Real Estate Agents
Haley Cutter, Pamela Cushing
Top Producer

Haley Cutter, Pamela Cushing


84 Atlantic Ave.
Boston, MA

Let this real estate agent know you found them on Boston magazine’s Find It Boston.

This is my business. I'd like to submit an update.


Live in Luxury Real Estate at Douglas Elliman is one of Boston’s leading full-service brokerage firms, specializing in the city’s most exclusive residential buildings and legendary luxury neighborhoods. Industry experts Pamela Cushing and Haley Cutter are known for bringing a gold standard of professional real estate service to every buying, selling, and renting opportunity.

From modern living at the Penthouse at Millennium Tower to an iconic brownstone in Beacon Hill, this boutique team understands the unique needs of their discerning clientele. The team has worked with business leaders, professional athletes, and families alike, bringing a concierge-level philosophy to every partnership. As a seller, the team designs a tailored marketing plan for each property to maximize impact and results. As a buyer, they combine intuition with expertise to find those rare opportunities that clients may not have otherwise discovered or considered. Backed by the “Power of Elliman,” their approach challenges what a typical real estate experience looks like by elevating the process from start to finish. Cushing and Cutter are sought after for their commitment to excellence, bearing extensive knowledge and integrity with a personal touch. They are eager to work with you this season and make your vision a reality.

Brokerage Firm:

Douglas Elliman Real Estate

Towns Served:

Boston Proper; South Boston

Team Name:

The Live in Luxury Team

Awards or Certifications:

#1 Douglas Elliman, Team Transactions, Boston 2018

#1 Douglas Elliman Boston Team, Q1 2019

Douglas Elliman, Platinum Award

Boston Agent Magazine’s Best Website (2018)

What's your background, education and training?

With a degree in Integrated Marketing and a Masters in Business Administration combined with over ten years of industry experience, Haley Cutter’s extensive market knowledge is a unique asset she brings to every real estate opportunity. Starting her career  in account management at Grey Worldwide and later moving to in-house marketing while pursuing her MBA at Northeastern University. Haley is excited for each unique opportunity to bring a home to the market with integrated advertising and PR as well as hosting curated gatherings.

Pamela Cushing has a business degree from Suffolk University, and spent many years as an Account Executive at Verizon. She is a proud Bostonian - having lived and worked in the city for 15 years. Pamela is seen as a true partner by each of her distinguished clients; from first-time homebuyers to families and professionals alike. Pamela's intimate knowledge of Boston gives her clients a strong advantage when buying and selling their home. Pamela leads with integrity, and her warm disposition yet fierce negotiation skills give clients absolute confidence.

Together, Haley and Pamela have a like-minded approach to exceptional client experiences delivered through their unmatched knowledge of the Boston real estate market, unwavering work ethic and exemplary track record.

What is your typical process for working with a new client?

With any relationship, we focus our energy on understanding our client and their goals, as well as their daily lifestyle and long-term vision for life. We think this is critical to truly acting in each client’s best interest and being able to communicate their needs as a trusted partner.

As a seller, our team takes time to understand the true objective - the price, timing, family and personal constraints. We do our due diligence to capitalize on the market in that moment while considering the next chapter in their lives. designs a tailored marketing plan for each property to maximize impact and results. We take all our knowledge of certain layouts would generate a higher purchase price based on factors including: orientation, view, level of renovation, etc… and produce a thorough market analysis that is easy to understand. We also have the “Power of Elliman” behind us with reports such as their Quarterly Marketing Reports and our global Knight Frank partner’s “Wealth Report” which analyzes trends of high net worth individuals and recently listed Boston as one of the top 5 “Future Cities” for real estate growth & appreciation.

As a buyer, we want to arm our clients with as much tangible knowledge as possible, so they feel completely confident with their decisions. Buying a home is an emotional and financial commitment - and we want to honor that process. We play the role of ‘match-maker,’ using our intuition and expertise to find those rare opportunities that our clients may not have otherwise discovered or considered. Of course, we assist in all search journeys, negotiations, inspections and closings for a flawless experience.

For those seeking a high end rental, our deep knowledge of each full-service luxury building in Boston proper surpasses the industry standard.

What advice would you give a client looking to find a provider in your specialty?

Understand your priorities and seek to work with a professional who offers deep expertise in the market and who advocates for you every step of the way. Challenges can arise and you want someone who you can trust implicitly to protect your investment. When hiring a Broker to represent your property, we highly recommend hiring a team with a proven track record in the building and area you are selling. We understand the market patterns and buyer mindset and consistently sell homes for record breaking prices and terms.

