Condos for Sale in Chester, NY

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ABOUT THIS HOME
Condo for sale in Chester, NY:
PRICED TO SELL! Bright and spacious 3-bedroom, 2-bath end-unit townhouse in Whispering Hills, offered at an attractive price compared with other condos in the community. Enjoy a cozy fireplace, double patio sliders to a private patio and open yard, generous bedrooms, ample storage, and a private garage with direct entry. Whispering Hills offers resort-style amenities, including a pool, tennis, basketball, dog runs, and fitness center. Conveniently located near Route 17, the NYS Thruway, Route 84, shopping, restaurants, and major attractions. A wonderful opportunity for first-time buyers, downsizers, or investors. Don't miss this value!

$299,900

3 beds2 baths1,316 sq ft

1223 Whispering Hls, Chester, NY 10918

Tennis • Open yard • Private patio

Listing by KW Hudson Valley United

ABOUT THIS HOME
Condo for sale in Chester, NY:
Discover a compelling combination of space, convenience and Chester accessibility at 3706 Whispering Hills. This 2-bedroom, 2-bath, approximately 1,086-sq-ft townhome-style residence is reported to offer central air, a fireplace, attached garage. Set within the established Whispering Hills community, the location provides convenient access to Route 17, Route 94 and the Chester Park & Ride, along with the Orange County Heritage Trail, Goosepond Mountain State Park and the arts and destinations of the greater Hudson Valley. An appealing alternative for buyers comparing condo and townhome living in Orange County.

$339,900

2 beds1.5 baths1,086 sq ft

3706 Whispering Hls, Chester, NY 10918

Convenient access • Central air • Fireplace

Listing by eXp Realty

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to 2107 Whispering Hills, a comfortable 2-bedroom, 1-bath condo offering 1,086 square feet of living space in a convenient Chester location. This home offers an easy, low-maintenance lifestyle with a practical layout and plenty of opportunity to make the space your own. Residents can enjoy community amenities including a swimming pool, providing a great place to relax and enjoy the warmer months without the maintenance of owning a private pool. The condo setting also offers the convenience of having exterior and community maintenance handled for you, allowing more time to simply enjoy your home and surroundings. Whether you're a first-time buyer, downsizing, looking for a weekend ge

$299,000

2 beds1.5 baths1,086 sq ft

2107 Whispering Hls, Chester, NY 10918

Swimming pool • Convenient location • $724 HOA

Listing by Wansor Realty

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to stress-free Hudson Valley living in the desirable Whispering Hills community! This end unit, bright and airy 2-bedroom, 1-bathroom condo features soaring cathedral ceilings, a cozy fireplace, and an updated kitchen complete with sleek stainless steel appliances. Enjoy fantastic turn-key amenities right outside your door, including two community pools, a clubhouse, gym, tennis, basketball courts, handball, and playgrounds. Conveniently located near major highways and shopping for an effortless commute, you are also just minutes away from local vineyards, Legoland, scenic hiking trails, and everything the vibrant Hudson Valley has to offer.

$269,000

2 beds1 bath1,084 sq ft

1212 Whispering Hls, Chester, NY 10918

Tennis • Clubhouse • Updated kitchen

Listing by Keller Williams Realty

ABOUT THIS HOME
Condo for sale in Chester, NY:
WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace! Master Bedroom Suite with Walk In Closet! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Dog Walk! Perfect Commuter Location! Close to Major Highways, Buses & Shopping! Walk to NYC Bus!

$364,900

3 beds2.5 baths1,331 sq ft

2921 Whispering Hls, Chester, NY 10918

End unit • Eat in kitchen • Largest unit

Listing by ARC Realty 1 in Sales

Property at 2124 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$289,000

2 beds1 bath1,084 sq ft

2124 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 4704 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$370,000

3 beds2.5 baths1,331 sq ft

4704 Whispering Hls, Chester, NY 10918

Listing by Sahagian Realty LLC

Property at 2522 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$355,000

3 beds2.5 baths1,331 sq ft

2522 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 1005 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$290,000

2 beds1.5 baths1,053 sq ft

1005 Whispering Hls, Chester, NY 10918

Listing by Century 21 Full Service Realty

Property at 2113 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$275,000

2 beds1 bath1,084 sq ft

2113 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Realty

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ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to Rolling Hills Condominiums in Monroe! This spacious 2-bedroom, 1.5-bath unit offers a thoughtfully designed layout with separate living and dining rooms. Enjoy the ease of low-maintenance living with heat, hot water, and cooking gas all included in the HOA fees. Ideally located for commuters, you're just minutes from the NYC bus and train, and only an hour from the city. Conveniently close to Woodbury Common Premium Outlets, parks, restaurants, schools, and shopping centers—everything you need is right at your doorstep!

