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Winter Park Luxury Homes, Winter Park Luxury Real Estate For Sale


(128) PROPERTIES

$6,995,000

1008 GENIUS - WINTER PARK, FL

1008 GENIUS WINTER PARK, FL 32789
6 Beds 7 Baths Square Ft: 10904
Single Family - MLS#: O5055027
Subdivision: windsong ests sec 1

Exquisite inside and out! This magnificent 6 bedroom American Tudor estate home is located in the Gated Estate Section of Windsong one of Winter Park's most desirable addresses and offers all the allure of fine lakefront living. Situated on a premier 2 acre lot with more than 532 linear feet of lakefront, this two level residence enjoys a picture perfect setting overlooking Lake Virginia & Lake Mizell part of the famed Winter Park chain of lakes offers spectacular sunrise & sunset views. Inside,…

Details for MLS# O5055027

$6,600,000

240 TRISMEN - WINTER PARK, FL

240 TRISMEN WINTER PARK, FL 32789
7 Beds 9 Baths Square Ft: 8000
Single Family - MLS#: S4679460
Subdivision: brewer e h

THIS LAKE FRONT ESTATE HOME IS LOCATED OFF THE BEAUTIFUL LAKE OSCEOLA AND WILL TRULY TAKE YOUR BREATH AWAY!TAKE YOUR BOAT FOR A SPIN OR SIMPLY ENJOY THE BEAUTY FROM YOUR MASTER BEDROOM WINDOW OR WIDOWS TOWER ON THE ROOF OF YOUR HOME. PLAY A GAME OF TENNIS AT YOUR VERY OWN PRIVATE TENNIS COURT THEN TAKE A DIP IN YOUR REFRESHING POOL OR RELAX IN YOUR HOT TUB. BESIDES THE MAGNIFICENT VIEWS, THIS EXTENSIVELY UPDATED & RENOVATED HOME OFFERS LOTS OF SPACE WITH A LIBRARY, EXERCISE ROOM, THEATER ROOM AND…

Details for MLS# S4679460

$5,250,000

1024 GENIUS - WINTER PARK, FL

1024 GENIUS WINTER PARK, FL 32789
7 Beds 7 Baths Square Ft: 13748
Single Family - MLS#: O5082831
Community: windsong Subdivision: windsong ests sec 1

Truly remarkable Lakefront Estate secluded on olde Winter Park's only gated private drive in the Estate Section of Windsong... Bermuda Traditional Island Colonial with contemporary elements... This 2 acre + site is situated on both Lk Virginia & Lk Mizell w/ panoramic sunrise & sunset views... This property is arguably the premier lakefront property on the Winter Park Chain of Lakes & affords the ultimate in privacy next to the Windsong Preserve... There are several expansive lanai's including a…

Details for MLS# O5082831

$4,950,000

1250 N PARK - WINTER PARK, FL

1250 N PARK WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 8207
Single Family - MLS#: O5098786
Subdivision: winter park

Exquisite lake front home situated on 157 ft on the shores of Lake Maitland in the heart of Olde Winter Park. Exclusive Winter Park chain of lakes. Amazing 1.5 acre lot is meticulously manicured. This gated estate custom built by Charles Clayton in 2001 with quality craftsmanship throughout. Downstairs master suite with sitting room and fireplace. Downstairs guest suite with private entrance. Rich mahogany paneled office/library with Fireplace. Gourmet kitchen boasts delightful breakfast nook. Fantastic…

Details for MLS# O5098786

$4,700,000

1551 VIA TUSCANY - WINTER PARK, FL

1551 VIA TUSCANY WINTER PARK, FL 32789
7 Beds 6 Baths Square Ft: 12800
Single Family - MLS#: O5019984
Subdivision: woodmere terr rep

Active With Contract. Accepting back-up offers. Beautiful 12,800 SqFt. mediterranean home designed by the Nasrallah Group currently under construction and is ready for stucco, drywall and finishes. This home is situated on 1.8 acres with approx. 250ft of waterfront on Lake Maitland, the largest lakeon the chain of lakes. Enjoy spectacular sunsets from its many porches from the covered outdoor living space and spa cabana. This home offers 7 bedrooms, 6 full baths and 2 powder rooms. It has a fantastic…

Details for MLS# O5019984

$3,495,000

1008 ANCHORAGE - WINTER PARK, FL

1008 ANCHORAGE WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 8973
Single Family - MLS#: O5031991
Subdivision: anchorage ests

Coastal Living in Winter Park, Enjoy this 'Santa Barbara' style home with expansive rooms detailed with river washed wood beams, Peruvian travertine and a reclaimed terra cotta roof.This fully furnished show place by Montanna & Associates boasts 5 bedrooms, includes 2 master suites, 5 full and 2 half baths, pool with fire pots, outdoor cigar terrace adjoining the gentlemen's lounge with theatre, and an extraordinary kitchen with every amenity. This fully gated estate is situated on a .58 acre lot,…

