We analyze thousands of real estate agents in Chilmark and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for September 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.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the Chilmark real estate market. *
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (May 2026 - Jul 2026).
Inventory in Chilmark has expanded sharply in this rolling three-month view, with active listings up more than triple from a year ago to 19. New listings have also more than doubled year over year, indicating many more properties are coming to market even as pending sales remain very low at just one home under contract.
Pricing is reacting to this supply shift with a mix of strength and volatility. The rolling three-month median list price is up dramatically from a year ago, rising more than 60 percent, yet it has edged down slightly compared with the prior three-month period as sellers test the upper end of the luxury range.
Longer-term data shows how conditions have become more favorable for buyers, moving from 3.1 months of supply at the end of 2022 to as high as 27 months by March 2026, and now registering as a clear buyer’s market on the local market gauge. With such a small number of actual sales and contract signings, every transaction can meaningfully influence local benchmarks, so working with someone who understands these nuances is crucial for both buyers and sellers, and Agent Pronto can help connect them with the right real estate agent for their needs.
Chilmark offers residents a serene coastal community with unspoiled beaches, open farmland, and a close-knit, nature-loving lifestyle that emphasizes privacy and outdoor living.
Chilmark is a rural, low-density town on the western side of Martha’s Vineyard, known for its scenic coastline, working farms, and strong emphasis on preservation. Life here feels quiet and spacious, yet residents still access daily needs and services in nearby Vineyard Haven and Oak Bluffs.
The town’s public beaches, including acclaimed Lucy Vincent Beach, offer dramatic cliffs and surf, while resident access and seasonal parking rules mean it helps to understand local regulations before you buy. Nearby Menemsha Hills Reservation and Great Rock Bight Preserve provide hiking, shoreline access, and expansive views that shape day to day recreation for locals.
Practical amenities are modest but meaningful. The Chilmark Free Public Library doubles as a community hub, and the seasonal Chilmark Flea Market draws both residents and visitors. Schools are part of the regional Martha’s Vineyard system, with older students commuting to Edgartown or Tisbury. Year round ferry service from Woods Hole via Steamship Authority connects islanders to the mainland.
Because Chilmark’s zoning, waterfront regulations, and seasonal rhythms are unique, working with a real estate agent who knows local rules, inventory cycles, and neighborhood nuances can significantly reduce stress. Agent Pronto helps both buyers and sellers connect with the right Chilmark expert so each move is better informed and more manageable.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Nina has exceeded all expectations. She has been such a perfect agent to work with, very knowledgeable and professional. Most importantly she is kind, supportive and genuinely cares about her clients, making every effort to understand their needs. We were so fortunate to have Nina as our agent.”
“Lisa helped my wife and I purchase a home in Warren, MA. She was on top of things and we're very satisfied with the outcome - I would use her again!”
“As first time home sellers, Amy Harbeck seamlessly guided us through an unfamiliar process. Her local market knowledge, attention to detail, patience and problem-solving expertise was evident from our first meeting. Amy was spot on with pricing our home and we had an offer above asking within 8 days. She certainly lived up to all the glowing reviews.”
“Outstanding knowledge and instincts in a tricky market. The assistance is so crucial to making the property presentable in the best possible light. I would not hesitate to recommend Kathy for any real estate transaction.”
“She was very helpful and knowledgeable. Even at time of frustrations she knows how to handle the situations with expertise. I would only use Sheri for any real estate needs. She is a professional”
“Liked him almost immediately. If I did,, others will also. He assessed my situation and treated it accordingly. He already knew how to proceed. I didn't have a clue. Excellent knowledge of the market and process. Experience. Drive. Availabllity. He literally took over and handeled the entire project. He works well at all levels of the project. Strongly recommend him.”
“Rosie embodies everything about what a top-notch realtor should be, and everything I could hope for and more in a partner in this process. She's the best at what she does-- extremely knowledgeable and relentlessly hard working and advocating in both roles as buyer's and seller's agent. She's also kind, supportive, and encouraging throughout the processes of buying, selling, and moving. I've enthusiastically recommended her to everyone in my life when I've heard that they're buying or selling, and I'd recommend her to anyone who wants to work with the best agent out there.”
“His knowledge, expertise and commitment to service excellence were evident throughout the entire process.”
“Spencer, you made the whole process from start to finish seem so easy! You were always such a calming influence and made my needs the top priority in both the selling of my home and the purchase of the condo that I am in love with. You have been so patient and never rushed me to make decisions. You took care of every detail and went far beyond what anyone would expect from their real estate agent. There are no words to express the level of care, expertise and professionalism that you exhibited at all times. I am forever grateful!”
“We had a challenging condo sale, and we couldn’t have asked for a better real estate agent. She was incredibly patient, persistent, and professional throughout the entire process. Despite several obstacles, she stayed focused, communicated with us every step of the way, and worked diligently to get the deal across the finish line. This wasn’t the first time we’ve worked with her, and once again she proved why we continue to trust her. We truly appreciate her dedication and would highly recommend her to anyone looking to buy or sell a property.”
“Lino was professional, knowledgeable, and great to work with. With a unique property he made the entire process smooth and was always available to answer questions. I highly recommend Lino to anyone looking for a dedicated real estate agent.”
“Stay with until finished purchase.”
“What a great experience! Beatriz knew exactly how to price our home and the marketing was outstanding. She is a strong advocate for her clients and the entire transaction went smoothly.”
“Shawn is the best! Both him and Dee are great to deal with. They go above and beyond! Would recommend them to anyone looking to buy or sell!”
“She's making very good good job with me”
“Craig is the best Realtor we have ever worked with and we have already been recommending him to family considering a move.”
“Jill Fitzpatrick went above and beyond in every way. Saying we were lucky to have her as our real estate agent is an understatement. Working with her was 10/10 in every category! Highly, highly recommend.”
“Christine was excellent throughout our process. She was very easy to talk with and provided a lot of valuable information to us as we were learning things throughout the process. I would highly recommended her to anyone looking for a new house.”
“Brad was the best Realtor around. He cared deeply and treated my family as his. I can't thank Brad enough. I will recommend him to every single person that I know who is looking to buy or sell a home.”
“Farrah worked with us for several months. She helped us to understand what to look out for when we viewed properties and was tenacious getting information to help us make good decisions. She was very thorough, knowledgeable, and patient. She organised viewings to make good use of our time and collaborated very effectively with our closing attorney. Farrah worked hard to make the house buying process as straightforward as possible and we highly recommend her.”
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 Chilmark. 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.
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.
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.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Chilmark Realtor® or real estate agent today.
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.