Real Estate Investing in Chestertown, New York

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

1 ZIP codes • Population: 2,023 • Warren County

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Should you buy in Chestertown, NY? Our answer, based on the numbers below.

🏠 For Homebuyers
CAUTION
Grade D (53/100)

Proceed carefully. Weak appreciation or affordability makes this a harder case for most buyers.

📈 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: 55.3% of homes vacant — above national norms.
  • Tenant-protective state: Landlord rating 1.0/5 — slower evictions, more regulations.

What’s happening in Chestertown, NY?

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3.0/ 5

Investability

Citywide average

4.0/ 5

Appreciation

7.7% 5yr CAGR

1.0/ 5

Landlord Climate

Regulatory friendliness

🏦 30-yr Fixed Rate: 6.95% as of Sep 17 Source: Freddie Mac PMMS
Avg Investability
Avg Home Value $389,188
Avg Monthly Rent $1,098
ZIP Codes 1

Investing in Chestertown Real Estate

This is a distressed-leaning corner of New York: Chestertown has 1 ZIPs and a sizable population, and the investment math only works for investors who truly understand the market.

Across Chestertown's 1 ZIPs, fundamentals run sluggish: thin appreciation, soft rents, and demographic trends that don't obviously reverse in the medium term.

Transaction volume in Chestertown has thinned in a way that amplifies price discovery risk. Meanwhile, investors without local context should treat every number on the page with skepticism.

Demographics in Chestertown show real pressure — median income of $N/AK is sluggish relative to rents, and the 0% renter share includes significant cost-burdened households.

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 Glens Falls, NY

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

Cash Flow → Appreciation → Affordable →

Landlord Ground Truth

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

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Avg Home Value
$389,188
Avg Monthly Rent
$1,098
1% Rule
✗ Below
Landlord Friendly (NY)

📉 Market Crash Risk Index

Based on Glens Falls, NY metro

1/10
Low Risk
Price YoY
0/3
N/A
Rent YoY
0/2
N/A
Below List
0/3
48%
Days Pending
1/2
46 days

View all metro crash risk rankings →

⚖️ Balanced Market — Glens Falls, NY metro
46
Days to pending
8.9%
Listings with price cuts
0.0%
Sale-to-list ratio
📅 Data as of August 29, 2026 — updated weekly

ZIP Codes in Chestertown, NY

Screen every ZIP in Chestertown

Filter Chestertown’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 Chestertown, NY

Is Chestertown in NY worth investing in?

The 3.0/5 investability rating in Chestertown, NY reflects its $389K prices and $1,098/mo rents. Investors generally consider it a solid option within NY.

How much do tenants pay in Chestertown, NY?

Rental rates in Chestertown, NY average $1,098/mo. Tenant demand and $389K home values make the yield look reasonable by investor standards.

Is Chestertown, NY landlord-friendly?

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

Does house hacking work in Chestertown, NY?

The house hack math a challenging in Chestertown, NY. Owner-occupant buyers benefit from the $1,098/mo rents and $389K home values.

What is the rental occupancy rate in Chestertown, NY?

Chestertown, NY carries elevated vacancy risk. Expect even-keeled absorption at market rents of $1,098/mo.

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