Cheap homes for sale & real estate in Chester, NY

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ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
UNLOCK UNLIMITED POTENTIAL IN WARWICK VALLEY SCHOOLS! Are you ready to stop renting, build instant equity, and design your dream home from the ground up? This hidden gem off Gibson Hill Road is your golden ticket into one of Orange County’s most desirable school districts at a rare and unbeatable entry-level price! Whether you are a savvy investor looking for your next high-margin flip, a contractor seeking a prime project, or a first-time homebuyer eager to earn serious sweat equity, the upside potential here is off the charts! Nestled in a peaceful setting with a shared private access setup off well-maintained Speranza Ct, you get the perfect balance of serene rural living with ea

$374,900

3 beds1.5 baths1,644 sq ft

Private access • Countryside retreat • Peaceful setting

260 Gibson Hill Rd, Chester, NY 10918

Listing by Keller Williams Realty

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level living in the desirable Whispering Hills community. As soon as you enter the welcoming two-story foyer, you’ll appreciate how bright, open, and impeccably maintained this home is. The spacious open-concept living area features vaulted ceilings and a beautiful Marble & Wood fireplace, creating a warm, inviting atmosphere. Sliding doors lead to your private deck provides easy access to enjoy the peaceful, beautifully landscaped surroundings. The renovated kitchen is both stylish and functional, featuring modern cab

$370,000

3 beds2 baths1,316 sq ft

Private deck • California shelving • Tennis court

3211 Whispering Hls, Chester, NY 10918

Listing by RE/MAX Benchmark Realty Group

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain with a new HVAC system. The kitchen boasts modern stainless-steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the commun

$360,000

3 beds2.5 baths1,331 sq ft

Handball courts • Community pool • Tennis courts

3409 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Cheap Home 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!

$374,900

3 beds2.5 baths1,331 sq ft

End unit • Eat in kitchen • Largest unit

2921 Whispering Hls, Chester, NY 10918

Listing by ARC Realty 1 in Sales

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Looking for the perfect weekend stay, peaceful getaway, or a one-of-a-kind place to call home? Step into the timeless charm of this historic 1800s farmhouse, where character, history, and a warm, inviting setting come together. Whether you envision weekends away from the hustle and bustle, a charming country retreat, or year-round living, this unique property offers an opportunity to own a true piece of history. Original details, classic craftsmanship, and the distinctive character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that refl

$289,000

2 beds1 bath1,004 sq ft

Historic farmhouse • Original deed • 1.8 acre lot

166 Bull Mill Rd, Chester, NY 10918

Listing by Keller Williams Valley Realty

Property at 241 Meadow Ave, Chester, NY 10918, 4 beds, 1.5 baths

$349,999

4 beds1.5 baths1,560 sq ft

241 Meadow Ave, Chester, NY 10918

Listing by Keller Williams 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 2124 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$299,000

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

$380,000

3 beds2.5 baths1,331 sq ft

4704 Whispering Hls, Chester, NY 10918

Listing by Sahagian Realty LLC

Property at 4008 Whispering Hills Dr, Chester, NY 10918, 2 beds, 1.5 baths

$290,000

2 beds1.5 baths1,072 sq ft

4008 Whispering Hills Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 151 Main St, Chester, NY 10918, 4 beds, 1 bath

$299,000

4 beds1 bath1,504 sq ft

151 Main St, Chester, NY 10918

Listing by Hudson Valley Griffith

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

$359,000

3 beds2.5 baths1,331 sq ft

2522 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 1367 Kings Hwy, Chester, NY 10918, 3 beds, 1.5 baths

$440,000

3 beds1.5 baths1,728 sq ft

1367 Kings Hwy, Chester, NY 10918

Listing by Greene Realty Group

Property at 66 Whitetail Run, Chester, NY 10918, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths1,500 sq ft

66 Whitetail Run, Chester, NY 10918

Listing by Howard Hanna Rand 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

Property at 7 Hambletonian Ave, Chester, NY 10918, 2 beds, 1 bath

$379,900

2 beds1 bath1,026 sq ft

7 Hambletonian Ave, Chester, NY 10918

Listing by HomeSmart Homes & Estates

Property at 492 Black Meadow Rd, Chester, NY 10918

$399,000

Land46.00 acres (lot)

