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 May 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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Information and statistics on the latest trends in the Chilmark real estate market, updated for May 2026. *
Inventory in Chilmark is limited but growing, with 9 homes for sale in March 2026 and 2 new listings added. Contract activity is slow, as only 1 home went under contract and the market sits firmly in a Buyer’s Market with a market gauge of 90.
Pricing is responding to these conditions, with the typical home value at a lofty $7,105,000 but homes selling for about 92 percent of list price. Homes are taking time to move, spending a median of 111 days on the market, which reflects a 117.65 percent increase from the prior month.
Compared with Dukes County overall, where the typical home value is $1,850,000, Chilmark sits at a much higher price tier even as the county has seen values fall 14.94 percent year over year. Looking ahead to April 2026, typical home values in Chilmark are projected to reach $8,495,000 while the median list price is expected to hold near $13,000,000 and inventory around 9 homes. Buyers and sellers who want to navigate these high prices and slower sales can use Agent Pronto to connect with an experienced local agent who understands Chilmark’s unique market dynamics.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.
“Lisa went above and beyond our expectations to sell our home. She guided us through every step of the way and answered all of our questions and concerns quickly. Never was she too busy to talk with us, never was she uncertain about the process, never was she less than professional. The partnership we experienced with Lisa brought a sense of trust and friendship and we are forever grateful to Lisa Caron.”
“Amy was excellent in every way. She sold the property in a short time, the price she recommended was very good, she kept me current on everything that was happening in regard to the sale, was helpful about advising workers to do the jobs required to ready the sale of the house, dealt with prospective buyers. I think that Amy did an excellent job and I would recommend her to anyone looking for help in selling a house.”
“Kurt was always available, kept up on market conditions and showed a difficult property that some agrnts may hav paid little attntion to. He was prompt with feedback. Definitely would reommend him.”
“James was an absolute pleasure to work with while buying our first home. The home buying process can be complex and stressful but James helped us feel confident and informed through each step, from the initial consult to closing day. He is knowledgeable, professional, personable, and was always prompt. We would highly recommend James!”
“I have known Jill Fitzpatrick, and her family long before she was a realtor. I was always impressed with their honesty, and strong work ethic. Knowing Jill had become a realtor I knew if I needed one I would use her. I was even more impressed with her knowledge, and expertise then I imagined I would be. I put my trust in her, sat back, and the results speak for themselves. I had 27 offers on my home, and sold well over asking price. Jill made it easy for me to negotiate the overwhelming offers I received, and helped me pick the most qualified buyer. My closing went off without a hitch. Jill had my house full of prospective buyers, which really produced results. I could not be more grateful, or impressed. Jill is simply the best, I'm blessed to have had her as a realtor, and even more blessed to call her my friend”
“Sheri Barrette was a really important resource in my home purchase. She was able to get me in the property quickly, had great insight into the property value, and was able to get me an excellent final price. She gave me helpful context about the condo market and the availability of units like the one I purchased. She was also able to recommend other professionals involved in the purchase process who were just as knowledgeable and professional as she was. If I ever buy or sell a property, I would work with Sheri again. She was trustworthy and showed that she was working with my best interest.”
“Christine was excellent to work with. She was knowlegeable, friendly and attentive. I would reccomend her to anyone looking or listing!”
“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.”
“Shawnai was so great to work with! She was incredibly helpful and knowledgeable of the area, which was a huge help since I was buying from out of state. Her response time was excellent. She was able to turn things around quickly so that we could work through any issues. She is patient and professional. I highly recommend her to anyone looking for a realtor! L”
“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.”
“Craig Celli was terrific from the very start and through to the very end of the transaction. When he came to view the property for the first time, he demonstrated knowledge, experience, and was friendly and communicative. I knew right after our meeting that he was the broker I would choose to market and sell the property. He also was very hands-on in preparing the home for sale - he worked on things himself and he personally knew and introduced me to a number of people who assisted in the work associated with preparing the home for sale (cleaners, electricians, etc.). All of the people he referred worked out perfectly. I was selling this property as a fiduciary so was not located in the area - Craig took on the responsibility of being my "boots on the ground" throughout the marketing and pre-sale. In short, I could not have asked for a better professional to market and sell this property. I would recommend him to anyone without reservation.”
“Fue más de lo que esperaba muy amable excelente profesional Y sobretodo muy rápido 10 días Wao todavía No lo creo jajaja muchas gracias Michelle Silverio eres la mejor Dios continué depositando su gracia sobre ti bendiciones y Asia delante porque se que es solo el comienzo de las cosas grandes que vendrán en el nombre de Jesús bendiciones”
“Sarah Rodewald was excellent, especially with being a first time home buyer. She was friendly and responsive when I had questions or concerns. Sarah was a strong advocate for me during negotiations to secure a fair price and credits towards closing. I would highly recommend Sarah for anyone looking for a dedicated expert agent.”
“Adam sold us our first home 23 years ago so we immediately thought of him for the sale of my mother's home. He was communicative, very knowledgeable and as an aside, very kind working with my mother who had recently been diagnosed with Alzheimers.”
“Friendly helpful all the way to the end and beyond. Made everything easy to understand answered all my questions within a few minutes of asking if she didn't have the answers, she got them for me”
“November, 2025 We had a very positive experience working with Kathy Tully. From start to finish, she was knowledgeable, responsive, and genuinely invested in helping us achieve our goals. Her understanding of the local market was helpful, and she provided clear guidance at every step of the process. What stood out most was her professionalism and communication. She answered every question promptly, explained each part of the transaction in a way that was easy to understand, and always made us feel like a priority. Whether it was scheduling showings, handling negotiations, or coordinating details behind the scenes, Kathy went above and beyond to make the entire experience smooth and stress-free. We are pleased with the results and highly recommend Kathy to anyone looking to buy or sell a home. Ken & Suzanne Malach”
“She is amazing... beyond words, honestly :-)”
“Spencer is a gem! From the start, his deep knowledge of the market and attention to detail when we were looking at properties blew us away. He’s always available, whether to answer questions or provide guidance, making us feel completely supported every step of the way. Spencer’s approachable, funny, and yet always professional—he truly made the process enjoyable and stress-free. He handled the sale of our home with perfection, the entire process was above expectations. Highly recommend him to anyone looking for an outstanding realtor!”
“I needed help finding a reputable real estate agent in my area, there are so many to choose from. Agent Pronto found Krista Dunn for me & we just closed on our house! Thank you Agent pronto, I will be using you again!”
“Nancy is professional, easy to communicate with, responsive to calls and text. She is a very experienced realtor who knows the market well and has many useful contacts for new home owners. I highly recommend her and for Fudge reators.”
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.
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