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Jeanine Montgomery Luxury Homes of Distinction Specialist,REALTOR®

Relax and Leave the Real Estate to Me!


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Relax and Leave the Real Estate To Me!

Jeanine Montgomery is a native of Norfolk and Virginia Beach and her family is 4th generation to Coastal Virginia and Hampton Roads. Jeanine has seen the changes and the growth that the area has experienced and understands what it takes to navigate through the process of both buying and selling a home. Whether you're a first time home buyer, an investor, looking for a luxury home or selling any residential property, Jeanine Montgomery can help you find what is important to you! Jeanine has a strong track record in closed sales in both buying and selling real estate. Her ability to navigate through the various details throughout the process and negotiate on behalf of her clients is one of the many features that set her apart during a real estate transaction.

For more than 30 years, Jeanine has been building relationships globally in her endeavors working with people. Locally she lives and breathes Coastal Virginia and is proud to call Virginia Beach her home. Jeanine and her husband Gaylon, live in the sought after Chic's Beach community and have raised their two boys, Garrett and Jordan, there. Jeanine is passionate about her work as a real estate agent for Howard Hanna Real Estate Services. Before real estate, Jeanine spent more than a decade as a international television producer and event planner for internationally recognized media companies such as Family Channel and WHRO as well as various Government contractors and in the music industry. Connecting people to what is important to them with their real estate needs is a big part of Jeanine’s process. It's essential to spend time with clients and listen to their needs and connecting all the dots for them is critical. Getting out in the community, finding the right property, and leading clients through the process of home buying or selling is essential. Jeanine is passionate about what she does for a living! That is why Jeanine’s slogan is "Relax and Leave the Real Estate to Me!"

When not selling real estate, Jeanine loves spending time at the beach with family and friends and enjoys sailing the Chesapeake Bay, gardening and spending time with her two dogs Kona and Bleu. Jeanine and Gaylon enjoy exploring the world and dining at the local restaurants on the Shore Drive corridor. Jeanine continues to be actively involved in the Chesapeake Beach Civic League, has served on the board of directors for the Virginia District of the Eastern Surfing Association and ESA All Star committee. Jeanine's husband, Gaylon, is also very involved in the local community and has spent many years on the CXB Civic League, as well as Little Creek American Baseball Pony League board of directors and has coached hundreds of children, both military and local, at Little Creek Amphibious Base in Norfolk, VA. Gaylon is the manager of video and training at Huntington Ingalls Industries, Newport News Shipbuilding. If you are looking for a local with global connections and a  passion to serve people, Choose A Realtor with a Proven Track Record! That is Jeanine Montgomery.


Specialties

Hanna Luxury
Certified Buyer Specialist
Country Property
Custom Home
Dream Home
Executive Home
Farm And Ranch
First Time Buyers
Historic Home
Investment
Land
Luxury Homes
Move-Up Home
New Construction
New Home
Quality Home
Relocation
Residential
Retirement

Photo for 2412 Beaufort AVE $545,000 Sold 7/21/2026
beds
 
2
full
baths
2
partial
bath
1
sq.ft.
 
1,500
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10637459
Photo for 54 N Willard AVE $595,000 Sold 7/2/2026
beds
 
5
full
baths
4
sq.ft.
 
3,293
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10629862
Photo for 4114 Roanoke AVE $249,000 Sold 6/12/2026
beds
 
3
full
baths
2
sq.ft.
 
1,034
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10623855
Photo for 2232 Chamberino DR $1,230,000 Sold 4/30/2026
beds
 
4
full
baths
3
partial
bath
1
sq.ft.
 
3,400
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10623438
Photo for 3811 Pretty Lake AVE $720,000 Sold 4/29/2026
sq.ft.
 
2,160
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10620347
Photo for 5041 Gatehouse WAY $224,500 Sold 4/24/2026
beds
 
2
full
baths
2
sq.ft.
 
1,148
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10628115
Photo for 2529 Bridge Side PL $385,000 Sold 4/14/2026
beds
 
2
full
baths
2
sq.ft.
 
1,204
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10618965
Photo for 5253 Bardith CIR $260,000 Sold 4/13/2026
beds
 
2
full
baths
2
partial
bath
1
sq.ft.
 
1,240
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10625120
Photo for 4936 Lauderdale AVE $830,000 Sold 3/27/2026
beds
 
4
full
baths
3
partial
baths
2
sq.ft.
 
2,595
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10614599
Photo for 9489 Mooring DR $500,000 Sold 3/9/2026
beds
 
3
full
baths
2
sq.ft.
 
2,064
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10617895
Photo for 1872 Lewisham WAY $440,000 Sold 3/2/2026
beds
 
3
full
baths
2
sq.ft.
 
1,272
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10623053
Photo for 3437 Sale DR $399,000 Sold 2/24/2026
beds
 
3
full
baths
2
sq.ft.
 
1,653
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10612413
Photo for 2441 Bayview AVE $745,000 Sold 2/17/2026
beds
 
3
full
baths
2
partial
bath
1
sq.ft.
 
2,218
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10617830
Photo for 601 Roland DR $450,000 Sold 1/27/2026
beds
 
4
full
baths
2
sq.ft.
 
1,859
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10613511
Photo for 4612 Islander CT $330,000 Sold 1/8/2026
beds
 
3
full
baths
2
partial
bath
1
sq.ft.
 
1,501
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10612372
Photo for 9409 Alpine CT $490,000 Sold 10/24/2025
beds
 
4
full
baths
2
partial
bath
1
sq.ft.
 
2,210
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10601409
Photo for 9404 Willow TER $449,900 Sold 10/16/2025
beds
 
4
full
baths
2
sq.ft.
 
2,300
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10600997
Photo for 1813 Jack Frost RD $524,900 Sold 8/29/2025
beds
 
3
full
bath
1
partial
bath
1
sq.ft.
 
1,665
Buyer's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10584459
Photo for 4812 Bay Landing DR $400,000 Sold 8/28/2025
beds
 
2
full
baths
2
sq.ft.
 
1,204
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10596124
Photo for 4928 Sunny Circle
$939,000
Sold 6/20/2025
4928 Sunny Circle
Virginia Beach, VA 23455
beds
 
4
full
baths
2
partial
bath
1
type
 
Detached
Seller's Agent:Jeanine Montgomery
Howard Hanna Real Estate Services
MLS # 10575767
Hanna Luxury

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