Jen Holden Group's Profile Photo

Jen Holden Group

jenholdengroup@compass.com
M: 443-803-7620

Revenue

2025 Sales Revenue: $41,851,430
2025 Average Sale Price: $775,000
2025 Number of Transactions: 60+

Awards

RealTrends Verified
Top Small Team in Maryland (2024)
Top 5 Small Team in Annapolis (2024)

FastExpert
#1 Agent in Severna Park: Jen Holden
#4 Agent in Annapolis: Jen Holden

Real Producers
#30 in Real Producers Magazine: Top 150 of the Chesapeake Region
Top 150 Realtor: Baltimore Real Producers (2025)

Local and Regional “Best Of” and Media
Top Agent: Best of Baltimore’s 2025 list
Washingtonian Magazine: 2025 list of Top Real Estate Agents

Quality Business Awards
#1 Best Annapolis Real Estate Agent (2024)

Zillow
Best of Zillow Team (2019 to 2024), top 10% in customer experience

Education

Certified Negotiation Expert
e-Pro Certification
Seniors Real Estate Specialist® (SRES®) designation
Certified Military Relocation Professional (MRP)
Accredited Buyer’s Representative (ABR®)
Trained Corporate Relocation Expert

Charity

Our love of helping and serving others in our community is at the heart of our business. The Jen Holden Group is very honored to support many fantastic local charities in our area that feed, educate, house, and nurture our neighbors:
  • SPAN (Severna Park Assistance Network)
  • 100 Women Who Care
  • Walk the Walk Foundation
  • HOBY Maryland Corporate Sponsor
  • Holiday Toy Drive - Belle Grove Elementary School
  • BARCS / AACSPCA
  • Downtown Sailing Center
  • Feed Anne Arundel
  • Homeowners Association - Board Member
  • Greater Severna Park Mom's Club Sponsor
  • Chesapeake Hospice Cup
  • Mentoring For Success
  • St. Vincent De Paul Baltimore
  • School Volunteer & Sponsor - Band, Music, Theater, & Sports
  • Back to School Supply Drive - Tyler Heights Elementary
About Jen Holden Group

The Jen Holden Group of Compass is a team of local real estate professionals serving Severna Park, Annapolis, and greater Anne Arundel County. We combine high-touch service with smart strategy, market insight, and strong negotiation to help our clients move with confidence.

In 2025, we closed nearly $42M in sales with 60+ transactions, and we are truly grateful to the buyers and sellers who trusted us with such an important moment. We’re grateful for the recognition we’ve received from RealTrends Verified, Washingtonian, Real Producers, Quality Business Awards, and Zillow’s Best of Zillow Team (2019–2024), and we’re proud to be ranked among the top agents in Severna Park and Annapolis by FastExpert.

What sets us apart is the way we tailor every plan to the client. No two moves are the same, so we create customized solutions that match your goals, timeline, and comfort level. From pricing and prep to targeted marketing and offer strategy, we focus on the details that protect your best interests and deliver strong results.

We’re also experienced in more complex transitions, including coordinating the sale of a home while purchasing the next one. Whether you need timing flexibility, contingency planning, bridge options, or a step-by-step roadmap to make everything line up, we will build a clear game plan and guide you through it with calm, proactive communication.

Whether you’re buying your first home, selling a longtime favorite, relocating, or moving up, our mission is simple: deliver outstanding results, simplify the process, and make the experience feel supported from start to finish.

Jen Holden Group of Compass team portrait with six women in professional attire, seated and standing in a bright, modern studio with neutral chairs and a leafy plant.

