Get A Personalized Quote: 413-675-5420
Get A Personalized Quote Today: 413-675-5420
About Ask Insurance
Local Insurance Experts You Can Trust
Proudly serving Massachusetts and Connecticut with personalized insurance solutions tailored to real life.
At Ask Insurance, our mission is simple: to take the stress out of finding the right insurance. As independent agents, we work for you — not the carriers — which means better options, better service, and better peace of mind.
Why Us?
Personal service with real people
Fast, pressure-free quotes
Licensed in both MA and CT
Access to a wide network of trusted insurance providers
We help you compare and save without the guesswork
Meet the Founders
Alan Stewart Jr.
Alan Stewart Jr. is a Fairfield & Milford native, multi-business founder, and award-winning real estate professional. Named 2017 NHMR Realtor of the Year and ranked #67 nationally by Real Trends in 2018, he has led over $30M in personal and $40M in team sales with 100+ successful property flips.
Alan founded ASJ Realty Partners, ASK Insurance, ASJ Development, True You Design & Development, and Cash Now CT - offering flexible home sale solutions through cash purchases, traditional listings, and private partnerships. A licensed loan officer with a construction background, Alan is driven by personal experience to help others build wealth through real estate across Connecticut.
Greg Kline
Greg Kline started his insurance career at 21 years old, working for a captive agency but knew quickly he wanted to run his own Agency one day. In 2021, Greg & Alan opened ASK Insurance in Stratford, CT. Greg now specializes in all things Real Estate related when it comes to insurance - from condo associations to apartment buildings, investors with hundreds of doors under management to commercial buildings and storefronts. Greg brings over a decade of expertise to the team and has helped launch the insurance careers of many successful agents, helping them grow both their personal & commercial lines books of business.
Meet the Founders
Meet the Founders
Alan Stewart Jr.
Alan Stewart Jr. is a Fairfield & Milford native, multi-business founder, and award-winning real estate professional. Named 2017 NHMR Realtor of the Year and ranked #67 nationally by Real Trends in 2018, he has led over $30M in personal and $40M in team sales with 100+ successful property flips.
Alan founded ASJ Realty Partners, ASK Insurance, ASJ Development, True You Design & Development, and Cash Now CT - offering flexible home sale solutions through cash purchases, traditional listings, and private partnerships. A licensed loan officer with a construction background, Alan is driven by personal experience to help others build wealth through real estate across Connecticut.
Meet the Founders
Greg Kline
Greg Kline started his insurance career at 21 years old, working for a captive agency but knew quickly he wanted to run his own Agency one day. In 2021, Greg & Alan opened ASK Insurance in Stratford, CT. Greg now specializes in all things Real Estate related when it comes to insurance - from condo associations to apartment buildings, investors with hundreds of doors under management to commercial buildings and storefronts. Greg brings over a decade of expertise to the team and has helped launch the insurance careers of many successful agents, helping them grow both their personal & commercial lines books of business.
Meet Your Massachusetts Branch Agents
Meet Your Massachusetts Branch Agents
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Your local partners for all things insurance. We provide tailored policy solutions for home, auto, renters, commercial and business needs.
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Massachusetts Office
96 Lyman St
South Hadley MA