Caitlyn Cleary

Caitlyn Cleary

Global Real Estate Advisor

Hartford County Regional Brokerage

45 East Main Street
Avon, CT 06001
  • Born In:
    Langhorne, PA
  • Live In:
    Avon, CT
  • Passion:
    Fantastic Food and Wine
  • Interests:
    Trying New Restaurants, Going to the Beach, Hiking with my Dog - Lexi, Traveling, and Spending Quality Time with Family
  • Can’t Live Without:
    Chocolate
  • Inspiration:
    My Mother

The Diane Barry Team: Your Global Real Estate Partner with a Concierge Focus.

Experience the difference expertise makes. As a mother-daughter, 4th-generation Connecticut real estate team, we offer trusted guidance for discerning luxury clients and first-time buyers looking to sell, buy or build a custom home. Our goal is to be your dedicated advocate for every real estate transaction, at any price point, now and in the future.

We deliver a seamless, concierge-level experience, backed by:

  • Global Reach: As part of the prestigious Sotheby's International Realty network, we connect you with expert agents worldwide for your international buying or selling needs.

  • A Trusted Resource Network: We provide our clients with a full ecosystem of vetted, trusted professionals—from attorneys and home inspectors to handymen—making every step of your transaction effortless. We guide you and proactively handle any challenge that arises, allowing you to move through your transaction with total confidence.

  • Proven Results: We are consistent top-producing Realtors serving Avon, Farmington, Simsbury, Canton, and West Hartford, with over $200+ million in sold properties, recognized as Top 2% Nationally.

Partner with The Diane Barry Team for concierge-level service and expert representation in the luxury real estate market.

 

The Diane Barry Team: Your Global Real Estate Partner with a Concierge Focus.

Experience the difference expertise makes. As a mother-daughter, 4th-generation Connecticut real estate team, we offer trusted guidance for discerning luxury clients and first-time buyers looking to sell, buy or build a custom home. Our goal is to be your dedicated advocate for every real estate transaction, at any price point, now and in the future.

We deliver a seamless, concierge-level experience, backed by:

  • Global Reach: As part of the prestigious Sotheby's International Realty network, we connect you with expert agents worldwide for your international buying or selling needs.

  • A Trusted Resource Network: We provide our clients with a full ecosystem of vetted, trusted professionals—from attorneys and home inspectors to handymen—making every step of your transaction effortless. We guide you and proactively handle any challenge that arises, allowing you to move through your transaction with total confidence.

  • Proven Results: We are consistent top-producing Realtors serving Avon, Farmington, Simsbury, Canton, and West Hartford, with over $200+ million in sold properties, recognized as Top 2% Nationally.

Partner with The Diane Barry Team for concierge-level service and expert representation in the luxury real estate market.

 

The Diane Barry Team: Your Global Real Estate Partner with a Concierge Focus.

Experience the difference expertise makes. As a mother-daughter, 4th-generation Connecticut real estate team, we offer trusted guidance for discerning luxury clients and first-time buyers looking to sell, buy or build a custom home. Our goal is to be your dedicated advocate for every real estate transaction, at any price point, now and in the future.

We deliver a seamless, concierge-level experience, backed by:

  • Global Reach: As part of the prestigious Sotheby's International Realty network, we connect you with expert agents worldwide for your international buying or selling needs.

  • A Trusted Resource Network: We provide our clients with a full ecosystem of vetted, trusted professionals—from attorneys and home inspectors to handymen—making every step of your transaction effortless. We guide you and proactively handle any challenge that arises, allowing you to move through your transaction with total confidence.

  • Proven Results: We are consistent top-producing Realtors serving Avon, Farmington, Simsbury, Canton, and West Hartford, with over $200+ million in sold properties, recognized as Top 2% Nationally.

Partner with The Diane Barry Team for concierge-level service and expert representation in the luxury real estate market.

 

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Testimonials

Working with Caitlyn was a dream. She was able to answer all our first time homebuyer questions. She was knowledgeable and had so many referrals which is great when you’re overwhelmed with options and never been in this position before. She was always very reachable and if she wasn’t able to call back right away she would be explicit on when we could get in touch. Caitlyn was calm and understanding as we navigated these very confusing and new waters. It was a difficult market out there when we were looking in the late winter/spring of 2025, but Caitlyn helped us curate competitive offers that we would be happy with if our offer won. If we weren’t sure on something structurally or house wise Caitlyn was able to steer us in the right direction. She is a wealth of knowledge and so easy to work with. We’d recommend her many times over!

sarasilvss

Very professional .helped make decision since not in town

Harvey Sprung

Our realtor provided our family, who was moving abroad for the first time, with a wealth of information and advice. Without her, our family's relocation might have been impossible. We are highly satisfied with her dedication and expertise.

Jooho Lee Seul Kim

Caitlyn Cleary is a really friendly and helpful person. She kept great communication with me and gave me a lot of useful advice. Really appreciate!

Yuanuye Chi

Thank you so much Caitlyn and William Pitt Sotheby's International Realty. My colleague had introduced me to Caitlyn. She did a fantastic job, she was quick, professional and very efficient. I didn't know how I was going to search a rental home. I needed some work and had tried to list online as well as a realtor with no success. She went out her way and beyond to assist us. Thank you again.

Mohammed Toufiq

I was looking for a house to live for a year while I visit Connecticut as a visiting scientist. Caitlyn was extremely helpful and professional to provide all the needs to find the right place for my family.