Details for MLS# O5031991

$3,399,000

110 OSCEOLA - WINTER PARK, FL

110 OSCEOLA WINTER PARK, FL 32789
5 Beds 4 Baths Square Ft: 6713
Single Family - MLS#: O4853377
Subdivision: osceola court

Sophisticated and stunning is this Winter Park Chain-of-Lakes estate. Only a short walk from Park Avenue, this five-bedroom pool home was custom built in 2004 with the finest materials and to the highest of standards and finishes. Brazilian Walnut and natural stone flooring is throughout the entire home. First floor amenities include a formal living room with fireplace, formal dining, a spectacular center-island kitchen overlooking the family room with stone fireplace, paneled library with fireplace…

Details for MLS# O4853377

$3,310,000

911 N PARK - WINTER PARK, FL

911 N PARK WINTER PARK, FL 32789
6 Beds 7 Baths Square Ft: 9161
Single Family - MLS#: O5090843
Subdivision: morseland gdns

Premier Park Avenue Winter Park Location! Crowned the Jewel of Winter Park this Stunning Mediterranean Style Residence features 6 Bedrooms, 7.5 Baths. Estate comprises approx. 9161 sq ft of gracious living accommodations sited on over half an acre. Home features solid oak hardwood flooring with decorative inlays and was professionally decorated with custom wall treatments. Walk to Winter Park's Renowned Park Avenue shopping district and golf course. Lushly landscaped exterior set behind Private…

Details for MLS# O5090843

$3,200,000

1020 N PARK - WINTER PARK, FL

1020 N PARK WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 8342
Single Family - MLS#: O4768678
Subdivision: mac donald robert dhu park sec

Breathtaking appointments at every turn! Collaboration between Maroon Fine Homes & Marquis Fine Homes offers a fully furnished classic estate on prestigious Park Avenue!There are too many features to list. The home has travertine marble flooring, beautiful wood finishes, and granite counters throughout. The bottom level boasts an eleborate movie theater, fitness center, fully equipped sports bar with all the audio visual equipment, and a large air/ humidity controlled wine cellar. The house is equipped…

Details for MLS# O4768678

$2,795,000

600 SEMINOLE - WINTER PARK, FL

600 SEMINOLE WINTER PARK, FL 32789
4 Beds 4 Baths Square Ft: 4957
Single Family - MLS#: O5088855
Subdivision: winter park old town

Wander down one of the most beautiful estate tree-lined brick streets in Winter Park and you'll find a private oasis on Lake Osceola. This home is nestled on approximately .87 acre and is truly within walking distance to Park Avenue, Farmers Market, Rollins and Winter Park Country Club. The spacious one-story floor plan takes advantage of stunning water views from almost every room, boasts open and inviting living spaces, large rooms and separate living and dining rooms. This home is perfect for…

Details for MLS# O5088855

$2,790,000

2219 AZALEA - WINTER PARK, FL

2219 AZALEA WINTER PARK, FL 32789
6 Beds 6 Baths Square Ft: 6684
Single Family - MLS#: O5100488
Subdivision: azalea place

Gorgeous Custom Lakefront home built by Liberty Development. First time offered. Feels like new! Situated on the lagoon that feeds into Lake Maitland. Stunning staircase that goes up three floors. Two Master Suites, one upstairs and one downstairs, both with wonderful lake views. Huge family room off the spacious kitchen, bonus room, exercise room, formal living and dining rooms, breakfast nook, and den with wet bar. Six total bedrooms and Six and one half baths. Three car garage and a roof top…

Details for MLS# O5100488

$2,695,000

1210 ALBERTA - WINTER PARK, FL

1210 ALBERTA WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 5245
Single Family - MLS#: O5099201
Subdivision: osceola summit

Premier English Manor Estate on secluded 3/4 acre site with lake frontage on Lake Osceola, exquisite craftsmanship, built-ins, moldings, soaring detailed ceilings, hardwood floors throughout, finest of finishes including slate, marble, granite, brick, extensive millwork/trim, 3 fabulous masonry gas fireplaces, expansive Master retreat with adjacent mahogany paneled library & private guest suite with separate outside entry on 1st floor, 2 secondary bedrooms are large suites upstairs... Elegant formal…

Details for MLS# O5099201

$2,695,000

1150 N PARK - WINTER PARK, FL

1150 N PARK WINTER PARK, FL 32789
4 Beds 4 Baths Square Ft: 4484
Single Family - MLS#: O5072506
Subdivision: macdonald robert dhu pk rep of

