Seaport Entertainment Group Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

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SEAPORT ENTERTAINMENT GROUP** **INC.

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A Letter from the CEO

Dear Fellow Shareholders,

In 2024, we set out to define what Seaport Entertainment Group could become as a newly public company. Our ambition was not simply to operate a portfolio of assets, but to shape a collection of destinations where people actively choose to spend their time. We sit at the intersection of hospitality, entertainment, and real estate, and our core focus is straightforward – to build on the strengths of our unique locations to develop community-driven destinations, grounded in live entertainment, retail, food & beverage, arts & culture, and event-based experiences. Against that backdrop, I’m very excited to share the progress we’ve made in my first annual letter to you as President & CEO of Seaport Entertainment Group.

In 2025, our first full year as a public company, we advanced our vision through structural changes and disciplined execution, leading to tangible progress in shaping experiences and programming designed to deliver cultural relevance and long-term customer engagement. In an ever-changing world fueled by digital consumption and the promise of AI, the value of authentic experiences will only increase with time. When something feels real, people respond, and our ability to create a connection through meaningful, in-person experiences gives our guests a reason to come back. This is how we increase visitation and demand, which in turn drives the long-term viability and success of our underlying businesses.

At the Seaport in New York City, our progress is visible. Over the past year, we leased and programmed more than 153,000 square feet, reaching 90% planned occupancy through a mix of retail, event, food & beverage, and experiential concepts. The Rooftop at Pier 17 concert series had a record year of visitation, benefitting from an expansive event calendar and increased investment in the fan experience. This success was further exemplified by the 2026 Rolling Stone Audio Awards, which recently named The Rooftop at Pier 17 the Best Outdoor Music Venue in the United States. We also continued to elevate the neighborhood’s visibility by hosting large-scale events, including the Macy’s 4 th of July Fireworks® and the New York City Wine & Food Festival, reinforcing the Seaport’s role as a leading destination for marquee experiences in New York City. These are not one-off events, but a central component of our long-term programming strategy, designed to give guests compelling reasons to return to the Seaport again and again.

In Las Vegas, the Aviators had a standout season, winning the 2025 Pacific Coast League Championship and competing for a national title in the Triple-A National Championship Game hosted at our Las Vegas Ballpark. Equally important, we built internal capabilities to scale our own non-baseball experiences. Enchant, our holiday-themed activation at the Las Vegas Ballpark is a good example of the types of non-baseball offerings we can deliver to the community; just one example of the kinds of opportunities we plan to pursue to increase the number of experiences that can drive consistent, off-season traffic to the Ballpark.

I’m pleased to say we’ve carried our momentum into 2026. In January, we sold the development site, 250 Water Street, strengthening our already solid balance sheet. In February, we announced the repositioning of the Tin Building through a long-term lease with Lux Entertainment to introduce the U.S. flagship of Balloon Museum, an innovative contemporary art experience, to the Seaport. Across our portfolio, we remain focused on providing curated and diverse experiences designed to deliver consistent guest engagement, which ultimately supports long-term sustainable cash flow.

None of this happens without our resilient, committed team. The work they did throughout 2025, which continued into 2026, required tough decisions, creative thinking, and a willingness to move quickly. Our people delivered on all of it. We continue to push the business forward, and the energy, ownership, and accountability across the organization is not just supporting our strategy, it is defining our culture.

Looking ahead, we have a strong foundation and real momentum. We are confident in our plan for our portfolio and remain focused on disciplined, thoughtful execution. We have a unique combination of operating businesses and real estate, a balance sheet that gives us flexibility, and a path toward long-term value creation. Most importantly, we are committed to creating meaningful experiences for every guest who comes to our destinations and engages with our organization, because we believe that consistent, differentiated value for our guests and partners is what drives sustained performance and long-term benefits for our stakeholders.

Thank you for your continued support, trust and confidence as we continue to build the future for Seaport Entertainment Group.

Matthew M. Partridge

President, Chief Executive Officer and Director

Seaport Entertainment Group Inc.

199 Water Street

New York, NY 10038

NOTICE OF 2026 ANNUAL MEETING OF STOCKHOLDERS

Dear Stockholders of Seaport Entertainment Group Inc.:

We cordially invite you to attend the 2026 Annual Meeting of Stockholders (the “Annual Meeting”) of Seaport Entertainment Group Inc., a Delaware corporation.

As permitted by the rules of the U.S. Securities and Exchange Commission, we have elected to furnish our proxy materials to stockholders by providing access to the proxy materials on the internet. Accordingly, we are sending our stockholders a Notice of Internet Availability of Proxy Materials (the “Notice”) rather than a paper set of the proxy materials, unless a stockholder has previously requested printed materials. The Notice includes instructions on how to access our proxy materials over the internet, as well as how to request the proxy materials in paper form.

Your vote is important. We encourage you to vote by proxy in advance of the Annual Meeting, whether or not you plan to attend the virtual meeting. The Notice includes instructions on how to vote, including by internet or telephone. If you hold your shares through a broker, bank or other nominee, please follow the instructions you receive from them.

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON JUNE 8, 2026

This notice of the Annual Meeting, the Proxy Statement and the related proxy card are first being distributed and made available on or about April 23, 2026. The Proxy Statement and our Annual Report on Form 10-K for the fiscal year ended December 31, 2025 are also available on our website, ir.seaportentertainment.com, as well as www.proxyvote.com.