Cheap Homes For Sale in Chester, MD

77 homes

Use arrow keys to navigate
NEW CONSTRUCTION
BUILDABLE PLAN
$701,990+
4 Beds
3 Baths
2,791 sqft
Simone Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
Use arrow keys to navigate
$712,000
4 Beds
3 Baths
2,870 sqft
266 Peregrine Dr,
Chester, MD 21619
RE/MAX Executive
Use arrow keys to navigate
0.43 ACRES
$744,500
5 Beds
3.5 Baths
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
Use arrow keys to navigate
$750,000
3 Beds
2.5 Baths
2,602 sqft
2000 Herons Nest Way #401,
Chester, MD 21619
Real Broker, LLC
Use arrow keys to navigate
NEW CONSTRUCTION
BUILDABLE PLAN
$752,990+
2 Beds
2.5 Baths
2,010 sqft
Taylor Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
Use arrow keys to navigate
$765,000
2 Beds
2.5 Baths
111 Marshgrass Way #43,
Chester, MD 21619
Coldwell Banker Realty
Use arrow keys to navigate
COMING SOON 5/22
$770,000
3 Beds
2.5 Baths
212 Switchgrass Way #34,
Chester, MD 21619
RE/MAX Executive
NEW CONSTRUCTION
BUILDABLE PLAN
$774,990+
2 Beds
2 Baths
2,143 sqft
Kelly Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
3D VIEW
$787,900
3 Beds
2.5 Baths
2,276 sqft
126 Claiborne St,
Chester, MD 21619
Samson Properties
NEW CONSTRUCTION
QUICK MOVE-IN
$789,990
2 Beds
2.5 Baths
1,900 sqft
110 Boatswain Way #42,
Chester, MD 21619
$799,900
2 Beds
2.5 Baths
2,003 sqft
132 Wheelhouse Way #11,
Chester, MD 21619
Real Broker, LLC
$799,999
3 Beds
3 Baths
2,795 sqft
135 Nauset Ln,
Chester, MD 21619
Real Broker, LLC - Annapolis
NEW CONSTRUCTION
BUILDABLE PLAN
$819,990+
3 Beds
3 Baths
2,789 sqft
Kerr Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
NEW CONSTRUCTION
QUICK MOVE-IN
$829,990
2 Beds
2.5 Baths
1,900 sqft
102 Boatswain Way #33,
Chester, MD 21619
NEW CONSTRUCTION
QUICK MOVE-IN
$829,990
2 Beds
2.5 Baths
1,900 sqft
102 Boatswain Way #32,
Chester, MD 21619
NEW CONSTRUCTION
BUILDABLE PLAN
$848,990+
5 Beds
4.5 Baths
3,225 sqft
Tuscaloosa Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
NEW CONSTRUCTION
BUILDABLE PLAN
$858,990+
3 Beds
3.5 Baths
2,930 sqft
Franklin Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
NEW CONSTRUCTION
QUICK MOVE-IN
$869,990
3 Beds
2.5 Baths
2,602 sqft
102 Boatswain Way #21,
