{"id":1851,"date":"2025-10-14T08:39:39","date_gmt":"2025-10-14T08:39:39","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-fl\/1851\/"},"modified":"2025-10-14T08:39:39","modified_gmt":"2025-10-14T08:39:39","slug":"photos-dave-portnoy-buys-florida-mansion-for-record-breaking-28m","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-fl\/1851\/","title":{"rendered":"Photos: Dave Portnoy buys Florida mansion for record-breaking $28M"},"content":{"rendered":"<p>Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while doing it.<\/p>\n<p>The unapologetic internet personality and Barstool Sports founder purchased an Islamorada mansion this week for $27,750,000, the highest property sale the village has ever seen.\u00a0<\/p>\n<p>Located at <a href=\"https:\/\/www.realtor.com\/realestateandhomes-detail\/76180-Overseas-Hwy_Islamorada_FL_33036_M61276-90414\" data-wplink-edit=\"true\" rel=\"nofollow noopener\" target=\"_blank\">76180 Overseas Highway<\/a>, the home has eight bedrooms, 10 bathrooms and a total 7,562 square feet across a main residence and a guest house.\u00a0<\/p>\n<p>The estate sits on 1.65 acres of waterfront land, and it comes with two pools, a private beach, a boat ramp and dock, an outdoor kitchen and 150 feet of private water access, per the listing. Inside, there are two laundry rooms, an elevator, a 180-bottle glass wine cellar, Sonos sound system and more.<\/p>\n<p>There are also two gated driveways, a four-car garage and lots of tropical landscaping.\u00a0<\/p>\n<p>Portnoy, 48, already owned more than $95 million worth of real estate in both Florida and other areas like Montauk, Nantucket and Saratoga Springs. He also is the owner of a $14 million home in Miami.<\/p>\n<p>All photos are from Realtor.com.<\/p>\n<p class=\"Text-c11n-8-112-0__sc-aiai24-0 fXfDch\">Every house has a story, and our mission is to tell Orlando\u2019s story through the lens of our community\u2019s most exceptional and historic homes. Orlando Weekly\u2019s real estate features are not ads and are assembled by our editorial department. But we love public input. Do you know of a unique Florida home we should highlight? Let us know, and email\u00a0<a href=\"http:\/\/cgreenberg@orlandoweekly.com\/\" target=\"_blank\" rel=\"noopener nofollow\">cgreenberg@orlandoweekly.com<\/a>.<\/p>\n<p><img loading=\"lazy\" data-recalc-dims=\"1\" decoding=\"async\" width=\"780\" height=\"519\" data-attachment-id=\"400699\" data-permalink=\"https:\/\/www.orlandoweekly.com\/news\/photos-dave-portnoy-buys-florida-mansion-for-record-breaking-28m\/attachment\/230156a8e00ad40317c7b603ef8abc83l-b760594291rd-w1280_h960-2\/\" data-orig-file=\"https:\/\/i0.wp.com\/www.orlandoweekly.com\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b760594291rd-w1280_h960-1.webp?fit=1280%2C853&amp;ssl=1\" data-orig-size=\"1280,853\" data-comments-opened=\"0\" 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src=\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b3500456510rd-w1280_h960.webp\" alt=\"\" class=\"wp-image-400802\"  \/><\/p>\n<p><img loading=\"lazy\" data-recalc-dims=\"1\" decoding=\"async\" width=\"780\" height=\"519\" data-attachment-id=\"400803\" data-permalink=\"https:\/\/www.orlandoweekly.com\/news\/photos-dave-portnoy-buys-florida-mansion-for-record-breaking-28m\/attachment\/230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960\/\" data-orig-file=\"https:\/\/i0.wp.com\/www.orlandoweekly.com\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960.webp?fit=1280%2C853&amp;ssl=1\" data-orig-size=\"1280,853\" data-comments-opened=\"0\" data-image-meta=\"{&quot;aperture&quot;:&quot;0&quot;,&quot;credit&quot;:&quot;&quot;,&quot;camera&quot;:&quot;&quot;,&quot;caption&quot;:&quot;&quot;,&quot;created_timestamp&quot;:&quot;0&quot;,&quot;copyright&quot;:&quot;&quot;,&quot;focal_length&quot;:&quot;0&quot;,&quot;iso&quot;:&quot;0&quot;,&quot;shutter_speed&quot;:&quot;0&quot;,&quot;title&quot;:&quot;&quot;,&quot;orientation&quot;:&quot;0&quot;}\" data-image-title=\"230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960\" data-image-description=\"\" data-image-caption=\"\" data-medium-file=\"https:\/\/i0.wp.com\/www.orlandoweekly.com\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960.webp?fit=300%2C200&amp;ssl=1\" data-large-file=\"https:\/\/i0.wp.com\/www.orlandoweekly.com\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960.webp?fit=780%2C519&amp;ssl=1\" src=\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2025\/10\/230156a8e00ad40317c7b603ef8abc83l-b4130764706rd-w1280_h960.webp\" alt=\"\" class=\"wp-image-400803\"  \/><\/p>\n<p>\n\tRelated<\/p>\n","protected":false},"excerpt":{"rendered":"Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while&hellip;\n","protected":false},"author":2,"featured_media":1852,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[11],"tags":[1624,2471,1625,2472,1626,2473,139,141,140,1627,1628],"class_list":["post-1851","post","type-post","status-publish","format-standard","has-post-thumbnail","category-orlando","tag-celebrity-real-estate","tag-dave-portnoy","tag-florida-celebrity-real-estate","tag-florida-keys","tag-florida-real-estate","tag-islamorada","tag-orlando","tag-orlando-headlines","tag-orlando-news","tag-rare-florida-homes","tag-slideshow-gallery"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/1851","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=1851"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/1851\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/1852"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=1851"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=1851"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=1851"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}