
Get to know Jack Gregory
Leasing / Residential Sales, Property Management............. for the small Investor & Homeowner..........30 Years Experience
Covering New Haven, Fairfield, Litchfield, Middlesex & Hartford Counties.
~ Open Listings available
Jack Gregory's listings & sales (75)
For Sale
For Rent (15)
Address | Bed/Bath | Listing price |
|---|---|---|
![]() 1690 Dixwell Ave #D4 Hamden, CT 06514
| 1 Bed, 1 Bath | $1,700/mo |
![]() 138 Wooster St #2F New Haven, CT 06511
| 3 Bed, 2 Bath | $2,800/mo |
![]() 1684 Dixwell Ave #B Hamden, CT 06514
| 1 Bed, 1 Bath | $1,395/mo |
![]() 170 Mill Plain Rd #B Branford, CT 06405
| 2 Bed, 1 Bath | $2,495/mo |
![]() 1676 Dixwell Ave FLOOR 2 Hamden, CT 06514
| 1 Bed, 1 Bath | $1,495/mo |
Sold (60)
Address | Sold date | Closing price | Represented | Flag Sale |
|---|---|---|---|---|
| 9/17/2025 | $220,000 | Seller | ||
| 8/18/2025 | $142,900 | Seller | ||
| 4/8/2025 | $850,000 | Seller | ||
| 2/25/2025 | $360,000 | Seller | ||
| 12/18/2024 | $820,000 | Seller |
Jack Gregory's reviews (5)
Write a review- Will never recommend||1.01.0
6/18/2025 - techaeri91
Airport heights, Anchorage, AK.Local knowledgeProcess expertiseResponsivenessNegotiation skillsSent him a message on the app and he spoke to my boyfriend on the phone. We scheduled a house tour as we were very interested in the property. Came the next day for the tour and the agent was not there. There was another family there who had just don...
Response from Jack Gregory on 6/28/2025
The fact of the matter is that we did 'NOT' schedule an appointment. I initially told them that a 6 pm appointment was possible.............However, once they told me that they had 4 pets ( 3 dogs and 1 cat )..... I informed them that I would need to speak to the Owner of the property to see if they were ok with the amount of pets, before I would schedule an appointment, .......... and I would "get back to them"...........and that's where we left off. ......It unfortunate that Aimee & Chris chose to write a negative review, when in reality the problem is either a lack of memory on their part or maybe they misunderstood.
- Highly likely to recommend||5.05.0
1/27/2025 - Rajiv Sethi
Helped me rent a Apartment home in Wooster square, New haven, CT.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJack’s a great guy. Super helpful and very professional. He worked with us to get a lease in place and also was very responsive when any issues arose at the apartment. He’s a great guy too. Not pushy and very patient. Would highly recommend - Will never recommend||1.01.0
4/24/2024 - George Germano
Property managed a home I rent.Local knowledgeProcess expertiseResponsivenessNegotiation skillsEdit: We were disappointed to see Jack’s response of calling us liars with no justification/explanation on the several issues we experienced working with him. We wish him the best and hopes he treats his tenants with a bit more respect going forward....
Response from Jack Gregory on 5/28/2024
In regards to George Germano's inaccurate & false claims .....I have been in the real estate business in CT for many years and I have never had anyone post a complaint. George decided to break his Lease which is fine, and so by breaking his lease, it offered me opportunity to earn a commission/get paid by re-renting the house. I am always motivated to do that, not advertise a "wildly outlandish listing", which is counterproductive and makes no sense. In regards to the other accusations & comments he made -they are all inaccurate....... and I hope some day this gentleman finds the peace of mind that we all deserve.
- Highly likely to recommend||5.05.0
6/13/2020 - Julia Skrainski
Helped me rent a Multiple Occupancy home in North haven, CT.Local knowledgeProcess expertiseResponsivenessNegotiation skillsContacted me back almost immediately after I left a message. Always got back to me right away through text as well. Was very quick with the process (which is what we wanted). Got the application approved and move quickly to have lease signed! overall... - Highly likely to recommend||5.05.0
10/10/2018 - user0328775
Bought a home in 2015 in CT 06511.Local knowledgeProcess expertiseResponsivenessNegotiation skillsI used Jack as an agent for years and it would be hard to find a harder working person than Jack. I have found him to be knoweledgeable and willing to do anything to get the deal closed. I have used him both for purchases and leasing and have been ha...














