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Chester, NY Homes for Rent

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    $2,000 per month

    • 1 Bed
    • 1.5 Baths
    • 970 Sq Ft
    • Apartment for Rent

    44 High St Unit 234, Chester, NY 10918

    Beautiful rental in Chester NY. The one bedroom 3rd floor unit offers so much. There are 9 foot ceilings, deck, central A/C, washer and dryer in each unit, granite counters in the kitchen, large closets, carpet in the bedrooms. Pavilion with a grilling area with beautiful views the Sugar Loaf Mountains. One hour to NYC, and close to highways, shopping, and transportation.

    Marisa Sinnott Curasi Realty, Inc.

    44 High St Unit 234, Chester, NY 10918
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    $2,600 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Townhouse for Rent

    3917 Whispering Hills, Chester, NY 10918

    TWO-LEVEL RENTAL in Whispering Hills!This freshly painted home features an updated galley kitchen with brand-new appliances, including a new dryer. The first level offers a convenient half bath, along with brand-new flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace and extend your living space outdoors with a private patio.Upstairs, you’ll

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 244-5124

    3917 Whispering Hills, Chester, NY 10918
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    $4,250 per month

    • 3 Beds
    • 2.5 Baths
    • 2,840 Sq Ft
    • House for Rent

    948 Craigville Rd, Chester, NY 10918

    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 excellent condition with high-efficiency radiant heated floors, central a/c and natural gas! There is also a stand-by generator. Enjoy beautiful wide-plank wood floors, meticulously maintained and

    Layla Rose Boyles Century 21 Realty Center

    948 Craigville Rd, Chester, NY 10918
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    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    63 Hudson St Unit 61A, Chester, NY 10918

    TENANT ACCEPTED. No more showings. 11/19. Quaint 2 bedroom rental in a quiet setting on a dead-end road at the edge of the Village of Chester. 1st floor apartment offers easy access to commuting routes, shops & restaurants. Requires RentSpree application per adult, credit report and proof of income. (Tenant pays gas, electric, cable)

    Kristine Many Keller Williams Realty

    63 Hudson St Unit 61A, Chester, NY 10918
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    $3,300 per month

    • 4 Beds
    • 2 Baths
    • 1,780 Sq Ft
    • House for Rent

    52 Surrey Rd, Chester, NY 10918

    Get ready to fall in love with this stunningly renovated home, just waiting for your family to make magical memories! With a flexible layout, shiny stainless steel appliances, a cozy fireplace, and a one-of-a-kind 3-car detached garage for all your rides and creative projects, this place has it all! Imagine spending summer evenings in the spacious backyard, where you can host barbecues or simply

    Jayne Mangieri Keller Williams Valley Realty

    52 Surrey Rd, Chester, NY 10918
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    $2,650 per month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    1418 Whispering Hills, Chester, NY 10918

    Looking for a 2 car garage for the winter months? 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 for extra storage. The first level offers a cozy fireplace in your spacious living room, dining area with sliding glass doors to your private patio, kitchen, half bath, and

    Erin Hansford Stonewall Realty Group LLC

    1418 Whispering Hills, Chester, NY 10918
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    $1,700 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    8 Main St, Chester, NY 10918

    Conveniently located in the Village of Chester, this spacious one-bedroom apartment is close to all amenities and Route 17. It is situated on the 3rd floor and features an open floor plan with exposed brick walls, providing plenty of natural light and windows.

    Jeanmarie Valentin HomeSmart Homes & Estates

    8 Main St, Chester, NY 10918
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    $2,450 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • House for Rent

    2208 Whispering Hills, Chester, NY 10918

    Welcome to 2208 Whispering Hills! This stunning townhouse will capture your heart with its impeccable features and unbeatable location. Step inside and be welcomed by the warm and inviting atmosphere. The main level boasts a beautifully designed open floor plan, allowing for seamless flow between the living room, dining area, and kitchen. Newer tiles in the kitchen, you'll find 2 bedrooms, each

    Mordechai Ungar HFA Realty Group

    2208 Whispering Hills, Chester, NY 10918
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    $3,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    25 Trotting Dr, Chester, NY 10918

    Welcome to 25 Trotting Drive, located in the heart of Chester, NY. This spacious rental offers the perfect blend of comfort and convenience with plenty of room for everyday living. The home is set in a quiet residential neighborhood, providing a peaceful setting with easy access to local shopping, schools, and major highways. Tenants will be responsible for all utilities. Trash collection & Lawn

    Anthony Rivas Keller Williams Hudson Valley

    25 Trotting Dr, Chester, NY 10918
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    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    82 High St Unit 2, Chester, NY 10918

