Real Estate Investing in Chilmark, Massachusetts

Everything the listing leaves out — vacancy, rent trend, cap rate, landlord climate. All free.

1 ZIP codes • Population: 2,393 • Dukes County

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Should you buy in Chilmark, MA? Our answer, based on the numbers below.

🏠 For Homebuyers
WEAK FIT
Grade F (36/100)

Multiple negative signals. Better options likely exist nearby.

📈 For Investors
MIXED
3.0 / 5 (47/100)

A middle-of-the-road market. Workable, but the best opportunities may be nearby ZIPs rather than this one.

⚠️ Risks to Know
2 flags
  • High vacancy: 64.0% of homes vacant — above national norms.
  • Tenant-protective state: Landlord rating 1.0/5 — slower evictions, more regulations.

What’s happening in Chilmark, MA?

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3.0/ 5

Investability

Citywide average

3.0/ 5

Appreciation

4.1% 5yr CAGR

1.0/ 5

Landlord Climate

Regulatory friendliness

🏦 30-yr Fixed Rate: 6.76% as of Sep 10 Source: Freddie Mac PMMS
Avg Investability
Avg Home Value $2,169,516
Avg Monthly Rent $2,097
ZIP Codes 1

Investing in Chilmark Real Estate

With a sizable population across 1 ZIPs, Chilmark shows the kind of modest fundamentals that keep most out-of-state capital on the sidelines.

Investors considering Chilmark, MA should understand what the ★★★☆☆ rating represents — a market with material structural headwinds, not a temporary rough patch.

Rents in Chilmark at $2,097/mo have struggled to keep pace with cost increases, and vacancy has risen in pockets — a dynamic that compresses realized returns well below headline cap rates.

Chilmark's population trends and income levels suggest a market where affordability is strained, which constrains how aggressively rents can rise without hurting collections.

A great house in the wrong ZIP is still a bad deal — screen every market by cash flow & cap rate.
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Best ZIP codes in Vineyard Haven, MA

Chilmark is part of this metro. Every ZIP in it, ranked. Free.

Cash Flow → Appreciation →

Landlord Ground Truth

Real numbers from people who own or manage rentals in Chilmark, MA. Anonymous, moderated, never written by AI.

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Avg Home Value
$2,169,516
Avg Monthly Rent
$2,097
1% Rule
✗ Below
Landlord Friendly (MA)

📉 Market Crash Risk Index

Based on Vineyard Haven, MA metro

0/10
Low Risk
Price YoY
0/3
N/A
Rent YoY
0/2
N/A
Below List
0/3
0%
Days Pending
0/2
0 days

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☀️ Warm Market — Vineyard Haven, MA metro
0
Days to pending
4.1%
Listings with price cuts
0.0%
Sale-to-list ratio
📅 Data as of August 29, 2026 — updated weekly

ZIP Codes in Chilmark, MA

Screen every ZIP in Chilmark

Filter Chilmark’s ZIPs by cap rate, vacancy, appreciation and 30+ more criteria, and export your shortlist to CSV — with the Investor plan ($19/mo).

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Frequently Asked Questions About Chilmark, MA

What is the typical home price in Chilmark, MA?

Median home price in Chilmark, MA is near $2.2M, with a 5-year CAGR of 0.0%. Prices have been measured and supportive of buy-and-hold strategies.

How strong is the working-renter base in Chilmark, MA?

Chilmark, MA offers a measured renter base at the $2,097/mo rent level. Tenant turnover is reasonable for well-managed properties.

What do rentals go for in Chilmark, MA?

Chilmark, MA rentals go for roughly $2,097/mo a month. That puts gross yield in solid territory relative to $2.2M acquisition costs.

How should investors approach Chilmark, MA?

Investors usually favor careful cash-flow rentals with hands-on management in Chilmark, MA. With home values at $2.2M and rents near $2,097/mo, other strategies can work but produce even-keeled rather than outsized returns.

Is Chilmark, MA good for landlords?

Rental owners in Chilmark, MA deal with a tenant-protective legal framework. Most standard eviction processes run on reasonable timelines.

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