Samantha Grimes

Responds Quickly

Trappe MD

5.0stars, 5 Reviews

Chesapeake Real Estate Associates, LLC

150 Closed Sales

$60M Total Value

$155K - $2M Price Range

$399.9K Average Price

Prior 5 years

About Samantha

I'm an owner/agent with Chesapeake Real Estate Associates, LLC in Chester, MD and the nearby area, providing home-buyers and sellers with professional, responsive and attentive real estate services. Want an agent who'll really listen to what you want in a home? Need an agent who knows how to effectively market your home so it sells? Give me a call! I'm eager to help and would love to talk to you.

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

Years of Experience: 24

Education: Wesley College, Delaware, Md. Leadership Academy

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	22
Total Value	$8,303,060
Average Sale Price	$377,412
Price Range	$130K - $1.1M

Buyer Deals
Total Deals	18
Total Value	$4,586,700
Average Sale Price	$254,817
Price Range	$13K - $600K

1 Year View by Quarter

Seller Deals
Total Deals	48
Total Value	$20,050,105
Average Sale Price	$417,711
Price Range	$130K - $1.1M

Buyer Deals
Total Deals	32
Total Value	$10,631,500
Average Sale Price	$332,234
Price Range	$13K - $827K

2 Year View by Quarter

Seller Deals
Total Deals	99
Total Value	$43,419,219
Average Sale Price	$438,578
Price Range	$22K - $2M

Buyer Deals
Total Deals	51
Total Value	$16,573,150
Average Sale Price	$324,964
Price Range	$13K - $827K

5 Year View

Neighborhoods Samantha is Experienced In

Samantha's Recent Active Listings

$519,900
- 3 Beds
- 2 Baths
- 1,805 Sq Ft
8047 Laurel Ln

Denton, MD
Welcome to 8047 Laurel Lane in Denton, Md. First time ever offered on the market! Tucked away on 1.4 private, wooded acres in Denton’s sought-after Forest Landing community, this custom-built 3BR/2BA home features a pristine inground pool, a brand-new roof, and water-privileged community access just minutes from the Tuckahoe Creek, leading into the Choptank River. Property Highlights:Move-In

Samantha Grimes Chesapeake Real Estate Associates, LLC

$359,900
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
29316 Will St

Easton, MD
Cute as a button Updated Rancher Easton – 29316 Will Street Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout.Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements

Samantha Grimes Chesapeake Real Estate Associates, LLC

$749,900
- 4 Beds
- 3.5 Baths
- 3,282 Sq Ft
127 Pleasant Springs Dr

Centreville, MD
Welcome to 127 Pleasant Springs Drive, a beautifully maintained home nestled in the highly desirable Claiborne Fields community of Centreville. This four‐bedroom, 3.5‐bath residence offers the perfect blend of comfort, style, and functionality—truly an ideal place to call home.Set on 4.0 picturesque acres, the property includes 2.1 acres owned plus an additional 1.937 acres under a 99‐year

Samantha Grimes Chesapeake Real Estate Associates, LLC

$539,000
- 5 Beds
- 2.5 Baths
- 3,120 Sq Ft
126 Meadowcroft Dr

Centreville, MD
Welcome to 126 Meadowcroft Drive — a beautifully updated 5‐bedroom, 2.5‐bath home tucked in one of Centreville’s most desirable neighborhoods. With a brand‐new roof within the last few years and newer dual‐zoned HVAC units, this spacious home offers modern comfort, low maintenance, and peace of mind from day one.Step inside to find fresh updates throughout, including stylish finishes, gas

Samantha Grimes Chesapeake Real Estate Associates, LLC

$275,000
- 3 Beds
- 3 Baths
- 2,128 Sq Ft
21245 Tanyard Rd

Preston, MD
Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

Samantha Grimes Chesapeake Real Estate Associates, LLC

Co-Listing Agent

$439,900
- 3 Beds
- 3.5 Baths
- 1,900 Sq Ft
108 John Patrick Dr

Stevensville, MD
Welcome to this well‐appointed 3‐level townhome located in the amenity‐rich Ellendale community, just minutes from the Bay Bridge. This spacious 1,900 estimated sq. ft. home offers 3 bedrooms, 3.5 baths, and a 2‐car rear‐entry garage with additional driveway parking. The entry level includes an inviting foyer and a private bedroom with a murphy bed and full bath, ideal for guests or flexible use,

