Chester, NY rental listings

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ABOUT THIS HOME
Chester, NY Rental Listings
This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways an

$2,950/mo

3 beds2.5 baths1,331 sq ft

4321 Whispering Hls, Chester, NY 10918

Parking • A/C • Dishwasher

NEW 30 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Rental Listings
Amazingly beautiful 1850's renovated home and horse property. Over 11 acres of land with approx. 3.5 acres of 4-board fenced-in pasture including 2 run-in sheds with access to water. The house is in

$4,250/mo

3 beds2.5 baths2,840 sq ft

948 Craigville Rd, Chester, NY 10918

Parking • A/C • Dishwasher

ABOUT THIS HOME
Chester, NY Rental Listings
Charming Colonial with 4 Bedrooms on Nearly an Acre - Prime Location! Welcome to this beautifully maintained Colonial-style home nestled on agenerous 0.92-acre lot, offering space, comfort, and conven

$3,950/mo

4 beds2 baths3,330 sq ft

114 Old Mansion Rd, Chester, NY 10918

Parking • A/C • Car-dependent

$6,915/mo

7 beds5.5 baths— sq ft

45 Conklingtown Rd Unit 1056815P, Chester, NY 10918

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
Chester, NY Rental Listings
2BD 1.5BA rental in Whispering Hills! This unit has been updated top to bottom, featuring LVP flooring throughout, new refrigerator, new stove and a brand new full bath! The entire space has been pro

$2,400/mo

2 beds1.5 baths1,072 sq ft

2805 Whispering Hls, Chester, NY 10918

Laundry in unit • Parking • A/C

ABOUT THIS HOME
Chester, NY Rental Listings
Looking for a 2 car garage? Look no further! Welcome to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage

$2,650/mo

2 beds1.5 baths1,086 sq ft

1418 Whispering Hls, Chester, NY 10918

Laundry in unit • Parking • A/C

Property at 2910 Whispering Hls, Chester, NY, 10918, 3 beds, 2.5 baths, [object Object]

$2,800/mo

3 beds2.5 baths1,331 sq ft

2910 Whispering Hls, Chester, NY 10918

Property at 3607 Whispering Hls, Chester, NY, 10918, 2 beds, 1.5 baths, [object Object]

$2,450/mo

2 beds1.5 baths1,086 sq ft

3607 Whispering Hls, Chester, NY 10918

Property at 2208 Whispering Hls, Chester, NY, 10918, 2 beds, 1.5 baths, [object Object]

$2,450/mo

2 beds1.5 baths1,072 sq ft

2208 Whispering Hls, Chester, NY 10918

Property at 3917 Whispering Hls, Chester, NY, 10918, 2 beds, 1.5 baths, [object Object]

$2,600/mo

2 beds1.5 baths1,072 sq ft

3917 Whispering Hls, Chester, NY 10918

Property at 2507 Whispering Hls, Chester, NY, 10918, 2 beds, 1.5 baths, [object Object]

$2,300/mo

2 beds1.5 baths1,086 sq ft

2507 Whispering Hls, Chester, NY 10918

Property at 26 Main St, Chester, NY, 10918, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath650 sq ft

26 Main St, Chester, NY 10918

Property at 25 Trotting Dr, Chester, NY, 10918, 4 beds, 1.5 baths, [object Object]

$3,000/mo

4 beds1.5 baths1,800 sq ft

25 Trotting Dr, Chester, NY 10918

Property at 82 High St Unit 2, Chester, NY, 10918, 2 beds, 1 bath, [object Object]

$2,200/mo

2 beds1 bath900 sq ft

82 High St Unit 2, Chester, NY 10918

Property at 8 Main St, Chester, NY, 10918, 1 bed, 1 bath, [object Object]

$1,700/mo

1 bed1 bath700 sq ft

8 Main St, Chester, NY 10918

Property at 7 Greycourt Ave Unit 4, Chester, NY, 10918, 1 bed, 1 bath, [object Object]

$2,000/mo

1 bed1 bath675 sq ft

7 Greycourt Ave Unit 4, Chester, NY 10918

Property at 7 Greycourt Ave Unit 6, Chester, NY, 10918, 1 bed, 1 bath, [object Object]

$2,100/mo

1 bed1 bath675 sq ft

7 Greycourt Ave Unit 6, Chester, NY 10918

Property at 7 Greycourt Ave Unit 5, Chester, NY, 10918, 1 bed, 1 bath, [object Object]

$2,200/mo

1 bed1 bath675 sq ft

7 Greycourt Ave Unit 5, Chester, NY 10918

End of results (Download All)

Here are some rentals close to your search

ABOUT THIS HOME
Chester, NY Rental Listings
The Regency Club offers 1 bedroom w/ den and 2 bedroom townhome-style rental homes. This pet-friendly community includes a Club House, fitness center, outdoor pool, tennis court, and playground. The

Contact for Price

1-2 bed1.5-2 baths1,148-1,172 sq ft

The Regency Club

| 1200 Regency Ct, Middletown, NY 10940

Pets welcome • Parking • Car-dependent

3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Rental Listings
Welcome to The Park at Main. Make this beautiful property your next home! Perfectly located just minutes away from Garnet Health Hospital in Middletown, NY, and The Galleria at Crystal Run Mall, The

