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9508 Windy Ridge Rd Windermere, FL 34786

$30,000,000
6 Beds
14 Baths
51,000 SqFt
Status Active
MLS # O5412382
Property Type Single Family Home
Private Windermere lakefront compound with 18 acres on Lake Down on the Butler Chain offering an unparalleled presence and prestige in Central Florida’s most desirable location. This walled and gated compound boasts a 25,000 sqft. state-of-the-art family residence, a 5,600 sqft grand lodge with catering kitchen and large entertainment hall, a 4,000 sqft paneled garage with 20 ft. ceilings for car collectors, a separate office with guest apartment, a 3,800 sqft storage building with 20 ft. ceilings, staff quarters, and massive 25 meter pool. The residence combines the warmth of classic Georgian architecture with modern comfort. The grand entry invites guests with a floating mahogany staircase, paneled walls, and distinctive Murano chandeliers. Generous art gallery leads to a grand living room with furniture quality mahogany walls and expansive lake views. The enormous kitchen and family room is perfect for gatherings within its warm cypress walls and honey-onyx floors. The chef’s dream kitchen with all amenities including a salamander for warming and broiling, a double convection oven, an extra stand-alone double convection oven, and a 72 cubic ft. refrigerator and 72 cubic ft. freezer. Two staircases or fully paneled ADA commercial elevator access the second floor featuring 4 bedroom suites, an 85' grand parlor with 20 ft. ceilings, and a screened porch with southern lakefront views and Disney fireworks nightly. An exceptional compound for the most discriminating buyer.

Windermere FL 34786

$18,950,000
9 Beds
17 Baths
20,240 SqFt
Status Active
MLS # O5498420
Property Type Single Family Home
Presenting Central Florida’s most exquisite Lake Butler estate tucked behind the secured manned gates of Lake Butler Sound. Offering 20,240 sq ft under air (31,000 gross), on nearly 5 acres and 547 feet of lake frontage, this double-lot oasis offers a magnificent residence with multiple outdoor living and entertaining areas, private guest quarters, 8-car garage, lighted tennis court with basketball, sand volleyball, citrus orchard, zip line, children's treehouse with electricity, and a resort pool with grotto and swim up bar with hibachi grill. Exceptional interior amenities in this 9 bedroom, 17 bath mansion include a two-lane bowling alley, complete fully-equipped sports bar with pool table, theater, full gym clubhouse, large arcade, elevator, caterers’ kitchen, formal dining room with adjacent children’s dining room, wine and ventilated smoking lounge- plus two private wings with bedrooms and separate living areas with kitchenettes. The spectacular master wing includes a bedroom retreat with sitting area, bath with double showers, private outdoor showers, double toilet rooms, a separate steam and sauna room bath, his and her closets, private salon, laundry room, and recreation room or second gym with motor court access. State of the art smart home technology controls music, lighting and video surveillance. Multiple balconies, outdoor kitchens, and recreation areas include a screened boat dock with sundeck. An unrivaled property securely positioned within one of Windermere’s most exclusive communities.

5536 Isleworth Country Club Dr Windermere, FL 34786

$15,000,000
7 Beds
9.5 Baths
13,519 SqFt
Status Active
MLS # O5394385
Property Type Single Family Home
Poised on a private cul-de-sac overlooking Isleworth’s 14th fairway and the beautiful Lake Butler, this island-inspired estate spans three home sites totaling 1.89 acres. The sprawling floor plan encompasses more than 13,000 square feet of living space, with elegant appointments throughout. The resplendent interior showcases formal living and dining rooms, each accented by elegant fireplaces and chandeliers. Designed for two chefs, the kitchen features three islands, two Jenn-Air stoves with gas cooktops and three Sub-Zero 700 Series refrigerators. Hand-tufted, leaf-patterned carpet and oculus windows adorn the distinguished master suite, which also boasts a private bath with two rain showerheads and a basin bathtub. A heated pool, grotto-style spa, shimmering waterfall and private boat dock create a breathtaking menagerie along the back nine. Additional highlights include an exercise room, guest house and separate caretaker’s cottage.

5115 Fairway Oaks Dr Windermere, FL 34786

$10,999,000
7 Beds
11 Baths
15,063 SqFt
Status Active
MLS # O5433535
Property Type Single Family Home
A sprawling floor plan and a prime setting on 3.76 acres along the shores of Lake Bessie define this exquisite seven-bedroom residence. Through a pair of arched French doors with glass and iron detail, the foyer opens to a stunning two-story living room where dramatic floor-to ceiling windows allow an abundance of natural light while capturing the stunning water views. A wealth of unique finishes such as imported stone and antique details travel throughout the master-designed floor plan, from the formal dining room, kitchen and breakfast area to six en -suite bedrooms and a detached guest house. Built for both business and leisurely pursuits, the 14,842-square-foot home also features an impressive two-story office with custom library as well as a large game room with beautiful hardwood floors, custom ceiling and a covered balcony from which to take in the panoramic water views. The expansive grounds capture the best in Florida lakefront living, with a custom swimming pool and spa, sparkling water fountains and impeccably manicured landscaping.

5318 Isleworth Country Club Dr Windermere, FL 34786

$8,500,000
6 Beds
8.5 Baths
11,182 SqFt
Status Active
MLS # O5441428
Property Type Single Family Home
Characterized by a lovely English garden designed to maximize its prime golf-front location, this estate is unparalleled in Isleworth. Beyond the circular driveway with fountain and porte-cochere entry, a pair of French doors open to the grand foyer featuring a curved staircase, wine cellar and polished marble floors with an intricate medallion inlay—all leading graciously into the more than 11,000-square-foot interior of this beautiful estate. Built by leading custom home builder Pellegrini Homes, the master-designed floor plan draws every room toward the home’s most impressive feature: a magnificent two-story indoor swimming pool. The main floor features formal living and dining rooms, a home office, kitchen and master suite, while the upper level hosts the game room and additional en-suite bedrooms. In each room, discover a ceiling unique to that particular space—a detail that was hand-selected by the homeowners to create a truly unique living experience. The grounds showcase sprawling gardens with a custom fountain, walking paths, a butterfly garden, and impeccably maintained landscaping as well as a private motor court flanked by a pair of two-car garages.

161 Palmer Ave Winter Park, FL 32789

$7,995,000
7 Beds
12 Baths
17,649 SqFt
Status Active
MLS # O5511735
Property Type Single Family Home
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!...

1204 N Park Ave Winter Park, FL 32789

$7,495,000
6 Beds
8.5 Baths
8,766 SqFt
Status Active
MLS # O5494384
Property Type Single Family Home
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 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...

5354 Isleworth Country Club Dr Windermere, FL 34786

$7,225,000
5 Beds
6 Baths
9,811 SqFt
Status Active
MLS # O5405442
Property Type Single Family Home
Seller Requirement: Buyer must produce proof of funds at full listing price. Beautifully mirrored in Hourglass Pond, this home was designed to reflect the elegance of an old, Italian villa positioned on an oversized lot with more than an acre of lush, manicured gardens. Globally sourced materials, including medallions of ancient terracotta, marble and granite retrieved from the same Vatican quarries outside Rome. Down the brick-paver driveway, through the honed-marble framed front doors, you are welcomed by Jerusalem limestone and a sweeping custom wrought iron crafted staircase. Overlooking hourglass pond is the kitchen encompassed by a great room, dining room and a breakfast nook and bar. The bathroom features beautiful ceilings, dual vanities, showers and his-and-her water closets, and leads to a private bath and Jacuzzi located on the outside terrace and garden area. The covered breezeways run from the main house to the five-car garage and golf-car garage. Nestled in the backyard is a 12-foot deep pool with spa, half-basketball court and summer kitchen. A walkway leads to the guest house, which includes a living room offering lake views and large bedroom with two king-sized beds, beautiful wood doors and a walk-in closet. Gracious living at its finest, this home offers a theater and billiard room. Additional unique features include Jacuzzi tubs in all bathrooms, a rose garden, fruit trees and a security system. Important works of art and select furniture may be available.