    This ground-floor apartment is ready for occupancy. The Primary bedroom has double closets and can fit a king-sized bed. The Living room/dining room combination is bright and sun-filled, with plenty of windows and a patio overlooking a private wooded area. The flooring is grey vinyl, and there is plush carpet in the bedrooms. The updated kitchen has stainless steel appliances and a subway tile

    Lynda Hoss Weichert Realtors

    82 High St Unit 2, Chester, NY 10918
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    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft
    • Apartment for Rent

    7 Greycourt Ave Unit 6, Chester, NY 10918

    Brand New 1-Bedroom Apartment in the Heart of Chester! Be the very first to live in this stunning, newly constructed 1-bedroom, 1-bathroom apartment located in the charming Village of Chester. This is a rare opportunity to rent a home where every detail is fresh and modern. Step inside to a bright and inviting living space with beautiful vinyl plank flooring throughout. The kitchen is a true

    Matthew Gibbs Keller Williams Hudson Valley

    7 Greycourt Ave Unit 6, Chester, NY 10918
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    $2,200 per month

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft
    • Apartment for Rent

    7 Greycourt Ave Unit 5, Chester, NY 10918

    Brand New 1-Bedroom Apartment in the Heart of Chester! Be the very first to live in this stunning, newly constructed 1-bedroom, 1-bathroom apartment located in the charming Village of Chester. This is a rare opportunity to rent a home where every detail is fresh and modern. Step inside to a bright and inviting living space with beautiful vinyl plank flooring throughout. The kitchen is a true

    Matthew Gibbs Keller Williams Hudson Valley

    7 Greycourt Ave Unit 5, Chester, NY 10918
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    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft
    • Apartment for Rent

    7 Greycourt Ave Unit 4, Chester, NY 10918

    Brand New 1-Bedroom Apartment in the Heart of Chester!Be the very first to live in this stunning, newly constructed 1-bedroom, 1-bathroom apartment located in the charming Village of Chester. This is a rare opportunity to rent a home where every detail is fresh and modern.Step inside to a bright and inviting living space with beautiful vinyl plank flooring throughout. The kitchen

    Matthew Gibbs Keller Williams Hudson Valley

    7 Greycourt Ave Unit 4, Chester, NY 10918
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    $1,900 per month

    • 1 Bed
    • 1.5 Baths
    • 717 Sq Ft
    • Condo for Rent

    118 Green Meadows Way Unit 10B, Chester, NY 10918

    This is a one-bedroom one and half one-and-a-half-bathroom first-floor unit. The unit has been freshly painted with updates in the bathrooms and Kitchen along with carpet and floors throughout. The landlord requires the tenant to pay 1 Month of rent, 1 month of security at lease signing. Please fill out and submit a rental application and also submit a credit report. Available NOV 1

    James Cosenza BHG Real Estate Green Team

    118 Green Meadows Way Unit 10B, Chester, NY 10918
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    $2,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Townhouse for Rent

    2805 Whispering Hills Unit 573, Chester, NY 10918

    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 professionally painted and feels like new. Updated kitchen including newer cabinets and granite countertops. The master bedroom offers a walk in closet. Washer and dryer in unit and private garage. The

    Joseph Trifono HomeSmart Homes & Estates

    2805 Whispering Hills Unit 573, Chester, NY 10918
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    $5,500 per month

    • 6 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • House for Rent

    3 Grand View Terrace, Chester, NY 10918

    Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

    Shalom Landau eRealty Advisors, Inc

    3 Grand View Terrace, Chester, NY 10918
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    $3,950 per month

    • 4 Beds
    • 2 Baths
    • 3,330 Sq Ft
    • House for Rent

    114 Old Mansion Rd, Chester, NY 10918

    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 convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms,and a versatile layout perfect for modern living. The first floor boasts gleaming hardwood floors, a warm wood

    Chaya Weiss Master Realty Group Inc.

    114 Old Mansion Rd, Chester, NY 10918
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    $2,300 per month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • House for Rent

    2507 Whispering Hills, Chester, NY 10918

    Prime Rental Opportunity in Whispering Hills! Unit Features: New Furnace - New Patio Door - New Refrigerator - • 2 spacious bedrooms • Skylight on second floor • 1.5 modern bathrooms • Cozyfireplace • In-unit washer and dryer • 2 car garage • Private outside fenced patio Community Amenities: • Refreshing swimming pool • Fun-filledplayground for kids • Tennis court for sports enthusiasts •

    Barbara Korabel Four Seasons Realty Group

    2507 Whispering Hills, Chester, NY 10918
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    $6,946 per month

    • 7 Beds
    • 5.5 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

    Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

Frequently Asked Questions

What are the most popular zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10918, 10924, 10950, 10990 and 10921.
How to Rent a Home