“Shawnai was extremely, professional, patient, and helpful during our search and ultimate purchase of our first home. I pay attention to small details (sometimes borderline neurotic...) and she met me on my level entirely. We had been searching for months and she was with us every step of the way. Even when there was a curveball with funding issues and other random hiccups, she was able to pivot and help us close on time. She understood exactly what we liked and didn't like about houses and helped find the perfect home. In a crazy market where people are rushing and overbidding, she kept our cool and was able to negotiate on a house under asking to stay in our budget, assuring us not to rush into a house just for the sake of having one. We so appreciate everything she did for us and are forever grateful for her. THANK YOU SHAWNAI!! :)”
- Agent Pronto
- Massachusetts
- Oak Bluffs
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 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.
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“We had a difficult situation due to a medical problem and Shelley, Christine and the Topsail people pulled together, worked around our problems and were able to accomplish a good sale for us. We are very happy.”
“Kathy was fantastic to work with. She was recommended highly by my wifes Mother who actuallyused to work with Kathy. It was like working with a close friend or family member, warm friendly and caring..not just another Broker. thanks so much for everything, Kathy. We really did appreciate you! Philip and Kelley”
“Lisa Caron was very helpful and just a wonderful agent. My husband had died just 10 months earlier and she made me feel so comfortable in dealing with this on my own. My home sold in just one day and for the asking price. She did a fantastic job in advertising it. I would recommend her very highly.”
“Thanks to Beatriz now l made one of the biggest dream, to own a house to secure my family”
“From the first phone call Jill communicated competence. She clearly knows the home buying process inside and out and helped my wife and I understand every step of the process. She's helped us all through the process, sending us recommendations and coming to showings with us. She pointed out things about the houses we were looking at that I would not have noticed and helped us get better at looking critically at properties.”
“Amy laid out the sales strategy and it happened just as she predicted. We achieved a rapid sale for a great price”
“I have used Brad in the past. He has repeatedly demonstrated a strong understanding of the housing market and how to best navigate through it. Brad's guidance was critical in helping us secure our dream home by being aggressive, concientious and thoughtful. Now more than ever it is important to have a strong realtor!”
“Attentive and on your side , Adam is there for the prospective buyer”
“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!”
“1st time working with Craig Celli. He was very professional. I was not selling my home, but my aunt's. While the home was on the market, Craig always kept me abrest of any open houses, what the interested buyers were saying about the home whether possitive or negative. Was very honest on what the sales price should be set at to open the market to reach more buyers. I would absolutely use Craig again.”
“Kurt service is excellent. He always give guidence one step ahead & give me enough time to prepare doucment without delay for closing. He send me enough data to decide price for my house and able to find buyer to purchase house on same price without any discount. Great communication skill and knowledge as a realtor. I work twice with him so far & I recomed him as a 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!”
“If not the most talented and detail-oriented realtor, Michelle Silverio, is among them. Thank you for your help acquiring our properties. We greatly appreciate all the long trips to help us achieve our goals. Thank you Michelle and we hope that your professionalism and charisma brightens many other families lives.”
“Sheri was incredibly knowledgeable, patient, and helpful throughout the process of buying our first home. Had great attention to detail and pointed out things we hadn’t even considered. We would highly recommend Sheri!”
“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.”
“James Laney was extremely knowledgeable throughout the sales process. He did an outstanding job in developing a strong marketing strategy which quickly resulted in the sale of my home. He planned, organized and single handedly managed a very successful Open House Event which resulted in the successful offer to purchase the house one day later. James was expremely organized and responded very quickly to any questions that I posed to him. Would highly recommend James to any potential seller or buyer.”
“Len went above and beyond during the whole process of selling my mother's home. He was kind, considerate, compassionate and extremely helpful, during an especially stressful time. I would definitely recommend him without hesitation.”
“El seńor Juan lopera,excelente agente vendedor respetuoso al entrar a la propiedad igual que su equipo de trabajo ,muy buena comunicación,siempre pendiente durante todo el proceso de venta. Gracias.”
“Marcia is a very knowledgeable and experienced realtor. She is always professional, prepared, friendly, and communicative. It was a pleasure working with her and I never felt anxious regarding the listing and sale of my co-op. Since I lived in that co-op for so many years, it was a scary decision to sell my unit. Marcia made it so easy. I would recommend Marcia to anyone looking for a realtor.”
Oak Bluffs real estate Market Report.
Information and statistics on the latest trends in the Oak Bluffs real estate market, updated for November 2025. *
The typical home value in Oak Bluffs is projected to be $944,380 for the month of October. September’s finalized data reported the typical value of a home in the city to be $1,143,250—down 13.72% over the previous 12 months. For comparison, county-level data pegged home values at $1,500,000 in Dukes County for the most recent reporting period. That number is expected to float around $1,433,500 in October.
Oak Bluffs had 3 new listings and 6 listings that went under contract in September, decreasing the area’s total available inventory to 36—down 10.0% from the previous month. Inventory is projected to have further decreased in October.
Of those 36 active listings, 30.56% reduced their price in the month of September. The median listing price for homes in Oak Bluffs fell 39.31% from August to September, bringing the current median listing price to $1,150,000. Based on projected data for October, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In September 2025, the median time for a listed property to go pending was 20 days, compared to -64 days in September 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this October.
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 Oak Bluffs has to offer.
Oak Bluffs offers residents a walkable harbor-side community with iconic Victorian cottages, a vibrant arts and dining scene, and easy access to beaches and parks within a close-knit, year-round atmosphere.
Oak Bluffs hums with seaside energy, from its postcard harbor and broad beaches to the celebrated gingerbread cottages of the Martha’s Vineyard Camp Meeting Association. Families and day-trippers converge on Ocean Park’s lawns and the waterfront boardwalk, then make a beeline for the hand-carved Flying Horses Carousel, the nation’s oldest platform carousel. Quick connections keep life moving: ferries via the Steamship Authority and island-wide buses on the Vineyard Transit Authority make commuting, shopping, and school drop-offs straightforward.
Education anchors the community. Oak Bluffs School serves K–8 with strong arts and STEM programs, while older students attend Martha’s Vineyard Regional High School right in town. Weekends fill easily: tee off amid salt marsh vistas at Farm Neck Golf Club, read and recharge at the Oak Bluffs Public Library, or watch the lighthouse glow from East Chop at dusk. Year-round healthcare is close by at Martha’s Vineyard Hospital. Signature traditions, including Illumination Night and summer concerts, bring neighbors together and keep the calendar lively.
Proximity to island hubs adds convenience without sacrificing character—shops and dining in Edgartown and the ferry bustle of Vineyard Haven are minutes away, and the town is part of scenic Dukes County. Whether you’re settling in for your first season or planning a long-term move, Agent Pronto can connect buyers and sellers with trusted Oak Bluffs real estate experts who know the market, the neighborhoods, and the island’s rhythm.
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 covering the housing market in and around Oak Bluffs. 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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