Recently Sold Homes in Chester, NY

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SOLD OCT 22, 2025

ABOUT THIS HOME
Recently Sold Home in Chester, NY:
Monroe's Stunning Mini Mansion Awaits Its New Owner! This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase. Before heading upstairs, prepare to be impressed by the spacious chef's kitchen, equipped with top-of-the-line stainless steel appliances. You'll also discover a grand formal dining room, a cozy family room with a fireplace, and ample closets and storage space. All of these wonderful features lead out to a large deck and a breathtaking heated inground saltwater pool! On the up

$850,000 Last sold price

5 beds3 baths3,485 sq ft

284 Bull Mill Rd, Chester, NY 10918

Listing by Keller Williams Valley Realty

SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in Chester, NY:
Nestled amidst the tranquil woods of Chester, NY, this stunning contemporary home offers a perfect sanctuary for those seeking a harmonious blend of modern design and natural beauty. The moment you step inside, floor-to-ceiling windows reveal breathtaking wooded vistas, flooding the interior with natural light and creating a seamless connection between indoor comfort and outdoor serenity. This residence is more than just a house; it’s a lifestyle, an oasis of privacy yet conveniently located near shopping, dining, and major highways for effortless commuting. The interior of the home is thoughtfully designed to maximize both style and functionality. The open-concept living areas invite

$765,000 Last sold price

3 beds2 baths2,020 sq ft

1711 Kings Hwy, Chester, NY 10918

Listing by Keller Williams Realty

SOLD SEP 15, 2025

ABOUT THIS HOME
Recently Sold Home in Chester, NY:
Serene Country Retreat in an Upscale Chester Neighborhood! Set on over 5 peaceful acres with sweeping mountain views, this stunning contemporary home offers the perfect mix of style, comfort, and privacy. With 4 bedrooms and 4 bathrooms, the layout is ideal for both everyday living and effortless entertaining. The sun-drenched living room is a true showpiece—featuring dramatic cathedral ceilings, oversized windows, custom built-ins with a rolling library ladder, and a beautiful marble wood-burning fireplace as the centerpiece. Skylights bathe the space in natural light, creating a warm and inviting atmosphere. Upstairs, the spacious master suite offers a quiet escape with its own priv

$800,000 Last sold price

5 beds4 baths4,496 sq ft

10 Spectrum Dr, Chester, NY 10918

Listing by eRealty Advisors, Inc

SOLD NOV 21, 2025

ABOUT THIS HOME
Recently Sold Home in Chester, NY:
Welcome to this stunning home nestled on 5 acres near the heart of Chester, NY. Tucked away for ultimate privacy, yet just minutes from shopping, dining, and major highways-it's the perfect blend of seclusion and convenience. Step inside this spacious 4-bedroom 3-bathroom retreat, designed for comfort and style. This open layout flows seamlessly with plenty of natural light pouring in through large windows. Each bedroom offers ample space, ideal for families or guests. Downstairs, discover a versatile walk-out basement-perfect for a home office, gym, or entertainment area. Plus, the attached 2-car garage provides easy access and storage solutions Out back, your private oasis awaits. Dive i

$740,000 Last sold price

4 beds2.5 baths3,063 sq ft

48 Brennan Ct, Chester, NY 10918

Listing by Keller Williams Realty

SOLD OCT 23, 2025

ABOUT THIS HOME
Recently Sold Home in Chester, NY:
CHARM, SPACE and OPPORTUNITY in the highly rated Monroe-Woodbury School District! Classic vintage 5 bedroom colonial on 3.10 level acres offering the perfect blend of character and potential - all just 50 miles from NYC yet a world away from the hustle and bustle of city life. Located on a winding country road, the home sits on a large, level lot with mature trees and an in ground pool (condition unknown) for summer fun. With its peaceful setting, you’ll enjoy country living while still being minutes from Woodbury Common Premium Outlets, shopping, parks, schools, public transportation to NYC, and major highways—a truly unbeatable location. Inside, you’ll find a home full o

