings
Downtown Winter Park Historic District is listed on the National Register of Historic Places, along with eight buildings including Knowles Memorial Chapel at Rollins College and The Winter Park Country Club Clubhouse, Central Florida’s second oldest golf club.
Rollins College, Florida’s oldest private college, ranked by U.S. News and World Report in a tie for the
number one regional university in the South for 2016. Awards
Winter Park is the recipient of more than 100
awards just since 2002, including recognition from Governor Jeb Bush, the Center for Public Safety Excellence, Government Finance Officers Association, and Florida League of Cities. City Amenities
This culture committed to quality of life has notable collections of things to see and do in this oasis with a purpose. Experience a vibrant heartbeat of experiences at an unhurried pace:
Four museums and galleries 75 small and large parks, many dedicated to specific sports or interactions with nature Six institutions of higher learning Upscale shopping and dining Free, outdoor Wi-Fi access to the city’s Metro-Wireless network two hours a day Art in Chambers houses the city’s collection and showcases works by local artists Martin Luther King, Jr Park features a lake, fountain, community-built bridge set on 23 acres of sports and recreation facilities, and extra large playground. Dinky Dock features a fishing pier and swimming, two docks, park benches, picnic tables, grills, a beach, two boat ramps and restrooms. Mead Botanical Garden, part of one of the Great Florida Birding Trails, has unique features like an amphitheater, butterfly garden, boardwalk, and Geocaches. Ward Park is dedicated for baseball/softball fields, soccer/multi-purpose fields, and a football-track stadium. Fitness and bike trails, asphalt walking path, little league complex, olympic-sized pool, and a modern, disabled accessible playground. Major City Events
Winter Park Sidewalk Art Festival hosts over 250,000 visitors each year for fine art and music.
The 2016 Great Duck Derby will be February 27, featuring the famous rubber duck race.
The new Amtrak station is in a designated Quiet Zone, a set of standards established to minimize impact of noise once its
new SunRail® commuter rail service begins.
Thanks to outstanding city planning, residents still feel at home when throngs of visitors gather for some of the city’s largest annual events. The right real estate broker can assist you in finding the perfect Winter Park home.
Winter Park Real Estate for Sale