Diane Barry
Diane Barry

Diane Barry

Global Real Estate Advisor

Member of Diane Barry Team
  • M
Hartford County Regional
45 East Main Street
Avon, CT 06001

About Me About Me

Looking for a full-time professional Realtor who is in tune with today's market?

LOOK NO MORE ... The Diane Barry Team will respect your goals, take time to understand your expectations and work seamlessly with others during your real estate transaction. Our clients also benefit from a Trusted Group of Advisors to include Mortgage Consultants, Real Estate Attorneys, Home Inspectors and Licensed Contractors.

Diane and Caitlyn offer personalized solutions to suit all selling, buying or renting needs. Sellers experience a creative, aggressive and customized approach to pricing, the latest technology in digital marketing, home staging and results-driven negotiating throughout the sale process. Buyers benefit from expertise in the local Real Estate market and a focused home search, with real-time feeds from MLS. As Third and Fourth Generation Realtors, clients experience a meaningful perspective to the residential Real Estate business. Our business is built upon referrals with devotion to serving clients before, during and after the sale. Relevant and current information on local Real Estate trends and industry knowledge is provided through our ongoing Client Appreciation Program.

Experience positive results with our knowledge, enthusiasm and expertise in negotiating hundreds of transactions.

  • $124+ million in sold properties
  • Top 2% Nationally 
  • Consistent top producing Realtors in the Farmington Valley, CT

We are passionate about giving back to the Healthcare Community and guiding Physicians, Nurses, Therapists, Scientists and Social Workers through seamless and stress-free transactions from start to finish. Contact us for current market information when you are buying or selling.


Your Dedicated Advocate Every Step of The Way.

  • Born In Waterbury, CT
  • Lives In Simsbury, CT
  • Passion Helping People Capture Their Dreams
  • Interests Beach Days, Enjoying Nature in the Farmington Valley, Sharing great food with loved ones, listening to live music at the Simsbury Meadows
  • Favorite Lyric "Shower the people you love with love" - James Taylor
  • Can't Live Without Family Time

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My Listings and Sales

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Testimonials (35)

