Ryan is a respected real estate expert.

North Shore and 

Merrimack Valley

"Bringing design and real estate together. Turning dreams into reality one client at a time." 

Ryan O'Connor-Crowe

Phone: 978.836.8761

Email: [email protected]

Ryan is an experienced agent with a wide variety of knowledge in the real estate world.  Graduating with his Bachelor's in Architecture from the University of Hartford and then with his Master's Degree in Architecture from Southern Illinois University, Ryan has been able to combine his passion for architecture with properties.  Growing up on the North Shore and now living in the Merrimack Valley, Ryan is highly knowledgable in the areas. 

Ryan has worked in both residential and commercial design, in addition to performing major home renovations. First time home buyers or sellers will be guided to making the decision that is best for them with the guidance of Ryan showing them possible improvements that could increase equity in their property. 

In addition to Ryan's Real Estate and Design career, he is also the Owner of the WINE LAB in North Andover, where you can see one of his passionate architecture designs (while enjoying some fantastic wine).

Areas of Expertise: North Shore and Merrimack Valley

Types of Properties: Experienced in Single Family Homes, Condominiums, Multi-Family Properties, New Construction, Home Renovation Properties and Commercial Properties.

Types of Clients: First time buyers and sellers, move-up buyers, down-sizers, investors, builders, new construction developers, estate & probate sales.

Start your home buying/selling journey 

with Ryan today!



North Andover

1 Kid


2 Dogs

Copley & Charlie


in Architecture

Why Choose Bentley's? 

  • #1 in Essex County Real Estate Team since 2011
  • We were ranked #159 in the United States 2017 by Wall Street Journal
  • As of 12/1 we are the 3# office in Essex County with a small but mighty team. This is a huge accomplishment. 
  • We Sold more homes traditionally in 2017 than any other Real Estate team in the entire state of MA.
  • We will quickly become #1 in New Hampshire  - 2019
  • #1 Essex County Real Estate office homes sold per agent 2017
  • Data from MLSPIN, Broker Metrics, Wall Street Journal


Essex County Team

since 2011


of Happy Clients


US Team



Per Agent Sales

Essex County 2018

See Some of Ryan's Recent Sales

7 Grandview, North Reading

Pete and Sue were looking for a single family home to downsize to that they would be able to easily retire in with low maintenance.  Ryan went above and beyond to work with these buyers to find them a property that had lots of privacy, a quiet neighborhood and would let the couple retire with very little maintenance to the property, so they could spend their time focusing on their grandchildren.

43 Castle Circle, Peabody

Ryan worked with the sellers on this beautiful property to have the home priced to sell.  The property had an accepted offer in less than 2 days of being on the market!  The sellers were so impressed that they used Ryan to find their property they planned to downsize to.

8 Sycamore, Dracut

This property was a new construction home in a development overlooking the golf course.  Ryan worked on the buying side of this transaction and guided selections from home-style, paint colors, interior finishes, and custom changes to the design of the home.

181 Storey Ave, Newburyport

Jared and Kelly were first time homebuyers and looking for a property to start their family together.  The couple loved the walkability and downtown in Newburyport.  Ryan worked with the couple to find a property that would suit their needs and give them the possibilities for future expansion.

17 Summit Terrace, Peabody

Frantz and Georgia were newlyweds looking for their first time home together.  Being a native of Peabody, Ryan took them to several properties to help them find a property that had plenty of room for entertaining.

66 Park Street, North Reading

Ryan was the agent (twice) and designer for this home-flip property.  The single family ranch had an amazing backyard but was in need of a makeover.  Ryan designed the first floor renovations to create an open floor plan and selected all finishes.  

487 Waverly St, North Andover

Nicholas and Katherine had a growing family with twin boys and a new baby girl and they were in need of a home with ample space, a backyard for the children to play, and a good school district.  Ryan took them straight to North Andover to find their forever family home. 

284 Princeton Street, Boston

Sean and Emily were newly married and looking to find their first home close to their jobs in Boston.  Ryan worked with the buyers to find a gorgeous newly renovated condo in East Boston that would keep their commutes short, and give them more living space.

Interested in Selling a property with Ryan?

Get to know some of the things Ryan & the North of Boston Living Group do to market your valuable home. 

Our Facebook Page

Our advanced and targeted Facebook marketing reaches thousands of potential home buyers. We create dedicated Facebook Ads to target locals and drive massive amounts of traffic to your listings using our advertising budget.

Lifecycle Marketing

We use Facebook to strategically advertise your home during all stages of the selling process. Coming Soon, Just Listed, and Open House posts help to build a "buzz" around your property and can even lead to multiple offers the moment its officially for sale! 

Want to know exactly how we do it? Call Ryan today.

Everyone talks about their marketing, but can they show you a proven history of success? 

Can they demonstrate exactly what they do when? 

We can & our clients LOVE It.

Reach Buyers with Email Marketing

Learn how we use email to reach buyers.

Video Marketing Strategy

We'll create custom, television quality video to market your home.

Ready to start to watch for the perfect home? 

See the latest local homes to hit the market below.

Be sure to ask Ryan about "off market & coming soon" listings not yet public.

Learn about Selling, Buying, Buying & Selling at the same time or, get to know the local hotspots, read our blog posts below. 

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