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Diane Dempsey

Diane Dempsey is best known for her nostalgic artwork that celebrates mid-century holiday charm, vintage advertising styles, and Americana. Her Retro Christmas series, with its warm colors and classic 1940s–60s aesthetic, has become especially popular, sparking feelings of nostalgia and cozy tradition. For Cobble Hill, her artwork resonates perfectly with puzzlers who love seasonal themes, family traditions, and retro style, making her puzzles perennial favourites and strong holiday sellers.

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  • Christmas Campers | 1000 Piece

    40219
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    Follow the road to the Christmas Campers decorating their trailers and trees for a wonderful winter celebration. A 1000 piece puzzle with a nostal...

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  • Santa's Flyby (Family) | Family Pieces 350

    47044
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    Diane Dempsey does it again with another festive Christmas puzzle to celebrate Santa and mid-century modern living. Catch Santa in the sky flying b...

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  • Holiday Drive In | 1000 Piece

    40293
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    Celebrate the holidays with the "Holiday Drive In" 1000 piece puzzle, featuring a festive double feature for Christmas and New Year's. This charmin...

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  • Santa's Parade | 2000 Piece

    49020
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    Santa's Parade by Diane Dempsey brings the warmth and charm of mid-century modern life in a festive winter scene. The Christmas spirit is in full s...

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  • Christmas Cats | 1000 Piece

    40272
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    Diane Dempsey does it again! This mid-mod creation of Christmas Cats is delightful, nostalgic, and full of festivity! Featuring a beautifully decor...

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  • Vintage Main Street | 1000 Piece

    40218
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    Diane Dempsey does it again with a spectacular Christmas scene in Vintage Main Street. Shop for trees, the latest in fashion, or some treats at Coc...

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  • Merry Catmas | 500 Piece

    45131
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    Diane Dempsey’s colourful compositions are packed with mid century high-style. Historically accurate ornaments, patterns, and textures bring the fa...

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  • Holiday Hustle | 1000 Piece

    40010
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    Holiday Hustle is a retro Diane Dempsey 1000 piece image in a portrait orientation. Vintage cars, trucks, and camper vans are headed out for the ho...

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  • Mid Mod Season's Greetings | 1000 Piece

    40217
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    It's that time of year for sending out our Mid-Mod Season's Greetings to friends and family. Remind yourself of the good old days of Christmas trad...

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  • Mid-Century Modern Dream Home | 1000 Piece

    40070
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    Architectural enthusiasts will enjoy this 1000 piece puzzle featuring silhouettes entertaining in their Mid-Century Modern Dream Home designed by D...

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