Jessica Dailey




Jessica Dailey's Listings

2829 N Howard St, BALTIMORE
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,161 SqFt

2829 N Howard St, BALTIMORE





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 sixteen-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.

Link to personal website




"As first time home buyers we relied on Jessica to help us every step of the way. She was patient, dependable and always had our best interest in mind. When it was time for us to move again for our expanding family we didn't hesitate to call Jessica. Like a true professional, she found us a great home that checked off all of our needs all while staying in budget and location. More impressively, she made the process of buying and selling easy. If you need an agent in the Baltimore area, look no further." -Vanessa P.

"Jessica first helped me by a home in 2008 and because I was so happy with her work and the overall experience, I recommended her to both of my sisters, whom she has also subsequently worked with. When I was considering buying an investment property, I consulted with her again. She was incredibly knowledgeable and helpful and gave sound advice, even though I wasn't quite ready to pull the trigger. About a year later, I was ready and reached out again. She was incredibly flexible in scheduling times to see homes and pragmatic and supportive when one offer wasn't accepted. While we were both keeping our eyes out for potential options, she was the one who sent the listing that ended up being the house I bought. I probably wouldn't have requested seeing in on my own, but she had a sense of how and why it could be a good fit. I especially appreciate her frank and practical manner and sense of humor. I highly recommend working with her." -Nellie P.

"Jessica Dailey was a pro! She quickly determined the market and was able to price our house perfectly. She knew all of the right people who could quickly fix any of the issues that arose - from plumbing to electrical to chimney work. Having a real estate agent with these connections is so important! And because of her excellent work - we had a contract on the house within 8 days of listing it! I would recommend Jessica Dailey to anyone!" -Karen K.

"We worked with Jessica when we first moved to Baltimore in 2013, and again when we left in 2019. Jessica was flexible when meeting with us and very communicative throughout the process. She clearly explained the factors to consider when pricing the house, how to make it look its best for showings, any updates we should make, etc. Showings were well-coordinated (I work from home) and we were receiving offers within a week of listing. Jessica helped us decide among our options, and negotiated professionally and effectively with the prospective buyers.The back-and-forth between offer acceptance and final closing went smoothly, and Jessica made sure we knew what was happening and when (and why) and was always quick to respond when we had any questions or concerns. I would unequivocally recommend her for anyone buying or selling in the area. Our experience with her when moving to Baltimore in 2019 was equally fantastic." -Ben B.

"I met with several real estate agents who specialized in our neighborhood before choosing Jessica. She was the most organized and persuasive about how we should price our house, improvements to make, and how to market it. We were selling from out of town and she was our eyes and ears on the house, even saving us from a mini-flood that another real estate agent had created in our kitchen. She pushed us in authoritative but pleasant ways during the negotiation process and was able to secure a purchase price of $20,000 over the estimate we had in our heads of the value of our house. She was also funny and easy to work with. Oh, and our house was under contract within three weeks of listing." -Sophie H.


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Listing information last updated on October 5th, 2022 at 6:15pm EDT.