John Middleton | Real Estate Realtor® / Agent


Real Estate. Redefined.

People often ask “How’s the market?”
If you’re considering acquiring or disposing of real estate that’s a reasonable question, but we often hear responses that miss the essence of the question in a meaningful way. The real estate market is neither hot nor cold, good nor bad. The real estate market is indifferent. It is dynamic. It can be stable or volatile. There are undervalued and overvalued offerings and throughout it all, there are equity-building opportunities. Since 2003, John Middleton’s history as a real estate and business leader includes sourcing properties, structuring capital, site selection, strategic conception and implementation, structuring transactions, property development and more. But according to John, the most important element is building lasting relationships based on trust.

“Our role as real estate advisors is to focus on developing fully transparent, relationship-based transactions which ultimately translates to providing the greatest value for our clients. Because trust, not necessarily agreement, is essential in the role of an advisor."

As a boutique real estate investment firm, John Middleton - Real Estate Advisors caters to individuals and investment groups looking for personalized service and real world-demonstrated acquisition and disposition advice and services.

“Our long-term relationships with brokers, builders, lenders, appraisers and other professionals throughout the real estate industry - paired with our comprehensive strategies and effective negotiations - allows us to connect our clients to the right people and the right properties using the right approach. The result is the greatest possible benefit to our client's objectives.”

The firm’s focuses include strategic investment advisory and facilitation processes for buyers and sellers, 1031 tax-deferred exchanges, single-tenant investment sales and acquisitions, net lease investments, joint venture advisory, capital structure advisory, build-to-suit developments, debt/equity, specialized search and family office/professional investor representation. Or, as John likes to put it, “It’s Real Estate. Redefined.”


"John is a distinguished professional and, unlike many in his field, operates with a real sense of dedication to service and results. If I ever needed to hire a real estate agent in northwest Montana again, then John would be my first choice. He is serious and extremely knowledgeable about his work, and also very gracious and patient. I'm honored to be able to recommend him to anyone who needs assistance buying or selling real estate in the region."
-David Groce, ESQ. Operations, Planning, Administration and Generalist



John assisted us in buying a house in NW Montana while we were still living in Virginia, and it was a very easy transaction. John directed us to the right property and handled the sale with impeccable integrity. He is someone who can be trusted and upholds the professional code."
-Karen Loving, Teacher of the Alexander Technique and CranioSacral Practitioner



"We have known and worked with John Middleton for over 8 years. During this time, he has shown integrity and hard work ethics. He works for his clients first and looks out for their interests. Would highly recommend him in all areas of his business."
-David Quinn, President at Quinn Home Inspection



"I've been fortunate to be able to work with John Middleton on real estate transactions in Flathead County, MT. For a couple of those deals, it was essential that "out of the box" deal making take place. John advised the buyers and kept the sellers motivated during challenging negotiations that were ultimately win-win solutions for both the buyer and seller. It is great to work with a guy like John in situations like that."
-David Boye, Broker/Owner at Black Diamond Mortgage Corp.


John Middleton displayed exceptional tenacity throughout my lengthy listing and eventual home sale. He never lost focus, remained committed and never became complacent when it came to pursuing a buyer for my house. He was always confident and positive, and I believe my home sale was a direct result of his dedication and professionalism. I hope to use his services again in the future and would not hesitate to recommend him to others. Kudos on a job well done

-Kevin Devine, Seller

We work closely with John to set realistic prices and list our properties. They sell quickly, negotiations are on point, and the closings are seamless.

We've referred several friends and acquaintances to John, and will continue to recommend him in the future.

-Scott Fair, Seller and Buyer

John found my husband and I the most perfect piece of property on Flathead Lake, a little piece of "heaven", that actually went over and beyond our wildest dreams or expectations! He was incredibly diligent and responsive, putting in many hours showing us potential lots. And then before our acreage was even listed, John heard about it through his wide network of contacts and knew he had found our dream property. The purchase transaction went very smoothly with absolutely NO hitches, and we could not be happier. I would highly recommend John for any of your real estate needs, from selling to purchasing.

-Gail Elizabeth, Seller and Buyer


John's Listings

Viewing 4 Listings

137 Headwaters Lane, Condon, MT 59826

Property Type


Come and see! This 15+ acre dream property offers the finest of views and terrain. A perfect place to build your Montana dream home and enjoy privacy, beauty and wildlife.

605 Geddes Avenue, Whitefish, MT 59937




ONLY ONE UNIT LEFT. This fantastic townhouse with excellent rental income is the lowest price townhouse per square foot in Whitefish. Completed in May of 2016, this unit is finely finished with granite, stainless, warm woods, master on the main floor (with additional master suite in the lower level) and a seasonal creek out the back door. Quiet neighborhood on the edge of town for easy access to all the amenities downtown Whitefish has to offer, including close proximity to the bike path. HOA dues cover all exterior maintenance making this a perfect property for investors, owner occupants or as a vacation home.

190 Cliff Creek Road, Whitefish, MT 59937




SHORT SALE. Bring the outdoors in with this custom log framed home in a very private location. Close to ''blue ribbon'' Bootjack Lake (full of trophy trout) with easy access to Whitefish and Kalispell. Oversize double attached garage, open floor plan providing lots of natural light and wonderful wooded views. Large deck overlooking a wildlife thoroughfare. There are not a lot of homes like this in Whitefish. Bonus: a nearly finished cottage house that could be made into an extraordinary guest home. All offers are subject to third party/lender approval.

3832 Tamarack Avenue, 2b, Whitefish, MT 59937




Only one unit left! One of the nicest mountainside condos at Whitefish Mountain Resort in the highly desirable ''Black Diamond'' building - just 100 yds from the Home Again Ski Trail for easy access to the slopes. Open floor plan, heated garage with parking for two vehicles, storage unit, ski locker and in-floor radiant heat. Private balcony with great views. Enjoy the new hot tub after a long day playing outdoors or warm up next to the cozy stacked stone gas fireplace. HOA dues cover water, sewer, heat, internet and cable. Only two units per floor provide peace and quiet for owners and guests. Meticulously maintained, quality furnishings and excellent rental history. Many recent updates including hot tub, gutters and heat tape.