Diane and Caitlyn have done it again for me! They professionally carried me to the finish line again. If i ever buy or sell in the future, they are the women I will call! Warm and compassionate, while always keeping their eyes on the finish line! What a dynamic team! Victoria Fortuna
This is the second time we have had the pleasure of working with Diane Barry and Caitlyn Cleary, and we could not possibly be more satisfied. We wouldn't think of having anyone else represent us for any future real estate needs. They were professional, honest, courteous and caring. They made us feel like they were members of our family which was especially appreciated as this time we were selling the home that I grew up in after my mother's passing. Diane and Caitlyn are a joy to work with. They are simply the best. Craig Garfinkel
I thoroughly enjoyed working with Diane and her team. From start to finish, they did exceptional work. I felt fully supported through the entire engagement. I will recommend them to others. Katrina and Elvin Turner
I was very grateful to have worked with Diane Barry and Caitlyn Cleary. They were very organized with excellent, clear communication.A great team to work with. I found them to be very professional and positve. They kept me informed every step of the way each day.Was very pleased with how smoothly the sale of my home went. Elizabeth Scully
Diane and Caitlyn were very easy to work with - they are very professional and were very helpful at every stage of the house selling process. They were excellent with communication and keeping us informed at every step. Priya Venugopalan Aurobindo Nair
The Diane Barry Team did an excellent job selling our home. She and her team were on top of every detail and made the entire process bearable for us (first home sale in 34 years). From the movers, to dealing with the buyers, to recommending excellent vendors for us to use for some home repairs, Diane and her team provided all the services we needed. Thank you! Maureen and James Giuffre
Diane Barry and Caitlyn Cleary are absolutely brilliant to work with. This is my second home sale using this team and they are always so kind, courteous, responsive, professional, knowledgeable, accommodating, helpful and supportive. I truly would not use anyone else. WPS is lucky to have them! And I am lucky to call them my friends!! Helen Thomas
Diane and Caitlyn are truly the professionals. They know the market well and help the clients with valuable advises. They are excellent communicators and get things done effectively and efficiently. I enjoyed very much working with them and had great experience with them when I bought and sold my house. Dongchun Jiang
Diane Barry and her daughter were an exceptional team. Because of their expertise the house sold in 3 days with many offers over the listed price. I am also extremely grateful to them for all of the advice they shared with me. My aunts home is in CT, and I am in NJ, which made things a little complicated, But their advice ranging from house clean out options, people who could fix smaller issues in the house quickly and with high quality, and many other questions answered made the process so easy. Every person recommended exceeded my expectations. It was a great pleasure to work with them, and i strongly recommend using Diane if you need a real estate agent. I can't say enough good things about her. Estate of Lois Ohare Exect. Kathy Hurley
Yhis iss a first=rate organization treating clients with respect and dignity and information so essential to a real estate transaction. My recent dealing in selling my home was treated with patience, kindness and extreme professionalism==relieving me of anxiety and concern. It is with the final result, I recommend Sotheby's to anyone considering a change in real estate. Jane W Hazen Trustee
The service and execution by Diane and Caitlyn were extraordinary. They explained everything and were extremely responsive. Their pricing was spot-on and we actually received over-asking on the sale of our house. Very satisfied. Peter Murphy
Diane Barry & Caitlyn Cleary were an absolute dream working with. They helped us navigate their turmoil of a market with precision. All steps were discussed and questions answered. They were organized and methodical with each phase and made sure we were on top of our deliverables. Could not be happier with our choice to go with Diane and her Team. Kirill and Valerie Forin
Diane Barry and her team are awesome. They are knowledgeable and professional. They know their business and have their clients’ best interest. Loretta Albert Trust
Diane and Caitlyn were amazing! In an incredibly challenging market for a buyer they were calm, strategic, and empathetic. They were focused on getting us in the right house and not just the first house. Further, once the contract was signed, their engagement didn't stop. They have supported us every step of the way, have gone above and beyond, and ensured that we got the right property for our family at a fair price. I couldn't recommend them more highly. Easily the best realtors that I have ever worked with. Thank you! Michael Lutz
The Diane Barry team were responsive, friendly and provided us with great guidance throughout the entire process. We would highly recommend them! Jennifer Wolfberg
I highly recommend WP/Sotheby's as highly knowledgable professionals in the high end real estate market. My agent (Diane Barry) was incredible detail focused, and always instantly responsive. She intimately knew the market, what the profile of the potential buyers would be, and found just the right buyer at the right price for all parties. The transaction was timely, and both parties were happy with the outcome. She knew how to keep the energy positive and moving in the right direction for all. April Lukasik
Very caring about your needs. Fredrick and Suzette Baker
We have used Sotheby's in Newport RI, Scottsdale AZ and Avon CT on the sale side and have been very pleased in all cases. We used another firm to purchase in Ocala FL, and quite frankly missed the excellent "on top of it service" during the transaction and the follow up. James Claffee Trustee Marja Claffee Trustee
