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Oak Bluffs, MA real estate

Compare top Oak Bluffs real estate agents.

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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See why so many people rely on Agent Pronto to make their real estate journey a success.

“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!! :)”

Shannon · Somerset, MA

Photo of Shawnai Matos
Century 21 Signature Properties
“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.”

Young Busch · Middletown, RI

Photo of Christine Farley
CENTURY 21 Topsail Realty
“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”

Philip and Kelley · Reading, MA

Photo of Kathryn Tully
Century 21 Northeast
“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.”

Rita Turnbull · Brookfield, MA

Photo of Lisa Caron
Exit Realty Exit Real Estate Executives
“Thanks to Beatriz now l made one of the biggest dream, to own a house to secure my family”

Carlos Escaño · Fitchburg, MA

Photo of Beatriz Gomez
Century 21 North East
“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.”

John Sawers · Danvers, MA

Photo of Jill Fitzpatrick
Century 21 C21 North East
“Amy laid out the sales strategy and it happened just as she predicted. We achieved a rapid sale for a great price”

Ann Cummings · West Chester, PA

Photo of Amy Harbeck
Kinlin Grover Compass
“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!”

Rob S · Leominster, MA

Photo of Brad Morse
Century 21 North East
“Attentive and on your side , Adam is there for the prospective buyer”

Nate Murphy · Kingston, MA

Photo of Adam  Yorks
Century 21 Tassinari & Associates
“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!”

Kealy · Worcester, MA

Photo of Spencer Fortwengler
Topp Realtors
“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.”

Cheryl Gard · Salem, MA

Photo of Craig Celli
CENTURY 21 CELLI
“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.”

Pranav Patel · Gardner, MA

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

Alison B. · S Yarmouth, MA

Photo of Krista Dunn
Exit Realty Cape Realty
“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.”

Leonardo · Springfield, MA

Photo of Michelle Silverio
Century 21 North East
“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!”

Sana Tharadra · Holden, MA

Photo of Sheri Barrette
Media Realty, LLC
“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.”

Karen Wiberg · Wilmington, MA

Photo of Nancy Fudge
Fudge Properties, Inc.
“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.”

R. Kahlau · Princeton, MA

Photo of James Laney
Century 21 North East
“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.”

Denise Kastrinakis · Beverly, MA

Photo of Len Ferrari
Century 21 North East - Integra
“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.”

Madeleyne & Martha · Revere, MA

Photo of Juan Lopera
eXp Realty
“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.”

Cynthia · Westborough, MA

Photo of Marcia Canter
Century 21 Metrowest Realty

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.

Oak Bluffs, MA real estate
60
Buyer’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

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

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.