Chester, NY Homes for Sale under $400,000

/11
$369,900
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
3910 Whispering Hills, Chester, NY 10918

Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

Randolph Rogers

eXp Realty

(845) 957-9249

3910 Whispering Hills, Chester, NY 10918
Explore Chester
/4
$350,000

$50K PRICE INCREASE
- Land
- 5.1 Acres
- $68,627 per Acre
0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

Theresa Powers

Keller Williams Realty

(845) 713-9754

0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
/50
$370,000
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
3815 Whispering Hills Dr, Chester, NY 10918

Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

David Kraus MK Realty Inc

3815 Whispering Hills Dr, Chester, NY 10918
/23
$400,000

$55K PRICE DROP
- 3 Beds
- 1 Bath
- 1,561 Sq Ft
33 Meadow Ave, Chester, NY 10918

One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

Ernie Acampora River Realty Services, Inc.

33 Meadow Ave, Chester, NY 10918
/39
$319,900

$20K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,320 Sq Ft
607 Mountain Laurel Dr, Monroe, NY 10950

Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

Rosalie Cook Weichert Realtors

607 Mountain Laurel Dr, Monroe, NY 10950
/29
$389,000

$8K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
1221 Whispering Hills, Chester, NY 10918

Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

Malia Leonard BUY NY REALTY LLC

1221 Whispering Hills, Chester, NY 10918
/11
$349,999

$25K PRICE DROP
- Land
- 4.9 Acres
- $71,428 per Acre
8 Camelback Rd, Chester, NY 10918

Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

James Feldhaus eXp Realty

8 Camelback Rd, Chester, NY 10918
/2
$350,000
- Land
- 2 Acres
- $175,000 per Acre
220 Oxford Rd, Chester, NY 10918

A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

Chaim Weiss Exit Realty Venture

220 Oxford Rd, Chester, NY 10918
/26
$399,900

$25K PRICE DROP
- 2 Beds
- 1 Bath
- 1,026 Sq Ft
7 Hambletonian Ave, Chester, NY 10918

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

William Scolza HomeSmart Homes & Estates

7 Hambletonian Ave, Chester, NY 10918
/32
$319,900

$4K PRICE INCREASE
- 2 Beds
- 1.5 Baths
- 1,072 Sq Ft
2820 Whispering Hills, Chester, NY 10918

Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

Anne Marie Scouarnec R2M Realty Inc.

2820 Whispering Hills, Chester, NY 10918
/32
$344,900

$10K PRICE DROP
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
1311 Whispering Hills Unit 96, Chester, NY 10918

Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

Michael Jenney Keller Williams Realty

1311 Whispering Hills Unit 96, Chester, NY 10918

New York Orange County Chester

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 54 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, NY over the last 12 months is $503,250, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$503,250

Median Single Family Sale Price

$667,000

Median Townhouse Sale Price

$337,450

Median 2 Bedroom Sale Price

$305,000

Average Price Per Sq Ft

$275

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

6.30

Median List Price

$550,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-4%

How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Chester, where you'll find 11 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Chester offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Chester, NY.

Chester Types of Homes for Sale

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