Pending Listings in Chester, MD

23 homes

Sort:

Recommended

UNDER CONTRACT3D WALKTHROUGH

ABOUT THIS HOME
Pending Listing in Chester, MD:
Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful

$789,000

3 beds2.5 baths2,787 sq ft

402 Macum Creek Dr, Chester, MD 21619

Double porches • Spacious deck • Fenced backyard

(703) 378-8810

UNDER CONTRACT

$645,000

6 beds2.5 baths2,700 sq ft

1351 Calvert Rd, Chester, MD 21619

0.34 acre lot • 2 garage spots • Built 2007

(443) 292-6767

UNDER CONTRACT3D WALKTHROUGH

ABOUT THIS HOME
Pending Listing in Chester, MD:
SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing conn

$500,000

4 beds3 baths3,000 sq ft

205 Anchor Ln, Chester, MD 21619

Half-acre lot • Expansive yard • Updated bathrooms

(703) 378-8810

UNDER CONTRACT3D WALKTHROUGH

ABOUT THIS HOME
Pending Listing in Chester, MD:
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 already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, c

$930,000

3 beds3 baths2,761 sq ft

275 Warbler Way, Chester, MD 21619

Upgraded chandeliers • Premium corner lot • Decorative molding

(703) 378-8810

UNDER CONTRACT3D WALKTHROUGH

ABOUT THIS HOME
Pending Listing in Chester, MD:
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-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add mod

$899,000

3 beds2.5 baths2,464 sq ft

148 Elinor St, Chester, MD 21619

Updated staircase • Extensive renovation • Upgraded lighting

(703) 378-8810

Property at 200 Church St, Chester, MD 21619, 2 beds, 2 baths

$350,000

2 beds2 baths1,274 sq ft

200 Church St, Chester, MD 21619

(443) 274-1900

Property at 2011 Stevens Dr, Chester, MD 21619, 3 beds, 2 baths

$489,900

3 beds2 baths1,663 sq ft

2011 Stevens Dr, Chester, MD 21619

(703) 378-8810

Property at 205 Riverside Dr, Chester, MD 21619, 3 beds, 2 baths

$699,000

3 beds2 baths1,524 sq ft

205 Riverside Dr, Chester, MD 21619

(443) 292-6767

Property at 202 Claiborne St, Chester, MD 21619, 4 beds, 3.5 baths

$915,000

4 beds3.5 baths3,424 sq ft

202 Claiborne St, Chester, MD 21619

(410) 224-2200

Property at 208 Blenny Ln, Chester, MD 21619, 4 beds, 3 baths

$374,900

4 beds3 baths1,899 sq ft

208 Blenny Ln, Chester, MD 21619

(443) 274-1900

Property at 41-D Queen Catherine Ct, Chester, MD 21619, 3 beds, 3 baths

$439,000

3 beds3 baths1,750 sq ft

41-D Queen Catherine Ct, Chester, MD 21619

(410) 465-1770

Property at 111 Marshgrass Way #21, Chester, MD 21619, 3 beds, 2.5 baths

$680,000

3 beds2.5 baths2,602 sq ft

111 Marshgrass Way #21, Chester, MD 21619

(301) 882-8710

Property at 208 Widgeon Way, Chester, MD 21619, 3 beds, 3.5 baths

$590,000

3 beds3.5 baths2,100 sq ft

208 Widgeon Way, Chester, MD 21619

(410) 224-3200

Property at 609 Blenny Ln, Chester, MD 21619, 3 beds, 3.5 baths

$450,000

3 beds3.5 baths2,100 sq ft

609 Blenny Ln, Chester, MD 21619

(410) 429-7425

Property at 207 Thomas White Blvd, Chester, MD 21619, 3 beds, 2.5 baths

$819,900

3 beds2.5 baths2,479 sq ft

207 Thomas White Blvd, Chester, MD 21619

(443) 353-5281

Property at 830 Warbler Way #2824, Chester, MD 21619, 3 beds, 2.5 baths

$749,990

3 beds2.5 baths2,602 sq ft

830 Warbler Way #2824, Chester, MD 21619

(410) 208-3500

Property at 2004 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2 baths

$369,900

3 beds2 baths1,524 sq ft

2004 Bridgepointe Dr, Chester, MD 21619

(443) 274-1900

Property at 313 Thomas White Blvd, Chester, MD 21619, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths3,291 sq ft

313 Thomas White Blvd, Chester, MD 21619

(443) 906-3848

Property at 532 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$799,990

3 beds3 baths2,772 sq ft

532 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 124 Riverside Dr, Chester, MD 21619, 4 beds, 2.5 baths

$499,000

4 beds2.5 baths1,979 sq ft

124 Riverside Dr, Chester, MD 21619

(866) 987-3937

Property at 323 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$949,990

5 beds4.5 baths3,225 sq ft

323 Kingfisher Ln, Chester, MD 21619

(410) 208-3500

Property at Lot 6 Norman Ct, Chester, MD 21619, 4 beds, 2.5 baths

$674,900

4 beds2.5 baths— sq ft

Lot 6 Norman Ct, Chester, MD 21619

(410) 729-7700

Property at 201 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$835,000

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

(410) 280-5600

Viewing page 1 of 1

Pending Listings in Chester

There are currently 23 pending listings for sale in Chester at a median listing price of $595K. 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 76 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 14 homes have been sold in Chester. In addition to houses in Chester, there were also 17 condos, 25 townhouses, and 0 multi-family units 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.

More real estate resources for Chester, MD

Nearby Cities

Zip Codes

Nearby Cities with Pending Listings

More to explore in Chester, MD

How to buy a house in Chester, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

9 Redfin agents serving Chester

287

Deals*

4.8

Satisfaction

2985

Homes closed*

* Data from the last year

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.