5410 Osprey Isle Ln Orlando, FL 32819

$6,900,000
7 Beds
13 Baths
14,477 SqFt
Status Active
MLS # O5421264
Property Type Single Family Home
One of a kind custom built fully furnished Grand Estate on 2.4 acres of lush Florida landscaping along 450 feet of waterfront on Lake Chase of the Butler Chain of Lakes. 23’ grand entrance with mosaic tile floor, stained glass rotunda and twin glass staircases welcome you inside. Explore the gourmet kitchen, formal dining room, formal living room with magnificent 2 story round glass wall over looking pool and waterfront, unique large round theater room, 2 elevators, huge game room and massive upstairs master suite complete with wet bar, fireplace, spa bath, his and hers steam showers, walk in closets, separate sitting room/nursery and tons of storage. Walk outside to large indoor gym with full bath, 2 outdoor fireplaces, outdoor theater, large hot tub, lighted tennis/basketball court, and covered multi-boat house. A true entertainers dream home complete with professional sound studio, disco and separate 2-story guest quarter’s with full kitchen and garage. Isle of Osprey is an exclusive guard gated community of only 19 homes located within the world famous Bay Hill Golf community, only minutes to the attractions, restaurant row, and shopping.

5018 Latrobe Dr Windermere, FL 34786

$6,875,000
7 Beds
10 Baths
12,353 SqFt
Status Active
MLS # O5460974
Property Type Single Family Home
Gracious living at its finest, this exquisite French chateau offers a prime location overlooking the beautiful Lake Bessie within the renowned Isleworth Golf & Country Club. Elegant finishes, stonework and extensive marble throughout set the tone for the three-story home encompassing more than 12,300 square feet of living space. The main level boasts a beautiful foyer with grand staircase and opens to the formal living room with volume ceilings, a stone fireplace and breathtaking water views. The spacious kitchen boasts a warm mix of custom cabinetry and smooth granite, with appliances by Miele and Wolf—all overlooking a large family room with built-in media center and access to the screened balcony. Seven bedrooms – including two well-appointed master suites – create expansive retreats complete with individual closets and private baths. The main master suite also boasts a two-story closet leading to the first level, which offers an immaculate home theater, game room and card room. The fenced grounds take full advantage of the lakefront setting with an open-air pool and spa, ample deck space for lounging in the sun, and a screened, covered lanai with summer kitchen. Further highlights include an air-conditioned seven-car garage, boat dock, elevator and a wine cellar.

1016 Genius Dr Winter Park, FL 32789

$6,795,000
6 Beds
9 Baths
10,314 SqFt
Status Active
MLS # O5496008
Property Type Single Family Home
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!

9200 Bentley Park Cir Orlando, FL 32819

$6,450,000
5 Beds
7.5 Baths
15,892 SqFt
Status Active
MLS # O5195598
Property Type Single Family Home
FURNISHED ESTATE! Orlando's most significant estate boasts the grandeur, elegance and quality of yesterday - with today's conveniences! Gently lived in - Lovingly cared for - Looks NEW! Custom designed to meet needs of today's family with large Family Rm, Kitchen, granite counters, rich Mahogany Office, large Bonus Rm/Billiard Rm, 31'equipped Gym and oversized formal rooms for entertaining! Enter this impressive pillared Greek Revival estate, and step into an impressive 40' two-story Reception Foyer with grand twin staircases, beautiful hand-painted murals and a magnificent crystal chandelier hanging from the rotunda ceiling. Furnishings are invitingly grouped around a beautifully hand-carved fireplace in the 40' formal Living Rm, which mirrors the wealth of 18th century European homes. Palladium windows throughout are dressed in imported silks. A columned Gallery, lined with shimmering chandeliers, joins east and west wings, defining living areas and leading to privileged areas including a 36' MasterSuite with adjoining 18' luxurious Bath. From the dignified classic Corinthian columns at the front porte-cochere entry to the charming poolside Pavillion, which houses the Guest House in the rear, this estate is embraced by a beautiful formal landscape on approx.2 Acres! The family-friendly yet splendid 14,600 Sq.Ft. interior mirrors the splendor of European 18th century homes and speaks quality and beauty throughout every room. See attached Addendum for add. INFO. SELLER FINANCING! SEE VIRTUAL TOUR !!