{"id":6499,"date":"2025-10-16T12:55:07","date_gmt":"2025-10-16T12:55:07","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-fl\/6499\/"},"modified":"2025-10-16T12:55:07","modified_gmt":"2025-10-16T12:55:07","slug":"dave-portnoy-just-dropped-27-75-million-on-a-waterfront-compound-in-islamorada-a-record-for-florida-keys","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-fl\/6499\/","title":{"rendered":"Dave Portnoy Just Dropped $27.75 Million On A Waterfront Compound in Islamorada, A Record for Florida Keys"},"content":{"rendered":"<p class=\"mb-4 text-lg md:leading-8 break-words\">Benzinga and Yahoo Finance LLC may earn commission or revenue on some items through the links below.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Dave Portnoy&#8217;s real estate portfolio just got bigger, as the Barstool Sports founder has purchased a $27.75 million property in Florida Keys, according to<a href=\"https:\/\/www.wsj.com\/real-estate\/luxury-homes\/dave-portnoy-barstool-florida-keys-home-97639208\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:The Wall Street Journal;elm:context_link;itc:0;sec:content-canvas\" class=\"link \"> The Wall Street Journal<\/a>.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">The mansion is situated on Islamorada, a string of six islands that&#8217;s located about 80 miles south of Miami and 80 miles north of Key West. The sale is a record breaker for Islamorada and Florida Keys, Leslie Leopold, who held the listing with Cheri Tindall, told the Journal.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Don&#8217;t Miss:<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">The land was sold in November 2017 for $2.1 million, and then again in December 2019 for $2.3 million, according to<a href=\"https:\/\/www.zillow.com\/homedetails\/76180-Overseas-Hwy-Islamorada-FL-33036\/306094884_zpid\/\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Zillow;elm:context_link;itc:0;sec:content-canvas\" class=\"link \"> Zillow<\/a>. The mansion home was recently built and listed in June for $31.2 million. As of Oct. 6, it&#8217;s been sold for $27.75 million.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">&#8220;Welcome to a rare offering in the heart of the Florida Keys, this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views,&#8221; says the<a href=\"https:\/\/www.sothebysrealty.com\/eng\/sales\/detail\/180-l-737-c53shr\/76180-overseas-highway-islamorada-fl-33036\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Sotheby&#039;s International Realty listing;elm:context_link;itc:0;sec:content-canvas\" class=\"link \"> Sotheby&#8217;s International Realty listing<\/a>. &#8220;With two gated driveways, serene lawns and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige and paradise.&#8221;<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">The property&#8217;s 7,562-square-foot main residence has five bedrooms and six full bathrooms. Its top-of-the-line kitchen features Miele and Wolf appliances, Sub-Zero refrigerators and two laundry rooms. There&#8217;s a media room, a 180-bottle glass wine cellar, an elevator and Toto toilets.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Trending: <a href=\"https:\/\/arrivedhomes.go2cloud.org\/aff_c?offer_id=8&amp;aff_id=1006&amp;aff_sub=yahoo\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Arrived Home&#039;s Private Credit Fund\u2019s has historically paid an annualized dividend yield of 8.1%*;elm:context_link;itc:0;sec:content-canvas\" class=\"link \">Arrived Home&#8217;s Private Credit Fund\u2019s has historically paid an annualized dividend yield of 8.1%*<\/a>, which provides access to a pool of short-term loans backed by residential real estate with just a $100 minimum.<a href=\"https:\/\/www.benzinga.com\/go\/arrived-private-credit-yf?utm_campaign=partner_feed&amp;utm_source=yahooFinance&amp;utm_medium=partner_feed&amp;utm_content=real_estate&amp;nid=48247237\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:\u00a0;elm:context_link;itc:0;sec:content-canvas\" class=\"link \">\u00a0<\/a><\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Then, there&#8217;s the 2,666-square-foot guest house that has its own three bedrooms, four bathrooms and fully equipped kitchen. It even has its own private pool that&#8217;s separate from the main house&#8217;s pool, according to the listing. Portnoy will get 150 feet of private waterfront views, along with dockage, a boat ramp, a private beach and mature tropical landscaping, too.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">&#8220;We welcome him to Islamorada and wish him all the best in his new private Florida Keys escape,&#8221; Leopold told<a href=\"https:\/\/www.boston.com\/real-estate\/luxury-homes\/2025\/10\/09\/barstool-sports-dave-portnoy-florida-keys-real-estate\/\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Boston.com;elm:context_link;itc:0;sec:content-canvas\" class=\"link \"> Boston.com<\/a>. &#8220;This property is the first of its quality and caliber in this area to trade. As more new construction, or totally remodeled homes and larger estate properties come on market, we believe we will see more trading in this price range, if not higher.&#8221;<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Portnoy has been dealing with construction delays and mold in his Miami mansion, though it&#8217;s unclear if he&#8217;s planning on offloading the property now that he&#8217;s a Florida Keys home owner. The professional pizza reviewer also owns real estate in New York and Massachusetts, including a record-breaking $42 million property on Nantucket, according to <a href=\"http:\/\/realtor.com\/\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Realtor.com;elm:context_link;itc:0;sec:content-canvas\" class=\"link \">Realtor.com<\/a>.<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Read Next:\u00a0<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">Image: Shutterstock<\/p>\n<p class=\"mb-4 text-lg md:leading-8 break-words\">This article <a href=\"https:\/\/www.benzinga.com\/markets\/25\/10\/48247237\/dave-portnoy-just-dropped-27-75-million-on-a-waterfront-compound-in-islamorada-a-record-for-florida?utm_campaign=partner_feed&amp;utm_source=yahooFinance&amp;utm_medium=partner_feed&amp;utm_content=real_estate\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Dave Portnoy Just Dropped $27.75 Million On A Waterfront Compound in Islamorada, A Record for Florida Keys;elm:context_link;itc:0;sec:content-canvas\" class=\"link \">Dave Portnoy Just Dropped $27.75 Million On A Waterfront Compound in Islamorada, A Record for Florida Keys<\/a> originally appeared on <a href=\"https:\/\/www.benzinga.com\" rel=\"nofollow noopener\" target=\"_blank\" data-ylk=\"slk:Benzinga.com;elm:context_link;itc:0;sec:content-canvas\" class=\"link \">Benzinga.com<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"Benzinga and Yahoo Finance LLC may earn commission or revenue on some items through the links below. Dave&hellip;\n","protected":false},"author":2,"featured_media":6500,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6],"tags":[7112,2471,28,30,2472,29,2473,7113,7114],"class_list":["post-6499","post","type-post","status-publish","format-standard","has-post-thumbnail","category-florida","tag-accredited-investors","tag-dave-portnoy","tag-florida","tag-florida-headlines","tag-florida-keys","tag-florida-news","tag-islamorada","tag-leslie-leopold","tag-the-wall-street-journal"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/6499","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/comments?post=6499"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/6499\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/6500"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=6499"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=6499"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=6499"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}