Chester, NY homes for sale & real estate

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3D WALKTHROUGH

ABOUT THIS HOME
Chester, NY Homes for Sale
Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm and inviting family room with a fireplace, creating an ideal space for entertaining. The spacious kitchen is appointed with granite countertops, a center island, abundant cabinetry, and sliders leading to an expansive deck overlooking the peaceful backyard. A formal dining room, powder room, and fir

$799,000

4 beds2.5 baths3,070 sq ft

197 Oxford Rd, Chester, NY 10918

Man-made pond • Granite countertops • Center island

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Chester, NY Homes for Sale
Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location. Don't wait this one is ready to go!

$275,000

2 beds1 bath1,084 sq ft

2113 Whispering Hls, Chester, NY 10918

New kitchen • New bathroom • Granite counter tops

Listing by Keller Williams Realty

FLOOR PLAN

ABOUT THIS HOME
Chester, NY Homes for Sale
Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom,

$539,000

4 beds2.5 baths2,698 sq ft

24 Walnut St, Chester, NY 10918

Sweeping lot • Park views • Full basement

Listing by Keller Williams Village Sq Rlt

FLOOR PLAN

ABOUT THIS HOME
Chester, NY Homes for Sale
* Rare Opportunity in Chester A rare opportunity in Chester, this beautifully designed 3-bedroom, 2 full and 2 half bathroom split-level home blends contemporary style, generous living space, and a peaceful connection to nature. The light-filled main level welcomes you with soaring ceilings, expansive windows, and an open, flowing layout designed for both everyday living and entertaining. At the heart of the home, the dramatic living room features a wood-burning fireplace and overlooks the beautifully landscaped backyard, where a custom-built pond, mature gardens, and bamboo privacy create a serene and private setting. The slick white kitchen was designed with entertaining in mind, featuri

$650,000

3 beds3 baths2,520 sq ft

29 Murray Dr, Chester, NY 10918

Large center island • Custom built pond • Private patio

Listing by eXp Realty

ABOUT THIS HOME
Chester, NY Homes for Sale
Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The Second beautiful structure offers hardwood floors, as seen, 2 bedrooms, a kitchen, a living room, and 1 full bath. In addition, there is a garage about 750 sq that can be rented out for another few hundred dollars a month. Enjoy the beautiful 1.1-acre property. This unique property has multiple opportuni

$575,000

6 beds2 baths— sq ft

68 Conklingtown Rd Unit 1&2, Chester, NY 10918

Separate structures • Own utilities • 1.1-acre property

Listing by MS Realty Group USA, Inc

Property at 3 Hilltop Ln, Chester, NY 10918, 5 beds, 2.5 baths

$750,000

5 beds2.5 baths2,700 sq ft

3 Hilltop Ln, Chester, NY 10918

Listing by MK Realty Inc

Property at 1 Hilltop Ln, Chester, NY 10918, 5 beds, 2.5 baths

$750,000

5 beds2.5 baths2,700 sq ft

1 Hilltop Ln, Chester, NY 10918

Listing by MK Realty Inc

Property at 58 Nancy Ln, Chester, NY 10918, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths2,718 sq ft

58 Nancy Ln, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 2119 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$295,000

2 beds1.5 baths1,086 sq ft

2119 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 487 Black Meadow Rd, Chester, NY 10918, 6 beds, 3.5 baths

$699,995

6 beds3.5 baths4,204 sq ft

487 Black Meadow Rd, Chester, NY 10918

Listing by Joseph Baratta Company Realty

Property at 3318 State Route 94, Chester, NY 10918, 3 beds, 2 baths

$549,900

3 beds2 baths2,138 sq ft

3318 State Route 94, Chester, NY 10918

Listing by Howard Hanna Rand Realty

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

$990,000

4 beds2.5 baths3,955 sq ft

1 Oakland Ave, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 49 Stone Mountain Trl, Chester, NY 10918, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths3,656 sq ft