Wonsoer Kang

My Listings

165 Bradford Walk $500,000 link

165 Bradford Walk

New Britain, CT 06053 | Hartford County
$500,000
2 Beds 2/1 Baths 2,170 Sqft

Discover the Art of Living at Bradford Walk. Imagine waking up to serene, elevated views from your primary suite before heading downstairs to a kitchen bathed in morning light....

2
bed
2/1
bath
2,170
sqft

My Sales

181 Mountain Spring Road $2,150,000 link

181 Mountain Spring Road

Farmington, CT 06032 | Hartford County
$2,150,000
6 Beds 6/3 Baths 10,392 Sqft 21.04 Acres

Nestled on prestigious Mountain Spring Road, Partridge Hollow presents a rare opportunity to own a magnificent estate. This white-washed brick Colonial, set amidst 21 acres of...

6
bed
6/3
bath
10,392
sqft
41 Mountain Road $1,580,000 link

41 Mountain Road

Farmington, CT 06032 | Hartford County
$1,580,000
5 Beds 4/2 Baths 4,242 Sqft 2.06 Acres

Living in the Historic Farmington Village offers treelined sidewalk streets, and opportunity to join the Farmington Country Club or Farmington Field Club. Enjoy the Hill-Stead...

5
bed
4/2
bath
4,242
sqft
133 Main Street $1,385,133 link

133 Main Street

Farmington, CT 06032 | Hartford County
$1,385,133
6 Beds 3/2 Baths 5,025 Sqft 1.12 Acres

Nestled in Historic Farmington Village, this exquisite residence presents a harmonious blend of classic New England charm and modern luxury. Set on 1.12 acres of professionally...

6
bed
3/2
bath
5,025
sqft
155 Mountain Spring Road $1,250,000 link

155 Mountain Spring Road

Farmington, CT 06032 | Hartford County
$1,250,000
5 Beds 3/1 Baths 4,612 Sqft 8.72 Acres

Elegant Georgian Colonial majestically poised on 8.72 acres of Farmington's most coveted landscapes. The graceful drive through verdant woodlands crosses a storybook bridge and...

5
bed
3/1
bath
4,612
sqft
181 Reverknolls $1,250,000 link

181 Reverknolls

Avon, CT 06001 | Hartford County
$1,250,000
4 Beds 4/1 Baths 3,707 Sqft 2.06 Acres

This stunning and newly renovated 4 bedroom and 4.5 bath home is situated on a sprawling 2.5 acres of land. Directly on the Farmington River, this home is surrounded by beautiful...

4
bed
4/1
bath
3,707
sqft
35 Mountain Farms Road $1,225,000 link

35 Mountain Farms Road

West Hartford, CT 06117 | Hartford County
$1,225,000
5 Beds 5/2 Baths 6,837 Sqft 2.7 Acres

Exquisite Estate~Spectacular Hartford Skyline Views~Beautifully sited on 2+Acres. Welcoming circular drive reveals a private enclave of lush and private grounds trimmed with handsome...

5
bed
5/2
bath
6,837
sqft
59 Garrett Road $1,150,000 link

59 Garrett Road

Canton, CT 06019 | Hartford County
$1,150,000
4 Beds 4/2 Baths 6,392 Sqft 2.37 Acres

David Stoner Custom Built Home with Exquisite Pool, Majestically Sited on 2+ Acres, complete with Luxury Amenities. Enjoy daybreak listening to nature on your bluestone patio....

4
bed
4/2
bath
6,392
sqft
65 Deer Run $1,125,000 link

65 Deer Run

Avon, CT 06001 | Hartford County
$1,125,000
4 Beds 4/2 Baths 6,730 Sqft 0.98 Acres

Welcome to 65 Deer Run, a beautifully appointed home nestled in one of Avon's most desirable neighborhoods. This expansive property offers elegant living with a first-floor primary...

4
bed
4/2
bath
6,730
sqft
133 Main Street $1,100,000 link

133 Main Street

Farmington, CT 06032 | Hartford County
$1,100,000
6 Beds 3/2 Baths 5,025 Sqft 1.12 Acres

Irresistible Historical Farmington Village Home, beautifully sited on 1.12 professionally landscaped acres. Luxury finishes seamlessly blend New England Charm with a Contemporary...

6
bed
3/2
bath
5,025
sqft
75 East Maxwell Drive $982,000 link

75 East Maxwell Drive

West Hartford, CT 06107 | Hartford County
$982,000
5 Beds 3/1 Baths 3,458 Sqft 0.3 Acres

Stunning Colonial on private cul-de-sac setting in a desirable West Hartford neighborhood. Lovely tree-lined yard offers the perfect blend of privacy & tranquility. Open Floor...

5
bed
3/1
bath
3,458
sqft
104 Meadow Ridge $941,000 link

104 Meadow Ridge

Avon, CT 06001 | Hartford County
$941,000
4 Beds 3/2 Baths 5,172 Sqft 2.76 Acres

This stunning home makes an impact from the moment you lay eyes on it. It radiates from the elegant central foyer w/ sweeping staircase! Gleaming, re-finished hardwood floors....

4
bed
3/2
bath
5,172
sqft
35 Uplands Drive $851,200 link

35 Uplands Drive

West Hartford, CT 06107 | Hartford County
$851,200
4 Beds 3 Baths 3,176 Sqft 0.51 Acres

Wonderful four bedroom colonial completely updated, nestled on a quiet cul de sac west of Mountain Road. Kitchen opens to family room with sliders to a large terrace, first floor...

4
bed
3
bath
3,176
sqft