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Top 30 Most Luxurious Homes for sale In Orlando 

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9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $30,000,000

Nestled on 18 acres of pristine lakefront property, this exceptional estate offers a sanctuary of unparalleled beauty. With approximately 627 feet of frontage on Lake Dow...

  • 7 Beds
  • 14.5 Baths
  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9291 Point Cypress Drive, Orlando image
9291 Point Cypress Drive, Orlando $19,500,000 ▼

Welcome to Entrelagos, an extraordinary estate located on a private peninsula between Lake Sheen and Lake Tibet on the prestigious Butler Chain of Lakes in Windermere Flo...

  • 12 Beds
  • 13.5 Baths
  • Cypress Point Ph 02 SubDv.
  • 32836 Zip Code
10242 Summer Meadow Way, Orlando image
10242 Summer Meadow Way, Orlando $19,000,000

There are very few times when one of the most exclusive properties in the world becomes available, but now is that time. Nestled within Golden Oak at the Walt Disney Worl...

  • 7 Beds
  • 7.5 Baths
  • Golden Oak Phase 3 SubDv.
  • 32836 Zip Code
1220 N Park Avenue, Winter Park image
1220 N Park Avenue, Winter Park $17,486,000 ▲

Casa del Mondo, known as House of the World on Park Avenue in Winter Park, is a gated estate situated on Winter Park Chain of Lakes in the the most exclusive location in ...

  • 7 Beds
  • 5.5 Baths
  • Twelve Oaks SubDv.
  • 32789 Zip Code
9306 Blanche Cove Drive, Windermere image
9306 Blanche Cove Drive, Windermere $16,500,000 ▼

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
1461 Via Tuscany, Winter Park image
1461 Via Tuscany, Winter Park $16,000,000

Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue...

  • 5 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
10151 Enchanted Oak Drive, Golden Oak image
10151 Enchanted Oak Drive, Golden Oak $13,800,000

This sprawling Mediterranean masterpiece welcomes you to a lifestyle defined by luxury and attention to detail. Enter through beautiful double doors into an exquisite gra...

  • 7 Beds
  • 7.5 Baths
  • Golden Oak Ph 1c SubDv.
  • 32836 Zip Code
9200 Bentley Park Circle, Orlando image
9200 Bentley Park Circle, Orlando $12,888,000 ▼

This incredible estate known as 'Bentley Hall' sits on a massive 2 Acre lot located in the heart of Central Florida just minutes from Walt Disney World and Universal! Wor...

  • 7 Beds
  • 8.5 Baths
  • Bentley Park 2nd Rep SubDv.
  • 32819 Zip Code
10297 Summer Meadow Way, Golden Oak image
10297 Summer Meadow Way, Golden Oak $11,995,000

Drawing inspiration from historic Italianate architecture, this exquisite home located in the Four Seasons Private Residences Orlando feels like a destination on its own....

  • 5 Beds
  • 6.5 Baths
  • Golden Oak Ph 3 SubDv.
  • 32836 Zip Code
11301 Bridge House Road, Windermere image
11301 Bridge House Road, Windermere $11,995,000

Stunning modern masterpiece situated in Windermere's Reserve on Lake Butler Sound's most coveted waterfront lot. Known as "Overjoy" for its location on the sparkling wate...

  • 5 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
4 Isle Of Sicily, Winter Park image
4 Isle Of Sicily, Winter Park $10,950,000

Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… Extremely RARE opportunity to purchase a spectacular re...

  • 5 Beds
  • 5.5 Baths
  • Isle Of Sicily SubDv.
  • 32789 Zip Code
310 Saddleworth Place, Lake Mary image
310 Saddleworth Place, Lake Mary $10,000,000 ▲

Welcome to a one of kind masterpiece located in North Seminole County's subdivision of Heathrow. Situated on over 3 acres as you enter this Estate the entire property is ...

  • 14 Beds
  • 14.5 Baths
  • Heathrow/Chestnut Hill SubDv.
  • 32746 Zip Code
10254 Summer Meadow Way, Orlando image
10254 Summer Meadow Way, Orlando $9,999,950

Indulge in a truly enchanting lifestyle in this masterpiece of modern luxury, Once Upon A Dream. Thoughtfully positioned on a coveted corner lot, this modern architectura...

  • 5 Beds
  • 5.5 Baths
  • Golden Oak Ph 3 SubDv.
  • 32836 Zip Code
1233 Castle Pines Court, Reunion image
1233 Castle Pines Court, Reunion $9,800,000 ▼

One of Orlando's most unique and successful short-term rental investment homes is for sale. This magnificent 3-story, 10 bedroom, 11,000sq ft brilliantly designed home...

  • 10 Beds
  • 12.5 Baths
  • Reunion West Village 03a SubDv.
  • 34747 Zip Code
11450 Nellie Oaks Bend, Clermont image
11450 Nellie Oaks Bend, Clermont $9,000,000

AMAZING 54 ACRE private LAKEFRONT home on the Clermont chain of lakes with incredible, steady INCOME. This is a fully furnished, turnkey property with bookings in place f...

