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Whether it's your first purchase or next purchase, let the expert guidance of Gateway Berkshire Real Estate make it a successful one.

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"We found Tom by lucky accident. We liked that he is licensed in New York, Massachusetts and Connecticut because we wanted more options. He guided us to our apartment and a short time later to our new home. Tom not only knows the market and the surrounding areas, he offers savvy advice. His personal attention carried over from our deposit to the closing, and made a complicated process much smoother. We are very grateful to Tom and we highly recommend him."

~ Monique Rainy Kirchoff

Luxury Living

Gateway Berkshire Real Estate is proud to announce the newest upscale condo development in the Berkshires: Highfield on Main. Experience luxury, carefree living in downtown Great Barrington, steps away from restaurants, theater, and more. This to-be-built development will feature state-of-the-art amenities including sub-level parking with access to your condo via a semi-private elevator opening directly into the condo unit.

More info coming soon...

Featured Home

This upscale country estate is a must see! Built on a pleasant ridge with multi-directional views of 50 miles plus, the residential or private retreat compound features two structures with elevators, four fireplaces, two wood burning stoves, radiant heating on all ground floors, enviroshake roofing, and Hardiplank siding, along with vast flower gardens and a pool!

$7,600,000

View this property...

View our Listings

Gateway Berkshire Real Estate & Services aims to be the most informed and up-to-date real estate agency in Berkshire County. We make the process of buying or selling your home comfortable, even if it’s your first time. View our listings or contact us for a custom list of all Berkshire properties, regardless of selling agent, that match your criteria. We can also continue to notify you when new listings come on the market or when a price change happens.

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CHECK OUT OUR REVIEWS!

Monique Rainy Kirchoff
Monique Rainy Kirchoff
2017-01-21T19:37:05+0000
We found Tom by lucky accident. We liked that he is licensed in New York, Massachusetts and Connecticut because we wanted more options. He guided us to our apartment and a short time later to our new home. Tom not only knows the market and the surrounding areas, he offers savvy advice. His personal attention carried over from our deposit to the closing, and made a complicated process much smoother. We are very grateful to Tom and we highly recommend him.read more
Alii Teele
Alii Teele
2016-10-04T17:07:50+0000
With the expert guidance of Tom Doyle, my husband and I recently took the amazing journey of buying our first home. We started out looking for another house to rent when we met Tom as a renter's broker. He was friendly and knowledgeable; we shared with him our situation and that our ultimate goal was to buy a house. Although we decided against renting the house, he gave us good financing suggestions and helpful tips. Then a week later he sent us a listing, just in case we were curious. I looked into the financing he suggested at Village Mortgage, here in town, and success! We were pre-qualified for more than I anticipated and, boom, we started off on the joyous and very involved process of buying a home. Tom was quick to respond, patient, and thorough as we searched for houses. He was always easy to contact and talk to; with answers and explanations for all my questions and inquires. As we narrowed things down, he guided us through several houses and was very obliging to go through several directions: move-in ready, fixer uppers, different areas. Although I grew up in the area, it still wonderfully helpful to have a realtor's perspective from someone who knew the ins and outs of the entire county. In the search for the perfect fit, he was able to point out potential concerns with the home or with the overall fit to our lifestyle. Not only that, but he was able to anticipate the trajectory the closing process; what strategy we may need or what kind of competition we might have. I found this to be extremely helpful because the journey was also important to me; I was expecting my third child and I wanted the process to go smoothly. Tom made that happen. When we finally found the place for us, he made the purchasing process smooth and more than successful. He was professional, direct, and meticulous with his expert negotiating and he got our family exactly what we needed. Knowing that we had a steadfast negotiator in our corner, took all the anxiety out of closing. He really made our experience a perfect one, and now we have the perfect house. I would recommend Tom and Gateway Berkshire Real Estate to anyone and everyone. I would imagine whether you are buying, selling, renting, or etcetera, with Tom's professional and experienced skill set, he is an asset you would want on your side. Thank you Tom!read more
Alexandra Beers
Alexandra Beers
2016-09-20T15:56:38+0000
Tom is fantastic. He stuck with us through much searching, and ultimately he showed us the perfect place-- a great fit. He was warm and knowledgable, personal and professional. Highly recommended!read more
Laurie Thorne-Conquest
Laurie Thorne-Conquest
2014-10-04T17:22:06+0000
David and Tom bring professionalism to a new level. Outstanding service in the Berkshires!
Jennifer DeSimone Lindsay
Jennifer DeSimone Lindsay
2014-09-11T02:56:21+0000
My husband and I have bought and sold numerous properties in our lifetime but have never had the pleasure of dealing with the utmost professional Tom Doyle. We now consider Tom and his gorgeous, sweet, and amazing wife Paula one of our great friends and good neighbors!!! You can't go wrong with Tom Doyle and Gateway Berkshire Real Estate & Services!!!read more
Karen W. Smith
Karen W. Smith
2014-09-05T01:40:00+0000
Tom Doyle is the realtor of my choice. The awesomest
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