Jessica Bailey

Responds Quickly

Chesapeake VA

The Real Estate Group

69 Closed Sales

$25.7M Total Value

$239.9K - $800K Price Range

$372.7K Average Price

Prior 5 years

About Jessica

If you are a Military Family relocating, Realtor Jessica Bailey can help. Whether you are moving from the West coast to the East coast, living out of suitcases, or your spouse is deployed, and you are doing everything yourself, Jessica knows how you feel. She has been there.

If you are a first-time home buyer, you may be nervous and not certain how the home buying process works; Jessica knows how you feel. She has been there.

If you are looking to sell your current property, her expertise and tenacious marketing plan will get your property sold and not just sitting on the market.

Contact her today for all your real estate needs! She wants to be more than just your Realtor for this one time move, she wants to be your Realtor for life.

Home Types: House, MultiFamily, Townhouse, Condo

Years of Experience: 21

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	7
Total Value	$2,201,500
Average Sale Price	$314,500
Price Range	$205K - $441K

Buyer Deals
Total Deals	3
Total Value	$1,307,990
Average Sale Price	$435,997
Price Range	$350K - $565K

1 Year View by Quarter

Seller Deals
Total Deals	13
Total Value	$4,693,950
Average Sale Price	$361,073
Price Range	$205K - $768K

Buyer Deals
Total Deals	11
Total Value	$4,557,770
Average Sale Price	$414,343
Price Range	$240K - $666K

2 Year View by Quarter

Seller Deals
Total Deals	40
Total Value	$15,114,700
Average Sale Price	$377,868
Price Range	$105K - $800K

Buyer Deals
Total Deals	29
Total Value	$10,601,405
Average Sale Price	$365,566
Price Range	$170K - $720K

5 Year View

Neighborhoods Jessica is Experienced In

Jessica's Active Listings

$430,000
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
1804 Barkading Ct

Virginia Beach, VA
Nestled on a tree lined cul-de-sac, this beautifully maintained 3-bed, 2-bath home offers the perfect blend of comfort and convenience. Head inside to discover soaring ceilings in this open floorplan home w/ abundant natural light streaming through the skylights, creating an airy, inviting atmosphere. The spacious living room centers around a stunning large stone fireplace, perfect for cozy

Jessica Bailey The Real Estate Group

$315,000
- 4 Beds
- 1.5 Baths
- 1,900 Sq Ft
419 Durham St

Hampton, VA
This waterfront home is priced to sell. Motivated seller! Bring your best offer! Get the home, then launch your kayak/canoe from your backyard! Lots of extra living space in this home with a sunroom, den, family room and a dining room!! Oversized garage and a detached shed for all your storage. Vapor barrier/garage service door/thermostat/doorbell new in 2026, LVP

Jessica Bailey The Real Estate Group

$325,000
- 3 Beds
- 2.5 Baths
- 1,870 Sq Ft
729 Lacy Oak Dr

Chesapeake, VA
A beautifully designed condo in Chesapeake’s Greenbrier area, this home features two spacious primary bedrooms with large closets that offer comfort and privacy, plus an additional flex room perfect as a bedroom, office, study, or creative space. Stylish luxury vinyl plank flooring flows throughout the main living areas, creating a modern, cohesive feel. The kitchen opens to the dining area,

Jessica Bailey The Real Estate Group

$385,000
- 3 Beds
- 2 Baths
- 1,550 Sq Ft
401 Cannon Dr

Carrollton, VA
Looking for a home tucked away from all the hustle and bustle yet close to the brand-new hospital, Publix shopping center, The Peninsula, military bases and more? Look no more and welcome home! This beautiful ranch that has been meticulously maintained and will wow you as you enter to the open floorplan with sprawling hardwood floors and soaring cathedral ceilings. Nicely appointed throughout

Jessica Bailey The Real Estate Group

Recently Sold

$365,000

Sold Jan 9, 2026
- 3 Beds
- 2 Baths
- 1,526 Sq Ft
210 Azalea Dr

Smithfield, VA
- $239/SF
- 11 Days On Market
- Current Est. Value $366K
Jessica Bailey The Real Estate Group

$205,000

Sold Nov 14, 2025
- 3 Beds
- 2 Baths
- 1,270 Sq Ft
5682 Landfall Dr

Virginia Beach, VA
- $161/SF
- 57 Days On Market
- Current Est. Value $198K
Jessica Bailey The Real Estate Group

$260,000

Sold Aug 4, 2025
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
2025 Allison Dr

Chesapeake, VA
- $217/SF
- 18 Days On Market
- Current Est. Value $265K
Jessica Bailey The Real Estate Group

$441,000

Sold Aug 1, 2025
- 3 Beds
- 2 Baths
- 1,676 Sq Ft
713 Barbury Arch

Chesapeake, VA
- $263/SF
- 20 Days On Market
- Current Est. Value $447K
Jessica Bailey The Real Estate Group

$356,000

Sold Jun 20, 2025
- 3 Beds
- 2 Baths
- 1,504 Sq Ft
4004 Wyant Ct

Chesapeake, VA
- $237/SF
- 10 Days On Market
- Current Est. Value $362K
Jessica Bailey The Real Estate Group

$240,000

Sold Jun 18, 2025
- 3 Beds
- 1 Bath
- 1,025 Sq Ft
1117 Baskerville Ln

Portsmouth, VA
- $234/SF
- 30 Days On Market
- Current Est. Value $255K
Jessica Bailey The Real Estate Group

Awards and Designations

NAR - National Association of Realtors
ABR - Accredited Buyer Representative
MRP - Military Relocation Professional

Other Experience

Distressed Properties, First Time Home Buyers, Military Families, New Construction, Short Sales, Veteran Programs

Agent License: Virginia #0225098252

Jessica Bailey

(757) 891-5392

Responds Quickly

(757) 891-5392

Homes for Sale by City

Jessica Bailey

About Jessica

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jessica is Experienced In

Jessica's Listings and Deals

Jessica's Active Listings

Recently Sold

Awards and Designations

Other Experience