Chester, NY homes for sale & real estate

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ABOUT THIS HOME
Chester, NY Homes for Sale
Perched beautifully atop a scenic hill, this lovingly maintained home has been cherished by its original owners and offers a rare combination of privacy, space, and timeless charm. Set on a stunning property in a desirable Chester location, the home contains unique features including a beautiful sunroom, a detached three-car garage, and an additional one-car attached garage, providing exceptional parking and storage. Inside, the home has been kept in immaculate condition and offers an excellent opportunity for its next owner to personalize and make it their own. A wonderful opportunity to own a spacious home on a beautiful piece of property in a great location.

$599,000

4 beds4.5 baths3,326 sq ft

111 Ayr Rd, Chester, NY 10918

Sunroom • 3 acre lot • 5 garage spots

Listing by Curasi Realty, Inc.

OPEN TODAY, 1PM TO 3:30PM

ABOUT THIS HOME
Chester, NY Homes for Sale
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand-new, ready-to-move-in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

$880,000

5 beds2.5 baths3,600 sq ft

2 Periwinkle Ct, Chester, NY 10918

Modern retreat • Oversized windows • 3,631 sq ft lot

Listing by MK Realty Inc

ABOUT THIS HOME
Chester, NY Homes for Sale
Why rent when you can own? Here’s a rare opportunity to make it your own. Check out this two bedroom end unit in desirable Whispering Hills Community. This 1084 Square Foot abode comes with one car garage parking and all the amenities Whispering Hills has to offer. You’ll enjoy the spacious living room featuring a cathedral ceiling and wood-burning fireplace while sipping coffee from your private deck overlooking the development. Make your appointment to view this unit today.

$239,900

2 beds1 bath1,084 sq ft

2313 Whispering Hls, Chester, NY 10918

Private deck • One car garage • Cathedral ceiling

Listing by R2M Realty Inc

ABOUT THIS HOME
Chester, NY Homes for Sale
THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential development, or a private sustainable sanctuary, this estate delivers on every front. THE RESIDENCE Built in 2002, the custom-designed 3,348 sq. ft. home features 4 spacious bedrooms and 3 full baths. The layout is thoughtfully crafted to maximize natural light and views of the sprawling grounds. The

$1,725,000

4 beds2.5 baths3,348 sq ft

20 Goshen Rd, Chester, NY 10918

53 acres • Marketable timber • Horse trails

Listing by eXp Realty

ABOUT THIS HOME
Chester, NY Homes for Sale
With vision and a little elbow grease, this split-level home can be brought back to its full potential. Offering 3 bedrooms, 2 full baths, central air, wood stove, a full basement with a fire place and a 2-car garage, the home is a great opportunity for buyers looking to make it their own. It is being sold as is and will require some work, reflected in the asking price. Located in the Tomahawk Lake community in Blooming Grove, residents can enjoy amenities including a basketball court, gated park and playground, and recreational facilities. Powered boats are allowed on Tomahawk Lake. Take advantage of the opportunity to create your vision in a beautiful lake community. Take advantage of the

$399,000

3 beds2 baths1,658 sq ft

45 Sayer Rd, Blooming Grove, NY 10914

Gated park • Full basement • Basketball court

Listing by eXp Realty

Property at 94 Booth Rd, Chester, NY 10918, 3 beds, 2.5 baths

$485,000

3 beds2.5 baths2,441 sq ft

94 Booth Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 3706 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$339,900

2 beds1.5 baths1,086 sq ft

3706 Whispering Hls, Chester, NY 10918

Listing by eXp Realty

Property at 1223 Whispering Hls, Chester, NY 10918, 3 beds, 2 baths

$299,900

3 beds2 baths1,316 sq ft

1223 Whispering Hls, Chester, NY 10918

Listing by KW Hudson Valley United

Property at 3561 Rte 94, Chester, NY 10918, 3 beds, 3 baths

$619,999

3 beds3 baths2,902 sq ft

3561 Rte 94, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 20 Mountainside Dr, Chester, NY 10918, 4 beds, 3 baths

$739,900

4 beds3 baths3,080 sq ft

20 Mountainside Dr, Chester, NY 10918

Listing by eXp Realty

Property at 8 Townsend Pl, Chester, NY 10918, 4 beds, 2 baths

$449,000

4 beds2 baths1,832 sq ft

8 Townsend Pl, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 5 Red Fox Run, Chester, NY 10918, 4 beds, 3.5 baths

$679,000

4 beds3.5 baths2,960 sq ft

5 Red Fox Run, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 2107 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths1,086 sq ft

2107 Whispering Hls, Chester, NY 10918

Listing by Wansor Realty

Property at 985 Craigville Rd, Chester, NY 10918, 4 beds, 3.5 baths

$750,000

4 beds3.5 baths3,100 sq ft

985 Craigville Rd, Chester, NY 10918

Listing by Houlihan Lawrence Inc.

