Luxury watches under $5000
4786 RESULTS
SORT BY
![Rolex Datejust 36mm 16013](https://cdn.grayandsons.com/s/rolex_datejust_36mm_16013_w520032_230f3994b6-w360.jpg.auto)
Rolex WatchDatejust 36mm
$4,990
W520032
![Fendi 25mm 750L](https://cdn.grayandsons.com/s/fendi_25mm_750l_w520128_ef48c09497-w360.jpg.auto)
Fendi OtherFendi 750L Stainless Steel 25mm Quartz watch
$390
W520128
![Hamilton Cocktail 14mm](https://cdn.grayandsons.com/s/hamilton_cocktail_14mm_w520131_4a6a3d4346-w360.jpg.auto)
Hamilton WatchCocktail 14mm
$2,900
W520131
![Cartier Santos 29mm w20041c4](https://cdn.grayandsons.com/s/cartier_santos_29mm_w20041c4_w520057_c87093bb29-w360.jpg.auto)
Cartier WatchSantos 29mm
$3,950
W520057
![Cartier Roadster 36mm 2510](https://cdn.grayandsons.com/s/cartier_roadster_36mm_2510_w520127_719d22f85a-w360.jpg.auto)
Cartier WatchRoadster 36mm
$4,400
W520127
![Rolex Datejust 26mm 69173](https://cdn.grayandsons.com/s/rolex_datejust_26mm_69173_w520085_84c95d861c-w360.jpg.auto)
Rolex WatchDatejust 26mm
$3,950
W520085
![Rolex Datejust 36mm 16013](https://cdn.grayandsons.com/s/rolex_datejust_36mm_16013_w520020_22b07cb1b2-w360.jpg.auto)
Rolex WatchDatejust 36mm
$3,950
W520020
![Cartier Pasha 35mm W31076M7](https://cdn.grayandsons.com/s/cartier_pasha_35mm_w31076m7_w516908_9259fe309f-w360.jpg.auto)
Cartier WatchPasha 35mm
$2,600
W516908
![Chopard Mille Miglia 42.5mm 8954](https://cdn.grayandsons.com/s/chopard_mille_miglia_42_5mm_8954_w520125_a_cd13ad740f-w360.jpg.auto)
Chopard WatchMille Miglia 43mm
$4,200
W520125
![Cartier Must 21 27.5mm](https://cdn.grayandsons.com/s/cartier_must_21_27_5mm_w520014_e57ff6d915-w360.jpg.auto)
Cartier WatchMust 21 28mm
$1,500
W520014
![Cartier Tank 20.5mm](https://cdn.grayandsons.com/s/cartier_tank_20_5mm_w519790_c08f63e1e5-w360.jpg.auto)
Cartier WatchTank 21mm
$4,450
W519790
![Cartier 8.4mm 8064269](https://cdn.grayandsons.com/s/cartier_8_4mm_8064269_w520093_c1b865d46e-w360.jpg.auto)
Cartier OtherVintage Cartier 8064269, 18k White Gold, White dial, Diamond case 8.4mm Manual
$3,900
W520093
![Tudor Tiger Woods 39mm 79280](https://cdn.grayandsons.com/s/tudor_tiger_woods_39mm_79280_w520089_b6fd6259e9-w360.jpg.auto)
Tudor WatchTiger Woods 39mm
$3,975
W520089
![Waltham pocket watch 29mm 144350](https://cdn.grayandsons.com/s/waltham_pocket_watch_29mm_144350_w520084_0b1cc238b1-w360.jpg.auto)
Waltham Pocket Watchpocket watch 29mm
$2,950
W520084
![Vacheron Constantin pocket watch 44mm 246783](https://cdn.grayandsons.com/s/vacheron_constantin_pocket_watch_44mm_246783_w516316_690e94b424-w360.jpg.auto)
Vacheron Constantin Pocket Watchpocket watch 44mm
$4,500
W516316
![Omega Seamaster 35mm 111](https://cdn.grayandsons.com/s/omega_seamaster_35mm_111_w520073_117546966f-w360.jpg.auto)
Omega WatchSeamaster 35mm
$1,950
W520073
![Breitling Avenger 45mm E13360](https://cdn.grayandsons.com/s/breitling_avenger_45mm_e13360_w520081_b5c4aedd79-w360.jpg.auto)
Breitling WatchAvenger 45mm
$3,840
W520081
![Bell & Ross vintage 126 39mm V126A](https://cdn.grayandsons.com/s/bell_and_ross_vintage_126_39mm_v126a_w520080_179c9a80e3-w360.jpg.auto)