What inspired your passion for your profession?

Having both spent nearly two decades living and working in Boston, we have witnessed the transformative changes to this city firsthand, and are excited for the future of this burgeoning real estate economy.

We enjoy working with a diverse clientele including high-profile business leaders, professional athletes, young professionals and families alike, and aim for the buying or selling experience to complement their unique lifestyles. We are driven by the personal relationships we cultivate with our clients - many of whom we have partnered with multiple times throughout their lives. We also bring a unique global intuition to every relationship, understanding the minutiae of corporate relocations, international moves and help you execute any virtual search seamlessly.

What services are you most excited to offer?

Our global intuition and varied experience working with clients from a variety of cultures plays a critical role in a smooth transition when relocating. We are excited to work with more international clients and those who may be relocating for new career opportunities. We are already exploring new creative avenues to market a home through intimate events, global partnerships, unique staging concepts and advertising tactics. Also, we are leveraging the strength of our Douglas Elliman network internationally, so we can bring that diverse knowledge and expertise to our local clients.

What is the best reaction you’ve ever received from a client?

At one point, we lost out on a rental listing for a 3BR home because we priced the home precisely for the market and a competitor came in with a significantly higher price. A few months later, the client called us back and apologized. He recognized that the other agent had given him a higher number to win the business. He then asked us to market his home for sale. The Seller’s home closed  in under 30 days for 95.5% of the asking price. This client later asked if they could join our real estate firm as they respected the way that we do business and wanted to learn from us.

What makes your business stand apart?

We commit to a concierge-level philosophy with our clients, and extend ourselves to the fullest for our clients – it’s part of our commitment to exceptional service as your real estate partner. We not only facilitate all aspects of the buying, selling or renting process but also help manage furniture deliveries and will outfit your apartment with all the comforts and essentials of home. We want your move to feel exciting and stress-free. We strive to serve each client far beyond the expectations of a traditional real estate experience.

As female entrepreneurs, we  are committed to mentoring the next generation of women professionals in this growing industry.

How many years have you been in business?

Live in Luxury Real Estate has over 25 years of combined experience, and our initial firm was founded five years ago. For the past year we have operated as a “company within a company” as The Live In Luxury Team at Douglas Elliman.

What do clients have to say about you?

“One of the best real estate teams I have ever encountered in over 30 years of experience. Pamela and Haley epitomize exceptional customer service. Live In Luxury is a true asset to any real estate transaction: they were prompt, courteous and professional in every facet of the transaction.  - Peter |  Beacon Hill, Boston, MA

My husband and I had a wonderful experience with Pamela and Haley. They know the Boston rental market. They listened to exactly what we were looking for and they did not waste our time. I really felt protected having them as our agents. They go above and beyond to make sure all your needs are met. They feel like friends now. That is rare. I would highly recommend them both. - Mary  |  Millennium Tower, Boston, MA

Live In Luxury really delivered results for us beyond expectations. Pamela and Haley helped us navigate some sticky points in the negotiation of the sale of our condo, was creative in their approach to marketing and problem solving, and always available. We highly recommend Live In Luxury for any needs you may have in Boston. - Janel  |  North End, Boston, MA

Any other information you’d like to provide – Hobbies, etc.

We love traveling to other cities and collaborating with other members of the Douglas Elliman team. This year alone, we have attended real estate events in NYC, Aspen, Miami, San Francisco & London. It is inspiring to learn about what is successful in other markets and bring new marketing ideas back to Boston. When others may be sightseeing iconic spots when traveling somewhere new, we often spend our time touring homes on the market, drawing inspiration for how we can strengthen our capabilities at home.

We prioritize family, and are so honored to call many of our clients part of our extended family. We spent Christmas Eve with a number of current and past clients alongside our own families and regularly celebrate our clients through the milestones in their lives.

We have admired Boston’s progressive growth and are committed to enhancing this community we are so proud to call home. We’re active in our children’s school systems and believe strongly in civic impact through organizations such as The St Francis House that support positive growth and development throughout Boston.


Top Producer: 2019


Full-service brokerage firm specializing in properties at Millennium Tower, Millennium Place, The Ritz Carlton and many more, including The Penthouse Collection. The Live in Luxury Real Estate team is skilled at selling, buying and renting in Boston’s most exclusive residential buildings and legendary luxury neighborhoods.