- Agent Pronto
- Massachusetts
- Winthrop
- Whinthrop Highlands
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.
Compare the top real estate agents in Whinthrop Highlands
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for July 2025. *
* 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.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.


Home buyers and sellers love Agent Pronto.
We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent. Here’s what some of them have had to say about our service.
“Great service and Chris Cassidy was professional, courteous, efficient and responsive. I would recommend him to anyone.”![]()
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”![]()
“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.”![]()
“Agent Pronto connected us with the perfect agent! Extremely professional, knowledgeable, helpful, and prompt to communicate throughout the entire process. Highly recommended!”![]()
“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.”![]()
“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.”![]()
“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.”![]()
“In one word: easy. They found the realtor for me. He was amazing, and did everything else. My job was basically to answer the phone when he called to give me updates it ask questions. Fantastic for someone living far from the house being sold.”![]()
“Kelly was great. When I was looking for a realtor, I was specifically looking for someone who communicated and made me feel like I was number 1. Kelly did that and more!!! She made me feel comfortable throughout the whole process and she get to see first hand some of the headaches I had with the tenants at the building. She was everything and more...highly recommend!!!”![]()
“I am extremely satisfied with the service I received. I would recommend your service to everyone.”![]()
Whinthrop Highlands real estate Market Report.
Information and statistics on the latest trends in the Whinthrop Highlands real estate market, updated for July 2025. *
The typical home value in Whinthrop Highlands is projected to be $696,250 for the month of July. June’s finalized data reported the typical value of a home in the neighborhood to be $655,000—up 8.89% over the previous 12 months. For comparison, city-level data pegged home values at $849,500 in Winthrop for the most recent reporting period. That number is expected to float around $930,250 in July.
Whinthrop Highlands had 9 new listings and 9 listings that went under contract in June, increasing the area’s total available inventory to 6—up 20.0% from the previous month. Inventory is projected to have further increased in July.
The median listing price for homes in Whinthrop Highlands fell 6.46% from May to June, bringing the current median listing price to $699,000. Based on projected data for July, 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 June 2025, the median time for a listed property to go pending was 45 days, compared to 69 days in June 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 July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.

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!
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!
Resources for buyers and sellers.
Tips and market insights to make your Winthrop real estate journey a success.

Frequently Asked Questions
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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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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents.