Gregory Chaplain Real Estate Agent - The Real Estate Group

4052 Wyndybrow Dr, Portsmouth, VA For Sale $315,000 - listed by Gregory Chaplain — For Sale $315,000

Gregory Chaplain listing agent for 815 Delaware Ave, Virginia Beach, VA - sold for $700,000 — Sold $700,000

1680 Dylan Dr, Virginia Beach, VA Under Contract $360,000 - listed by Gregory Chaplain — Under Contract $360,000

Gregory Chaplain buyer's agent for 2185 Bierce Dr, Virginia Beach, VA - sold for $795,000 — Sold $795,000

3316 Mapleton Crescent, Chesapeake, VA For Sale $500,000 - listed by Gregory Chaplain — For Sale $500,000

Gregory Chaplain

Chesapeake VA

The Real Estate Group

247 Closed Sales

$78.4M Total Value

$186K - $990K Price Range

$317.6K Average Price

Prior 5 years

About Gregory

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 devoted husband and proud father of two daughters, plus a son-in-law. His extracurricular activities include watching sports, enjoying live music and the theatre, exploring great restaurants, and boating the local rivers.

Home Types: House, MultiFamily, Lot/Land, Townhouse, Manufactured, Condo

Years of Experience: 16

Education: West Virginia University

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	25
Total Value	$6,920,999
Average Sale Price	$276,840
Price Range	$50K - $700K

Buyer Deals
Total Deals	4
Total Value	$1,962,899
Average Sale Price	$490,725
Price Range	$385K - $795K

1 Year View by Quarter

Seller Deals
Total Deals	55
Total Value	$17,040,779
Average Sale Price	$309,832
Price Range	$50K - $700K

Buyer Deals
Total Deals	28
Total Value	$11,422,529
Average Sale Price	$407,947
Price Range	$205K - $795K

2 Year View by Quarter

Seller Deals
Total Deals	140
Total Value	$42,660,354
Average Sale Price	$304,717
Price Range	$4K - $990K

Buyer Deals
Total Deals	107
Total Value	$35,784,328
Average Sale Price	$334,433
Price Range	$155K - $795K

5 Year View

Neighborhoods Gregory is Experienced In

Gregory's Active Listings

$315,000
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
4052 Wyndybrow Dr

Portsmouth, VA
Opportunity awaits in the desirable Merrifields neighborhood! Nestled in an established community, this home offers solid bones, generous living spaces, and the potential to build sweat equity with a little TLC. Inside, you'll find a functional layout featuring spacious living and dining areas, comfortable bedrooms, and plenty of natural light throughout. Outside, enjoy a generously sized

Gregory Chaplain The Real Estate Group

$500,000
- 5 Beds
- 3.5 Baths
- 2,528 Sq Ft
3316 Mapleton Crescent

Chesapeake, VA
Beautifully maintained brick ranch in the heart of Western Branch! Offering generous living spaces and a functional layout, this home is designed for both everyday comfort and effortless entertaining. Inside, you'll find a beautifully remodeled kitchen (2024) with ample cabinet space, including pantry storage and an appliance garage. Two living areas provide the flexibility for a playroom, formal

Gregory Chaplain The Real Estate Group

$540,000
- 5 Beds
- 2.5 Baths
- 2,956 Sq Ft
5308 Sidney Ct

Virginia Beach, VA
Welcome to 5308 Sidney Court—a spacious, traditional Virginia Beach home located in sought-after Brigadoon! Boasting 2,956 square feet of living space, this home offers the perfect blend of comfort and functionality, with plenty of room to grow. Inside, you'll find a formal living room with a cozy wood-burning fireplace, a bonus room ideal for a home office or playroom, and a beautiful eat-in

Gregory Chaplain The Real Estate Group

$360,000
- 4 Beds
- 1.5 Baths
- 1,900 Sq Ft
1680 Dylan Dr

Virginia Beach, VA
Convenient and modern Virginia Beach living! Located in sought-after Brandon subdivision is this well maintained, semi-detached twinhome. Inside features an update kitchen with stainless steel appliances, a breakfast area, formal dining room, a spacious living room, and an office space that can double as a fourth bedroom. The converted garage adds an additional living space -- perfect for a home

Gregory Chaplain The Real Estate Group

$152,500
- Land
- 0.25 Acre
- $610,000 per Acre
1836 Rockwood Dr

Chesapeake, VA
.258 acre lot in Parkview subdivision. Must be purchased with 1832 Rockwood Drive for a total of .5 acres. Both lots are located in the Chesapeake Bay Protection Area and will require extra due diligence to obtain a building permit.

Gregory Chaplain The Real Estate Group

Recently Sold

$700,000

Sold Jun 5, 2026
- 3 Beds
- 2 Baths
- 1,420 Sq Ft
815 Delaware Ave

Virginia Beach, VA
- $493/SF
- 16 Days On Market
- Current Est. Value $669K
Gregory Chaplain The Real Estate Group

$410,000

Sold Apr 30, 2026
- 4 Beds
- 2.5 Baths
- 1,610 Sq Ft
1290 Bridle Creek Blvd

Virginia Beach, VA
- 2% Above List
- $255/SF
- 11 Days On Market
- Current Est. Value $407K
Gregory Chaplain The Real Estate Group

$465,000

Sold Apr 15, 2026
- 4 Beds
- 3 Baths
- 2,263 Sq Ft
2945 Replica Ln

Portsmouth, VA
- 3% Above List
- $205/SF
- 10 Days On Market
- Current Est. Value $462K
Gregory Chaplain The Real Estate Group

$350,000

Sold Apr 7, 2026
- 2 Beds
- 2.5 Baths
- 1,725 Sq Ft
1005 Hanson Way

Virginia Beach, VA
- $203/SF
- 109 Days On Market
- Current Est. Value $369K
Gregory Chaplain The Real Estate Group

$72,500

Sold Mar 18, 2026
- Land
- 0.34 Acre Lot
.34ac S Military Hwy

Chesapeake, VA
- 3% Below List
- 7 Days On Market
Gregory Chaplain The Real Estate Group

$72,500

Sold Mar 18, 2026
- Land
- 0.93 Acre Lot
.93ac Indiana Ave

Chesapeake, VA
- 3% Below List
- 7 Days On Market
Gregory Chaplain The Real Estate Group

$515,000

Sold Mar 13, 2026
- 4 Beds
- 2.5 Baths
- 2,178 Sq Ft
3076 Damascus Trail

Virginia Beach, VA
- $236/SF
- 73 Days On Market
- Current Est. Value $504K
Gregory Chaplain The Real Estate Group

$420,000

Sold Feb 27, 2026
- 4 Beds
- 3 Baths
- 1,916 Sq Ft
127 Elwood Ave

Norfolk, VA
- $219/SF
- 21 Days On Market
- Current Est. Value $431K
Gregory Chaplain The Real Estate Group

$165,000

Sold Feb 20, 2026
- Land
- 0.35 Acre Lot
1041 Washington Dr

Chesapeake, VA
- 87 Days On Market
- Current Est. Value $240K
Gregory Chaplain The Real Estate Group

Awards and Designations

NAR - National Association of Realtors

Agent License: 0225091566

Gregory Chaplain

(757) 993-8145

Homes for Sale by City

Gregory Chaplain

About Gregory

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 Gregory is Experienced In

Gregory's Listings and Deals

Gregory's Active Listings

Recently Sold

Awards and Designations