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Apartments for Rent in Chester, NY

All rentals

105 Pine Hollow Way - Photo 1 of 1

7m ago

Apartment for rent in Chester

105 Pine Hollow Way, Chester, NY 10918

In-unit laundry | Air conditioning | On-site laundry

1 bed

1 bath

$1,750

Apartment for rent

8 Main St #1 - Photo 1 of 1

4d ago

Apartment for rent in Chester

Residential Lease, Chester, NY

8 Main St #1, Chester, NY 10918

Outdoor space

1 bed

1 bath

$1,600

Apartment for rent

1915 Kings Hwy - Photo 1 of 1

4d ago

House for rent in Chester

Residential Lease, Chester, NY

1915 Kings Hwy, Chester, NY 10918

In-unit laundry | On-site laundry | Walk-in closets

2 beds

2 baths

$2,800

House for rent

53 Main St #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Charming Single Unit on Main St in Chester, NY - Available 09/01 - $2100

53 Main St #4, Chester, NY 10918

In-unit laundry | Assigned parking | Hardwood floor

2 beds

1 bath

$2,100

Apartment for rent

Available Sep 1

3 Brookside Ave - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

3 Brookside Ave, Chester, NY 10918

In-unit laundry | Business center

3 beds

2.5 baths

$4,200

House for rent

3102 Whispering Hls #678 - Photo 1 of 1

5d+ ago

Condo for rent in Chester

Residential Lease, Chester, NY

3102 Whispering Hls #678, Chester, NY 10918

In-unit laundry | Furnished | Air conditioning

1 bed

1 bath

$1,600

Condo for rent

20 Goshen Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

Residential Lease, Chester, NY

20 Goshen Rd, Chester, NY 10918

In-unit laundry | Garage parking | Hardwood floor

4 beds

2.5 baths

$6,000

House for rent

Colonial 4-bed estate with horse trails & orchard

Quietly set in Chester, NY, this colonial-style 4-bed, 2.5-bath house spans 3,348 sqft on expansive grounds with private horse trails and a mature fruit orchard. The custom home features hardwood floors, high ceilings, central air, and a 3-car garage with 10-foot doors. An outdoor wood-burning furnace adds cost savings, while the brick exterior and 14 rooms provide ample space for those seeking a self-sufficient lifestyle with modern amenities.

2507 Whispering Hls - Photo 1 of 1

5d+ ago

Condo for rent in Chester

Condominium, Condo,Townhouse - Chester, NY

2507 Whispering Hls, Chester, NY 10918

In-unit laundry | Air conditioning | Garage parking

2 beds

1.5 baths

$2,450

Condo for rent

Available Aug 1

2-bed condo with garage and community pool

This 2-bed, 1.5-bath condo in Chester features a cozy fireplace, in-unit laundry, and second-floor skylight across 1,086 sqft. The unit includes a 2-car garage and private fenced patio, plus community amenities like a swimming pool, tennis court, and playground. Close to hiking and biking trails with top-rated schools nearby.

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1 Angel Rd #2 - Photo 1 of 1

3d ago

Apartment for rent in Monroe

APARTMENT - Other - Monroe, NY

1 Angel Rd #2, Monroe, NY 10950

2 beds

1 bath

$1,875

Apartment for rent

205 Tondo Cir - Photo 1 of 1

5d+ ago

Condo for rent in Harriman

Residential Lease, Harriman, NY

205 Tondo Cir, Harriman, NY 10926

In-unit laundry | Air conditioning | Hardwood floor

2 beds

2 baths

$2,650

Condo for rent

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On-Site Laundry

Air Conditioning

Garage Parking

In-Unit Laundry

649 Lakes Rd - Photo 1 of 1

5d+ ago

House for rent in Monroe

Residential Lease, Monroe, NY

649 Lakes Rd, Monroe, NY 10950

In-unit laundry | Furnished | Outdoor space

1 bed

1 bath

$2,100

House for rent

60 W Jeanibo Rd - Photo 1 of 1

2d ago

House for rent in Monroe

Residential Lease, Monroe, NY

60 W Jeanibo Rd, Monroe, NY 10950

Garage parking | Dishwasher

3 beds

1 bath

$2,850

House for rent

12 Lake Region Blvd - Photo 1 of 1

13h ago

House for rent in Monroe

Residential Lease, Monroe, NY

12 Lake Region Blvd, Monroe, NY 10950

In-unit laundry | Outdoor space

3 beds

1 bath

$3,100

$2,995

Price drop

House for rent

616 Lakes Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Monroe

616 Lakes Rd, Monroe, NY 10950

Air conditioning | On-site laundry | Assigned parking

4 beds

3 baths

$3,350

Apartment for rent

Find sweet deals near Chester

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$1,875

Monroe

$2,050

Monroe

$1,500

Monroe

$2,600

Florida

Listings within 10 miles
8 Woodland Cir N - Photo 1 of 1

3d ago

House for rent in Monroe

Charming 2 Bedroom Rental!