Team Agents

Jen Holden Group’s Listings

a front view of a house with a yard
an aerial view of a house with a yard and trees
an aerial view of a house with swimming pool next to a big yard
front view of a house with a yard
a front view of a house
a view of an entryway
a view of a room with wooden floor
a view of empty room with wooden floor and fan
a view of a hallway with wooden floor staircase and living room
a view of an entryway with wooden floor
a view of an entryway with a & window
an empty room with wooden floor fireplace and windows
a view of empty room with wooden floor and fan
a bathroom with a bathtub and a shower
a bathroom with a double vanity sink and a mirror
a view of a room with racks on the wall
a bathroom with a bathtub sink and mirror
a view of an empty room with wooden floor and a window
a kitchen with stainless steel appliances granite countertop a sink a oven and wooden cabinets
a kitchen with a stove a sink and windows
a kitchen with stainless steel appliances granite countertop a refrigerator a oven and a fireplace with wooden floor
a view of an empty room with wooden floor fireplace and a window
a view of an empty room with a window and wooden floor
a living room with a fireplace
a view of an entryway with wooden floor
a view of a livingroom with a window
a bathroom with a sink a toilet and shower
a view of an empty room with a window
a bathroom with a sink a toilet and shower
a view of an empty room with closet and entryway
a view of an empty room with a window
a bathroom with a tub and shower
a view of entryway and hall with wooden floor
a view of entryway and hall
an empty room with a window
a bathroom with a bathtub a sink a vanity and mirror
a view of an empty room with a window
a view of a room with windows and chandelier fan
a view of a livingroom with furniture a ceiling fan and window
a big room with windows and fireplace
a view of an empty room with a fireplace
a front view of a house
a front view of a house with a garden
a front view of a building with garden
a front view of a residential apartment building with a yard
a front view of a house with yard and green space
a view of a backyard with sitting area
a view of a house with a wooden deck
an aerial view of a house
a front view of a house with a garden
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
$1,350,000 | 1002 Covington Way, Annapolis, MD 21401
1/78
Listed By CompassActive Under Contract

$1,350,000

5
Bedrooms
8,955
Square Feet
2.15
Acres

1002 Covington Way, Annapolis, MD 21401

$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
$600,000 | 122 Waterline Court, Annapolis, MD 21401
1/44
Listed By CompassActive Under Contract

$600,000

4
Bedrooms
2,450
Square Feet
0.04
Acres

122 Waterline Court, Annapolis, MD 21401

a front view of a house with a yard
a view of entryway and hall with wooden floor
a view of a dining room with furniture
a view of a room with furniture and wooden floor
a view of a dining room with furniture and chandelier
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a fireplace
a living room with furniture
a living room with furniture fireplace and flat screen tv
a living room with furniture
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a stove a refrigerator and a sink
a view of a livingroom with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a sink and wooden floor
a kitchen with a sink and cabinets
a view of entryway and hall with a couch
a bathroom with a sink toilet and shower
a living room with furniture a flat screen tv and a window
a living room with furniture and a flat screen tv
a living room with furniture and a ceiling fan
a view of a workspace with furniture and a window
a bedroom with a bed a lamp and a chandelier
a bedroom with a bed and a window
a bathroom with a sink double vanity granite tub shower and a mirror
a bathroom with a shower and a glass door
a view of an entryway with hardwood
a bathroom with a sink toilet and shower
a bedroom with a bed and window
a bedroom with a large bed and a window
a view of swimming pool with a patio
a view of a brick house with a large window
a picture of a room with a floor and mirror
a black and white photo of a room
a front view of a house with garden
a backyard of a house with lots of green space
a view of a lake with a deck
a lake view with a wooden bridge
a view of a lake in middle of forest
a view of a tennis court
a front view of a house
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
$485,000 | 134 Spring Pl Way, Annapolis, MD 21401
1/59
Listed By CompassPending

$485,000

2
Bedrooms
2,021
Square Feet
0.06
Acres

134 Spring Pl Way, Annapolis, MD 21401

a plant of a tree in a garden
a front view of a house with garden
a view of a house with backyard and trees
a view of backyard with a garden and entertaining space
a view of a lake with a big yard
a view of a garden with a slide
a view of a park with a slide
a view of a field with an ocean
a view of a yard with an house
a view of a swimming pool with a yard
a view of a garden with an trees
a view of ocean from a balcony
a view of terrace with seating space
a view of a lake with a outdoor space
a view of a lush green forest
$110,000 | 0 Ackerman Drive, Stevensville, MD 21666
$110,000 | 0 Ackerman Drive, Stevensville, MD 21666
1/17
Listed By CompassActive Under Contract

$110,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.39
Acres

0 Ackerman Drive, Stevensville, MD 21666