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
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 4895000 Bedrooms 6 Bathrooms (Full) 7 Square Footage 10493 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 4595000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 7224 Square Footage Source Measured 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 4500000 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
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
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.
MLS # O5522419 Price 3700000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 6272 Square Footage Source Public Records 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 3700000 Bedrooms 5 Bathrooms (Full) 6 Square Footage 8310 Square Footage Source Appraisal Status Active
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!
MLS # O5519106 Price 3595000 Bedrooms 4 Bathrooms (Full) 4 Square Footage 5731 Square Footage Source Appraisal 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
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!
MLS # O5517710 Price 3495000 Bedrooms 4 Bathrooms (Full) 4 Square Footage 4686 Square Footage Source Builder 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
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 # O5513210 Price 3350000 Bedrooms 3 Bathrooms (Full) 3 Square Footage 4237 Square Footage Source Builder 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 3295000 Bedrooms 4 Bathrooms (Full) 3 Square Footage 4908 Square Footage Source Appraisal 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 3195000 Bedrooms 0 Bathrooms (Full) 0 Status Active
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.
MLS # O5473303 Price 3150000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 6025 Square Footage Source Public Records Status Active
This rustic modern Parade of Homes winner was custom built with extreme care and thought for the most discerning buyer. No detail has been overlooked, creating spaces that are excellent for both entertaining and living. Mahogany entry door leads to an outdoor lanai complete with pool, dining, and lounge. Retractable screens that can create indoor/outdoor space with a push of a button. Amazing chef’s kitchen with natural gas burners, a steam oven, three convection and a Wolf pizza oven surrounded by custom cabinetry and a barrel tiled ceiling. A separate entertaining grill area overlooking family room. Motorized sliding glass doors completely retract to blend interior and exterior. Luxurious downstairs master retreat with large sitting room, two-sided fireplace and access to lanai through motorized sliding doors. Master bath with his and her water closets, steam shower, massage room with adjoining cedar lined dry sauna. Downstairs office, attached and detached guest room, allows for one floor living. Second floor has two bedrooms, workout area, and flex living space with private balcony. Whole home automation system, theater room, foam insulation, double pane Hurd windows, refrigerated wine room, fifteen security cameras, Crestron audio system, Auto lighting system, and five car capacity garages. Located close to Downtown Winter Park, with quick access to Baldwin, Audubon, and Downtown Orlando makes this a prime location. Property is leased until 5/31/2018.
MLS # O5461972 Price 2990000 Bedrooms 5 Bathrooms (Full) 5 Square Footage 6345 Square Footage Source Public Records 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