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 is known as the “Ultimate Jeweler”. Born in New York City, he got an early start in the industry working for his father’s jewelry company. Winston opened his first store, "The Premier Diamond Company," in 1920 on Fifth Avenue. Soon after, Winston quickly established himself as a gem connoisseur earning his name through recutting gems he found at estate sales. His specialty was finding outdated creations at a fraction of the price and recutting the stone to enhance the sparkle and give it a modern look. His signature designs caught the attention of many societies, Hollywood stars, and collectors at the time. In 1947, Harry Winston was crowned ‘King of Diamonds’ by Cosmopolitan magazine. Today Harry Winston rings are some of the most sought-after by collectors items in the high jewelry market. Harry Winston rings are also a celebrity favorite. Elizabeth Taylor, Marilyn Monroe, Nicole Kidman and Jennifer Lopez have all worn Harry Winston rings.
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. | $14 million |
| 2 | Harry Winston Pear Shaped Diamond Ring | 32.42-carat D-color pear-shaped diamond with VVS1 clarity and baguette shoulders. | $3.7 million |
| 3 | Harry Winston Kashmir Sapphire Ring | 16.65-carat cushion-cut Kashmir sapphire, rich royal blue hue, flanked by diamonds. | $2.5 million |
| 4 | Harry Winston Pear Shaped Diamond Ring | 43.24-carat D-color Type IIa diamond, VVS1 clarity, signed Jacques Timey. | $2.4 million |
| 5 | Harry Winston Cushion Cut Diamond Ring | 51.52-carat cushion-cut F-color diamond, internally flawless, shield diamond accents. | $30 million |
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 - $14 million
In 2017, this spectacular 33.36-carat fancy light pink diamond sold for 12.6M CHF, approximately $14M. 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 - $3.7 million
This unique pear-shaped diamond ring sold at Sotheby’s auction for 3.3M CHF, approximately $3.7M 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 - $2.5 million
This Harry Winston sapphire ring sold at Sotheby's auction in Hong Kong for 19.8M HKD, approximately $2.5M 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 - $2.4 million
In 2021, Sotheby's sold a Harry Winton diamond ring for 2.1 CHF or $2.4 million. 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 - $2.1 million
This Harry Winston cushion set ring features a modified brilliant-cut diamond sold at Sotheby's Magnificent and Noble Jewels auction for 1.8M CHF, approximately $2.1M 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.
Frequently Asked Questions About the 5 Most Expensive Harry Winston Ring
Why are Harry Winston diamonds so valuable?
Harry Winston is renowned for sourcing the world’s finest gemstones, emphasizing D-color and Type IIa clarity in diamonds—qualities representing the pinnacle of purity. Each ring’s design enhances the stone’s brilliance, resulting in exceptional rarity and value.
What makes Kashmir sapphires so sought after?
Kashmir sapphires, like the one featured in Winston’s $2.5 million ring, are prized for their velvety royal blue color and exceptional saturation. Their rarity and provenance make them some of the most desirable colored gemstones in the world, especially when mounted by Harry Winston.
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.
- Exclusive Global Access: Shop Harry Winston rings through auctions and Buy Now marketplace, backed by a worldwide network of collectors, consignors, and trusted suppliers.
- 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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