$239,000

2 beds1.5 baths1,025 sq ft

40 Tanager Rd #4002, Monroe, NY 10950

Close to parks • Close to restaurants • Close to schools

Listing by eXp Realty

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to 2 Seeley Bull St, a stunning townhome nestled in the charming town of Monroe, NY. Built in 2013, this modern and well-maintained property boasts a sleek design and ample living space for a growing family or those who love to entertain. Located in the very desirable sought after community Hidden Creek. Amenities include sparkling in ground pool, elegant clubhouse, fitness center, basketball courts, playground, and steps away from Orange County’s beloved walking and biking Heritage trail. Upon entering the home, you are greeted by a spacious and bright living area that is perfect for relaxing or hosting guests. The open floor plan seamlessly flows into the dining area and gou

$489,900

2 beds3 baths1,777 sq ft

2 Seeley Bull St, Monroe, NY 10950

Fitness center • Elegant clubhouse • In ground pool

Listing by Greene Realty Group

ABOUT THIS HOME
Condo for sale in Chester, NY:
NEWLY RENOVATED Summer 2026! New Kitchen and appliances, new quality composite floors throughout, New bathroom and freshly painted. Turn key! Enjoy a sunny and spacious new home. Heat and Hot water included! Located close to the HOA amenities including an inground community pool, play ground, sports areas and more. Sidewalk-lined streets make it safe and relaxing for walks to the pool and the grocery store right at the complex entryway. Close to major shopping and restaurants and easily commutable to NYC by bus, car or train. Don't miss this great opportunity. Won't last.

$205,000

1 bed1 bath813 sq ft

26 Tanager Rd #2601, Monroe, NY 10950

Sports areas • New kitchen • New bathroom

Listing by Century 21 Realty Center

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to 15 Treza Lane, located in the beautiful Treza Development in Blooming Grove. Set on a quiet, brand-new dead-end street surrounded by greenery, this spacious home offers a unique combination of privacy, space, and modern living. With approximately 4,500 square feet of living space, this home occupies the full side of a two-unit building, providing the feel and privacy of a private home. As part of Phase 1 of the development, each building features only two residences, with each owner having their own complete side of the building. The first floor features a large dining room, spacious kitchen, study, and playroom, creating a comfortable and functional layout for everyday living. T

$1,200,000

5 beds3.5 baths4,500 sq ft

22 Treza Ln #101, Blooming Grove, NY 10950

Large dining room • Spacious kitchen • Two residences

Listing by eRealty Advisors, Inc

NEW CONSTRUCTION

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome to 15 Treza Lane, located in the beautiful Treza Development in Blooming Grove. Set on a quiet, brand-new dead-end street surrounded by greenery, this spacious home offers a unique combination of privacy, space, and modern living. With approximately 4,500 square feet of living space, this home occupies the full side of a two-unit building, providing the feel and privacy of a private home. As part of Phase 1 of the development, each building features only two residences, with each owner having their own complete side of the building. The first floor features a large dining room, spacious kitchen, study, and playroom, creating a comfortable and functional layout for everyday living. T

$1,200,000

5 beds3.5 baths4,500 sq ft

15 Treza Ln #102, Monroe, NY 10950

Large windows • Finished stairs • Unfinished basement

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Condo for sale in Chester, NY:
Welcome home to 14 Tanager Road, Unit 1404, a beautifully updated 2 bedroom, 1.5 bathroom garden style condo that combines low maintenance living with stylish modern upgrades! Come inside to discover a bright and open layout featuring fresh, durable flooring and updated windows that flood the living space with natural light. The renovated kitchen boasts upgraded cabinetry, beautiful countertops, and new appliances, perfect for meal prep and casual entertaining. Both bedrooms are comfortably sized, offering ample storage and easy access to the fully updated bathrooms. With 1.5 baths, mornings are a breeze for household members and guests alike. Situated in a peaceful, established community w