Chester, MD 21619
NEW CONSTRUCTION
BUILDABLE PLAN
$883,990+
4 Beds
3.5 Baths
3,601 sqft
Munich ESP Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
NEW CONSTRUCTION
BUILDABLE PLAN
$886,990+
4 Beds
3.5 Baths
3,512 sqft
Mykonos Plan in K. Hovnanian's® Four Seasons at Kent Island - Single Family,
Chester, MD 21619
NEW CONSTRUCTION
QUICK MOVE-IN
$929,990
3 Beds
3 Baths
2,789 sqft
307 Kingfisher Ln,
Chester, MD 21619
KOVO Realty
NEW CONSTRUCTION
QUICK MOVE-IN
$929,990
2 Beds
2.5 Baths
1,900 sqft
102 Boatswain Way #42,
Chester, MD 21619
$945,000
4 Beds
3.5 Baths
3,634 sqft
132 Kestrel Ln,
Chester, MD 21619
TTR Sotheby's International Realty
NEW CONSTRUCTION
QUICK MOVE-IN
$949,990
3 Beds
3 Baths
2,789 sqft
540 Warbler Way,
Chester, MD 21619
KOVO Realty
NEW CONSTRUCTION
QUICK MOVE-IN
$969,990
3 Beds
2.5 Baths
2,602 sqft
102 Boatswain Way #34,
Chester, MD 21619
NEW CONSTRUCTION
QUICK MOVE-IN
$999,990
5 Beds
4.5 Baths
3,225 sqft
121 Kinglet Ct,
Chester, MD 21619
KOVO Realty
NEW CONSTRUCTION
$1,000,000
2 Beds
2 Baths
1,993 sqft
127 Flycatcher Way,
Chester, MD 21619
KOVO Realty
3D VIEW
$1,045,000
5 Beds
4.5 Baths
3,353 sqft
233 Kingfisher Ln,
Chester, MD 21619
Samson Properties
$1,049,500
5 Beds
4.5 Baths
3,225 sqft
215 Kingfisher Ln,
Chester, MD 21619
RE/MAX Executive
OPEN SUN, 11-2PM
NEW CONSTRUCTION
0.55 ACRES
$1,167,890
4 Beds
3.5 Baths
1757 Harbor Dr,
Chester, MD 21619
Keller Williams Flagship
NEW CONSTRUCTION
$1,200,000
3 Beds
3 Baths
2,789 sqft
123 Flycatcher Way,
Chester, MD 21619
KOVO Realty
1.25 ACRES
$1,250,000
3 Beds
4.5 Baths
4,413 sqft
2855 Cox Neck Rd,
Chester, MD 21619
Wilson Realty & Staging LLC
NEW CONSTRUCTION
$1,300,000
5 Beds
4.5 Baths
3,225 sqft
111 Flycatcher Way,
Chester, MD 21619
KOVO Realty
NEW CONSTRUCTION
$1,300,000
3 Beds
3.5 Baths
2,930 sqft
117 Flycatcher Way,
Chester, MD 21619
KOVO Realty
0.35 ACRES
$1,495,000
3 Beds
4 Baths
4,208 sqft
1719 Harbor Dr,
Chester, MD 21619
Chesapeake Real Estate Associates, LLC
OPEN SUN, 11-1PM
2.3 ACRES
$2,450,000
4 Beds
4 Baths
4,717 sqft
2832 Cox Neck Rd,
Chester, MD 21619
Coldwell Banker Realty
2.58 ACRES
$5,900,000
7 Beds
8 Baths
9,974 sqft
330 Serenity Ln,
Chester, MD 21619
TTR Sotheby's International Realty

