Chester, MD - single-family homes for sale

43 of 43 results displayed

New
$749,000Active
4 beds 4 baths2,185 sq. ft.
134 Richard Ingle Way, CHESTER, MD 21619
MLS# MDQA2017930Listed by: REDFIN CORP
Coming Soon
$989,000Coming Soon
5 beds 4 baths
2702 Sherman Dr, CHESTER, MD 21619
MLS# MDQA2017858Listed by: SAMSON PROPERTIES
New
$974,990Active
5 beds 5 baths3,225 sq. ft.
323 Kingfisher Ln, CHESTER, MD 21619
MLS# MDQA2017978Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP
New
$929,990Active
3 beds 3 baths2,772 sq. ft.
532 Warbler Way, CHESTER, MD 21619
MLS# MDQA2017958Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP
$779,900Pending
2 beds 2 baths2,394 sq. ft.
169 Harrier Way, CHESTER, MD 21619
MLS# MDQA2017938Listed by: CENTURY 21 NEW MILLENNIUM
Open Sat, 11am to 4pmNew
$929,990Active
3 beds 3 baths2,789 sq. ft.
540 Warbler Way, CHESTER, MD 21619
MLS# MDQA2017926Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP
New
$719,900Active
2 beds 2 baths2,118 sq. ft.
121 Merlin Dr, CHESTER, MD 21619
MLS# MDQA2017900Listed by: COLDWELL BANKER REALTY
$535,000Active
5 beds 3 baths3,000 sq. ft.
205 Anchor Ln, CHESTER, MD 21619
MLS# MDQA2017856Listed by: SAMSON PROPERTIES
Coming Soon
$629,900Coming Soon
3 beds 2 baths
315 Bentons Pleasure Rd, CHESTER, MD 21619
MLS# MDQA2017854Listed by: DOUGLAS REALTY LLC
$375,000Pending
3 beds 2 baths3,128 sq. ft.
114 Cedar Rd, CHESTER, MD 21619
MLS# MDQA2017822Listed by: KELLER WILLIAMS LEGACY
$749,900Active
4 beds 3 baths3,151 sq. ft.
233 Peregrine Dr, CHESTER, MD 21619
MLS# MDQA2017836Listed by: ROSENDALE REALTY
$2,840,000Active
3 beds 2 baths1,704 sq. ft.
300 Woods Point Rd, CHESTER, MD 21619
MLS# MDQA2017820Listed by: TIDEWATER PROPERTIES
$749,000Active
3 beds 2 baths1,524 sq. ft.
205 Riverside Dr, CHESTER, MD 21619
MLS# MDQA2017690Listed by: ENGEL & VOLKERS ANNAPOLIS
$520,000Active
4 beds 3 baths1,979 sq. ft.
124 Riverside Dr, CHESTER, MD 21619
MLS# MDQA2017718Listed by: DOUGLAS REALTY LLC
$995,000Pending
3 beds 3 baths3,434 sq. ft.
154 Bluebell Ct, CHESTER, MD 21619
MLS# MDQA2017710Listed by: WILSON REALTY & STAGING LLC
$2,049,000Pending
5 beds 4 baths3,250 sq. ft.
328 Bentons Pleasure Rd, CHESTER, MD 21619
MLS# MDQA2017668Listed by: HOMEZU BY SIMPLE CHOICE
Open Sun, 11am to 1pm
$399,500Active
3 beds 2 baths1,192 sq. ft.
2645 Cox Neck Rd, CHESTER, MD 21619
MLS# MDQA2017640Listed by: COMPASS
$1,350,000Active
5 beds 2 baths2,700 sq. ft.
2513 Cecil Dr, CHESTER, MD 21619
MLS# MDQA2017588Listed by: REAL BROKER, LLC - CHESTER
$569,000Pending
3 beds 2 baths1,944 sq. ft.
206 Anchor Ln, CHESTER, MD 21619
MLS# MDQA2017536Listed by: COLDWELL BANKER WATERMAN REALTY
$1,199,000Pending
5 beds 4 baths4,334 sq. ft.
108 Carriage Heath, CHESTER, MD 21619
MLS# MDQA2017422Listed by: COLDWELL BANKER REALTY
$840,000Active
4 beds 4 baths3,312 sq. ft.
232 Evelyne St, CHESTER, MD 21619
MLS# MDQA2017378Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$216,000Pending