$249,600

2 beds1.5 baths1,025 sq ft

14 Tanager Rd #1404, Monroe, NY 10950

Updated windows • Peaceful community • Renovated kitchen

Listing by Keller Williams Realty

Property at 31 Tanager Rd #3103, Monroe, NY 10950, 2 beds, 1.5 baths

$255,000

2 beds1.5 baths1,025 sq ft

31 Tanager Rd #3103, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 11 Hidden Creek Blvd, Monroe, NY 10950, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,176 sq ft

11 Hidden Creek Blvd, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 607 Mountain Laurel Dr, Monroe, NY 10950, 3 beds, 2.5 baths

$250,000

3 beds2.5 baths1,320 sq ft

607 Mountain Laurel Dr, Monroe, NY 10950

Listing by Weichert Realtors

Property at 338 Lake Shore Dr #102, Monroe, NY 10950, 5 beds, 2.5 baths

$765,000

5 beds2.5 baths2,622 sq ft

338 Lake Shore Dr #102, Monroe, NY 10950

Listing by MS Realty Group USA, Inc

Property at 213 Eagleton Dr, Monroe, NY 10950, 3 beds, 2.5 baths

$389,900

3 beds2.5 baths1,694 sq ft

213 Eagleton Dr, Monroe, NY 10950

Listing by Keller Williams Valley Realty

Property at 11 Forest Rd #414, Monroe, NY 10950, 3 beds, 2 baths

$660,000

3 beds2 baths1,451 sq ft

11 Forest Rd #414, Monroe, NY 10950

Listing by MK Realty Inc

Property at 11 Forest Rd #314, Monroe, NY 10950, 3 beds, 2 baths

$660,000

3 beds2 baths1,410 sq ft

11 Forest Rd #314, Monroe, NY 10950

Listing by MK Realty Inc

Property at 11 Forest #214, Monroe, NY 10950, 3 beds, 2 baths

$660,000

3 beds2 baths1,416 sq ft

11 Forest #214, Monroe, NY 10950

Listing by MK Realty Inc

Property at 3 San Marcos Dr #101, Monroe, NY 10950, 5 beds, 3.5 baths

$910,000

5 beds3.5 baths3,048 sq ft

3 San Marcos Dr #101, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 804 Swan Hollow Rd, Monroe, NY 10950, 2 beds, 1 bath

$250,000

2 beds1 bath1,062 sq ft

804 Swan Hollow Rd, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 50 Cropsey St, Warwick, NY 10990, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths2,482 sq ft

50 Cropsey St, Warwick, NY 10990

Listing by BHG Real Estate Green Team

Property at 26 Peddler Hill Rd #2602, Monroe, NY 10950, 1 bed, 1 bath

$205,000

1 bed1 bath813 sq ft

26 Peddler Hill Rd #2602, Monroe, NY 10950

Listing by KW Hudson Valley United

Property at 47 Tanager Rd #4702, Monroe, NY 10950, 2 beds, 1.5 baths

$204,999

2 beds1.5 baths1,025 sq ft

47 Tanager Rd #4702, Monroe, NY 10950

Listing by KW Hudson Valley United

Property at 19 Tanager Rd #1902, Monroe, NY 10950, 2 beds, 1.5 baths

$235,000

2 beds1.5 baths1,025 sq ft

19 Tanager Rd #1902, Monroe, NY 10950

Listing by Weichert Realtors

Based on information submitted to the MLS GRID as of Mon Oct 12 2026. 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.

Condos for Sale in Chester

There are currently 10 condos for sale in Chester at a median listing price of $299K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 35 days and receive 4 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 4 homes have been sold in Chester. In addition to houses in Chester, there were also 14 condos, 1 townhouse, and 1 multi-family unit for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Condos for Sale in Chester, NY

Condos for Sale in Chester

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