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Rolex Over $20,000

Welcome to the Rolex Over $20,000 page at Bob's Watches! Here, you'll find an exceptional collection of Rolex timepieces that represent the pinnacle of luxury and craftsmanship. Our selection includes some of the most coveted and prestigious models, each meticulously verified for authenticity and quality. Whether you're a seasoned collector or seeking a truly special investment piece, our expert buying guides and detailed descriptions will help you make an informed decision. Explore our collection and experience the ultimate in elegance and sophistication with a Rolex over $20,000.

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Rolex Day-Date 40 228349 White Gold
Rolex Day-Date
228349
40MM 18k White Gold, Diamond Bezel
Diamond Paved Dial , B&P (2023)
Rolex Day-Date President 128239 Blue Diamond Dial
Rolex Day-Date
128239
Blue Vignette Diamond Dial
36MM 18k White Gold, B&P (2024)
Rolex Daytona 116506 Platinum
Rolex Daytona
116506
40MM Platinum, Ice Blue Dial
Oyster Bracelet, B&P (2022)
Rolex Day-Date II Ref 218349 18k White Gold
Rolex Day-Date
218349
41MM 18k White Gold, President Band
Silver Diamond Dial, B&P (2015)
Rolex Sky-Dweller 336934 Oyster
Rolex Sky-Dweller
336934
Intense White Chromalight Dial
42MM Stainless Steel, B&P (2023)
Rolex GMT- Master II Ref 116719 White Gold Oyster Pepsi
Rolex GMT-Master
116719
Blue & Red Ceramic Pepsi
40MM 18k White Gold, B&P (2016)
Rolex Sky-Dweller 326135 Rose Gold
Rolex Sky-Dweller
326135
Chocolate Arabic Dial, Rolex Strap
42MM 18k Everose Gold, B&P (2013)
Used Rolex Submariner 18k Gold Model 16618
Rolex Submariner
16618
40MM 18k Yellow Gold, Oyster Band
Blue Dial & Timing Bezel (2000)
Pre-Owned Rolex Yacht-Master II Ref 116680
Rolex Yacht-Master
116680
44MM Stainless Steel, Oyster Band
Blue Ceramic Bezel, B&P (2016)
Rolex Daytona 116515 Rose Gold
Rolex Daytona
116515
Sundust Baguette DIAMOND Dial
40MM 18k Everose Gold, B&P (2017)
Rolex President 218235 Rose Gold
Rolex Day-Date
218235
Day-Date II Presidential Diamond Dial
41MM 18k Everose Gold, B&P (2013)
Pre-Owned Ladies Rolex Datejust 278384 Stainless Steel
Rolex Datejust
278384
31MM Stainless Steel, Diamond Bezel
Azzurro Blue Floral Motif, B&P (2024)
Rolex Daytona 116509 Black Mother of Pearl
Rolex Daytona
116509
40MM 18k White Gold, Oyster Band
Roman MOP Dial, B&P (2006)
Vintage Rolex Explorer II Ref 1655 Stainless Steel
Rolex Explorer
1655
Steve McQueen, Matte Black Dial
40MM Stainless Steel, Circa 1972
Rolex Day-Date 118238 White Roman Dial
Rolex Day-Date
118238
36MM White Roman Dial, Fluted Bezel
18k Yellow Gold, B&P (2005)
Rolex GMT-Master II Ref 116718 18k Yellow Gold
Rolex GMT-Master
116718
40MM 18k Yellow Gold, Ceramic Bezel
Black Superluminova Dial, B&P (2007)
Rolex Submariner 126619LB 18k White Gold
Rolex Submariner
126619
41MM 18k White Gold Cookie Monster
Blue Ceramic Bezel, B&P (2021)
Rolex President Day-Date 118348 Yellow Gold
Rolex Day-Date
118348
36MM 18k Yellow Gold, President Band
Champagne Wave Dial, B&P (2008)
Rolex Day-Date II Ref 218238 Roman Dial
Rolex Day-Date
218238
41MM 18k Yellow Gold, Fluted Bezel
Black Roman Dial, President Band
Rolex GMT-Master II Ref 116719 18k White Gold Pepsi
Rolex GMT-Master
116719
40MM 18k White Gold, Pepsi Bezel
Oyster Bracelet, B&P (2017)