This is Yueyang Qin and Shaobo Pang. They help us buy our first townhouse in Framington CT, and they are really nice and responsible. I highly recommend choosing them as your realtor. Shaopo Pong Yuegang Qin
Diane Barry was professional knowledgable and thorough. She is a true professional in all aspects of real estate representation. Rober and Grace Cerritelli Lynne Cerritelli
Diane Barry and Caitlyn Cleary are awesome. They are highly professional and knowledgeable. They deliver results! Loretta Albert Trust
Diane and Caitlin are just ideal partners when you want to sell a home Jacques Banchereu
Working with Diane and Caitlyn to sell our home was a truly great experience. They simplified the sales process, provided invaluable presale guidance, addressed our concerns, and responded very promptly with sage advice to our questions. The Sotheby’s marketing machine, and the data that was shared with us, was awesome. Over 50 showings were set up before the house was officially on the market. A generous offer was accepted before the end of the first full day on the market. Deposits, inspections, closings, finding suitable temporary housing – processes all overseen with the assistance and support of Diane and Caitlyn. We can’t praise them enough! Bob & Cathy Catharine and Robert Jarvis
Virtually from the moment I signed the conract with the Diane Barry Team, Diane began "staging" my house. She did not stop until it was done. From then on she and her partner, Caitlyn Cleary, did all those things that must be done to sell my house and helped me through the prossses to sell my house. They guided and supported me right up to, and includig, the "closisng". They also found time to resond to each off my calls and emails, and they even initiated several contacts to keep me encouraged. Caitlyn even got up on a ladder to make a small repair, Most importanly, the Team sold my house within four days of its listing--and for more than the asking price. Because of the energy and effetiveness of the Diane Barry Team, I woulld recommend Sotheby's. John J. Allison Jr.
The Diane Barry Team of Diane and Caitlyn were phenomenal to work with from taking the listing, to coaching me on the sale price and offers while navigating me through each phase and making the final stretch to the closing an easy one. I have no hesitation in recommending them to friends and family who are in the market to buy or sell a house. Beth Allison
There are very few people people we would trust guiding us through one of the biggest decisions of our lives. Diane Barry and Caitlyn Cleary were the perfect team for the job. Extremely professional, but also respectful, kind and empathetic. We will absolutely recommend you to our friends and coworkers. Thank you again for everything! Scott Leigner Trustee Laura Patrick Trustee
Diane and Caitlyn were excellent communicators and kept us updated throughout the process. John and Elaine Guillot
Both Diane and Caitlyn, were professional, helpful and responsive. I could not have asked for a better duo to assist me in purchasing my new home. Highly recommend them. Debra Angelina
Diane & Caitlyn went above and beyond helping to clean out and stage our house to sell, and encouraging us to set up a weekend of just non-stop showings, which in turn got us 13 offers! And they helped walk us through the offers with a spreadsheet that made it easy to pinpoint the best offers and choose that way. They then helped us to find our dream home and handled all the behind the scenes duties so we didn't need to stress! Highly recommend, and have recommended them to others! Anna Mowrey
Diane Barry and her team offer truly professional advice and total support throughout the sales process. She is available 24/7 to answer and resolve any and all questions and she moves the sales transaction forward with the utmost attention to detail. We would highly recommend Diane to anyone looking to work with a highly skilled, value-added partner during the complexities of a real estate transaction. tomangers
I can't speak highly enough about Diane's professionalism, industry knowledge, integrity and attention to her clients. She provided expert advice and guidance and was a pleasure to work with! Her positive energy, support and responsiveness made a stressful situation much more manageable. She's the agent to go to in Farmington Valley! zuser20150923035824896
Diane is a great realtor! She makes you feel comfortable throughout the hole process and understands her clients needs and wants. She has great communication with her clients and the other realtors making the whole experience a positive one! peanuts65000
We highly recommend Diane Barry. She knows everything about this area and always responded to our request very quickly. She provided us her opinion in a straight way and tried to make information as transparent as possible. dodidoes
Diane is a top notch realtor and a joy to work with. Her marketing plan to help us sell our home was well thought out and her pricing and staging suggestions were right on. Pictures and descriptions for the on line listing were excellent. Not only did we sell our home quickly (28 days with two offers in a slow market), her advice on resources to help seal the deal and get us moved to our new home were invaluable. We would and have highly recommended Diane to our friends and former neighbors. wjterry4
Diane is the most professional, dedicated realtor I have worked with. She works tirelessly to make sure the home fit is right for her client, and every detail attended to. I recommend her highly ccweldon0

Additional Communities


Diane Barry in the News

The Hartford Courant

Property of the week: Classic Cape Cod style CT home in historic old village section…

The Hartford Courant

Property of the Week: Exquisite Avon Home Is Perfect for Entertaining, Inside and Outside…


Asking $675K, This Eccentric Connecticut Midcentury Is a World Unto Its Own…

The Hartford Courant

Property of the Week: 19 Thistle Hollow, unit 19, Avon…

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  • Diane Barry

    Diane Barry

    Global Real Estate Advisor
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