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Chilmark, MA real estate

Compare top Chilmark real estate agents.

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.

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Chilmark real estate Market Report.

Information and statistics on the latest trends in the Chilmark real estate market. *

Quarterly Pricing Trends for Chilmark

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Chilmark Q3 '21 Q3 '22 Q3 '23 Q3 '24 Q3 '25 Q2 '26 Median list price in Jan 2022 - Mar 2022: $14M Median list price in Apr 2022 - Jun 2022: $3.5M Median list price in Jul 2022 - Sep 2022: $2M Median list price in Apr 2023 - Jun 2023: $15M Median list price in Oct 2023 - Dec 2023: $5.8M Median list price in Apr 2024 - Jun 2024: $13M Median list price in Oct 2024 - Dec 2024: $1.5M Median list price in Apr 2025 - Jun 2025: $4M Median list price in Jul 2025 - Sep 2025: $2.5M Median list price in Oct 2025 - Dec 2025: $1.6M Median list price in Jan 2026 - Mar 2026: $2M Median list price in Apr 2026 - Jun 2026: $5M Jul 2021 - Sep 2021 Median list price Unknown Oct 2021 - Dec 2021 Median list price Unknown Jan 2022 - Mar 2022 Median list price $14M Apr 2022 - Jun 2022 Median list price $3.5M Jul 2022 - Sep 2022 Median list price $2M Oct 2022 - Dec 2022 Median list price Unknown Jan 2023 - Mar 2023 Median list price Unknown Apr 2023 - Jun 2023 Median list price $15M Jul 2023 - Sep 2023 Median list price Unknown Oct 2023 - Dec 2023 Median list price $5.8M Jan 2024 - Mar 2024 Median list price Unknown Apr 2024 - Jun 2024 Median list price $13M Jul 2024 - Sep 2024 Median list price Unknown Oct 2024 - Dec 2024 Median list price $1.5M Jan 2025 - Mar 2025 Median list price Unknown Apr 2025 - Jun 2025 Median list price $4M Jul 2025 - Sep 2025 Median list price $2.5M Oct 2025 - Dec 2025 Median list price $1.6M Jan 2026 - Mar 2026 Median list price $2M Apr 2026 - Jun 2026 Median list price $5M
Median list price
* Data provided by Redfin, a national real estate brokerage.
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Seller’s Market
Seller’s Market
Buyer’s Market
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Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jun 2026 - Aug 2026).

Inventory in Chilmark has expanded notably in this rolling three-month view, with active listings up more than threefold compared with a year ago. Months of supply has surged as well, rising dramatically year over year and signaling far more options on the market than in the past.

Contract activity is also higher, with pending sales more than doubling from last year and new listings rising sharply over the same period. Even so, only one home closed in the latest three-month window, underscoring how thin individual sale data can be in such a small, high-end market.

Pricing is reacting unevenly to these shifts, as the typical home value has dropped markedly from a year ago while the median list price has climbed strongly. Homes are taking slightly longer to sell than last year, and the average sale-to-list ratio has edged down, suggesting buyers may have a bit more room to negotiate. With this mix of more inventory, shifting prices, and limited closed sales, buyers and sellers can both benefit from Agent Pronto’s help in finding an agent who understands the nuances of the Chilmark market.



Learn more about what Chilmark has to offer.

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.

Find your Chilmark real estate agent today →


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“I would strongly rcomend Farrah to anyone looking for a real estate agent. I started my search with another agent that didn't quite work out. I was lucky to find Farrah, her knowledge of the business from top to bottom was invaluable. She was professional honest and driven. I not only found a home at the right price, but exactly the right one! What I appreciate most along with her drive, is that Farrah has a network of excellent people to draw on from home inspector to lawyer. This made closing easier and less stressful.”

Liam Toland · Plymouth, MA

Photo of Farrah DiPietro
Coldwell Banker Realty
“I wouldn't use anyone else. She's great.”

Mark · Milford, MA

Photo of Beatriz Gomez
Century 21 North East
“Christine was very experienced and knowledgeable of the area. We met with her once and she was able to create a list of houses for us to see that same week that fit our needs. One of those same houses ended up being our perfect fit! She worked diligently to get our offer in and it was accepted! She made the process so effortless, and she put all our negotiations as a priority to ultimately get us exactly what we wanted! We appreciated her help so much!”

Samantha · East Providence, RI

Photo of Christine Farley
CENTURY 21 Topsail Realty
“La mejor de todos los tiempos”

Dioris Perez · Lawrence, MA

Photo of Michelle Silverio
eXp Realty
“Thank you Sue for your hard work in selling our home. Your market knowledge and recommendations were spot on and made the whole process easy for us. We appreciate how much time, effort and care you put into every detail. We are very happy with the result and would gladly recommend you to our friends and family. Thanks again for everything !”

Rob and Cindy DiGirolamo · Barre, MA

Photo of Susan Getz
LAER Realty Partners
“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.”

Marilyn D'Alessandro · Northborough, MA

Photo of Nina Sable
Berkshire Hathaway Commonwealth
“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!”

Joe B · Warren, MA

Photo of Lisa Caron
Exit Realty Exit Real Estate Executives
“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.”

Darla Kilroy · Salem, MA

Photo of Kathryn Tully
Century 21 Northeast
“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”

Justine Trautwein · Leicester, MA

Photo of Sheri Barrette
Media Realty, LLC
“Working with Sarah was the easiest and most rewarding decision I've made. She came highly recommended by someone I trust in the industry, and she absolutely delivered. I owned my home in Somerville for 21 years, and when it was time to sell, it needed some attention. Sarah helped me prioritize where to invest and where to hold back so I got the most out of every dollar. She had wonderful contacts to get the work done, along with a genuine eye for design that guided the interior choices - and she came by herself to help with the final touches. She was thoughtful about timing, invested real care in the marketing and the open houses, and was patient with my endless questions from start to finish. Sarah held my hand through the whole process. I would work with her again in a heartbeat and recommend her to anyone.”

Lisa Colucci · Somerville, MA

Photo of Sarah Rodewald
SR Realty
“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.”

Fred Barksdale · Fitchburg, MA

Photo of The HomesJustForYou Team
RE/MAX Liberty
“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.”

Katie K · Winchester, NH

Photo of Rosemarie Ledogar
RD Ledogar Real Estate
“His knowledge, expertise and commitment to service excellence were evident throughout the entire process.”

Craig Costa · Webster, MA

Photo of James Laney
Century 21 North East
“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!”

Sheila Flaherty · Clinton, MA

Photo of Spencer Fortwengler
Topp Realtors
“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.”

Rosa Croughwell · Lowell, MA

Photo of Aline Roy
Keller Williams Merrimack Valley
“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.”

Rob · Auburn, MA

Photo of Marcelino Viereck
Coldwell Banker Realty
“Stay with until finished purchase.”

Maksud Africawala · Billerica, MA

Photo of Firojkhan Pathan
Pathan Realty
“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!”

Dan Salois · Dracut, MA

Photo of Team Blades Realty
RE/MAX Remax Innovative Properties
“She's making very good good job with me”

Eveline Augustin · Boston, MA

Photo of Betty Mosley
Keller Williams realty
“Craig is the best Realtor we have ever worked with and we have already been recommending him to family considering a move.”

Tyler · Stoneham, MA

Photo of Craig Celli
CENTURY 21 CELLI

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 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.


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