A Closer Look At The Top 5 Most Expensive Harry Winston Rings
A deep dive into the most expensive Harry Winston rings, showcasing the rarest stones and finest craftsmanship.
Brief History of Harry Winston
Harry Winston stands as one of the most influential names in high jewelry, closely associated with some of the world’s most important diamonds and gemstones. Born in New York City, Winston entered the jewelry trade through his father’s business before founding The Premier Diamond Company on Fifth Avenue in 1920. He quickly distinguished himself as a gem connoisseur, known for acquiring historic stones from estate sales and recutting them to enhance brilliance and modern appeal.
By the mid‑20th century, Winston’s creations had become synonymous with exceptional quality, rare gemstones, and refined design. In 1947, he was famously dubbed the “King of Diamonds,” a reputation reinforced by the brand’s continued association with important diamonds, colored gemstones, and record‑setting auction results. Today, Harry Winston rings remain among the most sought‑after signed jewels in the high jewelry market, prized by collectors for their gemstone quality, provenance, and enduring significance. Below, we explore the five most expensive Harry Winston rings sold at auction, offering insight into the factors that place these jewels at the top of the market.
Most Expensive Harry Winston Rings
| Rank | Model | Notable Features | Price (USD) |
| 1 | Harry Winston Fancy Light Pink Diamond Ring | 33.36-carat Fancy Light Pink diamond, emerald-cut, VVS1 clarity, record-setting sale. | $14M |
| 2 | Harry Winston Pear Shaped Diamond Ring | 32.42-carat D-color pear-shaped diamond with VVS1 clarity and baguette shoulders. | $3.7M |
| 3 | Harry Winston Kashmir Sapphire Ring | 16.65-carat cushion-cut Kashmir sapphire, rich royal blue hue, flanked by diamonds. | $2.5M |
| 4 | Harry Winston Pear Shaped Diamond Ring | 43.24-carat D-color Type IIa diamond, VVS1 clarity, signed Jacques Timey. | $2.4M |
| 5 | Harry Winston Cushion Cut Diamond Ring | 51.52-carat cushion-cut F-color diamond, internally flawless, shield diamond accents. | $2.1M |
Top 5 Most Expensive Harry Winston Rings
Take a closer look at the most expensive Harry Winston rings sold at auction since 2017.
1. Harry Winston Fancy Light Pink Diamond Ring, $14M
In 2017, this spectacular 33.36-carat fancy light pink diamond sold for 12.6M CHF, approximately $14M USD. This remarkable ring remains one of the most expensive Harry Winston rings ever sold at auction and set a benchmark for the value of large pink diamonds. At the time of this sale, it set a world record for the highest-priced fancy light pink diamond sold at auction. Fancy light pink diamonds are extremely rare. Additionally, the flawless cut and near-perfect clarity add to this spectacular ring's value. The one-of-a-kind gem was mounted by Harry Winston in 1970; the diamond is a step-cut in a fancy Light pink Color with VVS1 clarity. Very few pink diamonds of this size are emerald cut since step cut diamonds require very high clarity to result in a beautiful finished diamond.This ring represents both the craftsmanship and the superiority of Harry Winston's diamonds.
2. Harry Winston Pear Shaped Diamond Ring, $3.7M
This unique pear-shaped diamond ring sold for 3.3M CHF, approximately $3.7M USD in 2017. The pear-shaped diamond weighs 32.42 carats and is D colored with VVS1 clarity. This diamond is almost internally flawless which is extremely rare for a diamond this size. A 32.42-carat diamond is roughly the size of a cherry tomato. The center diamond is set between two tapered baguette diamond shoulders.
3. Harry Winston Kashmir Sapphire Ring, $2.5M
This Harry Winston sapphire ring sold for 19.8M HKD, approximately $2.5M USD in 2024. This ring features an exceptional 16.65 cushion-shaped sapphire. The sapphire is flanked by two triangular diamonds and set in 18-karat gold. In the SSEF report it states the sapphire is from Kashmir origin. Kashmir sapphires are highly desirable and are known for having the deepest royal blue color. This Harry Winston sapphire ring is no exception - the sapphire is a rich velvety blue. Additionally, this is a remarkable size and weight for a sapphire from this region of the world. High quality sapphires of notable size and deep color have been strong performers at auction, especially from top brands like Harry Winston.
