Greg Chaplain leads the Real Estate Home Team and is a licensed agent and Associate Broker. Having grown up in Lakeville, Massachusetts, he completed his BS in Business Administration & Finance from West Virginia University. He relocated to Hampton Roads in 1989 and has called the 757 home ever since. After spending more than a decade managing sales teams in the wine industry, Greg brings a wealth of business experience to his real estate career. Licensed since 2005, Greg's attentiveness and communication skills ensure his clients feel comfortable and content. Clients love the way he goes the extra mile and helps them navigate the whole buying or selling process. Greg is a member of the National Association of REALTORS(R), Virginia Association of REALTORS(R), the Hampton Roads REALTORS(R) Association, and North Carolina Association of REALTORS(R). He is a devoted husband and proud father of two daughters, plus a son-in-law. Greg's extracurricular activities include watching sports, enjoying live music and the theatre, exploring great restaurants, and boating the local rivers.
Read More About Greg
Credentials
LICENSE
Real Estate - Virginia - # 0225091566
Designation
Top Producer
Licensed Realtor
Real Estate Broker
Military Relocation Professional
Broker / Associate Broker
REALTOR
Specialties
Sellers
Buyers
Residential Property
Awards
2026
TOP AGENT
Norfolk, VA
2026
TOP AGENT
Portsmouth, VA
Other Awards
Circle of Excellence, 2017 Extra Large Diamond Team, Hampton Roads Realtors Association. Circle of Excellence 2018-2022 Mega Team Diamond Award, Hampton Roads Realtors Association.
View All Awards
FAQ
1. What advice would you give a buyer trying to purchase a home?
It's never a bad time to purchase a primary residence. It is one of the first steps to creating wealth. The net worth of the average home owner is 40+ times greater than the average renter.
2. What advice would you give a seller trying to sell their home?
While the sticker price is very important, there are other elements that may be just as important when revieing offers to purchase. Working with an agent that understands that is key to maximizing the return on investment and for making a smooth transition.
3. What types of clients have you worked with?
I help people buy and sell residential real estate. My team serves over 400 families each year purchase or sell. We work with first time home owners, military and corporate relocations, second homes in our attractive area and clients who are looking for investment opportunities.
4. Describe a recent transaction you are fond of. How did it go?
We successfully close on residential real estate properties every day of the year. (Over 400 on average each year) Recently I helped a friend and former client secure and transition his growing family to a larger, new construction property in Norfolk, Virginia.
5. How did you get started in Real Estate?
I am a cooperate refugee! After 13 years in a cooperate sales/sales management role, I was let go in an acquisition. I landed in real estate as a place where I could use my extensive sales and customer service skills but, where I also worked for myself. The only person who can fire me now, is me.
6. Do you have any special education or training that will benefit your clients?
BSBAd. Finance - West Virginia University
Associate Broker
Vast negotiation and contract management background
Contact Information
Location
1112-F Eden Way NChesapeake, VA, 23320
Social Media
Greg Chaplain's Reviews & Ratings
90 Reviews
(5/5)
Note: Reviews may include other agents on their team
What clients say about this agent....
Responsive
Communicative
Professional
Knowledgeable
Outstanding
Great for new buyers
Available Remotely
Trustworthy
Hard working
Excellent negotiator
Amy G.
Review for Member: Greg Chaplain
March 23, 2023
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
ZillowVERIFIED
Greg did an amazing job with finding a home for us. He was in constant communication with us and I never felt like I was left behind or put aside with him. He had our best interest at heart and I could not have chosen someone better than him. He is extremely knowledgeable of the area when it comes to buying a home but he was also knowledgeable about the many stipulations that come with a VA loan. The process was an absolute breeze and he explained things multiple times so that I was able to understand everything that was happening. He responded to texts, calls, and emails in a timely manner and I was not caught off guard by anything at all. I cannot boast about him enough. If you are planning on buying in Hampton Roads, he is the guy to go to!
Rasheedacanario
Review for Member: Greg Chaplain
December 22, 2022
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
ZillowVERIFIED
Greg did an amazing job helping us throughout the process of purchasing our first home. Me being in japan was difficult enough, but he was there every step of the way and always had our backs. He will reply to you fast and is very knowledgeable. Me and my wife will definitely be working with Greg in the future!! I appreciate you greg!
Hientdang96
Review for Member: Greg Chaplain
November 30, 2022
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
ZillowVERIFIED
Oh man. Greg is wonderful. He helped me find a gem in Portsmouth and sell it when it came time to move on. Greg is communicative, quick to respond, quick to get you an answer and if he doesn?t have it, he gets back to you with it in less than 24 hrs. He?s organized and all business if need be. He treated me like family and I love that. He gives it to me straight and doesn?t sugar coat things. He still follows up with me even tho I?m not working with him anymore! Seriously, I?d recommend him to all my friends and family if they were looking. He even linked me up with someone at my next location that?s pretty awesome too. Not as great as him of course, but he?s literally the best. If you?re looking for a good, honest home, Greg?s your man.
Dr G.
Review for Member: Greg Chaplain
June 13, 2022
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
ZillowVERIFIED
Greg and his team were top notch through all aspects of the sale of our home. They took care of everything despite us being out of town for the entire sale. Great job!
Beccawelsh14
Review for Member: Greg Chaplain
May 28, 2022
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
ZillowVERIFIED
Greg was great! Extremely professional, helpful and kind. We were out of state buyers who had limited time to buy and little knowledge of the area. He did a great job showing us tons of options when we came into town and made the process as easy as possible. Highly recommend!