Samantha Grimes Chesapeake Real Estate Associates, LLC

$1,395,000
- 3 Beds
- 5 Baths
- 4,208 Sq Ft
1719 Harbor Dr

Chester, MD
Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a

Samantha Grimes Chesapeake Real Estate Associates, LLC

$1,053,900
- 3 Beds
- 2.5 Baths
- 2,575 Sq Ft
LOT 4 Finley Creek Dr

Centreville, MD
Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

Samantha Grimes Chesapeake Real Estate Associates, LLC

Co-Listing Agent

$659,900
- 4 Beds
- 3.5 Baths
- 2,437 Sq Ft
1033 Avalon Ct

Stevensville, MD
Welcome to 1033 Avalon Court, thoughtfully nestled on a quiet cul-de-sac in one of Kent Island’s most desirable neighborhoods, Mayfair Glen. This beautifully maintained home offers a perfect blend of comfort, space, and everyday livability, all just minutes from shopping, dining, schools, and an easy commute to Annapolis, DC, and Baltimore.Step inside to discover a light-filled interior with

Samantha Grimes Chesapeake Real Estate Associates, LLC

Recently Sold

$475,900

Sold Apr 17, 2026
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
108 Springbrook Ln

Millington, MD
- $284/SF
Samantha Grimes Chesapeake Real Estate Associates, LLC

$552,000

Sold Apr 17, 2026
- 4 Beds
- 3 Baths
- 2,400 Sq Ft
216 Blakefield Dr

Chestertown, MD
- $230/SF
- 94 Days On Market
- Current Est. Value $554K
Samantha Grimes Chesapeake Real Estate Associates, LLC

$365,000

Sold Mar 27, 2026
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
24029 Meadows Dr

Ridgely, MD
- $204/SF
- 67 Days On Market
- Current Est. Value $376K
Samantha Grimes Chesapeake Real Estate Associates, LLC

$450,000

Sold Feb 24, 2026
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
208 Grasonville Cemetery Rd

Grasonville, MD
- 3% Below List
- $220/SF
- 14 Days On Market
- Current Est. Value $473K
Samantha Grimes Chesapeake Real Estate Associates, LLC

$165,000

Sold Nov 25, 2025
- Land
- 2.29 Acre Lot
0 Cabin Cove Road ( Lot 7) Rd

Sherwood, MD
- 6 Days On Market
Samantha Grimes Chesapeake Real Estate Associates, LLC

$140,000

Sold Nov 17, 2025
- Land
- 2.64 Acre Lot
0 Private Spry ( Lot 50) Ln

Worton, MD
- 120 Days On Market
Samantha Grimes Chesapeake Real Estate Associates, LLC

$140,000

Sold Nov 14, 2025
- Land
- 1.00 Acre Lot
435 Eagle Manor Dr

Church Hill, MD
- 113 Days On Market
- Current Est. Value $147K
Samantha Grimes Chesapeake Real Estate Associates, LLC

$399,000

Sold Nov 6, 2025
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
216 Olde Point Ln

Queenstown, MD
- $311/SF
- 4 Days On Market
- Current Est. Value $414K
Samantha Grimes Chesapeake Real Estate Associates, LLC

$400,000

Sold Oct 28, 2025
- 3 Beds
- 2.5 Baths
- 1,874 Sq Ft
209 Kesley Ct

Queen Anne, MD
- $213/SF
- 52 Days On Market
- Current Est. Value $418K
Samantha Grimes Chesapeake Real Estate Associates, LLC

Other Experience

Distressed Properties, First Time Home Buyers, Foreclosures, Investments, Luxury Homes, New Construction, Senior Communities

6/16/23Amy Hudock

Google Review

Sam is a professional. She was very genuine and patient throughout the sale of our home. She listened to my wife and I very intently and with no judgement. For example, when Sam came to us to sign papers making the offer we received official, my wife and I expressed concern, not about the offer, but about the decision to sell. Sam listened to us, provided options and suggestions in order for us to move forward. We highly recommend Sam and appreciated the respect and professionalism she demonstrated throughout the entire process. - Ken Hudock

5/31/23Katrina Gestole

Google Review

Sam was a huge help in all aspects of preparing and selling my property. Sam went above and beyond in getting the job done. Her recommendations were spot on! If you are looking for a thorough realtor, give Sam a call!!

1/24/23Beatrice Kelley

Google Review

We’ve used the professional real estate services of Samatha Grimes on several occasions. She knows the market but goes the extra step to know her clients, whether on the buying side or as the seller, she works to make the experience the best while gauging your needs, preferences and guiding you with her expertise. Samatha is a prime example of who you want when in comes to honesty, integrity and knowledge and reflects the very best in the real estate industry.

Agent License: Maryland 535569

Samantha Grimes

(855) 952-1010

Chesapeake Real Estate Associates, LLC

Responds Quickly

(855) 952-1010

Homes for Sale by City

Samantha Grimes

About Samantha

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 Samantha is Experienced In

Samantha's Listings and Deals

Samantha's Recent Active Listings

Recently Sold

Other Experience

Samantha's Reviews