Find the perfect real estate agent in Whinthrop Highlands, Winthrop, MA

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

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Real estate in Winthrop’s Whinthrop Highlands 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
AT
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
“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
“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
“My Agent, Jean, was wonderful. She is very knowledgeable of all things real estate so don't worry if you aren't. Jean will guide you through the entire process and you will feel confident your agent is doing everything she can. She is such a pleasure to work with.”
5 stars
AJ
Audrey J.
Aquinnah, MA
“Cory was such a professional, but more than anything, she felt like a friend you could trust, you could ask questions and feel comfortable with. There was never any pressure...we sold a house in one day. It was great working with her and I plan to work with her again in the future. ”
5 stars
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Carol W.
Fitchburg, MA
“Annemarie LaTulip did a great job with selling our house. She created a youtube video with a walkthrough of our house and also advertised our house on other social media sites such as Instagram and Facebook. She held a few open houses and she was able to sell our house within a few months! Annemarie was a pleasure to work with and I recommend her as a real estate agent for any sellers out there looking to sell their own house.”
5 stars
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Kathi L.
Chelmsford, MA
“My agent was Susan Whitehead. I have sold a number of houses in my 77-year life. I found that Susan is the best agent I have ever had. My wife and I sincerely appreciate her tireless help. We are so impressed with her professionalism and hard working. Our house was sold much quicker than we expected. Susan guided us through every step in the tedious selling process. In the process, Sharon was also helping us a lot. Elizabeth was a great manager for this sales project and was the key helper for this sale. Thank you, Susan, Sharon, and Elizabeth! Thank you SRG!”
5 stars
SW
Shouhong W.
Dartmouth, MA

Whinthrop Highlands real estate Market Report.

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

The typical home value in Whinthrop Highlands is projected to be $597,500 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $590,000—down 6.79% 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.

Whinthrop Highlands had 9 new listings and 6 listings that went under contract in April, increasing the area’s total available inventory to 7—up 16.67% from the previous month. Inventory is projected to have further increased in May.

The median listing price for homes in Whinthrop Highlands fell 21.84% from March to April, bringing the current median listing price to $619,000. Based on projected data for May, listing prices may continue to fall.

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 31 days, compared to 48 days in April 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this May.

Real estate in Winthrop’s Whinthrop Highlands neighborhood.
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Seller’s Market
Seller’s Market
Buyer’s Market
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25
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75
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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 Whinthrop Highlands has to offer.

Whinthrop Highlands offers residents a vibrant community with stunning waterfront views, scenic outdoor spaces, and convenient access to local amenities that enrich everyday living.

Whinthrop Highlands offers a delightful blend of coastal character and convenient proximity to the best of Winthrop. Residents are treated to sweeping views of the Atlantic and Boston skyline, especially from the scenic vantage points around Yirrell Beach and Deer Island, which offer inviting walking trails and fresh ocean breezes. The neighborhood’s walkability is a standout, with friendly streets leading to charming local cafes and small businesses that exude a close-knit community feel.

Families are drawn to Whinthrop Highlands thanks to its commitment to quality education, anchored by Winthrop Public Schools and a vibrant local library scene at the Winthrop Public Library & Museum. Students have access to enriching programs and extracurriculars designed to foster both academic growth and community spirit. The Highland area’s easy access to Boston via nearby public transit makes it a practical choice for commuters, while remaining just far enough to offer peace and tranquility after a busy day.

Outdoor enthusiasts enjoy quick outings to the Belle Isle Marsh Reservation, where marshland habitats provide unique birdwatching opportunities. For dining and socializing, the scene is ever-evolving, with well-loved local institutions like Alia Ristorante providing standout experiences for both newcomers and long-time residents.

Whether you’re seeking a serene setting with urban accessibility or a welcoming neighborhood centered on community and the outdoors, Whinthrop Highlands offers a distinct coastal lifestyle with authentic New England charm. If you are considering buying or selling in this beautiful community, Agent Pronto is ready to connect you with the perfect real estate professional for your needs.

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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 Whinthrop Highlands 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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