WOW!! A Park Avenue Lakefront home only a short stroll to the Park Avenue shops. This magnificent Winter Park chain of lakes home offers the best of the old and new.Totally renovated and updated in 2002. Beautiful hardwood floors throughout. Stunning lake views from most rooms. Gorgeous new kitchen featuring an open kitchen/family room, cherry wood cabinets, granite counters, Sub-Zero refrigerator and freezer drawers, gas cook top, and oversized island. Relax in your spacious family room with built-ins…

Details for MLS# O5072506

$2,600,000

789 BONITA - WINTER PARK, FL

789 BONITA WINTER PARK, FL 32789
5 Beds 6 Baths Square Ft: 6926
Single Family - MLS#: O5021307
Subdivision: comstock park

Stunning, one-of-a-kind five bedroom Winter Park estate home - meticulously designed with a Parisian and Tuscan influence. All details and finishes have been hand selected: imported French limestone and black walnut wood floors, hand plastered walls with organic limewash paints from Australia, solid Florida bald cypress beams hand hewn by a Florida artisan, custom fireplaces/mantles, large steel windows and French doors imported from England, and much much more. The European farm kitchen offers…

Details for MLS# O5021307

$2,395,000

1610 VIA TUSCANY - WINTER PARK, FL

1610 VIA TUSCANY WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 5980
Single Family - MLS#: O5089827
Subdivision: woodmere terr rep

Glamorous Tuscan Estate in the heart of the Via's. Impeccable construction with superb finishes. Every detail considered. Beautiful arched entry with wrought iron doors. Wonderful open floor plan offers views of the luxurious pool and covered lanai area. High-end custom kitchen with large island, china closet, butler's pantry, built-in desk and breakfast area. Summer kitchen with automatic screen great for entertaining. Master on the main with extravagant bath and closet. Four additional bedrooms,…

Details for MLS# O5089827

$2,365,000

1800 VIA AMALFI - WINTER PARK, FL

1800 VIA AMALFI WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 7530
Single Family - MLS#: O5097870
Subdivision: sicilian shores

Live in the Via's of Winter Park in this brand new Italian Inspired Tuscan Farm House Design. Walk to the Racquet Club! Dramatic floating Grand Staircase topped with silver flaked dome and magnificent chandelier as you enter the front door. These are someof the special features of this Five En Suite Bedroom home: Oversized kitchen and fully equipped service bar for entertaining, top of the line appliances, Bali imported Teak columns in family room, 23' ceilings throughout first floor, imported granite…

Details for MLS# O5097870

$2,200,000

275 E WEBSTER - WINTER PARK, FL

275 E WEBSTER WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 6712
Single Family - MLS#: O5086385
Subdivision: golfview terr

Outstanding Winter Park property.Every detail has been taken care of during the award winning renovation by one of the top kitchen and design companies in the country.Names like Siematic, Wolf, Miele, Smallbone and Sub Zero will greet you in this award winning kitchen. Music room, formal dinning room,casual dining room and family room grace the first floor of the property along with an amazing master bedroom with fireplace and soaring ceilings. Master bedroom opens to a patio area and pool.Master…

Details for MLS# O5086385

$2,199,999

4583 TIGUA ISLAND - WINTER PARK, FL

4583 TIGUA ISLAND WINTER PARK, FL 32792
5 Beds 4 Baths Square Ft: 6403
Single Family - MLS#: O5015501
Subdivision: antigua pointe

ANTIGUA POINTE. STUNNING MEDITERRANEAN DECOR. FORGED IRON FRONT DOORS LEAD TO TRAVERTINE AND GRANITE FOYER AND CIRCULAR STAIRCASE. EMBELLISHED WROUGHT IRON BANISTER AND LOFT WRAP AROUND 2ND FLOOR WHICH OPENS UP TO 24FT CREATIVE CEILING DESIGNS. FIVE BEDROOMS, FOUR FULL BATHS, HUGE GAMEROOM WITH LAKEVIEW TERRACE, CUSTOM BILLIARD AND HOME THEATRE ROOM COMPLETE WITH COMFORT CHAIRS. FIRST FLOOR 30X40 MASTER SUITE, LIVING, KITCHEN, FAMILY ROOM W/ GAS FIREPLACE OVER LOOK BEAUTIFUL BEAR GULLY LAKE. EXERCISE…

Details for MLS# O5015501

$2,100,000

2150 LAKE - WINTER PARK, FL

2150 LAKE WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 6022
Single Family - MLS#: O5101389
Subdivision: killarney point