$499,000 Last sold price

5 beds2.5 baths3,120 sq ft

358 Bull Mill Rd, Chester, NY 10918

Listing by Corcoran Baer & McIntosh

Property at 9 June Rd, Chester, NY 10918, 4 beds, 2.5 baths

$620,000 Last sold price

4 beds2.5 baths2,402 sq ft

9 June Rd, Chester, NY 10918

Listing by eXp Realty

Property at 4 Wood Rd, Chester, NY 10918, 4 beds, 1.5 baths

$475,000 Last sold price

4 beds1.5 baths1,554 sq ft

4 Wood Rd, Chester, NY 10918

Listing by HomeSmart Homes & Estates

Property at 15 Mari Rd, Chester, NY 10918, 4 beds, 2 baths

$500,000 Last sold price

4 beds2 baths1,888 sq ft

15 Mari Rd, Chester, NY 10918

Listing by HomeSmart Homes & Estates

Property at 114 Old Mansion Rd, Chester, NY 10918, 4 beds, 2 baths

$555,000 Last sold price

4 beds2 baths3,330 sq ft

114 Old Mansion Rd, Chester, NY 10918

Listing by Master Realty Group Inc.

Property at 3915 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$382,000 Last sold price

3 beds2.5 baths1,331 sq ft

3915 Whispering Hls, Chester, NY 10918

Listing by Century 21 Full Service Realty

Property at 2503 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$340,000 Last sold price

3 beds2.5 baths1,316 sq ft

2503 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Hudson Valley

Property at 3911 Whispering Hls, Chester, NY 10918, 3 beds, 2 baths

$367,500 Last sold price

3 beds2 baths1,316 sq ft

3911 Whispering Hls, Chester, NY 10918

Listing by Master Realty Group Inc.

Property at 2409 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$365,000 Last sold price

3 beds2.5 baths1,331 sq ft

2409 Whispering Hls, Chester, NY 10918

Listing by Hudson Valley Griffith

Property at 8 Hom St, Chester, NY 10918, 3 beds, 1.5 baths

$425,000 Last sold price

3 beds1.5 baths1,410 sq ft

8 Hom St, Chester, NY 10918

Listing by Preferred Properties Real Esta

Property at 22 Bridle Ln, Chester, NY 10918, 4 beds, 1.5 baths

$498,000 Last sold price

4 beds1.5 baths1,570 sq ft

22 Bridle Ln, Chester, NY 10918

Listing by Keller Williams Realty

Property at 12 Bianca Blvd, Chester, NY 10918, 4 beds, 2.5 baths

$575,000 Last sold price

4 beds2.5 baths3,200 sq ft

12 Bianca Blvd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 3708 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$310,000 Last sold price

2 beds1.5 baths1,072 sq ft

3708 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Realty

Property at 81 Hambletonian Rd, Chester, NY 10918, 3 beds, 2 baths

$612,500 Last sold price

3 beds2 baths1,938 sq ft

81 Hambletonian Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 165 Creamery Pond Rd, Chester, NY 10918, 4 beds, 2.5 baths

$675,000 Last sold price

4 beds2.5 baths2,548 sq ft

165 Creamery Pond Rd, Chester, NY 10918

Listing by Christie's Int. Real Estate

$48,750

2 beds1.5 baths1,052 sq ft

4608 Whispering Hls, Chester, NY 10918

$325,000

2 beds1.5 baths1,086 sq ft

2206 Whispering Hls, Chester, NY 10918

$277,500

3 beds1 bath984 sq ft

8 Shaw Rd, Chester, NY 10918

$105,000

— beds— baths696 sq ft

222 Lehigh Ave, Chester, NY 10918

$200,000

1 bed1 bath1,381 sq ft

79 Greycourt Rd, Chester, NY 10918

$315,800

4 beds1.5 baths1,780 sq ft

108 Pine Hill Rd, Chester, NY 10918

$799,900 Last sold price

4 beds2.5 baths2,500 sq ft

40 Mountainside Dr, Chester, NY 10918

Listing by Our House Real Estate Group

$210,000

— beds— baths— sq ft

145 Kings Highway Byp, Chester, NY 10918

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Based on information submitted to the MLS GRID as of Thu Nov 27 2025. 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.

Recently Sold Homes in Chester

There are currently 27 recently sold homes for sale in Chester at a median listing price of $499K. 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 39 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 was also 1 condo, 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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