Rolex President Day-Date II Ref 218239 Black Dial
Rolex Day-Date
218239
41MM 18k White Gold, President Band
Black Roman Dial, Rolex Box (2009)
Vintage Rolex Pepsi GMT-Master 1675
Rolex GMT-Master
1675
40MM Black Dial, Pepsi Bezel
Stainless Steel Jubilee, Circa 1966
Pre-Owned Rolex Yacht-Master 268655 Everose Gold
Rolex Yacht-Master
268655
37MM 18k Everose Gold, Black Dial
Oysterflex Rubber Strap, B&P (2017)
Rolex Day-Date 118208 Oyster
Rolex Day-Date
118208
36MM 18k Yellow Gold, Smooth Bezel
Black Dial, Oyster Bracelet (2000)
Rolex Cosmograph Daytona 116503 Black Dial
Rolex Daytona
116503
40MM Steel & Yellow Gold Chronograph
Black Chromalight Dial, B&P (2022)
Rolex GMT-Master 16758 18K Yellow Gold Jubilee
Rolex GMT-Master
16758
Vintage 40MM Black Dial, Rolex Box
18k Yellow Gold Jubilee, Circa 1984
Rolex Sky-Dweller 336934 Stainless Steel
Rolex Sky-Dweller
336934
Intense White Chromalight Dial
42MM Stainless Steel, B&P (2024)
Rolex Sea-Dweller 1665 Tropical Dial
Rolex Sea-Dweller
1665
40MM Stainless Steel, Tropical Dial
Oyster Bracelet, Rolex Box (1972)
Pre-Owned Rolex GMT-Master II 16718 Black
Rolex GMT-Master
16718
40MM 18k Yellow Gold, Black Dial
Oyster Bracelet, Automatic (1991)
Rolex GMT- Master II 116719 Ceramic 'Pepsi' Bezel
Rolex GMT-Master
116719
40MM 18k White Gold, Pepsi Bezel
Black Dial, Rolex Papers (2015)
Vintage Rolex GMT-Master 1675 Nipple Dial
Rolex GMT-Master
1675
40MM 18k Yellow Gold, Oyster Band
Black Nipple Dial, Circa 1978
Rolex GMT-Master II Ref 16718 18k Gold
Rolex GMT-Master
16718
40MM 18k Yellow Gold, Oyster Band
Black Dial, Rolex Box (1994)
Rolex Sky-Dweller 336933 Steel & 18k Yellow Gold
Rolex Sky-Dweller
336933
42MM Steel & 18k Gold, Oyster Band
White Chromalight Dial, B&P (2023)
Ladies Rolex Datejust 279178 18k Yellow Gold
Rolex Datejust
279178
Silver Diamond Star Dial, Automatic
28MM 18k Yellow Gold, B&P (2018)
Rolex Daytona 116515 Everose Gold
Rolex Daytona
116515
Eversose Gold on Oysterflex Strap
Sundust Chromalight Dial, B&P (2019)
Rolex Submariner 16808 18K Yellow Gold
Rolex Submariner
16808
Champagne Serti Dial, Oyster Band
40MM Yellow Gold, Rolex Box (1981)
Pre-Owned Rolex Submariner 16808
Rolex Submariner
16808
40MM 18k Yellow Gold, Oyster Band
Silver Serti Dial, Rolex Box (1987)
Vintage Rolex "Pre-Daytona" Oyster Chronograph 6034
Rolex Daytona
6034
36MM Vintage Pre-Daytona
Stainless Steel Rivet Oyster
Pre-Owned Rolex Sky-Dweller 326135 Rose Gold
Rolex Sky-Dweller
326135
42MM Rose Gold, Chocolate Arabic Dial
Rolex Leather Band, B&P (2016)
Rolex Day-Date II Ref 218235 18k Everose Gold
Rolex Day-Date
218235
Black Roman Dial
41MM 18k Everose Gold, B&P (2012)
Rolex White Gold Day-Date President 228239
Rolex Day-Date
228239
40MM White Gold, Grey Tapestry Dial
Index Hour Markers, B&P (2017)
Vintage Rolex GMT-Master 1675 Glossy Gilt Dial
Rolex GMT-Master
1675
40MM Glossy Gilt Pepsi, Circa 1966
Stainless Steel Rivet Oyster
Vintage Rolex Explorer II 1655 Albino GMT Hand
Rolex Explorer
1655
39MM Stainless Steel Steve McQueen
MK II Bezel & MK II Dial (1975)
Vintage Rolex 5512 Submariner No Date
Rolex Submariner
5512
Vintage 40MM Black Dial, Circa 1976
Stainless Steel Oyster Rivet
Rolex Submariner 5513 Glossy Gilt Dial
Rolex Submariner
5513
40MM Black Glossy Dial, Circa 1966
Stainless Steel Rivet Oyster
1 - 45 of 49 results
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