The best way to find top real estate agents in Cheswolde, Baltimore, MD

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Real estate in Baltimore’s Cheswolde neighborhood.

Compare top Cheswolde real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for April 2026. *


* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

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Cheswolde real estate Market Report.

Information and statistics on the latest trends in the Cheswolde real estate market, updated for April 2026. *

Cheswolde has seen striking year-over-year growth, with typical home values up 64.5 percent. That stands in sharp contrast to the broader Baltimore market, where values are down 3.73 percent. Buyers looking here are encountering a neighborhood that has appreciated well above the city’s typical home value of $216,600.

In February 2026, the typical home value in Cheswolde reached about $380,000, while the median list price sat lower at $259,900. Homes spent a median of 52.5 days on the market, which is down more than 50 percent from a year ago, and roughly 14 percent of recent sales closed above the asking price with an average sale-to-list ratio near 0.96.

Inventory remains tight, with only 5 homes available in February and 6 new listings, both down notably from last year as inventory fell 37.5 percent and new listings dropped 33.33 percent. Pending sales also eased 14.29 percent year over year, yet the market gauge of 8 still points to clear seller leverage, and inventory is projected to dip to 4 homes next month while the typical home value edges up to about $383,750. In this kind of seller’s market, both buyers and sellers can benefit from Agent Pronto’s help in finding an agent who knows how to navigate Cheswolde’s conditions.

Real estate in Baltimore’s Cheswolde neighborhood.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Cheswolde has to offer.

Cheswolde offers residents a welcoming, family-friendly neighborhood with tree-lined streets, ample green space, and convenient access to parks, schools, and local amenities.

Cheswolde stands out in Baltimore for its quiet, close-knit feel paired with easy access to key city corridors and nearby areas like Pikesville and Mount Washington. Tree-lined residential streets, a strong sense of routine, and long-term residents give the neighborhood a distinctly stable character that many buyers seek when trading up from busier parts of Baltimore.

Locals appreciate proximity to everyday essentials along Smith Avenue and Greenspring Avenue, along with convenient routes to the Baltimore Metro SubwayLink and I‑83. Families are drawn to area schools such as Baltimore City College and nearby private options, plus community resources like the Weinberg Park Heights JCC and Baltimore County Public Library’s Pikesville branch just a short drive away. Green spaces, including Western Run Park, offer room for walking and unwinding without leaving the neighborhood orbit.

Housing in Cheswolde is mainly single-family homes and duplexes, many with generous yards and off-street parking. Inventory can be tight, and updated homes in prime locations often move quickly, especially when buyers are also considering nearby Roland Park or Cross Country.

In a neighborhood where word of mouth and timing matter, having the right local expert is crucial. Agent Pronto connects Cheswolde buyers and sellers with agents who understand the area’s nuances, helping you prepare strategically and act at the right moment.

Find your Cheswolde real estate agent today →


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“Working with Makeda Phillander to sell our home in Maryland was truly a great experience. From the beginning, she was professional, knowledgeable, and very responsive, which made the entire process feel much less stressful. She guided us through every step, from pricing the home correctly to handling showings and negotiations, and we always felt confident that everything was being managed the right way. What we appreciated most was her patience, honesty, and the genuine effort she put into making sure the sale went smoothly. We're very grateful for her support throughout the process and would absolutely recommend her to anyone looking to sell their home.”

Johnson · Randallstown, MD

Photo of Makeda Phillander
Execuhome Realty
“Donte was knowledgeable and patient with me during the entire process. I had a lot of anxiety but he calmed me down and helped me through. His expertise in the Northern Virginia market shined and I would definitely recommend his services and use him for all my real estate needs.”

Taylor Ferguson · Chantilly, VA

Photo of Donte Wade
Century 21 New Millennium
“She is an awesome real estate agent We would not hesitate to recommend her to multiple clients, She is a very understanding and patient person. We do love our new home ,the right one did came ..we would work with her again and again.. Thank u miss Kay.. We appreciate you !!”

Jeniffer and Trevaughn · Baltimore, MD

“Daniel, Thank you so very much for helping making this next chapter and dream of my life a reality. Since our initial meeting, you've been nothing short of amazing - you listened, to shared valuable knowledge and insights - which truly made this experience seamless at every step. You have a great passion and care for what you do, and it translated very well - as I was able to brief very easily - feeling reassured me that I was in the right hands. Teamwork made the dream work in every since of the word, and if I am ever blessed to sell/or buy another home - I will be coming to find you. Thank you so much, Daniel, I will always remember this time as a stamp of new beginning.”

Earl Scott · Fort Washington, MD

Photo of The Washingtonian Group
Real Living Real Estate RLAH @properties
“After speaking with Tyrone, it's clear he possesses the experience, expertise, local market knowledge and professionalism I was looking for in a realtor. Throughout the entire home buying process he patiently listened to me and quickly understood what my needs were in terms of amenities, community, location, proximity to work, and convenient access to shopping, dining entertainment, etc. And when it came to preparing and presenting our offer, it was collaborative because he valued my input! He had the foresight to establish rapport and an open line of communication with the listing agent early on in the negotiation phase, which helped tremendously! Aside from being a top tier real estate professional, Tyrone is good people...he's an honest guy and his integrity is beyond reproach!!! I recommend him highly, without reservation.”