8 Woodland Cir N, Monroe, NY 10950

Air conditioning | Outdoor space | Microwave

2 beds

1 bath

$2,050

House for rent

Available Aug 19

87 Arcadian Trl - Photo 1 of 1

3d ago

House for rent in Monroe

Cottage style home, 3 Beds, 1 Bath with lots of upgraded ammenities.

87 Arcadian Trl, Monroe, NY 10950

In-unit laundry | Balcony | Fireplace

3 beds

1 bath

$2,500

House for rent

Available Sep 1

11 Hopkins Ter - Photo 1 of 1

2d ago

House for rent in Goshen

Residential Lease, Goshen, NY

11 Hopkins Ter, Goshen, NY 10924

In-unit laundry | Garage parking | On-site laundry

3 beds

2.5 baths

$4,200

House for rent

1093 Orange Tpke - Photo 1 of 1

4d ago

House for rent in Monroe

House for rent

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43 Glenmere Homesites Rd #1F - Photo 1 of 1

5d+ ago

Apartment for rent in Florida

Residential Lease, Florida, NY

43 Glenmere Homesites Rd #1F, Florida, NY 10921

In-unit laundry | Dishwasher

3 beds

1 bath

$2,600

Apartment for rent

249 Ridge Rd - Photo 1 of 1

5d+ ago

House for rent in Highland Mills

Residential Lease, Highland Mills, NY

249 Ridge Rd, Highland Mills, NY 10930

In-unit laundry | Garage parking | Fitness center

3 beds

2.5 baths

$3,300

House for rent

15 Tusten Ave #2 - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

15 Tusten Ave #2, Goshen, NY 10924

Hardwood floor | Storage

1 bed

1 bath

$1,900

Apartment for rent

28 Lexington Hl #6 - Photo 1 of 1

4d ago

Condo for rent in Harriman

Residential Lease, Harriman, NY

28 Lexington Hl #6, Harriman, NY 10926

In-unit laundry | On-site laundry | Swimming pool

2 beds

2 baths

$2,450

Condo for rent

155 Main St #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

155 Main St #4, Goshen, NY 10924

1 bed

1 bath

$1,600

Apartment for rent

153 Greenwich Ave #201 - Photo 1 of 1
New construction

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

153 Greenwich Ave #201, Goshen, NY 10924

In-unit laundry | Air conditioning | Assigned parking

2 beds

1.5 baths

$2,850

Apartment for rent

105 Canter Ct - Photo 1 of 1

5d+ ago

Apartment for rent in Goshen

Residential Lease, Goshen, NY

105 Canter Ct, Goshen, NY 10924

In-unit laundry | Garage parking | Elevator

2 beds

2 baths

$3,295

Apartment for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: August 22, 2026

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Chester, NY apartments for rent

Renting in Chester, NY at a glance

As of today, Chester's median rent price is $2,695 per month.

Median rent

$2,695

Rentals, last 30 days

19

Rent by unit type
SizeValueYoY
All bedrooms$2,695N/A
1 bedroom$1,750N/A
2 bedroom$2,400N/A
Not sure what you can afford? Try our rent calculator

Local insights: What it's like to live in Chester, NY

Chester, NY, is appreciated for its scenic views and access to outdoor activities like hiking and fishing, making it a desirable spot for nature enthusiasts. Residents often mention the friendly atmosphere and the quiet, laid-back lifestyle that comes with living in a small town. While many enjoy the slower pace, some express concerns about limited shopping and dining options, which can make day-to-day life a bit inconvenient for renters. Overall, locals find it a pleasant place to live, particularly for those who value tranquility and natural surroundings.

Frequently asked questions

Are utilities usually included in rent in Chester, NY?

Based on our current listings, utilities-included rentals are extremely rare in Chester, appearing in under 1% of units. One-bedrooms show the highest rate at just 0.09% of listings.

Are most apartments in Chester, NY largely older buildings or new developments?

Based on Zumper's listings data, Chester's rental market is dominated by ranch-style homes, which make up 34.2% of all properties. These single-story homes with open floor plans and horizontal lines became popular in post-World War II America, reflecting the area's mid-20th century suburban development.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Looking for apartments in Chester, NY near you?

Chester, NY rental availability
🔑Available apartment rentals25
💰Best rent deal3102 Whispering Hls #678
✨Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos