Portland Foreside is a transformative 10-acre mixed-use development located along the historic eastern waterfront of Portland, Maine. This revitalised neighbourhood will seamlessly integrate residential, commercial, and recreational areas, creating a vibrant atmosphere for residents and visitors.
The key features include around 400 residential units, such as oceanfront condominiums, multi-story townhouses, and approximately 180 rental apartments, along with a luxury hotel featuring 128 rooms. Additionally, 50,000 square feet is allocated for retail, dining, and service enterprises, promoting a vibrant commercial hub.
At the same time, the site’s historic buildings are being repurposed into a nationally recognised public market, highlighting Maine’s top food and beverage innovators and entrepreneurs.
The marina features 150 boat slips, boosting Portland’s waterfront attractiveness. Sixty percent of the region is allocated as open space, providing parks, coastal walking and biking trails, and waterfront access for activities such as paddling and fishing.
To learn more about how this project is taking a new approach, we speak to Casey Prentice, founder and CEO of The Prentice Organization, about his vision for a new kind of mixed-use development and the importance of authentic, community-minded real estate development.
A steward, not just a buyer
After graduating in 2009, Prentice had a job offer in real estate. However, when the economy collapsed, he instead found himself bartending in Portland, Maine.
“My dad, an attorney, suggested forming an LLC to take on freelance real estate work. That led me to the Portland Foreside project. Initially, the site was marketed as a condo project, but its owner, Phineas Sprague, wanted more. He sought a steward, not just a buyer.”
Prentice immediately saw the site’s potential.
“I created an image overlaying Portland’s Old Port onto his property to show its scale. That resonated with him, and he told me, ‘If you can find the money, I’ll sell it to you.’”
Over the next four years, Prentice worked to raise the $7 million to buy the site. “We closed in 2013, and the vision became clear: to seamlessly extend Portland’s downtown into a mixed-use neighbourhood that feels organic, not like a project.
“If people can tell where the old city ends and our development begins, we’ve failed.”
True mixed-use space
Prentice and his team are in the process of developing 1.5 million square feet of what he calls true mixed-use space with ground-floor retail throughout, aiming to create a real neighbourhood.
After acquiring the property in 2013, five years were spent rezoning and securing entitlements. From 2018 to 2020, the company built Fore Points Marina, a 16-acre marina with 150 slips and space for mega yachts.
“People thought we were crazy. But I had a ‘build it and they will come’ mentality, and COVID worked in our favour, as yachts didn’t head to Europe, stabilising the asset quickly. That project has been a success and has greatly impacted the local economy.”
The second project was the US headquarters for Sun Life Financial, which was completed in 2023.
“Currently, we’re under construction on the Promenade Hotel, a five-star urban resort with 130 branded residences, 200 apartments, 130 luxury condos, 800 parking spaces, and 100,000 square feet of retail, including a new public market.
“We’re aiming for something like London’s Borough Market; an iconic, authentic place to shop. We’re also mapping out the ground floor carefully, focusing on the movement of people and ensuring the right mix of uses.
“I’ve always been fascinated by the human nature side of urbanisation, why certain stores are strategically placed next to each other, like Coca-Cola paying to be at the end of a grocery aisle. It’s the same with our retailers; we’re not using brokers, because not all coffee shops are created equal.
“We’re intentionally crafting a flow that creates a cohesive, functional space. While the public may not notice the effort, the best spaces are always meticulously planned.”
Shared experiences at Portland Foreside
In terms of the project as an urban collective, he says:
“Shared experiences in our development are rooted in creating a vibrant, engaging environment, not a theme park.”
The key is population density, high foot traffic, and keeping people engaged throughout the day. The attractions will be the retail experiences and the overall user experience on the ground with almost a “block party” atmosphere.
“We want it to feel timeless, as if it’s always been here, rather than brand new—a festival of culture. We focus on details like weathered stone and copper with a natural patina, and we make sure the first experience feels the same as the fifth. We’re also incorporating experiences like farmers markets, ice skating rinks, swings along the waterfront, and dog parks with local breweries.
“We want to create safe, welcoming spaces for people to enjoy, whether with family or pets.”
The development will also host 200 small, free events each year. For example, Cinco de Mayo, a Pride parade, or outdoor movies.
“By designing spaces that are easy to activate, we make it simple for our team to organise these events, creating a social hub that feels lively and always has something going on. Our goal is for residents to think, ‘Let’s head down to the Foreside neighbourhood because there’s always something cool happening.’
“That’s the entertainment and activation we’re aiming for—a place that’s vibrant, energetic, and the spot to be.”
A positive impact on the city
In 2018, Prentice’s team conducted an economic impact analysis, which highlighted the broader effects of a tourism-based neighbourhood.
“It’s not just about employee numbers or tax revenue; it’s about the trickle-down effect of tourism, hotel rooms, restaurants, and shops. Our project alone, once complete, will represent over 10% of Portland’s property tax value. We estimate $19 million in sales and use tax for Maine annually, $222 million in annual retailer earnings on the property, and $678 million in sales activity.”
Portland Foreside will generate 3,400 permanent jobs and 2,600 construction jobs with $700 million in construction spending. It’s the largest private development ever approved in Maine.
But the economic impact goes beyond what’s measurable. Portland’s outdoor lifestyle, vibrant arts and music scenes, great restaurants, and access to both the ocean and ski mountains have made it a desirable place to live.
“COVID has accelerated this, benefiting the city’s growth. Portland is like a teenage boy, still figuring things out as it grows from a small town to a small city. It’s not without challenges, like managing transportation, public services, and real estate development. But that’s where we come in, helping guide smart growth.