Clay · Columbia, MD

Photo of Tyrone Eugene
CENTURY 21 Envision
“The service was great, and for the agent, you couldn't ask for anyone better.”

John E. · Pittsville, MD

Photo of The Harrington Group
Coldwell Banker Realty
“My agent, Nisha Smithrick, was the ideal agent. We had tried to work with other Baltimore agents over the past year and they were terrible. Nisha was amazing from the get-go. She reached out immediately. She asked questions to understand our specific desires for my son's first home. She presented relevant listing within a day. She made herself available for appointments to fit our schedules. She showed us a great selection of homes. She followed up, gave her honest advice. She then was a great sounding board for creating an offer and negotiating with the seller. She was responsive and proactive through the whole process including to inspections and closing. She answered all our questions thoroughly and quickly. I highly recommend Nisha.”

Jen L. · Baltimore, MD

Photo of Nisha Smithrick
NextHome Forward
“I loved John and Susan like they were my own family! Absolutely loved working with them! Communication was great and just the experience from start to finish was amazing! I would highly recommend John to anybody who needs a realtor! Words can't express nor describe what a wonderful experience I had working with John and Susan! They deserve the highest level of appreciation! Thank you for aligning me with them through my sale! The world needs more people like John and his sister Susan in the realtor community! Hugs to them!”

Chari G. · Pasadena, MD

Photo of John Collins
Long & Foster Real Estate Long and Foster Real Estate, Inc.
“This is our second time working with Tanya Cunningham and she continues to be incredible in all aspects of real estate transactions. She went above & beyond several times throughout our sale process to make it as easy on us as possible. I want to be like Tanya when I grow up. Would highly recommend to anyone in need.”

Will H · Silver Spring, MD

Photo of Tanya Cunningham
Century 21 New Millennium
“Vicki was excellent. She handled every detail quickly, accurately, and professionally. She was available every time we needed to contact her. We were in Florida during the process of selling our home so Vicki had to handle all details and necessary actions without our help and she did. We are totally satisfied.”

Anne B. · Middle River, MD

Photo of Vicki King
Samson Properties
“Thx. Karren!”

Darren · MD

Photo of Karen Eagle
Century 21 New Millennium
“Matt Arnold is a superior agent. He helped me sell my home and buy my new home. Matt made the process happen quickly and seamlessly. I would highly recommend Matt to everyone.”

Cathy Y. · Odenton, MD

Photo of Matt Arnold
REAL Brokerage LLC
“Kelly was a pleasure to work with. She was very professional and helpful throughout this entire process. Kelly has always made herself available to any questions or concerns that I had. I would definitely recommend her to any future home buyers.”

Tasha G. · Martinsburg, WV

Photo of Kelly Steichen
EXIT Realty Center
“Paula was very knowledgeable, patient and helpful. She got me EXACTLY what I wanted for less than what I was expecting to pay! Paula iistened to what I wanted and what my concerns were. She walked me through several properties reminding me of what I said was important to me while keeping me within my budget. Paula is a true professional with a very approachable personality and friendly demeanour. She is the epitome of what first class customer service should look like. I couldn't be more satisfied!”

Willie Stewart · Waldorf, MD

Photo of Paula Thaxton
Century 21 Envision Realty
“My overall experience was well achieved and your Agent, Don Roberts, made my transition very smooth. Great Don went above and beyond to make sure all my questions were answered. He was always available to help me in any matter concerning my house. What a great person Don was, showing nothing but compassion and was very organized. I will rate Don Roberts as a five-star Realtor. Job well done. ”

Johnetta T. · Baltimore, MD

Photo of Don Roberts
Revol Real Estate
“Our experience with Greg Chamish was excellent. He was attentive, prompt, knowledgeable and very helpful. We highly recommend him to anyone looking to sell their home.”

Jim D. · Phoenix, MD

Photo of Greg  Chamish
Black Dog Realty
“Pitina was fast and effective.”

Roberta L. · Randallstown, MD

Photo of Pitina Stucky De Juan
Monument Sotheby's International Realty
“Fantastic agent was referred, super knowledgeable. I couldn't be more pleased. Easy to use service. Thanks again!”

Lauren C. · Huntingtown, MD

Photo of Debbie Balderson
O Brien Realty ERA Powered
“Working with Gary was a great experience. He was was very helpful, knowledgeable, and patient.”

Irma M. · Baltimore, MD

Photo of Gary Addington
Cummings & Co. Realtors
“Awesome, enjoyed every moment of it, no tensions at all. A REAL realtor. ”

Jaya M. · Clarksburg, MD

Photo of Lavina Samtani
Real Living Real Estate RLAH properties

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Cheswolde. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


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