Homes, values and local insight for Oak Bluffs, Dukes County, Massachusetts. Typical home value $1,264,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Oak Bluffs is a vibrant Massachusetts community known for its distinct character, quality of life, and strong community values. Located in Dukes County, the town attracts families, professionals, and investors seeking the perfect blend of New England tradition and modern amenities.
The Oak Bluffs real estate market reflects the diverse interests of buyers seeking Massachusetts properties. Whether you're looking for historic homes, contemporary builds, or investment opportunities, the local market offers options across various price points and property types.
Winslow Homes serves Oak Bluffs buyers and sellers across FL, MA, CT, and RI. Ryan and Megan Winslow provide both brokerage and mortgage services (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.
Regular town events and community gatherings.
Parks, trails, and recreational facilities throughout town.
Restaurants and cafes serving community.
Town parks and recreational facilities.
Purchase undervalued homes and renovate for appreciation.
Strong rental market supports cash flow investing.
Massachusetts market historically appreciates 3-4% annually.
The typical home in Oak Bluffs is worth $1,264,000, 19% below the Dukes County typical value of $1,558,000 and 91% above the Massachusetts typical value of $662,000.
Zillow Home Value Index for Oak Bluffs, August 2026. The middle of the market for single family homes and condos.
Home values in Oak Bluffs moved +32.3% over five years and +120.2% over ten.
Share of occupied homes in Oak Bluffs lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Oak Bluffs.
Median age of residents in Oak Bluffs.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Oak Bluffs home of $1,264,000:
Ryan and Megan price Oak Bluffs homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $1,348,000 · 4,927 residents
Area guide →Typical value $1,664,000 · 3,637 residents
Area guide →Typical value $1,869,000 · 5,328 residents
Area guide →Typical value $856,000 · 33,227 residents
Area guide →Typical value $708,000 · 15,482 residents
Area guide →Typical value $2,406,000 · 1,249 residents
Area guide →See the full Dukes County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Oak Bluffs was $1,264,000 in August 2026, +3.8% over the past year.
Oak Bluffs is in Dukes County, Massachusetts.
About 5,407 people as of the 2024 Census Bureau estimate, up from 5,337 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
71% of occupied homes in Oak Bluffs are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
No in-person meeting or phone call needed for most addresses. See your estimated value, price range and value trend in seconds.
Get coming-soon homes, pocket listings and price drops in Oak Bluffs, MA before they hit the big home search sites.
The typical home in Oak Bluffs is worth $1,257,406 as of August 2026 in ZIP code 02557. Values moved +4.0% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 02557 | $1,257,406 | +4.0% | +33.1% |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
