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34 Properties Available In Chester
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$670,000
Single Family Home
106 WOODS RD, Chester, MD 21619
This beautifully updated Kent Island retreat in the Benton's Pleasure community offers space, style, and serenity, with ...
MLS# MDQA2013010
Listed by Northrop Realty


$405,000
Condo
202 RINGNECK CT, Chester, MD 21619
Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community!<br><br>This spacious 2-bedroom, 2.5-bath end-u...
MLS# MDQA2012442
Listed by Benson & Mangold, LLC


$449,900
Single Family Home
122 DUNDEE AVE, Chester, MD 21619
$10K Price Drop!!!! Rare Opportunity to Own this Amazing 3 BR/2.5BA SFH w/ large backyard on Kent Island. Bonus NO HOA!!...
MLS# MDQA2012730
Listed by Taylor Properties


$779,000
Single Family Home
137 WARBLER WAY, Chester, MD 21619
No waiting on the builder here! Treat yourself to this STUNNING move-in-ready Four Seasons beauty- Boasting soaring ceil...
MLS# MDQA2012712
Listed by Chaney Homes, LLC


$750,000
Single Family Home
1771 HARBOR DR, Chester, MD 21619
This beautifully crafted waterfront home boasts five spacious bedrooms and 2.5 baths, offering ample space for comfortab...
MLS# MDQA2011784
Listed by Coldwell Banker Realty


$400,000
Single Family Home
2747 CECIL DR, Chester, MD 21619
Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable Harbor View community—perfect for first-time bu...
MLS# MDQA2012772
Listed by Anne Arundel Properties, Inc.


$525,000
Single Family Home
2008 PALM DR, Chester, MD 21619
You've been waiting for this!! Beautiful Cape Cod with spacious wrap around porch! Upon entering, you will be greeted ...
MLS# MDQA2013054
Listed by EXP Realty, LLC


$375,000
Condo
206 BLENNY LN, Chester, MD 21619
This town home has a 1 car garage and offers 1900' of space with interesting options on the first floor. Family room w/...
MLS# MDQA2013078
Listed by Long & Foster Real Estate, Inc.


$850,000
Single Family Home
194 SAILCLOTH WAY, Chester, MD 21619
Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlif...
MLS# MDQA2012962
Listed by Coldwell Banker Realty


$625,000
Condo
170 HARRIER WAY #32, Chester, MD 21619
Welcome to Four Seasons at Kent Island, a premier 55+ waterfront community offering luxury, lifestyle, and leisure. This...
MLS# MDQA2013032
Listed by Redfin Corp


$870,000
Condo
170 HARRIER WAY #34, Chester, MD 21619
New listing price! Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with am...
MLS# MDQA2012790
Listed by Long & Foster Real Estate, Inc.


$535,000
Single Family Home
327 CROSS CREEK CT, Chester, MD 21619
Do not miss! Clayborne Woods is a private community with one way in and one way out! Neighbors describe it as close knit...
MLS# MDQA2012426
Listed by Long & Foster Real Estate, Inc.


$599,000
Condo
121 SWITCHGRASS WAY #22, Chester, MD 21619
This beautifully appointed home offers the perfect blend of elegance, comfort, and convenience in one of Maryland's most...
MLS# MDQA2012984
Listed by RE/MAX Executive


$599,000
Condo
170 HARRIER WAY #11, Chester, MD 21619
Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island!<br><br>Discover this stunning 2-bedroom, 2.5-bath condo in...
MLS# MDQA2012944
Listed by Redfin Corp


$929,500
Single Family Home
235 BAYBERRY DR, Chester, MD 21619
Experience Kent Island living at its finest in this upgraded luxurious San Sebastian model in the prestigious Four Seaso...
MLS# MDQA2012918
Listed by RE/MAX Executive


$1,450,000
Single Family Home
1622 BAYSIDE DR, Chester, MD 21619
Eastern Shore Luxury with Sweeping Bay Views<br><br>Every room tells a story in this impeccably crafted waterfront resid...
MLS# MDQA2012740
Listed by Sullivan Select, LLC.


$545,000
Condo
1000 HERONS NEST WAY #22, Chester, MD 21619
Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, an...
MLS# MDQA2012894
Listed by RE/MAX Executive


$925,000
Condo
200 HARRIER WAY #44, Chester, MD 21619
Four Seasons at Kent Island is an active 55+ community on Maryland's Eastern Shore, offering island resort-style & maint...
MLS# MDQA2012742
Listed by RE/MAX Executive


$329,900
Condo
53-C QUEEN CAROLINE CT #C, Chester, MD 21619
Experience the best of comfort and convenience in this charming townhome located in the sought-after Queens Landing comm...
MLS# MDQA2012564
Listed by Realty Navigator


$649,500
Single Family Home
154 HARRIER WAY, Chester, MD 21619
*** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND***<br>The Donegal model is a spacious and airy 2 bedroom...
MLS# MDQA2012554
Listed by RE/MAX Executive


$780,000
Single Family Home
132 CLAIBORNE ST, Chester, MD 21619
Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Community, w/ beautiful landscaping, ...
MLS# MDQA2012512
Listed by RE/MAX Professionals


$255,000
Condo
7-C QUEEN VICTORIA WAY #7C, Chester, MD 21619
Price Improvement!! Discover the charm of waterfront living with this unique studio condominium in the sought-after comm...
MLS# MDQA2012500
Listed by Realty Navigator


$679,500
Condo
141 SWITCHGRASS WAY #34, Chester, MD 21619
K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resor...
MLS# MDQA2012530
Listed by RE/MAX Executive


$504,500
Single Family Home
312 HANNA CT, Chester, MD 21619
** This home is connected to public water and sewer.<br><br>Welcome to 312 Hanna Ct, a beautifully updated 4-bedroom, 2....
MLS# MDQA2012348
Listed by Berkshire Hathaway HomeServices PenFed Realty