Elegant traditional lakefront home on the N shore of Lake Killarney, picturesque lake views, expansive back yard with private boathouse, bright-open sophisticated floor plan, extensive moldings/columns, built-ins & ceiling details, beautiful hardwood floors, formal dining & living rooms, all generous size rooms, chef's island kitchen open to wonderful-warm family room w/ FP, French doors, Private spacious master retreat w/ sitting area & 2-sided FP along with his/her closets... This is a one owner…

Details for MLS# O5101389

$1,975,000

1099 N PARK - WINTER PARK, FL

1099 N PARK WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 5706
Single Family - MLS#: O5061692
Subdivision: morseland gdns

Don't miss this classic 5,706 square foot pool home situated on beautiful ? acre lot located in the heart of downtown Winter Park, Stroll casually to the stylish shops and cozy restaurants of Park Avenue and the popular Winter Park Golf Course.High end finishes are evident the minute you walk in this custom built home. Formal living and dining rooms, family room, gourmet kitchen with custom cabinetry, 3 fireplaces, hardwood flooring, extensive millwork & built-ins, spacious covered lanai, private…

Details for MLS# O5061692

$1,950,000

800 MAYFIELD - WINTER PARK, FL

800 MAYFIELD WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 5256
Single Family - MLS#: O5091276
Subdivision: kronenberger j

Le Manguier, an incomparable Winter Park estate replicated from a villa in the South of France. This Neo-Classical Regency inspired home is the pinnacle of luxurious comfort, privacy and unsurpassed elegance. Uniquely situated private location with canal frontage to WP chain of lakes. Seven foot high masonry ivy clad walls enclose entire property. House and poolhouse reappointed in 1988 with a new bedroom and bath addition in 2006 and new boathouse in 2004. Numerous Elegant Architectural Details…

Details for MLS# O5091276

$1,950,000

4095 SCARLET IRIS - WINTER PARK, FL

4095 SCARLET IRIS WINTER PARK, FL 32792
5 Beds 5 Baths Square Ft: 6895
Single Family - MLS#: O5086642
Subdivision: bear gully pointe

Luxurious Lakefront Estate in Gated Bear Gully Pointe. You will not want for anything! Enter the foyer to a dramatic double staircase, on the first floor you have a handsome library, elegant formal living and dining rooms, a wet bar complete with a salt water fish tank opening up to the dramatic family room and eat-in kitchen, then around the corner a welcoming bar and game room, you will love the spacious laundry room/craft room. Also a plus on the first floor is a Guest Suite off the pool. Three…

Details for MLS# O5086642

$1,899,000

475 LAKEWOOD - WINTER PARK, FL

475 LAKEWOOD WINTER PARK, FL 32789
4 Beds 3 Baths Square Ft: 5102
Single Family - MLS#: O5039667
Subdivision: osceola shores

Amazing Waterfront Home on Lake Osceola. Spectacular views from this stunning estate of Lake Osceola. The four bedroom three and three half bath home boasts over 5100 square feet and is located in Winter Park's Osceola Shores. Walk to Park Avenue!Mature landscaped grounds, pool with summer kitchen, dock, boat house with boat lift. A must see grand dining room with panoramic lake views perfect for entertaining. Gourmet kitchen with eating area overlooking family room with gorgeous arched windows…

Details for MLS# O5039667

$1,875,000

- WINTER PARK, FL

WINTER PARK, FL 32789
4 Beds 3 Baths Square Ft: 2894
Single Family - MLS#: O5070791
Subdivision: none

PARADISE. PERFECT FOR CELEBRITY OR ATHLETE OR ANYONE ELSE WHO DESIRES PRIVACY, NATURE AND CONVENIENCE. It is impossible to really describe the peacefulness this property brings to its owners day in and day out. When living at this refuge, it ispossible to have both extreme privacy while still being in the hub of activity and convenience. Your journey home begins along a 1,000 foot gravel drive through woods and over a small creek, passing by your private gated entrance. Once home, you have the feeling…

Details for MLS# O5070791

$1,850,000

1627 LOOKOUT LANDING - WINTER PARK, FL

1627 LOOKOUT LANDING WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 6108
Single Family - MLS#: O5046005
Subdivision: windsong lookounit landing

2002 Street of Dreams winner. This is a one of a kind residence with the finest finishes throughout. Some of those finishes include a gourmet chef's kitchen with granite counters and a marvelous island, stone fireplace, high-tech wiring throughout, winecellar, billiard and media rooms, full wet bar, indoor/outdoor FL room w/ picturesque views overlooking a beautiful pond with a fountain. Windsong is bordering Lakes Mizell, Berry and Virginia, and features 2 neighborhood pools one with a waterfront…

Details for MLS# O5046005
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The Chris Brown Team
Charles Rutenberg Realty

933 Lee Road
Suite 300
Orlando, FL 32810
Direct Phone: 407-327-6997
Email: ChrisBrown@Realtor.com