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Princeton Douglass

Associate | net lease retail | Tampa, FL
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About Princeton

Princeton Douglass is a real estate professional specializing in the acquisition and disposition of single-tenant retail properties with a particular focus on drugstores and dollar stores throughout Florida. He brings a strong drive for consistently expanding his market knowledge. Princeton is committed to representing his client’s best interests and advising them toward achieving their short and long-term investment goals while providing exceptional service that sets him apart in the industry.


B.A., International Business and Spanish, minor in Economics

Dickinson College – Carlisle, PA


Professional Accomplishments
  • 2025 – Five Star Award – Matthews

Affiliations & Memberships
  • Florida Real Estate Commission
  • License No. SL3632851 (FL)
Contact Princeton

Affiliated Agents

Princeton Douglass in the Media

2025 Cap Rate Recap

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The State of Florida’s Walgreens Market image

The State of Florida’s Walgreens Market

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Q225 Florida Drugstore Tenant Report image

Q225 Florida Drugstore Tenant Report

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Case Studies

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How Matthews'™ Strategic Positioning Led to the Rapid Disposition of a 3-Property Retail Portfolio in Arkansas

A three-property portfolio of Family Dollar assets located throughout Arkansas was brought to market under urgent circumstances, requiring a swift and strategic disposition. The Matthews™ agents were engaged to facilitate the sale, aligning pricing, buyer targeting, and execution speed to meet the developer’s immediate liquidity needs while navigating evolving market conditions.   Challenge The assignment involved a three-property portfolio of Family Dollar assets located throughout Arkansas. The developer faced a pressing need for immediate liquidity to pay off existing debt, requiring a swift and certain execution. However, the timing of the sale presented a significant hurdle. Just as the properties were brought to market, Dollar Tree announced the divestiture of the Family Dollar brand. This shift meant the lease guarantees were no longer backed by Dollar Tree’s investment-grade credit, but rather by Family Dollar’s private credit. This change in credit quality intimidated many traditional net-lease investors and fundamentally altered the exit expectations and valuation of the assets.   Strategy Recognizing that the credit downgrade would be the primary concern for the market, the agents developed a strategy focused on aggressive pricing and transparent market education. They advised the client to price the portfolio competitively, factoring in the shift from investment-grade to private credit to ensure the properties stood out in a crowded market. While the developer was initially hesitant about the adjusted valuation, real-time market data was used to demonstrate that this was the only viable path to achieving the client’s goal of a rapid closing. By leveraging a reputation as specialists in the dollar store sector, which led to the initial referral from an outside broker, the Matthews™ agents instilled confidence in the pricing strategy.   Result By utilizing the Matthews™ specialized marketing platform and deep database of private equity and 1031 exchange buyers, the agents identified one of the few active buyers specifically seeking higher-yield opportunities in the dollar store space. The strategy proved successful as the entire three-property portfolio was sold to a single buyer. This consolidated sale streamlined the closing process and met the developer’s urgent timeline for liquidity.   Despite the credit challenges, the Matthews™ agents facilitated a successful exit that satisfied the client’s debt obligations and demonstrated the effectiveness of market-driven pricing.

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Daniel Gonzalez

First Vice President & Associate Director

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How Matthews™ Facilitated the Sale of a Three-Site Walmart Portfolio

Matthews™ agents facilitated the acquisition of a Walmart portfolio which included three properties located in Albany, GA, Hinesville, GA, and Clemson, SC. Representing the buyer, Matthews™ agents sourced and executed an all-cash transaction involving an institutional seller seeking to dispose of multiple assets in a single portfolio. The offering, which included an investment-grade tenant and a high price point, is notable given the scarcity of Walmart assets and the complexity associated with acquiring them. Within hours of identifying the opportunity through the seller’s in-house brokerage channel, the Matthews™ agents successfully connected the parties and drove the deal to a streamlined closing.   Challenge Walmart-leased properties are among the most difficult retail assets to acquire, as Walmart owns the majority of its real estate and frequently exercises rights of first refusal (ROFRs), limiting transaction opportunities. When assets do become available, sellers are often opportunistic and seek above-market pricing. In this case, the seller was highly motivated by timing due to exchange requirements, while the buyer remained focused on acquiring assets at market pricing.   The transaction was further complicated by varying ROFR timelines across multiple assets and the need to align two sophisticated institutional parties with differing priorities. Successfully navigating these dynamics required precise coordination, strong relationships, and advanced negotiation capabilities.   Strategy Once engaged in the portfolio opportunity, the Matthews™ agents immediately leveraged their network and proprietary database to identify a buyer with the financial strength and acquisition history to execute quickly. The agents structured a deal that balanced the seller’s urgency with the buyer’s pricing discipline. Continuous communication and responsiveness ensured that negotiations progressed efficiently, while careful management of ROFR timelines across all three assets minimized execution risk.   The Matthews™ agents emphasized the rarity of acquiring multiple Walmart assets in a single transaction and positioned the portfolio accordingly to maintain deal momentum. Their ability to align expectations, anticipate institutional concerns, and maintain a fast-moving process was critical in bringing both parties to agreement.   Result The agents closed the transaction within an accelerated timeline, an exceptional outcome given the institutional nature of both parties and the complexity introduced by multiple assets and ROFR considerations. The seller achieved a market price while meeting strict exchange deadlines. Concurrently, the buyer secured multiple Walmart assets in one transaction, expanding their holdings with investment-grade tenancy at pricing rarely achieved in such a competitive segment.   The transaction highlights the Matthews™ agents’ ability to navigate high-level negotiations while maintaining momentum from sourcing to close.

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Levi Veleanu

Associate