1 bd: $2,375

2 bd: $2,500

The Park at Main

| 430 E Main St, Middletown, NY 10940

7 units match • Pets welcome • Dishwasher

3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Rental Listings
Welcome to Country Manor Apartments in Middletown, NY! Tucked into a peaceful suburban neighborhood, our pet-friendly community offers spacious and thoughtfully designed one- and two-bedroom homes per

1 bd: $1,850

2 bd: $2,200

Country Manor Apartments

| 700 Stratford Ln, Middletown, NY 10940

3 units match • Pets welcome • Somewhat walkable

DEAL

ABOUT THIS HOME
Chester, NY Rental Listings
Tower Ridge Grande: Luxury Living in the Heart of Orange County Tower Ridge Grande sets a new standard for refined living in Scotchtown, a desirable enclave of Middletown, NY. This upscale apartment c

1 bd: $2,300

2 bd: $2,600

Tower Ridge Grande

| 200 Tower Dr, Scotchtown, NY 10941

7 units match • Dishwasher • Patio/Balcony

NEW 3 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Rental Listings
Welcome Home to Imperial Gardens Apartments in Middletown, NY! Located in a country setting, our fabulous location is about an hour from New York City. Just minutes from the Metro North, and major hig

1 bd: $1,840

2 bd: $2,075

Imperial Gardens Apartment Homes

| 225 Berkman Dr, Middletown, NY 10941

31 units match • Pets welcome • Parking

3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Rental Listings
Get a FREE month off any of our unitslimited time Black Friday offer! Welcome to Stevens Manor Apartments in Middletown, NY! Tucked into a peaceful suburban neighborhood, our pet-friendly community o

1 bd: $1,900

2 bd: $2,150

Stevens Manor Apartments

| 644 Silver Lake Scotchtown Rd, Middletown, NY 10941

3 units match • Pets welcome • Car-dependent

Property at Summit Terrace Luxury Apartments - 1000 Clark St, New Windsor, NY, 12553, 2 beds, 2 baths, [object Object]

$2,300+/mo

2 beds2 baths1,062-1,179 sq ft

Summit Terrace Luxury Apartments

| 1000 Clark St, New Windsor, NY 12553

Property at Reserve at Lakeside 55+ - 7 Lakeside Rd, Newburgh, NY, 12550, 2 beds, 1 bath, [object Object]

$2,476/mo

2 beds1 bath900 sq ft

Reserve at Lakeside 55+

| 7 Lakeside Rd, Newburgh, NY 12550

Property at Boulder Pointe Apartments - 201 Genung St, Middletown, NY, 10940, 1-2 bed, 1-2 bath, [object Object]

$2,071+/mo

1-2 bed1-2 bath767-954 sq ft

Boulder Pointe Apartments

| 201 Genung St, Middletown, NY 10940

Property at Rockwood Gardens Apartments - 51 Rockwood Cir, Middletown, NY, 10941, 1-2 bed, 1 bath, [object Object]

$1,915+/mo

1-2 bed1 bath— sq ft

Rockwood Gardens Apartments

| 51 Rockwood Cir, Middletown, NY 10941

Property at 2 Edgewood Trl, Monroe, NY, 10950, 2 beds, 1 bath, [object Object]

$2,900/mo

2 beds1 bath959 sq ft

2 Edgewood Trl, Monroe, NY 10950

Property at 656 Jersey Ave, Greenwood Lake, NY, 10925, 5 beds, 3 baths, [object Object]

$3,500/mo

5 beds3 baths2,600 sq ft

656 Jersey Ave, Greenwood Lake, NY 10925

Property at 157 Johnsontown Rd, Sloatsburg, NY, 10974, 5 beds, 2.5 baths, [object Object]

$4,200/mo

5 beds2.5 baths2,060 sq ft

157 Johnsontown Rd, Sloatsburg, NY 10974

Property at 88 W Mombasha Rd, Monroe, NY, 10950, 3 beds, 2 baths, [object Object]

$3,000/mo

3 beds2 baths1,920 sq ft

88 W Mombasha Rd, Monroe, NY 10950

Property at 186 Highland Ave Unit 1, Middletown, NY, 10940, 3 beds, 2 baths, [object Object]

$2,800/mo

3 beds2 baths2,160 sq ft

186 Highland Ave Unit 1, Middletown, NY 10940

Property at 122 Golf Links Rd Unit 411, Middletown, NY, 10940, 1 bed, 1 bath, [object Object]

$2,694/mo

1 bed1 bath810 sq ft

122 Golf Links Rd Unit 411, Middletown, NY 10940

Property at 53 Woods Rd, Tuxedo Park, NY, 10987, 4 beds, 4 baths, [object Object]

$8,500/mo

4 beds4 baths5,264 sq ft

53 Woods Rd, Tuxedo Park, NY 10987

Property at 31 Denman Rd, Middletown, NY, 10940, 4 beds, 2.5 baths, [object Object]

$3,800/mo

4 beds2.5 baths2,176 sq ft

31 Denman Rd, Middletown, NY 10940

Property at 4 Edgewood Dr, Central Valley, NY, 10917, 3 beds, 1.5 baths, [object Object]

$3,250/mo

3 beds1.5 baths1,836 sq ft

4 Edgewood Dr, Central Valley, NY 10917

Property at 492 Midland Lake Rd Unit 1, Middletown, NY, 10941, 3 beds, 2 baths, [object Object]

$3,150/mo

3 beds2 baths1,880 sq ft

492 Midland Lake Rd Unit 1, Middletown, NY 10941

Based on information submitted to the MLS GRID as of Tue Dec 02 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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