“I’m focused on sustainable development. My interest in real estate started during my internship in New York, where I saw the construction of the Bank of America headquarters, the most sustainable building in the US at the time.
“I fell in love with the idea of sustainable real estate and urbanisation, especially when I saw how smart, dense urban spaces reduce car usage and improve public transportation. The key to sustainability in urban development is density, which, though not as flashy as solar panels, is the most impactful in terms of societal benefits.”
Portland Foreside and AOA
One of the companies the developer has partnered with to support its goals is AOA, a design firm renowned for its work in themed entertainment and the art of gathering.
“AOA’s involvement has been joyfully evolving throughout the project,” says Prentice. “I met Tom [Acomb, co-founder of AOA] through mutual friends. For years, it was just a cordial, professional exchange of ideas and friendship. He genuinely loves Portland and has deep family roots here, and we had a good rapport based on the admiration for the culture of the city.”
Over time, Prentice realised the value of officially having AOA on the team. “I wanted them to be a part of the ownership side, acting as a bridge between our consultants and ensuring that everyone was moving in the right direction to create a truly special, activated space.”
AOA’s primary role is to oversee the big picture, helping to coordinate the work of architects, landscape architects, civil engineers, lighting designers, and more, with a watchful eye on the authenticity of storytelling and soundscape.
It is focused on ensuring everything is integrated, down to the most minor details, such as strategically placing power, water, and sewer lines for items like food trucks or kiosks, so they don’t become a logistical headache.
“AOA’s job is to ensure that every design decision aligns with the larger vision of creating a space that meets people’s expectations and stays true to the neighbourhood vibe.
Placemaking
Another key area AOA is helping with on the Portland Foreside project is visualisation and story refinement:
“After seeing their creative team’s work product at their studio in Orlando, I knew we needed this. They’re providing us with tools for everything from world-class 3D design to investor presentations, sales materials, and overall placemaking refinement.”
“The digital data will also help with property management, like tracking the precise location of water lines, so we can make repairs more efficiently without digging up large areas unnecessarily.
“This is just one of the additional services AOA is helping us integrate, and their support is invaluable.”
AOA also brought the recently retired, long-time president of Walt Disney Imagineering, Bob Weis, into the conversation. “Having Bob take a look at what we are doing has been an honour and a unique privilege. We are hoping to host Bob in Portland soon.”
“Being able to support Casey and his team with their vision and their goal of the protection of the heritage of Portland has been energising and refreshing. We rarely encounter a team that places history and culture so staunchly at the top of the priority list and really means it,” says Jackie Wolford, AOA’s vice president of master planning and concept development, who is the lead for the project.
See also: From rides to retail: inside SEVEN’s Transformers-themed entertainment destinations
Rising to the challenge
Portland Foreside is an ongoing project; something on this scale is never without challenges. However, Prentice says:
“I’m an eternal optimist. I always see challenges as opportunities. But real estate development definitely comes with its share of challenges. It has a bad reputation, and a lot of development is done poorly. But the reality is that development affects everyone because it’s part of their everyday lives. People are protective of their city, and that’s understandable.”
We believe in building spaces where people live, work, and experience significant moments. These are places where people celebrate and grieve. We take that responsibility seriously. Buildings, whether people like it or not, define a place.
He says that he sees real estate development as a moral obligation:
“It’s about making places better than we found them. Our focus is on urban revitalisation and densification, not suburban sprawl or housing. We believe in building spaces where people live, work, and experience significant moments. These are places where people celebrate and grieve. We take that responsibility seriously. Buildings, whether people like it or not, define a place.”
The built environment shapes the character of a city or town. “If we do our part well, it contributes to making Portland feel like Portland.
“Convincing the public that we’re good stewards of their city is always a process, and building trust takes time. In my early days, I wanted everyone to love what I was doing, but I quickly learned that trust isn’t something you earn by broadcasting your plans—it’s earned by showing up and delivering.
“We faced referendums and public votes, but we won every polling location by a 60% margin. After that, we knew it was best to focus on doing good work rather than trying to get everyone’s approval. Over time, as we delivered well-received projects, it built more confidence in the process and our team.”
Now, other municipalities are reaching out to Prentice and his team because they see the results and understand what they are trying to achieve.
A long-term vision for Portland Foreside
The Portland Foreside project has been structured intentionally for the long term.
“The common mentality in private equity often focuses on the short term, where there’s this ‘build it, sell it’ approach. This can contribute to subpar construction because there’s no incentive to build things to last. It’s more about grabbing a fee and moving on. However, we view development as an opportunity to build something that creates lasting value for a community.
“Our approach is to hold onto our properties indefinitely. We design with the mindset that we won’t need to sell. This property is one of the most significant opportunities I’ll probably ever have, and it’s not just the location—it’s the size, the oceanfront position, and the impact it can have on the community. So, the main thing is not messing it up. It’s about protecting and enhancing what we’ve built.”
A microgrid has been integrated into the property. This centralised utility plant will supply power, heat, and hot water to the entire campus. “We’re also implementing a snowmelt system using waste heat, eliminating the need for salts or sand, protecting the fishery. These are significant investments—$60 million focused on sustainability, carbon reduction, and ensuring the project’s long-term success.
“We want to ensure that the project and the people using it are positioned well for the future.”
Prentice’s long-term vision is for it to become an integral part of Portland, to the point where people won’t even think of it as a single project.
“I want it to feel like a neighbourhood, like Soho in New York or any cool area in London. When people visit Portland, they’ll know that this area is a part of what makes the city great. It will be so well integrated into the city’s fabric that it feels timeless.”