Property at 1 Sanford Ave, Chester, NY 10918, 4 beds, 3 baths

$750,000

4 beds3 baths2,280 sq ft

1 Sanford Ave, Chester, NY 10918

Listing by Redfin Real Estate

Property at 19 Meadow Ave, Chester, NY 10918, 2 beds, 2 baths

$499,999

2 beds2 baths1,910 sq ft

19 Meadow Ave, Chester, NY 10918

Listing by RE/MAX Town & Country

Property at 147 Main St, Chester, NY 10918, 4 beds, 2 baths

$549,000

4 beds2 baths2,824 sq ft

147 Main St, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 1212 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$269,000

2 beds1 bath1,084 sq ft

1212 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Realty

Property at 7 Greycourt Rd, Chester, NY 10918, 3 beds, 2.5 baths

$1,850,000

3 beds2.5 baths2,404 sq ft

7 Greycourt Rd, Chester, NY 10918

Listing by KW Hudson Valley United

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

$399,999

3 beds1.5 baths1,500 sq ft

66 Whitetail Run, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 2921 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$364,900

3 beds2.5 baths1,331 sq ft

2921 Whispering Hls, Chester, NY 10918

Listing by ARC Realty 1 in Sales

Property at 33 Meadow Ave, Chester, NY 10918, 3 beds, 1 bath

$370,000

3 beds1 bath1,561 sq ft

33 Meadow Ave, Chester, NY 10918

Listing by River Realty Services, Inc.

Property at 101 Beverly Rd, Chester, NY 10918, 4 beds, 3 baths

$879,000

4 beds3 baths3,764 sq ft

101 Beverly Rd, Chester, NY 10918

Listing by Greene Realty Group

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 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 11 Chandler Dr, Chester, NY 10918, 3 beds, 2.5 baths

$499,999

3 beds2.5 baths1,908 sq ft

11 Chandler Dr, Chester, NY 10918

Listing by Coldwell Banker Realty

Property at 69 Cedar Pond Ln, Chester, NY 10918, 6 beds, 7.5 baths

$1,599,999

6 beds7.5 baths— sq ft

69 Cedar Pond Ln, Chester, NY 10918

Listing by Prominent Properties Sotheby's International Realty-Alpine, (201) 768-9300

Property at 412 Laroe Rd, Chester, NY 10918, 3 beds, 2 baths

$605,000

3 beds2 baths1,848 sq ft

412 Laroe Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 19 Grand View Ter, Chester, NY 10918, 5 beds, 4 baths

$789,900

5 beds4 baths4,697 sq ft

19 Grand View Ter, Chester, NY 10918

Listing by eXp Realty

Property at 424 Laroe Rd, Chester, NY 10918, 4 beds, 3 baths

$634,999

4 beds3 baths2,316 sq ft

424 Laroe Rd, Chester, NY 10918

Listing by Epique Realty

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 3 Garnett Hill Rd, Chester, NY 10918, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,516 sq ft

3 Garnett Hill Rd, Chester, NY 10918

Listing by Keller Williams 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 1168 Craigville Rd, Chester, NY 10918, 4 beds, 2.5 baths

$779,900

4 beds2.5 baths2,616 sq ft

1168 Craigville Rd, Chester, NY 10918

Listing by ARC Realty 1 in Sales

Property at 70 Main St, Chester, NY 10918, 3 beds, 2 baths

$419,000

3 beds2 baths1,357 sq ft

70 Main St, Chester, NY 10918

Listing by Curasi Realty, Inc.

Property at 65 Oxford Springs Rd, Chester, NY 10918, 5 beds, 3.5 baths

$699,000

5 beds3.5 baths3,463 sq ft

65 Oxford Springs Rd, Chester, NY 10918

Listing by HomeSmart Homes & Estates

Property at 1 Oakland Ave, Chester, NY 10918, 4 beds, 2.5 baths

$980,000

4 beds2.5 baths3,955 sq ft

1 Oakland Ave, 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 44 Sayer Rd, Blooming Grove, NY 10914, 3 beds, 1.5 baths

$540,000

3 beds1.5 baths2,332 sq ft

44 Sayer Rd, Blooming Grove, NY 10914

Listing by Sage Realty Center LLC

Property at 24 Walnut St, Chester, NY 10918, 4 beds, 2.5 baths

$525,000

4 beds2.5 baths2,698 sq ft

24 Walnut St, Chester, NY 10918

Listing by Keller Williams Village Sq Rlt

Property at 58 Nancy Ln, Chester, NY 10918, 4 beds, 2.5 baths

$744,999

4 beds2.5 baths2,718 sq ft

58 Nancy Ln, Chester, NY 10918

Listing by Howard Hanna Rand Realty

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Based on information submitted to the MLS GRID as of Sun Oct 18 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.

Average home prices near Chester, NY

Cities

Zip Codes

Chester, NY real estate trends

All Home Types trends in Chester, NY

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$384,817

+1.0% YoY | Sep 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2026

Growth

% YoY

Chester, NY

$384,817

+1.0%

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