Samantha Grimes

Responds Quickly

Trappe MD

5.0stars, 5 Reviews

Chesapeake Real Estate Associates, LLC

148 Closed Sales

$59.1M Total Value

$155K - $2M Price Range

$399.3K 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

Total Value

$6,910,160

Average Sale Price

$363,693

Price Range

$130K - $1.1M

Buyer Deals

Total Deals

Total Value

$2,751,800

Average Sale Price

$211,677

Price Range

$13K - $391K

1 Year View by Quarter

Seller Deals

Total Deals

Total Value

$18,657,205

Average Sale Price

$414,605

Price Range

$130K - $1.1M

Buyer Deals

Total Deals

Total Value

$8,796,600

Average Sale Price

$325,800

Price Range

$13K - $827K

2 Year View by Quarter

Seller Deals

Total Deals

102

Total Value

$44,362,219

Average Sale Price

$434,924

Price Range

$22K - $2M

Buyer Deals

Total Deals

Total Value

$14,738,250

Average Sale Price

$320,397

Price Range

$13K - $827K

5 Year View

Neighborhoods Samantha is Experienced In

Samantha's Open Houses

Co-Listing Agent

$459,900 Open Sun 12PM - 2PM
- 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 full bath, ideal for guests or flexible use, such as an

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

Samantha's Active Listings

$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

$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

Co-Listing Agent

$1,495,000
- 3 Beds
- 2 Baths
- 3,344 Sq Ft
2238 Pig Neck Rd

Cambridge, MD
Rare opportunity in Dorchester County to purchase 108 +/- acres on Pig Neck Road just outside of Cambridge. Estimated 93 +/- acres tillable with 11.9 acres +/- acres woodland. Gorgeous old home in need or major repair or tear down. Value is in the land only. Numerous outbuildings, 20 x20 garage is newer and in good shape. Please enter home at your own risk and call local health department and

Samantha Grimes Chesapeake Real Estate Associates, LLC

$474,900
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
108 Springbrook Ln

Millington, MD
108 Springbrook Lane New Construction A must see Forget everything you know about "builder grade." This home boost a tasteful design throughout, nestled on 1.76 semi-secluded wooded acres, offering a level of custom detail and material quality not often found in todays new construction.Unmatched Curb Appeal, The exterior is a masterclass in texture and design. A massive 52-foot front porch

Samantha Grimes Chesapeake Real Estate Associates, LLC

$384,000
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
24029 Meadows Dr

Ridgely, MD
Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also

Samantha Grimes Chesapeake Real Estate Associates, LLC

$559,000
- 4 Beds
- 3 Baths
- 2,400 Sq Ft
216 Blakefield Dr

Chestertown, MD
The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample

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

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 Open Houses

Samantha's Active Listings

Other Experience

Samantha's Reviews