Bell & Ross Watchvintage 126 39mm
$2,200
W520080
![Zenith Chronomaster 42mm 03.2080.4021/01.C494](https://cdn.grayandsons.com/s/zenith_chronomaster_42mm_03_2080_402101_c494_w520083_8726d3b74b-w360.jpg.auto)
Zenith WatchChronomaster 42mm
$4,730
W520083
![Rolex Cellini 26.5mm 183](https://cdn.grayandsons.com/s/rolex_cellini_26_5mm_183_w520090_8b9a381b6f-w360.jpg.auto)
Rolex WatchCellini 27mm
$2,400
W520090
![Cartier Roadster 37mm W62002V3](https://cdn.grayandsons.com/s/cartier_roadster_37mm_w62002v3_w517760_04d8ecf01c-w360.jpg.auto)
Cartier WatchRoadster 37mm
$3,950
W517760
![Cartier Panthere](https://cdn.grayandsons.com/s/cartier_panthere_w52000_f_b947cfdebc-w360.jpg.auto)
Cartier WatchPanthere
$2,500
W52000
![Rolex Classic 22.5mm 3652](https://cdn.grayandsons.com/s/rolex_classic_22_5mm_3652_w520018_8a743e1db5-w360.jpg.auto)
Rolex WatchClassic 23mm
$3,250
W520018
![Rolex Datejust 36mm 1601](https://cdn.grayandsons.com/s/rolex_datejust_36mm_1601_w519800_f358cecf11-w360.jpg.auto)
Rolex WatchDatejust 36mm
$2,500
W519800
![Rolex Datejust 26mm R69173](https://cdn.grayandsons.com/s/rolex_datejust_26mm_r69173_w520050_2a704f8dde-w360.jpg.auto)
Rolex WatchDatejust 26mm
$4,550
W520050
![IWC Classic 20mm](https://cdn.grayandsons.com/s/iwc_classic_20mm_w520003_4b4ce43b05-w360.jpg.auto)
IWC WatchClassic 20mm
$950
W520003
![Rolex Date 34mm 15223](https://cdn.grayandsons.com/s/rolex_date_34mm_15223_w519920_4ab9cbe62e-w360.jpg.auto)
Rolex WatchDate 34mm
$4,450
W519920
![Rolex Datejust 36mm 15000](https://cdn.grayandsons.com/s/rolex_datejust_36mm_15000_w519946_f78efb1e90-w360.jpg.auto)
Rolex WatchDatejust 36mm
$3,550
W519946
![Cartier Tank Francaise 20.5mm 345520CD](https://cdn.grayandsons.com/s/cartier_tank_francaise_20_5mm_345520cd_w520060_01a0add50e-w360.jpg.auto)
Cartier WatchTank Francaise 21mm
$4,250
W520060
![Cartier Roadster 38.5mm W62001V3](https://cdn.grayandsons.com/s/cartier_roadster_38_5mm_w62001v3_w520027_907d90ec5b-w360.jpg.auto)
Cartier WatchRoadster 39mm
$3,995
W520027
![Elgin Classic 22mm 4518](https://cdn.grayandsons.com/s/elgin_classic_22mm_4518_w519935_5904cbdff3-w360.jpg.auto)
Elgin WatchClassic 22mm
$1,700
W519935
![Cartier Chronoscaph 21 38mm w10172t2](https://cdn.grayandsons.com/s/cartier_chronoscaph_21_38mm_w10172t2_w520061_320d6d6b15-w360.jpg.auto)
Cartier WatchChronoscaph 21 38mm
$3,450
W520061
![Vacheron Constantin Classic 26mm 6840](https://cdn.grayandsons.com/s/vacheron_constantin_classic_26mm_6840_w519643_f3742ea0a4-w360.jpg.auto)
Vacheron Constantin WatchClassic 26mm
$2,950
W519643
![Rolex Datejust 26mm 69173](https://cdn.grayandsons.com/s/rolex_datejust_26mm_69173_w520051_661f64ef99-w360.jpg.auto)
Rolex WatchDatejust 26mm
$3,450
W520051
![Rolex Thunderbird 36mm 16264](https://cdn.grayandsons.com/s/rolex_thunderbird_36mm_16264_w517767_c571950062-w360.jpg.auto)
Rolex WatchThunderbird 36mm
$4,890
W517767
![Cartier Tank Francaise 20mm W51007Q4](https://cdn.grayandsons.com/s/cartier_tank_francaise_20mm_w51007q4_w518480_7ec042a2b5-w360.jpg.auto)
Cartier WatchTank Francaise 20mm
$3,700
W518480
...
...