4. Harry Winston Pear Shaped Diamond Ring, $2.4M
This Harry Winston pear-shaped diamond ring was sold for 2.1 million CHF, or approximately $2.4 million in 2021. The Harry Winston engagement ring featured a pear shaped diamond 43.24 carats that was D color, VVS1 clarity and Type IIa classification. The Acompanied by Gübelin report no. 21010052 also stating that the diamond is D Color and Internally Flawless. The Harry Winston ring also features tapered baguette diamonds and is signed Jacques Timey.
5. Harry Winston Cushion Cut Diamond Ring, $2.1M
This Harry Winston cushion set ring features a modified brilliant-cut diamond sold for 1.8M CHF, approximately $2.1M USD in 2023. This simple setting and cut by the iconic jeweler exemplifies timeless beauty. The cushion cut diamond is 51.52 carats. It is enhanced by two shield-shaped diamonds on either side of the center diamond. The impressive size of this diamond makes it stand out, additionally, this diamond is F colored and internally flawless.
What Makes Harry Winston Rings So Valuable
Harry Winston rings are renowned for their exceptional gemstones, meticulous craftsmanship, and strong auction performance. The brand is especially associated with rare diamonds graded D-color, Internally Flawless, or Type IIa, which represent the highest standards of purity and brilliance. Rings featuring large diamonds, historic provenance, or rare colored gemstones such as pink diamonds and Kashmir sapphires consistently command premium prices at auction. As a result, the most important Harry Winston rings are often among the most valuable pieces of signed jewelry sold in the global market.
Collector Demand for Harry Winston Rings Today
Harry Winston rings continue to attract strong global demand due to the brand’s reputation for sourcing exceptional gemstones and creating timeless designs. Collectors increasingly seek rings featuring large D-color diamonds, rare colored diamonds, and gemstones with documented provenance. As supply remains limited, high-quality signed Harry Winston rings consistently perform well at auction, reinforcing their status among the most desirable pieces in the high jewelry market.
Frequently Asked Questions About Harry Winston Rings
Why are Harry Winston rings so highly valued at auction?
Harry Winston rings are valued for their exceptional gemstones, particularly large D‑color, Type IIa, and internally flawless diamonds, as well as rare colored stones. Strong provenance, meticulous craftsmanship, and limited supply further contribute to their desirability among collectors.
What types of gemstones define important Harry Winston rings?
The most significant Harry Winston rings typically feature large colorless diamonds, rare colored diamonds, and exceptional gemstones such as Kashmir sapphires. These stones are prized for their rarity, quality, and historical importance within the jewelry market.
Are vintage Harry Winston rings especially collectible?
Vintage Harry Winston rings are highly collectible due to their association with historic gemstones, early craftsmanship, and limited production. Pieces from earlier periods often carry added significance when accompanied by original documentation or notable auction history.
Buy and Sell Harry Winston Rings with Sotheby’s
Whether you're a seasoned collector or new to the world of high jewelry, Sotheby’s offers a trusted, seamless way to buy and sell exceptional Harry Winston rings on the secondary market.
Why Choose Sotheby’s?
- Expertly Vetted Selection: Explore rare and iconic Harry Winston rings, from elegant diamond bands starting at $10,000 to stunning diamond engagement rings and colored gemstone pieces exceeding $100,000.
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- Flexible Ways to Buy: Purchase online or in person at our locations in New York, Hong Kong, and London—or work with a dedicated jewelry concierge for bespoke assistance.
- Exceptional Value: Every Harry Winston ring is authenticated and priced by Sotheby’s specialists to reflect true market value, with many pieces available below their original retail price.
- Constantly Evolving Inventory: Discover a curated selection of Harry Winston rings, including vintage treasures and unique custom creations, with new pieces added regularly.
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