Chester Homes for Sale

Welcome to Chester, a charming city located in the United States that offers a perfect blend of history, culture, and modern amenities. Known for its picturesque streets, beautiful parks, and friendly community, Chester is a fantastic place to call home.

In Chester, you will find a wide range of homes for sale to suit every lifestyle and budget. Whether you are looking for a cozy apartment in the heart of the city, a spacious family home in a peaceful neighborhood, or a luxurious estate with stunning views, Chester has something for everyone.

With a strong real estate market and a variety of properties available, finding your dream home in Chester is easier than ever. From historic homes with character to modern developments with all the latest features, the options are endless.

Explore the vibrant neighborhoods, excellent schools, and convenient amenities that Chester has to offer. Whether you are a first-time homebuyer, a growing family, or a retiree looking for a peaceful retreat, Chester has something for everyone.

Contact us today to learn more about the homes for sale in Chester and start your journey to finding the perfect property in this wonderful city.

Newest Chester Homes for Sale

402 Macum Creek Dr, Chester $789,000

Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This though...

3 Beds
3 Baths

Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

326 Castle Marina Rd, Chester $550,000

Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this ...

5 Beds
4 Baths

Courtesy of Coldwell Banker Waterman Realty

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

641 Warbler Way, Chester $649,990 ▼

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful desig...

2 Beds
2 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

200 Church St, Chester $350,000

Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bed...

2 Beds
2 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact: 4432741900

275 Warbler Way, Chester $944,900

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and a...

3 Beds
3 Baths

Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

1868 Roberta Dr, Chester $400,000

List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and ver...

5 Beds
4 Baths

Courtesy of Alex Cooper Auctioneers, Inc.

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

1717 Harbor Dr, Chester $1,250,000

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with ...

3 Beds
3 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

920 E 20th St, Chester $279,900

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3 Beds
1 Baths

Courtesy of BHHS Fox & Roach - Chester

Listing courtesy of BHHS Fox & Roach - Chester. Contact: (484) 483-9660

14519 Sonnenburg Dr, Chester $365,000

Nestled in the quiet Mistwood Forest neighborhood, this charming home offers comfort, space, and convenience. The main level features a large primary bedroom with a priva...

3 Beds
2 Baths

Courtesy of Move4Free Realty, LLC

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460

233 Cross Creek Ct, Chester $569,900

Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of...

4 Beds
3 Baths

Courtesy of Rory S. Coakley Realty, Inc.

Listing courtesy of Rory S. Coakley Realty, Inc.. Contact:

2513 Cecil Dr, Chester $1,290,000 ▼

Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property...

5 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

148 Elinor St, Chester $899,000

Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedr...