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Homes for sale in Chester, MD

Figures for Chester, MD, week ending September 15, 2026.

Paige
watching Chester · 78 homes for sale
Paige
The biggest price change in town this week happened at 54 Queen Caroline Court, where the price dropped from $365,000 to $299,900. If you want to take a look at what is available right now, 117 Flycatcher Way in Four Seasons At Kent Island is a 3 bedrooms residential listed 43 days ago at $1,100,000, which reduced from $1,200,000. Nearby, 110 Boatswain Way #3042 in Four Seasons At Kent Island is a 2 bedrooms residential listed 63 days ago for $699,990, down from $749,990. Right now, 0 homes came on the market in the last 7 days, while 11 asking prices were reduced by a median reduction of 4.5%. What is currently listed has a median days on market of 44, compared to 14 homes sold in the last 30 days at a median of 55 days on market before selling. Those recent sales had a median sold price of $653,495 across the month, while the overall median asking price sits at $629,990. Are you looking to buy or sell a home in Chester soon?
117 FLYCATCHER WAYFor SaleBright MLS
$1,100,000
117 FLYCATCHER WAY, Chester
3 bd · 4 ba · House · 44 DOM
MDQA2018162, Berkshire Hathaway HomeServices PenFed Realty - OP
110 BOATSWAIN WAY Unit 3042For SaleBright MLS
$699,990
110 BOATSWAIN WAY Unit 3042, Chester
2 bd · 3 ba · Condo · 64 DOM
MDQA2017928, Berkshire Hathaway HomeServices PenFed Realty - OP
12 QUEEN ANNE WAY Unit JFor SaleBright MLS
$379,900
12 QUEEN ANNE WAY Unit J, Chester
1 bd · 1.5 ba · Townhouse · 10 DOM
MDQA2018696, Chesapeake Real Estate Associates, LLC
6005 BRIDGEPOINTE DRIVEFor SaleBright MLS
$349,000
6005 BRIDGEPOINTE DRIVE, Chester
3 bd · 3 ba · Townhouse · 11 DOM
MDQA2018634, Rosendale Realty
200 CHURCH STREETFor SaleBright MLS
$350,000
200 CHURCH STREET, Chester
2 bd · 2 ba · House · 14 DOM
MDQA2018584, RE/MAX Executive
641 WARBLER WAYFor SaleBright MLS
$639,990
641 WARBLER WAY, Chester
2 bd · 2 ba · House · 14 DOM
MDQA2018602, Berkshire Hathaway HomeServices PenFed Realty - OP
275 WARBLER WAYFor SaleBright MLS
$944,900
275 WARBLER WAY, Chester
3 bd · 3 ba · House · 15 DOM
MDQA2018566, Samson Properties
1717 HARBOR DRIVEFor SaleBright MLS
$1,250,000
1717 HARBOR DRIVE, Chester
3 bd · 3 ba · House · 16 DOM
MDQA2018534, Chesapeake Real Estate Associates, LLC
326 CASTLE MARINA ROADFor SaleBright MLS
$550,000
326 CASTLE MARINA ROAD, Chester
5 bd · 4 ba · House · 16 DOM
MDQA2018594, Coldwell Banker Waterman Realty
1868 ROBERTA DRIVEFor SaleBright MLS
Auction
1868 ROBERTA DRIVE, Chester
5 bd · 4 ba · House · 16 DOM
MDQA2018570, Alex Cooper Auctioneers, Inc.
736 WARBLER WAY Unit 2733For SaleBright MLS
$719,990
736 WARBLER WAY Unit 2733, Chester
2 bd · 3 ba · Condo · 19 DOM
MDQA2018548, Berkshire Hathaway HomeServices PenFed Realty - OP
233 CROSS CREEK COURTFor SaleBright MLS
$569,900
233 CROSS CREEK COURT, Chester
4 bd · 3 ba · House · 20 DOM
MDQA2018296, Rory S. Coakley Realty, Inc.
2513 CECIL DRIVEUnder ContractBright MLS
$1,290,000
2513 CECIL DRIVE, Chester
5 bd · 2 ba · House · 21 DOM
MDQA2018504, Real Broker, LLC - Chester
41 QUEEN CATHERINE COURTFor SaleBright MLS
$439,000
41 QUEEN CATHERINE COURT, Chester
3 bd · 4 ba · Townhouse · 22 DOM
MDQA2018508, Northrop Realty
536 WARBLER WAYFor SaleBright MLS
$749,990
536 WARBLER WAY, Chester
2 bd · 3 ba · House · 29 DOM
MDQA2018316, Berkshire Hathaway HomeServices PenFed Realty - OP
108 BLENNY LANEFor SaleBright MLS
$389,900
108 BLENNY LANE, Chester
3 bd · 3 ba · Townhouse · 38 DOM
MDQA2018242, RE/MAX Leading Edge
402 MACUM CREEK DRIVEFor SaleBright MLS
$789,000
402 MACUM CREEK DRIVE, Chester
3 bd · 2.5 ba · House · 40 DOM
MDQA2018418, Samson Properties
207 THOMAS WHITE BOULEVARDFor SaleBright MLS
$819,900
207 THOMAS WHITE BOULEVARD, Chester
3 bd · 3 ba · House · 40 DOM
MDQA2018222, RE/MAX Components
118 BROADWATER DRIVEUnder ContractBright MLS
$660,000
118 BROADWATER DRIVE, Chester
2 bd · 2 ba · House · 41 DOM
MDQA2018202, RE/MAX Executive
214 BAYBERRY DRIVEFor SaleBright MLS
$924,000
214 BAYBERRY DRIVE, Chester
3 bd · 3 ba · House · 42 DOM
MDQA2018216, Benson & Mangold, LLC
201 SWITCHGRASS WAY Unit 34For SaleBright MLS
$835,000
201 SWITCHGRASS WAY Unit 34, Chester
3 bd · 3 ba · Condo · 43 DOM
MDQA2018120, TTR Sotheby's International Realty
148 ELINOR STREETFor SaleBright MLS
$899,000
148 ELINOR STREET, Chester
3 bd · 3 ba · House · 44 DOM
MDQA2018244, Samson Properties
320 BAYBERRY DRIVEFor SaleBright MLS
$862,750
320 BAYBERRY DRIVE, Chester
3 bd · 2 ba · House · 45 DOM
MDQA2018158, Mr. Lister Realty
230 SWITCHGRASS WAY Unit 12For SaleBright MLS
$524,999
230 SWITCHGRASS WAY Unit 12, Chester
2 bd · 3 ba · Condo · 72 DOM
MDQA2017860, Real Broker, LLC - Chester

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