  • 12 Beds
  • 8.5 Baths
  • Acreage & Unrec SubDv.
  • 34711 Zip Code
9725 Vista Falls Drive, Golden Oak image
9725 Vista Falls Drive, Golden Oak $8,995,000

Artfully designed as a conversation piece for the ages, this elegant Tuscan retreat exemplifies the fairytale lifestyle. Disney touches throughout are inspired by legenda...

  • 5 Beds
  • 5.5 Baths
  • Golden Oak Ph 1c SubDv.
  • 32836 Zip Code
5200 Isleworth Country Club Dr, Windermere image
5200 Isleworth Country Club Dr, Windermere $8,975,000

This magnificent estate is located on the eighth fairway of the Isleworth Golf and Country Club golf course. Step through the front doors and be captivated by the grandeu...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
510 Muirfield Loop, Reunion image
510 Muirfield Loop, Reunion $8,650,000

Discover unmatched luxury in this modern masterpiece spanning 15,319 square feet, blending indoor and outdoor living seamlessly. Live the ultimate Florida luxury lifestyl...

  • 12 Beds
  • 14.5 Baths
  • Reunion West Vlgs North SubDv.
  • 34747 Zip Code
350 Muirfield Loop, Reunion image
350 Muirfield Loop, Reunion $8,425,000

Prepare to embark on a journey where luxury knows no bounds. This extraordinary 13,000 square feet custom property boasts 12 bedrooms, each accompanied by its own ensuite...

  • 12 Beds
  • 12.5 Baths
  • Reunion West Vlgs North SubDv.
  • 34747 Zip Code
6432 Deacon Circle, Windermere image
6432 Deacon Circle, Windermere $8,300,000

Welcome to this magnificent lakefront estate in the Isleworth Country Club Community. This exceptional property offers the epitome of luxury living, combining a classic ...

  • 5 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11035 Schooner Way, Windermere image
11035 Schooner Way, Windermere $8,250,000 ▲

Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineering in the tranquility of the so...

  • 7 Beds
  • 5.5 Baths
  • Marina Bay Estates SubDv.
  • 34786 Zip Code
6120 Kirkstone Lane, Windermere image
6120 Kirkstone Lane, Windermere $7,900,000 ▼

Lake Butler Luxurious Lakefront Estate - Exquisite Custom-Built Residence! Welcome to an opulent lakefront estate that epitomizes luxury living. This magnificent cust...

  • 6 Beds
  • 6.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
654 W Morse Boulevard, Winter Park image
654 W Morse Boulevard, Winter Park $7,600,000

Distinctive, inspirational & harmonious. This newly constructed contemporary estate was designed by internationally respected architect, Kamal Rizk. The unique fusion of ...

  • 5 Beds
  • 7.5 Baths
  • Morse & Pennsylvania Twnhms SubDv.
  • 32789 Zip Code
10988 Down Park Lane, Windermere image
10988 Down Park Lane, Windermere $7,440,000 ▼

One or more photo(s) has been virtually staged. Pre-Construction. To be built. New Street name. New photos/renderings capturing the actual design finishes included in pl...

  • 4 Beds
  • 4.5 Baths
  • Lake Down Estates SubDv.
  • 34786 Zip Code
901 Golden Bear Drive, Reunion image
901 Golden Bear Drive, Reunion $7,299,000

Under Construction. One of the last opportunities to own a brand new custom vacation home on beautiful Golden Bear Dr. One of the first truly modern homes in Reunion Re...

  • 11 Beds
  • 11.5 Baths
  • Reunion West Village North SubDv.
  • 34747 Zip Code
11019 Bridge House Road Unit R, Windermere image
11019 Bridge House Road Unit R, Windermere $7,250,000

This Jones- Clayton built masterpiece set behind the guarded gated entrance of Reserve at Lake Butler Sound will leave you speechless around every corner. This custom one...

  • 7 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
6125 Grosvenor Shore Drive, Windermere image
6125 Grosvenor Shore Drive, Windermere $7,150,000 ▼

Welcome to this marvelous lakefront home at the desirable Keene’s Pointe community! Built by highly regarded custom home builders Goehring & Morgan on a 4-acre lot, this ...

  • 6 Beds
  • 7 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9086 Mayfair Pointe Drive, Orlando image
9086 Mayfair Pointe Drive, Orlando $6,950,000 ▼

The 2017 New American Home is perfectly situated along the back nine of Lake Nona Golf & Country Club’s world-renowned championship golf course, cutting-edge sustainabili...

  • 5 Beds
  • 6.5 Baths
  • Lake Nona Estates SubDv.
  • 32827 Zip Code
1014 Jack Nicklaus Court, Reunion image
1014 Jack Nicklaus Court, Reunion $6,600,000 ▼

Come tour this completely turn-key Luxury Mansion which sits directly behind the Jack Nicklaus 18th hole in Reunion Resort. Located within the Exclusive BEAR'S DEN priva...

  • 10 Beds
  • 10.5 Baths
  • Reunion West Fairways 17 & 18 SubDv.
  • 34747 Zip Code
9139 Tibet Pointe Circle, Windermere image
9139 Tibet Pointe Circle, Windermere $6,500,000

Windermere Lakefront on Butler Chain of Lakes in guard-gated Keene’s Pointe Neighborhood. Entertainer’s paradise featuring over 10,000 square feet of Mediterranean luxury...

  • 6 Beds
  • 6.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
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