492 Black Meadow Rd, Chester, NY 10918

Listing by eXp Realty

Property at 552 Pine Hill Rd, Chester, NY 10918

$299,000

Land5.70 acres (lot)

552 Pine Hill Rd, Chester, NY 10918

Listing by eRealty Advisors, Inc

Property at Shaw Rd Off Oxford Rd, Blooming Grove, NY 10914

$85,000

Land1.70 acres (lot)

Shaw Rd Off Oxford Rd, Blooming Grove, NY 10914

Listing by Keller Williams Realty

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NEW 34 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Welcome to this charming 3-bedroom, 1.5-bath home located in the heart of the Village of Monroe. Featuring durable vinyl siding and beautiful curb appeal, this property beautifully combines comfortable indoor living with outdoor enjoyment. Key Interior Highlights • Spacious Living & Dining: Large, inviting main-level rooms perfect for entertaining and everyday living. Bay window in dining room adds additional light. • Comfort Features: Ceiling fans throughout most rooms ensure year-round airflow. Downstairs offers large window air conditioning unit. • Bedrooms: Staircase with wide wooden bannister leads upstairs to the bedrooms. The spacious primary suite features a dou

$419,900

3 beds1.5 baths1,159 sq ft

Private deck • Covered porch • Double closet

27 Ash St, Monroe, NY 10950

Listing by HomeSmart Homes & Estates

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Looking for a home you can make truly your own? This spacious 3-bedroom, 1.5-bath Cape Cod sits on 1.3 beautiful acres in the conveniently located Town of Goshen and offers a wonderful opportunity for updating and creating a home that reflects your own style. The first floor features a large sunken living room, separate dining room, renovated kitchen, full bath, office/family room, mud room with side entrance, and laundry room. Upstairs, you'll find a spacious primary bedroom with en-suite bath, along with two additional nicely sized bedrooms. The location is ideal for commuters and those who enjoy nearby amenities less than a mile to Route 17 and the Park & Ride, approximately 10 min

$425,000

3 beds2 baths2,191 sq ft

Close to restaurants • Separate dining room • Renovated kitchen

41 Police Dr, Goshen, NY 10924

Listing by Compass Greater NY, LLC

FLOOR PLAN

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Welcome to this beautifully updated 4-bedroom single-family home conveniently located just outside the Village of Goshen. Offering a comfortable blend of modern updates and everyday functionality, this home is move-in ready and thoughtfully maintained. The updated kitchen features granite countertops, a mosaic tile backsplash, and brand-new stainless steel Frigidaire appliances. Throughout the home, updated luxury vinyl flooring and new baseboards create a clean, modern feel, complemented by new vinyl siding and windows replaced in 2016. Additional major improvements provide peace of mind, including a roof redone in 2016, a new well installed in 2020, and a new well pump with alarm system i

$349,999

4 beds2 baths1,536 sq ft

New baseboards • Updated kitchen • Granite countertops

11 Strack Rd, Goshen, NY 10924

Listing by Keller Williams Realty

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Built for easy, manageable living. Set on a corner lot, this 3-bed, 1-bath ranch has a welcoming presence from the moment you approach, complemented by an oversized driveway and front deck. Inside, the main living spaces feel open and connected while maintaining a sense of distinction, offering a comfortable layout with functionality in mind. A nicely-sized entrance foyer invites you in before giving way to the living, dining, and kitchen areas, while the bedrooms and bathroom are positioned on the opposite side. Laundry is tucked away and conveniently located between the bedrooms, and the utility room can be accessed through the bathroom or outside around the back. Adding another layer to

$412,000

3 beds1 bath1,288 sq ft

Front deck • Utility room access • Oversized driveway

21 Midway Dr, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Fall in love with this beautiful 3 Bedroom, 1.5 Bath Colonial. Gracious entrance opens to Living Room & Amazing Eat in Kitchen with Stainless Steel Appliances & Granite Countertops. Dining Area off Kitchen has sliders to a nice deck. Enjoy morning coffee on your large back deck overlooking the beautiful level yard. Basement offers a good amount of storage space & a laundry area. Nice large driveway can accommodate quite a few cars. Great location close to restaurants & shops. Make your appointment today!

