Jason Gillespie

Lamacchia Realty

Looking to sell your property, buy a new home, or just need some expert real estate advice?

About
After buying his first condo, Jason realized not all agents are created equal. Years later, when selling and buying again, a better experience sparked his own career in real estate. Today, he’s passionate about guiding first-time buyers, making the process less overwhelming and more rewarding. With 25 years in retail, including 20 as a Meat Manager at Stop & Shop, Jason honed strong customer service skills and the ability to work with all kinds of people. A lifelong South Shore local, he grew up in Brockton and Stoughton, bought his first condo in Weymouth, and now lives in Raynham with his wife and two daughters.
Highlights *
34
Recent sales
$109K-$1.94M
Price range
$501K
Median price
4
Years experience

Recent Listings & Sales

Ratings & Reviews
5.0 (6)

Jason Anker
Wrentham, MA - Aug 27, 2025

If you’re looking for professionalism, market knowledge, and the best representation possible look no further. Jay knows the market and how to negotiate deals. You couldn’t be in better hands.

Source: Other

Ben Naranjo
Rehoboth, MA - Aug 26, 2025

Great realtor with a great attention to detail! Jason is truly one of the best out there, with a quick response time, always kept us updated during the home buying process about each step. Jason is truly one of the most dedicated realtors around and comes highly recommend, thank you Jason!

Source: Other

Jocelyn F
Wrentham, MA - Aug 26, 2025

I recently worked with Jay on a transaction where I represented the sellers and he represented the buyers. He was professional, communicative, and a pleasure to work with throughout the process. His collaborative approach made for a smooth and successful closing.

Source: Other

John Ganara
Haverhill, MA - Feb 26, 2025

My wife and I recently purchased a home and had the pleasure of working with Jason as our buyer’s agent. We couldn’t be happier with the experience — both personally and professionally.

Anyone who has been through the home-buying process knows it can be overwhelming, especially in today’s competitive market. Jason’s knowledge, professionalism, and steady guidance kept us grounded and confident throughout. He was with us every step of the way, always available to answer questions and provide support when we needed it most.

We’re incredibly grateful to have had Jason by our side and would highly recommend him to anyone looking to buy a home.

Source: Other

Ian Kenney
Abington , MA - Jan 2, 2025

Jay went above and beyond every step of the way as my family and I looked for our house. He made a normally stressful process seamless and easy. We are so grateful he was the person we had by our side in our home buying journey.

Source: Other

Professional Info

Brokerage

Lamacchia Realty
31 Belmont Street
Easton, MA 02375

Licensed

Licensed REALTOR®
MA 9577644

Specialties

  • First-time buyers

Hobbies

  • Family
  • Food & Cooking
  • Sports

Top Cities *

Quincy

3 sales past 3 years

Weymouth

3 sales past 3 years

Abington

  • 2 sales past 3 years
  • 36 days on market
  • $520K median price

Service Areas (138 cities)

Abington, MA Accord, MA Assonet, MA Attleboro, MA Avon, MA Bellingham, MA Berkley, MA Blackstone, MA Boston, MA Braintree, MA Braintree Town, MA Brant Rock, MA Bridgewater, MA Bridgewater Town, MA Brockton, MA Bryantville, MA Buzzards Bay, MA Canton, MA Carver, MA Cedar Crest, MA Cedar Hill, MA Chartley, MA City Mills, MA Cohasset, MA Dedham, MA Dighton, MA Dover, MA Duxbury, MA East Bridgewater, MA East Taunton, MA East Walpole, MA East Weymouth, MA Easton, MA Elmwood, MA Fall River, MA Foxborough, MA Franklin, MA Franklin Town, MA Freetown, MA Green Harbor, MA Green Harbor-Cedar Crest, MA Greenbush, MA Halifax, MA Hanover, MA Hanson, MA Haverhill, MA Hingham, MA Holbrook, MA Holliston, MA Hopedale, MA Hull, MA Humarock, MA Kingston, MA Lakeville, MA Manomet, MA Mansfield, MA Mansfield Center, MA Marshfield, MA Marshfield Hills, MA Medfield, MA Medway, MA Mendon, MA Middleboro, MA Middleborough, MA Middleborough Center, MA Milford, MA Millis, MA Millis-Clicquot, MA Milton, MA Milton Village, MA Minot, MA Monponsett, MA Natick, MA Needham, MA Norfolk, MA North Attleboro, MA North Attleborough, MA North Attleborough Town, MA North Carver, MA North Dighton, MA North Lakeville, MA North Marshfield, MA North Pembroke, MA North Plymouth, MA North Scituate, MA North Seekonk, MA North Weymouth, MA Norton, MA Norton Center, MA Norwell, MA Norwood, MA Ocean Bluff, MA Ocean Bluff-Brant Rock, MA Pembroke, MA Plainville, MA Plymouth, MA Plympton, MA Quincy, MA Randolph, MA Randolph Town, MA Raynham, MA Raynham Center, MA Rehoboth, MA Rochester, MA Rockland, MA Sagamore, MA Scituate, MA Seekonk, MA Sharon, MA Sheldonville, MA Sherborn, MA Silver Lake, MA Somerset, MA South Carver, MA South Duxbury, MA South Easton, MA South Walpole, MA South Weymouth, MA South Yarmouth, MA Southfield, MA Stoughton, MA Swansea, MA Taunton, MA The Pinehills, MA Three Rivers, MA Walpole, MA Wareham, MA Wellesley, MA West Bridgewater, MA West Foxboro, MA West Wareham, MA Westwood, MA Weymouth, MA Weymouth Town, MA White Horse Beach, MA White Island Shores, MA Whitman, MA Wrentham, MA

* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.