Gregory Chaplain Real Estate Agent - The Real Estate Group

3316 Mapleton Crescent, Chesapeake, VA Pending $489,000 - listed by Gregory Chaplain — Pending $489,000

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

5308 Sidney Ct, Virginia Beach, VA For Sale $520,000 - listed by Gregory Chaplain — For Sale $520,000

Gregory Chaplain buyer's agent for 504 Tuskegee Ave, Chesapeake, VA - sold for $386,000 — Sold $386,000

1928 Rockwood Dr, Chesapeake, VA For Sale $645,000 - listed by Gregory Chaplain — For Sale $645,000

Gregory Chaplain

Chesapeake VA

The Real Estate Group

237 Closed Sales

$74.9M Total Value

$186K - $990K Price Range

$316.1K 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, Mobile Homes, 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	5
Total Value	$2,348,899
Average Sale Price	$469,780
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	29
Total Value	$11,808,529
Average Sale Price	$407,191
Price Range	$205K - $795K

2 Year View by Quarter

Seller Deals
Total Deals	134
Total Value	$40,387,354
Average Sale Price	$301,398
Price Range	$4K - $990K

Buyer Deals
Total Deals	103
Total Value	$34,529,328
Average Sale Price	$335,236
Price Range	$155K - $795K

5 Year View

Areas Gregory is Experienced In

Gregory's Listings and Deals

Gregory's Active Listings

$520,000
- 5 Beds
- 2.5 Baths
- 2,956 Sq Ft
5308 Sidney Ct

Virginia Beach, VA
Spacious 5-bedroom home in sought-after Brigadoon, offering nearly 3,000 sq. ft. and a flexible layout with room for everyone. Enjoy a formal living room with a wood-burning fireplace, a bonus room ideal for a home office, playroom, or gym, and an eat-in kitchen with stainless appliances replaced in 2023. The expansive primary suite provides a relaxing retreat, while the covered paver patio is

Gregory Chaplain The Real Estate Group

$645,000
- 4 Beds
- 2.5 Baths
- 3,146 Sq Ft
1928 Rockwood Dr

Chesapeake, VA
Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting

Gregory Chaplain The Real Estate Group

$525,000
- 4 Beds
- 2.5 Baths
- 2,657 Sq Ft
963 Speight Lyons Loop

Chesapeake, VA
Located in the highly sought-after Grassfield High School district, this home offers an incredible opportunity to make a home of your own in one of Chesapeake's most desirable areas. Inside features a spacious, functional floor plan boasting nearly 2700 square feet of living space. The living areas are generous with comfortable bedrooms and plenty of room to personalize. Head outside to the

Gregory Chaplain The Real Estate Group

$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

$489,000

Pending
- 5 Beds
- 3.5 Baths
- 2,528 Sq Ft
3316 Mapleton Crescent

Chesapeake, VA
Move-in ready brick ranch offering 2,528 sq ft, 5 bedrooms, and 3.5 baths, including a first-floor primary suite with private bath. Two living areas and a wood-burning fireplace provide flexible space. The remodeled 2024 kitchen features ample cabinetry, pantry, appliance garage, new gas range and dishwasher, included refrigerator, and eat-in area. A finished room over the garage offers a 5th

Gregory Chaplain The Real Estate Group

$450,000

Pending
- 4 Beds
- 2.5 Baths
- 1,821 Sq Ft
3512 Royal Palm Arch

Virginia Beach, VA
Charming split-level home nestled in the heart of Virginia Beach! 3512 Royal Palm Arch offers a versatile layout with plenty of space to spread out. The beautifully remodeled kitchen (2022) features modern finishes and serves as the heart of the home. Upstairs, you'll find three bedrooms, including the primary suite, while the lower level offers a fourth bedroom and an additional living area with

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
- 16 Days On Market
- $493/SF
- Current Est. Value $638K
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
- 11 Days On Market
- $255/SF
- Current Est. Value $408K
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
- 10 Days On Market
- $205/SF
- 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
- 109 Days On Market
- $203/SF
- Current Est. Value $370K
Gregory Chaplain The Real Estate Group

$72,500

Sold Mar 18, 2026
- Land
- 0.34 Acres 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 Acres 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
- 73 Days On Market
- $236/SF
- 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
- 21 Days On Market
- $219/SF
- Current Est. Value $423K
Gregory Chaplain The Real Estate Group

$165,000

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

Chesapeake, VA
- 87 Days On Market
- Current Est. Value $260K
Gregory Chaplain The Real Estate Group

Awards and Designations

NAR - National Association of Realtors

Agent License: 0225091566

Gregory Chaplain

(757) 993-8145

Nearby Homes

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

Areas Gregory is Experienced In

Gregory's Listings and Deals

Gregory's Active Listings

Recently Sold

Awards and Designations