49 Stone Mountain Trl, Chester, NY 10918

Listing by eRealty Advisors, Inc

Property at 2 Hemlock Ct, Chester, NY 10918, 5 beds, 2.5 baths

$750,000

5 beds2.5 baths2,700 sq ft

2 Hemlock Ct, Chester, NY 10918

Listing by MK Realty Inc

Property at 2 Garnett Hill Rd, Chester, NY 10918, 5 beds, 2.5 baths

$999,999

5 beds2.5 baths4,772 sq ft

2 Garnett Hill Rd, Chester, NY 10918

Listing by Platinum Realty Associates

Property at 19 High St, Chester, NY 10918, 9 beds, 6.5 baths

$1,145,000

9 beds6.5 baths4,965 sq ft

19 High St, Chester, NY 10918

Listing by Keller Williams Realty

Property at 2 Primrose Ln, Chester, NY 10918, 4 beds, 3 baths

$849,900

4 beds3 baths2,370 sq ft

2 Primrose Ln, Chester, NY 10918

Listing by Weichert Realtors

Property at 5 N Hudson St, Chester, NY 10918, 3 beds, 2 baths

$500,000

3 beds2 baths2,688 sq ft

5 N Hudson St, Chester, NY 10918

Listing by Keller Williams Realty

Property at 5 Hilltop Ln, Chester, NY 10918, 5 beds, 2.5 baths

$850,000

5 beds2.5 baths3,200 sq ft

5 Hilltop Ln, Chester, NY 10918

Listing by MK Realty Inc

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 16 Lori Ln, Chester, NY 10918, 4 beds, 4 baths

$1,139,900

4 beds4 baths4,624 sq ft

16 Lori Ln, Chester, NY 10918

Listing by eXp Realty

Property at 3 Hemlock Ct, Chester, NY 10918, 5 beds, 2.5 baths

$750,000

5 beds2.5 baths2,700 sq ft

3 Hemlock Ct, Chester, NY 10918

Listing by MK Realty Inc

Property at 1414 Kings Hwy, Chester, NY 10918, 4 beds, 2.5 baths

$879,900

4 beds2.5 baths3,200 sq ft

1414 Kings Hwy, Chester, NY 10918

Listing by Keller Williams Realty

Property at 22 Goshen Rd, Chester, NY 10918, 4 beds, 3.5 baths

$1,195,000

4 beds3.5 baths4,281 sq ft

22 Goshen Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 19 Greentree Ln, Chester, NY 10918, 4 beds, 4 baths

$3,400,000

4 beds4 baths7,750 sq ft

19 Greentree Ln, Chester, NY 10918

Listing by Serhant LLC

Property at 90 Pewter Cir, Chester, NY 10918, 4 beds, 2.5 baths

$759,900

4 beds2.5 baths2,250 sq ft

90 Pewter Cir, Chester, NY 10918

Listing by Keller Williams Realty

Property at 2 Pine Hill Rd, Chester, NY 10918, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths2,302 sq ft

2 Pine Hill Rd, Chester, NY 10918

Listing by Ellis Sotheby's Intl Realty

Property at 220 Oxford Rd, Chester, NY 10918, 3 beds, 3.5 baths

$894,000

3 beds3.5 baths3,535 sq ft

220 Oxford Rd, Chester, NY 10918

Listing by Blooming Realty

Property at 12 Damian Ct, Chester, NY 10918, 5 beds, 4 baths

$949,000

5 beds4 baths3,136 sq ft

12 Damian Ct, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Property at 63 Whitetail Run, Chester, NY 10918, 4 beds, 2.5 baths

$1,200,000

4 beds2.5 baths2,711 sq ft

63 Whitetail Run, Chester, NY 10918

Listing by SPIRAL NY Real Estate LLC

Property at 19 Bull Mine Rd, Chester, NY 10918, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths3,332 sq ft

19 Bull Mine Rd, Chester, NY 10918

Listing by BHG Real Estate Green Team

Property at 60 Whitetail Run, Chester, NY 10918, 4 beds, 2.5 baths

$900,000

4 beds2.5 baths2,588 sq ft

60 Whitetail Run, Chester, NY 10918

Listing by Realty Blue Corp

Property at Museum Village Rd, Monroe, NY 10914

$950,000

Land3.50 acres (lot)

Museum Village Rd, Monroe, NY 10914

Listing by Metrex Realty INC

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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Based on information submitted to the MLS GRID as of Wed Sep 02 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)

$369,715

-10.9% YoY | Jul 2026

1 year
3 year
5 year

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

Location

Data

Jul 2026

Growth

% YoY

Chester, NY

$369,715

-10.9%

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