Jessica Dailey

Jessica Dailey

REALTOR® at Compass
MARYLAND: 600667
  •   5   (196 reviews)

Jessica's sales performance at a glance

See how Jessica has performed in the last 12 months on RateMyAgent*

32
Reviews
11
Properties for sale
63
Sold properties
$498k
Average sale price
$31.4m
Total sales value

*Includes all properties sold (last 12 months) where the agent was a part of the transaction and published on ratemyagent.com. It may not be complete and can exclude off-market, private sales and undisclosed pricing and sold dates. Contact agent for full sales history.

  • priceExpertbadge

    Consistently meets client expectations for property purchase price.

  • aotybadge

    Recognized for going above & beyond for their clients.

Jessica's customer service awards

See what RateMyAgent awards Jessica has won

  • National Top 100United States
  • Region Top 20Mid-Atlantic Region
  • State WinnerMaryland
  • County WinnerBaltimore County
  • 4x County Top 5Baltimore County - 2026, 2025, 2024, 2023
  • 3x County WinnerBaltimore County - 2026, 2025, 2024
  • 3x City WinnerBaltimore - 2026, 2025, 2024
  • 2x State Top 10Maryland - 2026, 2024

About Jessica

Baltimore Magazine Top Agent 2025 #1 Solo Sales Agent Compass Central Maryland in 2024 Baltimore Magazine Top Agent 2024 #1 Solo Sales Agent Compass Central Maryland in 2023 Baltimore Magazine Top Agent 2023 #1 Solo Sales Agent Compass Central Maryland in 2022 Baltimore Magazine Top Agent 2022 Baltimore Magazine Top Agent 2021 Baltimore Magazine Top Agent 202 When you are looking for a top real estate agent in the Greater Baltimore Metropolitan area and beyond, including Baltimore City and County, Anne Arundel, Harford, Howard, and Montgomery Counties, no one wants to rely on an apprentice or an outsider. You want an experienced Realtor, preferably one who has lived in the area and even contributed to the community. Jessica loves the challenge of matching people to property and believes that there is something for everyone if you’re willing to take the journey. As one of the top agents in town, year after year, she has participated in hundreds of millions in transactions, though she is more interested in celebrating the number of people that she has successfully guided towards achieving their real estate goals. When you work with Jessica, you work only with Jessica Dailey. Jessica strives to provide the best representation for all of her buyer and seller clients. She is accessible and responsive to her client's needs full-time, seven days a week by phone, email, and text. She is professional, knowledgeable, articulate, and affable. Jessica appreciates her clients and continuously earns their trust through her driven, diligent work on their behalf, as well as her careful handling of their transactions. Most of Jessica’s business is by way of referrals from past clients and friends. Her rigorous mission is simply that all clients deserve above and beyond service that exceeds expectations. She achieves success through clear communication, organization, detailed follow-through, and advocating for her clients throughout the transaction. Jessica is always negotiating and strategizing on behalf of her clients so that no stone is left unturned. Jessica's relationship with her clients goes far beyond that of contract and settlement. She works directly with home sellers through the entire process of marketing and selling their properties. She hosts an in-person meeting to discuss their specific needs, staging advice, professional photography for every home she lists, custom marketing, and possesses an innate ability to handle all details up and through closing to create a seamless experience. As a buyer’s agent, Jessica walks the buyers through every facet of the transaction, managing expectations and holding their hand from offer to settlement. Originally from Capitol Hill in Washington DC, Jessica grew up in Baltimore's Charles Village neighborhood. She has a BFA from Tufts University and School of the Museum of Fine Arts in Boston. While living in Boston for thirteen years, she owned multiple investment properties before moving back to Baltimore in 2004. Jessica and her husband, accomplished chef, and restaurateur, George Dailey, live in Bolton Hill with their eighteen year old son, a student at Friends School of Baltimore, along with their two dogs and cat. Jessica and George own the two well-known Bolton Hill signature restaurants CookHouse and On the Hill Cafe. In her free time, Jessica enjoys spending time with her family, traveling, food, art and enjoying whatever life brings her way.

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Jessica's reviews

  5  
Jessica has 196 reviewsacross 25 different locations, showing 6.
Review Jessica
Jessica's qualities as told by our client reviews: reliable, great negotiation, well-prepared, clear communication, supportive, responsive, local expert.
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Buyer review
Just listen to Jessica and everything will work out!
20 days ago
Just listen to Jessica and everything will work out!

I had interviewed 5 other realtors before meeting with Jessica. After we first met I was confident that Jessica would be the best fit for me. She has a lot of experience in the field, knowledge of Baltimore communities, and does not waste any time getting you into your perfect house. Jessica was not afraid to tell me when a house was not for me and took the time to educate me about why exactly that is. As a first-time homebuyer it was a daunting experience but I never felt like I was making a wrong decision with Jessica on my team. It didn’t take long for us to find the right home and we ended up having to move quick and put an offer in the day of the tour. Jessica tailored the offer perfectly to fit the needs of the seller and I ended up getting the house the next day! Jessica remained helpful throughout the whole process and had many great connections for the inspections/ renovations. Jessica continues to be helpful after closing and I feel like I have all of the tools I need to be a successful homeowner. I would recommend her to anyone buying a home in a heartbeat!