Real Estate & Homes For Sale Near Chester, MD

We found 30 more homes matching your filters just outside Chester

Use arrow keys to navigate
NEW - 2 DAYS AGO
$239,900
3 Beds
2 Baths
949 sqft
1603 Marion Quimby Dr,
Stevensville, MD 21666
Northrop Realty
Use arrow keys to navigate
$249,900
2 Beds
1.5 Baths
968 sqft
1 Compass Cir #2,
Stevensville, MD 21666
Berkshire Hathaway Homeservice Homesale Realty
Use arrow keys to navigate
$259,900
2 Beds
1.5 Baths
968 sqft
17 Mariners Way #2,
Stevensville, MD 21666
Up-County Realty, Inc.
Use arrow keys to navigate
0.61 ACRES
$315,000
3 Beds
1 Bath
1,119 sqft
126 State St,
Stevensville, MD 21666
Benson & Mangold, LLC
Use arrow keys to navigate
$374,900
2 Beds
2.5 Baths
1,161 sqft
1305 Marion Quimby Dr,
Stevensville, MD 21666
Keller Williams Realty Centre
Use arrow keys to navigate
$400,000
2 Beds
2.5 Baths
1,161 sqft
1205 Marion Quimby Dr,
Stevensville, MD 21666
Taylor Properties
Use arrow keys to navigate
NEW
COMING SOON 5/22
0.37 ACRES
$400,000
3 Beds
2 Baths
1,260 sqft
607 Kimberly Way,
Stevensville, MD 21666
Samson Properties
0.35 ACRES
$405,000
3 Beds
1 Bath
1,248 sqft
920 Cloverfields Dr,
Stevensville, MD 21666
Benson & Mangold, LLC.
COMING SOON 5/18
0.36 ACRES
$425,000
2 Beds
2 Baths
1,518 sqft
501 Love Point Rd,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
$425,000
3 Beds
3.5 Baths
2,044 sqft
109 Bayview,
Grasonville, MD 21638
Coldwell Banker Realty
$449,995
3 Beds
3.5 Baths
1,900 sqft
108 John Patrick Dr,
Stevensville, MD 21666
Chesapeake Real Estate Associates, LLC
COMING SOON 5/26
0.39 ACRES
$459,000
4 Beds
3 Baths
1,800 sqft
708 Dixon Dr,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
0.34 ACRES
$469,000
3 Beds
2.5 Baths
1,620 sqft
729 Davol Rd,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
$479,900
2 Beds
3 Baths
2,304 sqft
131 John Patrick Dr,
Stevensville, MD 21666
Coldwell Banker Waterman Realty
NEW
COMING SOON 5/27
0.37 ACRES
$489,000
4 Beds
2 Baths
1,596 sqft
756 Kimberly Way,
Stevensville, MD 21666
Samson Properties
OPEN SUN, 11-1PM
0.34 ACRES
$495,000
4 Beds
2 Baths
1,896 sqft
15 Dixon Ct,
Stevensville, MD 21666
Cottage Street Realty LLC
$505,000
2 Beds
2 Baths
1,464 sqft
854 Moorings Cir #12,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
0.36 ACRES
$519,500
4 Beds
2.5 Baths
1,704 sqft
606 Kimberly Way,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
COMING SOON 5/29
0.34 ACRES
$525,000
3 Beds
4 Baths
1,828 sqft
702 Dixon Dr,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
OPEN SUN, 12-2PM
0.42 ACRES
$539,900
4 Beds
3 Baths
2,588 sqft
225 Nichols Manor Dr,
Stevensville, MD 21666
Berkshire Hathaway HomeServices PenFed Realty
3D VIEW
$540,000
3 Beds
3.5 Baths
2,044 sqft
114 Bayview,
Grasonville, MD 21638
Samson Properties
$540,000
4 Beds
3.5 Baths
2,280 sqft
205 Jessica Lyn Ave,
Stevensville, MD 21666
RE/MAX Executive
OPEN SAT, 10-12PM
COMING SOON 5/19
0.41 ACRES
$549,900
3 Beds
2.5 Baths
2,128 sqft
726 Davol Rd,
Stevensville, MD 21666
RE/MAX Executive
$574,900
2 Beds
2 Baths
2,088 sqft
845 Moorings Cir #138,
Stevensville, MD 21666
Coldwell Banker Realty
3D VIEW
$610,000
2 Beds
2.5 Baths
2,031 sqft
118 Bayview,
Grasonville, MD 21638
LPT Realty, LLC
$624,900
3 Beds
3 Baths
2,074 sqft
222 Moorings Cir #126,
Stevensville, MD 21666
Coldwell Banker Chesapeake Real Estate Company
NEW CONSTRUCTION
QUICK MOVE-IN
$629,990
2 Beds
2.5 Baths
2,003 sqft
102 Boatswain Way #2911,
Chester, MD 21619
KOVO Realty
NEW CONSTRUCTION
QUICK MOVE-IN
$629,990
2 Beds
2.5 Baths
2,003 sqft
102 Boatswain Way #2912,
Chester, MD 21619
KOVO Realty
$649,900
3 Beds
2.5 Baths
2,843 sqft
438 Web Foot Ln,
Stevensville, MD 21666
Berkshire Hathaway HomeServices PenFed Realty
$650,000
4 Beds
4 Baths
2,630 sqft
322 Allison Jane Dr #H-4,
Stevensville, MD 21666
Mr. Lister Realty

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Cheap Homes For Sale in Chester, MD

77 homes

We found 30 more homes matching your filters just outside Chester

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Maryland

Chester Neighborhoods

Chester Property Types

Real Estate Guides

Find Rental Properties