Find the perfect real estate agent in Downtown Winthrop, Winthrop, MA

We analyze top real estate agents in Winthrop’s Downtown Winthrop neighborhood and across the country to find you the most proven local agents, for free.

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Real estate in Winthrop’s Downtown Winthrop neighborhood.

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Home buyers and sellers love Agent Pronto.

Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.

“Great service and Chris Cassidy was professional, courteous, efficient and responsive. I would recommend him to anyone.”
5 stars
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Anne G.
Boston, MA
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”
5 stars
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Sharon R.
Boston, MA
“I can't thank John Dean enough for handing the sale of my home. John's knowledge of the industry and the area was exceptional. He kept me informed of all the issues and guided me with decisions that had to be made. He offered to make several trips to the house to meet and coordinate the inspections and other people that assisted me with the move. Not being available to make it to the property for various reasons being the distance and caring for a disabled husband, John saved me from having to be there. John was there to manage everything for me. If you need a professional agent, look no further than John Dean.”
5 stars
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Anna T.
Malden, MA
“Great real estate experience with Charlotte. I recently had the pleasure of working with Charlotte as my realtor, and I cannot express how grateful I am for her outstanding service throughout the entire home buying process. From our initial meeting to the closing day, Charlotte demonstrated a level of professionalism, expertise, and dedication that greatly met my expectations. One of Charlotte's standout qualities is her extensive knowledge of the local real estate market. She took the time to understand my preferences and priorities, providing valuable insights into neighborhoods, property values, and future market trends. Her expertise not only streamlined the decision-making process but also ensured that I made informed choices.”
5 stars
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Kheang T.
Lowell, MA
“Ms. Diane Franklin along with our representing attorney have both proved themselves to be highly reliable and proficient in performing the services necessary to assist in bringing our single-family home to market, and successfully consummating a mutually acceptable sale of the latter property. We would highly recommend Ms. Franklin for her proven level of effort, dedication, professionalism and reliability.”
5 stars
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Frank E.
Springfield, MA
“Agent Pronto connected us with the perfect agent! Extremely professional, knowledgeable, helpful, and prompt to communicate throughout the entire process. Highly recommended!”
5 stars
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Anne F.
Newton, MA
“Heather was outstanding! ”
5 stars
JH
Jeffrey L H.
Lakeville, MA
“Initial contact from Agent Pronto was very quick-everyone we spoke with was very pleasant and helpful. I can't speak highly enough about our experience with Kelly McKeown. She was awesome and very patient with our "little quirks". She walked us through the whole process, making our purchase as smooth as it could possibly be. Agent Pronto and Kelly McKeown are both highly recommended!”
5 stars
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Barbara D.
Wareham, MA
“The first day I met Carol to show her the house, she spent a good deal of time checking it out and gave me many tips for improvement, which is exactly what I needed. The listing to closing period was about thirty days, which was also important to me since we were approaching winter, and I did not want to worry about freezing pipes in an empty house. Carol took care of all the important deadline dates. She was personable, competent, and professional in everything she did to sell my house. I did not have any worries due to my confidence in Carol. If I had another house to list, I would call her back tomorrow!”
5 stars
SF
Sharyn F.
Somerset, MA
“Superlative! Mirella deserves the highest praise! Mirella knows how to work smart. Renovating and selling a home and moving into a retirement community obviously are difficult tasks! Mirella has a take-charge persona! She has a vision on the best way to create a positive atmosphere motivating the buyer and seller!”
5 stars
BL
Barry L.
Canton, MA

Downtown Winthrop real estate Market Report.

Information and statistics on the latest trends in the Downtown Winthrop real estate market, updated for June 2025. *

The typical home value in Downtown Winthrop is projected to be $680,000 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $655,000—down 17.01% over the previous 12 months. For comparison, city-level data pegged home values at $635,000 in Winthrop for the most recent reporting period. That number is expected to float around $591,250 in May.

Downtown Winthrop had 32 new listings and 26 listings that went under contract in April, decreasing the area’s total available inventory to 10—down 9.09% from the previous month. Inventory is projected to have further decreased in May.

The median listing price for homes in Downtown Winthrop grew 11.71% from March to April, bringing the current median listing price to $687,000. Based on projected data for May, listing prices may continue to grow.

The number of days that homes have been on the market prior to going under contract fell year-over-year. In April 2025, the median time for a listed property to go pending was 28.5 days, compared to 36 days in April 2024. In recent months the median number of days from listed to pending appears to be decreasing. That trend is predicted to have carried through to this May.

Real estate in Winthrop’s Downtown Winthrop neighborhood.
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Seller’s Market
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Buyer’s Market
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25
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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 Downtown Winthrop has to offer.

Downtown Winthrop offers residents a vibrant mix of charming local shops, diverse dining options, and scenic waterfront views, making it a lively and inviting neighborhood to call home.

Downtown Winthrop offers an inviting blend of small-town appeal and seaside sophistication, making it an appealing location for both settling down and exploring new possibilities. With its walkable streets, the downtown is brimming with independent shops, cozy cafes, and popular local bistros such as Blackstrap BBQ, all set against the scenic backdrop of the harbor. Residents and visitors alike enjoy summer evenings at Ingleside Park, where community events and waterfront views foster an energetic yet relaxed atmosphere.

Education is a central feature of the neighborhood’s appeal. Families benefit from proximity to Winthrop High School and Arthur T. Cummings Elementary School, ensuring excellent educational opportunities within walking distance. The Winthrop Public Library is more than a resource – it's a community hub, hosting cultural programs and activities for all ages.

Despite its intimate size, Downtown Winthrop is conveniently situated near the heart of Boston, allowing easy access to world-class amenities while preserving its distinctive coastal charm. Enjoy fresh seafood at local icons or catch a show at the Winthrop Playmakers, all without leaving town. The neighborhood’s proximity to East Boston expands your opportunities for dining and recreation just minutes away.

Whether you envision leisurely strolls along the Belle Isle Marsh or afternoons discovering the historic streets, Downtown Winthrop delivers a unique balance of character and convenience. If you’re ready to buy or sell your home here, Agent Pronto can connect you with the right real estate agent to ensure a smooth and successful experience.

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Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!

Sarah W.

Take the guesswork out of finding an agent.

With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.

We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Downtown Winthrop to qualify the best agents for your specific needs.

We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.

Data analysis with a human touch.

Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winthrop. But we don’t stop there.

Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.

Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!


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. 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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