Seller review
Our experience with Jessica was nothing short of amazing
23 days ago
Our experience with Jessica was nothing short of amazing

Jessica was so helpful, attentive, thoughtful, knowledgeable from the very get go, when we started our process of thinking about selling our house. She made this otherwise painstaking and grueling process, so easy and efficient. She made sure to be available throughout the entire process and made sure to make us feel comfortable and reassured. We did not think we would be able to sell our house in such a short span of time, but Jessica made sure to get things rolling and made us her priority even though she had other projects that she was working on concurrently. We would not hesitate to work with Jessica if we ever decide to come back to the area and would recommend to anyone who is looking for an experienced, competent and amazing realtor.

Buyer review
Committed, resourceful, knowledgeable...with integrity
28 days ago
Committed, resourceful, knowledgeable...with integrity

I first met Jessica at an open house, and what immediately stood out was her deep knowledge of the neighborhood paired with a refreshingly low-pressure approach. Unlike many agents, she didn’t try to “capture” me as a client on the spot. Instead, she was confident, informative, and let me come to my own decision—which I did. I ended up reaching out to her, and I’m very glad I did. Over the next two years, Jessica showed me a wide range of properties across multiple neighborhoods, always tailoring her guidance to what made sense for me—not what would be quickest or most profitable for her. In fact, at one point she advised me to rent out my current home rather than sell it, even though that meant less immediate business for her. That kind of integrity is rare and speaks volumes about how she operates. When it came time to make an offer on the home I ultimately purchased, Jessica was an outstanding strategist and negotiator. She took the time to understand the sellers’ specific needs and used that insight to help me craft a highly targeted offer. In a competitive situation with multiple bidders, mine was the one that was accepted—and I credit her expertise and judgment for that outcome. Beyond the transaction itself, Jessica was an invaluable resource. She connected me with a lender, an inspector, and reliable contacts to help me prepare my current home for rental. Even after closing, she continued to go above and beyond—when I discovered I was missing a key to one of the doors, she arranged and paid for a locksmith. Jessica combines market knowledge, strategic thinking, and genuine client advocacy in a way that’s hard to find. I would recommend her without hesitation.

Seller review
The best real estate agent I ever used
2 months ago
The best real estate agent I ever used

Jessica is a delightful agent so has done a fantastic job selling a few of my properties. She knows the market, knows how to close a deal, and is a delightful person to spend time with. I wouldn't hesitate to recommend her to anyone.

Buyer review
The absolute best realtor
2 months ago
The absolute best realtor

My partner and I couldn’t be happier with the home that Jessica found for us. From the moment I fist reached out to her til the moment she handed us the keys to our new place, everything with Jessica was wonderful. We enjoyed working and talking to her so much and we completely trusted her throughout the process. Nothing in our work together raised flags or felt against common sense. She was so attentive to what we were looking for, from the very beginning, and it only took 2 short house tours for her to find the perfect place for us, which was a house that was not in the market yet, so that we got to see it first. Then after we put in an offer on the house, Jessica made the closing experience effortless. She led us to an incredible local lender that was very knowledgeable and accessible, and a wonderful title company as well. We always knew exactly what was going on throughout the process. Jessica went out of her way to reassure us any time we had questions or concerns and we never felt any pressure whatsoever to do something we did not want to do. Jessica has our gratitude and admiration for her exceptional work. We could not recommend her more!

Seller review
Jessica Dailey is great to work with!
3 months ago
Jessica Dailey is great to work with!

Jessica was the best realtor I can imagine: prompt in her communication, knowledgable, creative and flexible in figuring a way to match me as the seller with the buyers. I recommend her to others without reservation. The market for condominiums n Baltimore was slow; the wait for a solid offer was long, but she encouraged me to stay the course. Her knowledge of Baltimore real estate and ability to network were invaluable. Thank you!

Show all 196 reviews
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Jessica's properties

Jessica has 11 properties for sale and sold 63 properties in the last 12 months, showing 4, sorted by most recent activity

For Sale
$345,000
5503 Fair Oaks Avenue
Baltimore MD 21214
4
2
Single-Family
Listing courtesy of Compass
For Sale
$228,000
1030 N Gilmor St
Baltimore MD 21217
3
2
Townhouse
Listing courtesy of Compass
For Sale
$750,000
1700 Park Avenue
Baltimore MD 21217
7
5
2
Condo
Listing courtesy of Compass
Under Contract
$450,000
256 Waxter Way
Baltimore MD 21217
4
4
2
Townhouse
Listing courtesy of Compass
Show all 74 properties

Jessica's sold properties

Jessica has sold 63 properties in the past 12 months, showing 4.

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Property imageAddressBedroomsBathroomsCarparksProperty TypeClosing PriceDate Sold
2446 Eutaw Place, Baltimore, MD, 21217
2446 Eutaw Place
Baltimore MD 21217
6
3
1
Townhouse$800,000Apr 26, 2026
211 Bolton Place, Baltimore, MD, 21217
211 Bolton Place
Baltimore MD 21217
2
3
Townhouse$422,900Apr 24, 2026
8412 Stevenson Road, Pikesville, MD, 21208
8412 Stevenson Road
Pikesville MD 21208
6
5
6
Single-Family$1,169,000Apr 24, 2026
1718 Eutaw Place, Baltimore, MD, 21217
1718 Eutaw Place
Baltimore MD 21217
6
5
1
Townhouse$750,000Apr 23, 2026

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