3 beds 2 baths1,160 sq. ft.
108 Price Rd, CHESTER, MD 21619
MLS# MDQA2017080Listed by: THURSTON WYATT REAL ESTATE, LLC
$620,000Active
3 beds 3 baths2,119 sq. ft.
265 Evelyne St, CHESTER, MD 21619
MLS# MDQA2017258Listed by: SAMSON PROPERTIES
$5,900,000Active
7 beds 9 baths9,974 sq. ft.
330 Serenity Ln, CHESTER, MD 21619
MLS# MDQA2016472Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$775,000Pending
3 beds 3 baths2,276 sq. ft.
126 Claiborne St, CHESTER, MD 21619
MLS# MDQA2017106Listed by: SAMSON PROPERTIES
$579,000Pending
3 beds 3 baths1,839 sq. ft.
134 Mchenny Ct, CHESTER, MD 21619
MLS# MDQA2017004Listed by: COLDWELL BANKER REALTY
$999,000Active
5 beds 5 baths3,225 sq. ft.
233 Kingfisher Ln, CHESTER, MD 21619
MLS# MDQA2016936Listed by: SAMSON PROPERTIES
$420,000Pending
3 beds 3 baths1,296 sq. ft.
200 Newtown Rd, CHESTER, MD 21619
MLS# MDQA2016754Listed by: SAMSON PROPERTIES
$559,000Active
3 beds 3 baths1,536 sq. ft.
126 Watermans Cove Ln, CHESTER, MD 21619
MLS# MDQA2016908Listed by: COLDWELL BANKER REALTY
$1,049,500Active
5 beds 5 baths3,225 sq. ft.
215 Kingfisher Ln, CHESTER, MD 21619
MLS# MDQA2016702Listed by: RE/MAX EXECUTIVE
$455,000Pending
3 beds 2 baths1,486 sq. ft.
1872 Harbor Dr, CHESTER, MD 21619
MLS# MDQA2016514Listed by: CROSS STREET REALTORS LLC
$945,000Pending
4 beds 4 baths3,634 sq. ft.
132 Kestrel Ln, CHESTER, MD 21619
MLS# MDQA2015732Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$899,990Pending
3 beds 3 baths2,789 sq. ft.
307 Kingfisher Ln, CHESTER, MD 21619
MLS# MDQA2016408Listed by: KOVO REALTY
$724,500Active
5 beds 4 baths3,250 sq. ft.
1868 Roberta Dr, CHESTER, MD 21619
MLS# MDQA2016194Listed by: COLDWELL BANKER REALTY
$707,000Pending
4 beds 3 baths2,870 sq. ft.
266 Peregrine Dr, CHESTER, MD 21619
MLS# MDQA2016140Listed by: RE/MAX EXECUTIVE
$299,900Active
3 beds 3 baths1,400 sq. ft.
1025 Dundee Ct, CHESTER, MD 21619
MLS# MDQA2016050Listed by: RE/MAX EXECUTIVE
$915,000Pending
6 beds 5 baths4,165 sq. ft.
109 John Gibson Dr, CHESTER, MD 21619
MLS# MDQA2015674Listed by: COLDWELL BANKER REALTY
$429,900Active
4 beds 2 baths1,750 sq. ft.
1906 Harbor Dr, CHESTER, MD 21619
MLS# MDQA2015604Listed by: FIVE STAR REAL ESTATE
$470,000Active
3 beds 3 baths1,728 sq. ft.
1916 Stevens Dr, CHESTER, MD 21619
MLS# MDQA2015554Listed by: COLDWELL BANKER REALTY
$799,999Pending
3 beds 3 baths2,795 sq. ft.
135 Nauset Ln, CHESTER, MD 21619
MLS# MDQA2015026Listed by: REAL BROKER, LLC - ANNAPOLIS
$19,500Active
2 beds 1 baths764 sq. ft.
1405 Little Creek Rd, CHESTER, MD 21619
MLS# MDQA2014252Listed by: THE PARKER GROUP
$1,294,800Active
4 beds 4 baths
1757 Harbor Dr, CHESTER, MD 21619
MLS# MDQA2014542Listed by: KELLER WILLIAMS FLAGSHIP
$674,900Pending
4 beds 3 baths
Lot 6 Norman Ct, CHESTER, MD 21619
MLS# MDQA2008126Listed by: KELLER WILLIAMS FLAGSHIP

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.