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Top 30 Most Luxurious Homes for sale In Orlando 

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9291 Point Cypress Drive, Orlando image
9291 Point Cypress Drive, Orlando $25,000,000

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
9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $24,995,000 ▼

Perfectly positioned on 18 acres of lakefront property with meticulously manicured grounds, this walled and gated compound includes apprx 614 feet of pristine lake fronta...

  • 7 Beds
  • 14.5 Baths
  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9306 Blanche Cove Drive, Windermere image
9306 Blanche Cove Drive, Windermere $17,500,000

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
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
525 E Jackson Street Unit 28 units, Orlando image
525 E Jackson Street Unit 28 units, Orlando — The Jackson $16,000,000

The Jackson is a Boutique Mid-rise Condo Building Located in The charming Thornton Park Arts and Theatre District in Downtown Orlando Florida. Buy 28 condominiums in this...

  • 61 Beds
  • 52 Baths
  • Jackson SubDv.
  • 32801 Zip Code
9200 Bentley Park Circle, Orlando image
9200 Bentley Park Circle, Orlando $15,000,000

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
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… This spectacular residence is located on the Isle of Sic...

  • 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
1233 Castle Pines Court, Reunion image
1233 Castle Pines Court, Reunion $9,999,000

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
350 Muirfield Loop, Reunion image
350 Muirfield Loop, Reunion $9,650,000

Indulge in the ultimate vacation experience at this incredible expansive 13,000+-sq ft custom holiday retreat just moments from Disney in the one and only Reunion Resort ...

  • 12 Beds
  • 12.5 Baths
  • Reunion West Vlgs North SubDv.
  • 34747 Zip Code
10030 Enchanted Oak Drive, Golden Oak image
10030 Enchanted Oak Drive, Golden Oak $9,500,000

Located in the coveted Carolwood Reserve neighborhood of Golden Oak at Walt Disney World® Resort, this elegant, custom-built home offers a harmonious blend of modern comf...

  • 6 Beds
  • 6.5 Baths
  • Golden Oak Ph 01c SubDv.
  • 32836 Zip Code
510 Muirfield Loop, Reunion image
510 Muirfield Loop, Reunion $9,250,000 ▲

Transferrable Active Reunion Resort Memberships. Interior of Home is Complete! Pool & Screen Enclosure to be completed by March 31, 2023. List Price reflects home to be c...

  • 12 Beds
  • 14.5 Baths
  • Reunion West Vlgs North SubDv.
  • 34747 Zip Code
1190 N Park Avenue, Winter Park image
1190 N Park Avenue, Winter Park $8,500,000 ▼

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acre...

  • 8 Beds
  • 5.5 Baths
  • 0000 SubDv.
  • 32789 Zip Code
11940 Lake Butler Boulevard, Windermere image
11940 Lake Butler Boulevard, Windermere $8,250,000 ▲

UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300’ SEAWALL. This private, gated lakefront home is set on 2.4 acres in old Windermere, with over 6,500 S...

  • 5 Beds
  • 6.5 Baths
  • Metcalf Park Rep 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
525 Hillview Drive, Altamonte Springs image
525 Hillview Drive, Altamonte Springs $8,000,000 ▼

If your dream was to build your PERFECT community in the heart of Altamonte Springs then these lots are for you! These beautiful lots are located in a unique, plated sin...

  • 2 Beds
  • 1 Baths
  • 300 SubDv.
  • 32714 Zip Code
529 Hillview Drive, Altamonte Springs image
529 Hillview Drive, Altamonte Springs $8,000,000

If your dream was to build your PERFECT community in the heart of Altamonte Springs then these lots are for you! These beautiful lots are located in a unique, plated sin...

  • 4 Beds
  • 2 Baths
  • 300 SubDv.
  • 32714 Zip Code
11205 Bridge House Road, Windermere image
11205 Bridge House Road, Windermere $7,900,000

A home designed for entertaining and intimate gatherings focused on comfort, convenience, and functionality. Welcome to the guarded gated community of Reserve at Lake But...

  • 6 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code
1311 Via Tuscany, Winter Park image
1311 Via Tuscany, Winter Park $7,900,000 ▲

Casa Bianca, the extraordinary Winter Park estate, has entered the market for the first time available in over 40 years. Perfectly positioned on the corner of Via Tuscany...

  • 7 Beds
  • 6.5 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
10217 Symphony Grove Drive, Orlando image
10217 Symphony Grove Drive, Orlando $7,800,000

Imagine a fairytale residence where dreams really come true. A masterpiece in every sense of the word; a home elegantly crafted with the finest hand-selected materials on...

  • 5 Beds
  • 5.5 Baths
  • Golden Oak Phase 5 SubDv.
  • 32836 Zip Code
5139 Isleworth Country Club Dr, Windermere image
5139 Isleworth Country Club Dr, Windermere $7,500,000

With a fabulous location along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this expansive estate showcases just under 14,000 squar...

  • 7 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
501 Muirfield Loop, Reunion image
501 Muirfield Loop, Reunion $7,499,000 ▼

THE MAGICAL MANSION – Dreams do come TRUE. Welcome to Reunion Resort, and one of the most iconic one-of-a-kind properties in the world. This 9 bedroom, 11.5 bath, 13,58...

  • 9 Beds
  • 11.5 Baths
  • Reunion West Vlgs North SubDv.
  • 34747 Zip Code
10988 Down Yonder Lane, Windermere image
10988 Down Yonder Lane, Windermere $7,495,000 ▲

Pre-Construction. To be built. Rare, Exclusive Lakefront property in Windermere, Florida. Front and rear water views! Gated community with only three home sites. Herein l...

  • 4 Beds
  • 4.5 Baths
  • Lake Down Estates SubDv.
  • 34786 Zip Code
9736 Chestnut Ridge Drive, Windermere image
9736 Chestnut Ridge Drive, Windermere $7,388,000

Pre-Construction. To be built. Featuring an exceptional setting along the shores of beautiful Lake Bessie with gorgeous sunset views, this five-bedroom estate will be bui...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9832 Laurel Valley Drive, Windermere image
9832 Laurel Valley Drive, Windermere $7,250,000 ▼

Stunning water views and **captivating sunsets** will take your breath away at this exquisite lakefront Estate. Perfectly situated on the shores of Lake Butler and the 1...

  • 6 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11947 Lake Butler Boulevard, Windermere image
11947 Lake Butler Boulevard, Windermere $7,035,000

Pre-Construction. To be built. Your contemporary work of art awaits. Located in the Town of Windermere on the famed Lake Butler Blvd. is a beautiful 1.2-acre plot of land...

  • 6 Beds
  • 6.5 Baths
  • Lake Butler Estates SubDv.
  • 34786 Zip Code
9838 Laurel Valley Drive, Windermere image
9838 Laurel Valley Drive, Windermere $7,000,000

Majestic Lake Butler lakefront, Sunset views, Disney fireworks and the 15th hole of Isleworth's renowned championship golf course. As far as location goes, this home has ...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
1014 Jack Nicklaus Court, Reunion image
1014 Jack Nicklaus Court, Reunion $6,900,000 ▼

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
5020 Down Point Lane, Windermere image
5020 Down Point Lane, Windermere $6,750,000 ▼

This stunning estate is the epitome of luxury Windermere lakefront living. Designed by legendary architect John Henry, this exquisite lakefront residence is perfectly pos...

  • 8 Beds
  • 8 Baths
  • Sunset Bay Rep SubDv.
  • 34786 Zip Code
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