“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!”
Ian Handel Real Estate LLC
- Agent Pronto
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for July 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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Oak Bluffs real estate Market Report.
Information and statistics on the latest trends in the Oak Bluffs real estate market. *
Latest Rolling 3-Month Snapshot
Mar 1, 2026 - May 31, 2026
Median sale price
$1.6M
+1.5%
from
Q1 '26
Median list price
$1.8M
+32%
from
Q1 '26
Active listings
36
+64%
from
Q1 '26
Homes sold
5
-29%
from
Q1 '26
New pendings
13
+117%
from
Q1 '26
New listings
23
+109%
from
Q1 '26
Quarterly Pricing Trends for Oak Bluffs
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oak Bluffs
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oak Bluffs
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Oak Bluffs
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oak Bluffs
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oak Bluffs
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
28
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Year-over-year, Oak Bluffs is showing strong price growth in this rolling three-month view, with the typical home value up about 77 percent. Activity has picked up as well, with homes sold rising roughly 71 percent compared with a year ago. New listings have more than doubled over the same period, giving buyers more choices than they had last year.
In the latest three-month window through May 2026, typical home values are around $1.62 million while the median list price is higher at about $1.78 million. Inventory has expanded to 36 active listings, and months of supply has climbed to roughly 15 months, signaling that homes are staying on the market longer overall.
Even with more inventory, some homes are moving relatively quickly, with a median of 74 days on market and about 20 percent of sales closing above the asking price. Pending sales have surged dramatically compared with last year, more than tripling and indicating that buyers are still writing offers despite the added supply. With an average sale-to-list price ratio near 96 percent, sellers are often negotiating but still achieving prices close to asking. Whether you are a buyer trying to interpret these shifting conditions or a seller aiming to price confidently, Agent Pronto can connect you with an Oak Bluffs agent who understands this market.
Learn more about what Oak Bluffs has to offer.
Oak Bluffs offers residents a vibrant coastal town lifestyle with scenic beaches, a close-knit community, and easy access to parks, cultural events, and everyday amenities.
Oak Bluffs stands out from neighboring Vineyard towns with its colorful gingerbread cottages, lively harbor, and walkable downtown that stays active well into the evening. While nearby Edgartown leans historic and formal, Oak Bluffs offers a more casual coastal feel that appeals to year round residents, summer homeowners, and day trippers alike.
The town’s identity centers on community gathering spots like Ocean Park, with its bandstand and sweeping water views, and the iconic Flying Horses Carousel, a National Historic Landmark. Families appreciate easy access to public beaches, including Inkwell Beach, and the convenience of the seasonal ferry terminal for commuters and visitors. The Oak Bluffs Public Library and town events help tie together long established neighborhoods and newer homeowners.
Local flavor is a big part of daily life, from waterfront dining along the harbor to quick trips to nearby Vineyard Haven for errands or connections to the rest of Dukes County. Buyers will find a mix of historic cottages, classic shingled homes, and properties tucked away from the summer bustle, each moving differently with seasonal demand. For sellers, timing around the ferry and tourist calendar can significantly affect visibility and pricing. Agent Pronto can connect both buyers and sellers with a local real estate professional who understands Oak Bluffs, its market rhythms, and how to prepare effectively for a successful move.
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“Mr. Firoz khan were referred by his brother Mr. Jibran khan who does my business tax filled. It was very pleasure to work with my my first real estate agent Mr. Firoz khan. He was very knowledgeable about home . Whatever questions arise he explained very clearly, nicely and friendly way. I was very happy to work with him and any of my friends or family looking to buy home, I will recommend about Mr. Firoz khan. Thank you very much for helping me to get my family's dream home. I also thank Mr. Jibran khan for recommending him and for his help too. Thanks to Mr. Jibran khan and Mr. Firoz khan again .”
Pathan Realty
“We enjoyed working with Amy who was very attentive and sensitive to our needs. Choosing a real estate agent in an unfamiliar area was a gamble and we count ourselves extremely fortunate to have selected Amy. Professional, responsive and knowledgeable are just some of the adjectives to describe Amy, we feel lucky to have chosen her.”
Kinlin Grover Compass
“Thank you, Spencer!! An absolute no-brainer to put this task in your capable hands. You're a credit to the Real Estate profession, tireless master of the craft, and most importantly a genuine great human being! Anyone preparing for the roller-coaster ride of buying or selling a home can do no better than to seek your skill, guidance and exceptional execution. Truly thrilled with the support, guidance and ultimate sale of this home. Very much consistent with it's purchase and sale of my previous residence handled by you five years previous!! Just grateful!! Well done.”
Topp Realtors
“She's making very good good job with me”
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.”
CENTURY 21 CELLI
“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.”
Century 21 C21 North East
“Kurt Thompson was fantastic to work with. Throughout the entire process, we knew we had someone looking out for our best interests. His years of experience were exactly what we needed to navigate a journey that can be exciting, stressful, and exhausting all at once. Highly recommend!”
RE/MAX Liberty
“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.”
CENTURY 21 Topsail Realty
“Lisa was incredible. She was always available whenever we had any questions and was always quick to reply. You could tell her main goal was to help find the perfect house. And she did just that. I would highly recommend Lisa to anyone.”
Exit Realty Exit Real Estate Executives
“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!”
Century 21 North East
“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.”
Media Realty, LLC
“This is about the 8th house tgst Beatriz Gomez sold to me. I am always amazed at her attention to all of the details. We negotiated strongly and eventually we got this property. Thank-you Beatriz. Don Bellofatto”
Century 21 North East
“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.”
Century 21 North East
“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.”
Coldwell Banker Realty
“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”
Century 21 North East
“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.”
SR Realty
“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.”
Century 21 Tassinari & Associates
“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”
Foundation Brokerage Group
“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”
Century 21 Northeast
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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