$415,000

3 beds1.5 baths1,458 sq ft

Large back deck • Level yard • Eat in kitchen

7 Nelson St, Goshen, NY 10924

Listing by Hudson Valley Griffith

ABOUT THIS HOME
Cheap Home for sale in Chester, NY:
Discover the possibilities in this charming 2-bedroom, 1-bath home situated on a spacious . 37-acre lot in Monroe, NY. Whether you're searching for the perfect weekend retreat, first home, downsizing opportunity, or investment property, this home offers flexibility and potential to fit a variety of lifestyles. Enjoy the convenience of being close to major highways, shopping, dining, schools, and everyday amenities, while still having your own space to relax and unwind. The manageable size and generous lot make this property an appealing option for those looking for a simpler lifestyle without sacrificing location. With its desirable Monroe location and multiple possibilities for use, this h

$350,000

2 beds1 bath600 sq ft

Front covered porch • Level lot • 2 sheds

33 E Crossman Ave, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 46 Midway Dr, Monroe, NY 10950, 3 beds, 2 baths

$449,000

3 beds2 baths1,050 sq ft

46 Midway Dr, Monroe, NY 10950

Listing by Sage Realty Center LLC

Property at 37 Marian Ct, Warwick, NY 10990, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,392 sq ft

37 Marian Ct, Warwick, NY 10990

Listing by Capital Estate Realty LLC

Property at 570 Lakes Rd, Monroe, NY 10950, 3 beds, 2 baths

$449,000

3 beds2 baths1,304 sq ft

570 Lakes Rd, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 47 Lake Region Blvd, Monroe, NY 10950, 2 beds, 2 baths

$449,000

2 beds2 baths1,359 sq ft

47 Lake Region Blvd, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 499 Old Dutch Hollow Rd, Monroe, NY 10950, 2 beds, 1 bath

$435,000

2 beds1 bath1,280 sq ft

499 Old Dutch Hollow Rd, Monroe, NY 10950

Listing by eXp Realty

Property at 6 Old Dominion Rd, Blooming Grove, NY 10914, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths2,116 sq ft

6 Old Dominion Rd, Blooming Grove, NY 10914

Listing by RE/MAX Prime Properties

Property at 124 Rye Hill Rd, Monroe, NY 10950, 3 beds, 1 bath

$425,000

3 beds1 bath1,107 sq ft

124 Rye Hill Rd, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 24 Round Lake Ave, Monroe, NY 10950, 2 beds, 1 bath

$375,000

2 beds1 bath616 sq ft

24 Round Lake Ave, Monroe, NY 10950

Listing by eXp Realty

Property at 149 Valley View Ave, Monroe, NY 10950, 3 beds, 2 baths

$350,000

3 beds2 baths2,032 sq ft

149 Valley View Ave, Monroe, NY 10950

Listing by Redfin Real Estate

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

$299,000

3 beds2.5 baths1,320 sq ft

607 Mountain Laurel Dr, Monroe, NY 10950

Listing by Weichert Realtors

Property at 20 Meadow Ave, Washingtonville, NY 10992, 3 beds, 1 bath

$425,000

3 beds1 bath1,196 sq ft

20 Meadow Ave, Washingtonville, NY 10992

Listing by RE/MAX Benchmark Realty Group

Property at 92 Walton Ter, Monroe, NY 10950, 2 beds, 1 bath

$275,000

2 beds1 bath672 sq ft

92 Walton Ter, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 16 Upper Hillman Rd, Warwick, NY 10990, 3 beds, 2 baths

$419,500

3 beds2 baths1,482 sq ft

16 Upper Hillman Rd, Warwick, NY 10990

Listing by Howard Hanna Rand Realty

Property at 110 Purgatory Rd, Campbell Hall, NY 10916

$225,000

Land8.60 acres (lot)

110 Purgatory Rd, Campbell Hall, NY 10916

Listing by Howard Hanna Rand Realty

Based on information submitted to the MLS GRID as of Mon Sep 14 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.

Cheap Homes for Sale in Chester

There are currently 19 cheap homes for sale in Chester at a median listing price of $377K. 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, 3 homes have been sold in Chester. In addition to houses in Chester, there were also 15 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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