Skip to main content
blue-therapy-logo-white
blue-therapy-logo-white
  • Thyme’s Heart Fund
  • Search Waterfront & Waterview
    • Waterfront
    • Water View
    • Water Access
  • Buyers
    • Buy a Home
    • Perfect Home Finder
    • Mortgage Calculator
    • Helpful Guides
  • Sellers
    • Sell a House
    • What’s My Home Worth?
    • Helpful Guides
  • About
    • About us
    • Meet the Team
    • Vlog/Blog
  • Get in Touch
  • 302-690-0245
  • Email Me
  • Thyme’s Heart Fund
menu
302-690-0245   [email protected]
 
Menu
  • Listings
  • Buyers
  • Sellers
  • Search Waterfront
  • Home Valuation
  • About us
  • Get in touch
  • Listings
  • Buyers
  • Sellers
  • Search Waterfront
  • Home Valuation
  • About us
  • Get in touch
  • Our Team
  • Perfect Home Finder
  • What’s My Home Worth?
  • Thyme’s Heart Fund
  • Discover Blue Therapy

Phone
302-690-0245

Email
[email protected]

Address
4628 Benoni Point Rd,
Royal Oak, MD 21662

Dashboard
Listings
Searches
Sign in / Sign up
Price
Beds
Baths
More
Save Search
Chestertown, MD
City
Reset
Share
Newest Listings
CROMWELL CLARK ROAD CHESTERTOWN MD 21620
1 / 19
$3,000,000
Land For Sale
Active
87.34
ACRES
KENT
COUNTY
CROMWELL CLARK ROAD
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of The Land Group
7989 QUAKER NECK ROAD CHESTERTOWN MD 21620
1 / 90
$2,400,000
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
4,305
SQFT
7989 QUAKER NECK ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
200 HIGH STREET CHESTERTOWN MD 21620
1 / 23
$2,300,000
Commercial Sale For Sale
Active
9
TOTAL BATHS
6,918
SQFT
200 HIGH STREET
CHESTERTOWN, MD 21620
DOWNTOWN CHESTERTOWN Subdivision
Listing courtesy of Taylor Properties
LITTLE HARBOR WAY 1 CHESTERTOWN MD 21620
1 / 29
$1,800,000
Condominium For Sale
Active
4
BEDS
4
TOTAL BATHS
3,540
SQFT
LITTLE HARBOR WAY 1
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
117 WATER STREET N 1A, 1B, 2A, & 2B CHESTERTOWN MD 21620
1 / 73
$1,600,000
Condominium For Sale
Active
7
BEDS
6
TOTAL BATHS
5,400
SQFT
117 WATER STREET N 1A, 1B, 2A, & 2B
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
8276 BROAD NECK ROAD CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 82
$1,495,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,383
SQFT
8276 BROAD NECK ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
LITTLE HARBOR WAY 1 CHESTERTOWN MD 21620
1 / 25
$1,459,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
2,231
SQFT
LITTLE HARBOR WAY 1
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
105 HIGH STREET CHESTERTOWN MD 21620
1 / 48
$1,395,500
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
3,243
SQFT
105 HIGH STREET
CHESTERTOWN, MD 21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
231 RICHARD DRIVE CHESTERTOWN MD 21620
1 / 51
$1,279,000
Single Family Residence For Sale
Active
5
BEDS
3
TOTAL BATHS
2,956
SQFT
231 RICHARD DRIVE
CHESTERTOWN, MD 21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of TTR Sotheby's International Realty
329 HIGH STREET CHESTERTOWN MD 21620
1 / 19
$1,190,000
Mixed Use For Sale
Active
4,500
SQFT
329 HIGH STREET
CHESTERTOWN, MD 21620
 
Listing courtesy of Cross Street Realtors LLC
#25 LANDING LANE CHESTERTOWN MD 21620
1 / 22
$1,099,900
Condominium For Sale
Active
4
BEDS
4
TOTAL BATHS
2,784
SQFT
#25 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
205 RIVER ROAD CHESTERTOWN MD 21620
1 / 14
$949,000
Single Family Residence For Sale
Coming Soon
3
BEDS
3
TOTAL BATHS
2,877
SQFT
205 RIVER ROAD
CHESTERTOWN, MD 21620
SARAH SKIPPER LANDS Subdivision
Listing courtesy of Clark & Co Realty, LLC
515 WASHINGTON AVENUE CHESTERTOWN MD 21620
1 / 4
$899,000
Commercial Sale For Sale
Active
0.0
SQFT
515 WASHINGTON AVENUE
CHESTERTOWN, MD 21620
 
Listing courtesy of EShore
228 S WATER ST CHESTERTOWN MD 21620
1 / 32
$878,000
Townhouse For Sale
Active
3
BEDS
4
TOTAL BATHS
2,310
SQFT
228 S WATER ST
CHESTERTOWN, MD 21620
HISTORIC CHESTERTOWN Subdivision
Listing courtesy of Gunther-McClary Real Estate
106 QUEEN STREET S CHESTERTOWN MD 21620
Open House Sat, Apr 4, 10 AM
1 / 70
$865,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,472
SQFT
106 QUEEN STREET S
CHESTERTOWN, MD 21620
HISTORIC CHESTERTOWN Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
104 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 23
$849,900
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
1,980
SQFT
104 LITTLE HARBOR WAY
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
102 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 23
$839,500
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
102 LITTLE HARBOR WAY
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
104 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$813,900
Condominium For Sale
Active
3
BEDS
4
TOTAL BATHS
2,192
SQFT
104 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
106 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$799,900
Condominium For Sale
Active
3
BEDS
4
TOTAL BATHS
2,092
SQFT
106 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 3
$795,000
Land For Sale
Active
0.1
ACRES
KENT
COUNTY
201 N LYNCHBURG STREET
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of RE/MAX Associates-Hockessin
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 13
$795,000
Single Family Residence For Sale
Active
2
TOTAL BATHS
2,045
SQFT
201 N LYNCHBURG STREET
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of RE/MAX Associates-Hockessin
201 N LYNCHBURG STREET CHESTERTOWN MD 21620
1 / 13
$795,000
Commercial Sale For Sale
Active
3,527
SQFT
201 N LYNCHBURG STREET
CHESTERTOWN, MD 21620
 
Listing courtesy of RE/MAX Associates-Hockessin
#35 LANDING LANE CHESTERTOWN MD 21620
1 / 26
$786,900
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#35 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
#37 LANDING LANE CHESTERTOWN MD 21620
1 / 24
$765,900
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#37 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
#36 LANDING LANE CHESTERTOWN MD 21620
1 / 26
$753,500
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
1,964
SQFT
#36 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
7844 CHESTER COURT CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 51
$695,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
3,248
SQFT
7844 CHESTER COURT
CHESTERTOWN, MD 21620
HEATHER HEIGHTS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
10087 JOHN CARVILL ROAD CHESTERTOWN MD 21620
Open House Sat, Apr 11, 11 AM
1 / 63
$695,000
Single Family Residence For Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,566
SQFT
10087 JOHN CARVILL ROAD
CHESTERTOWN, MD 21620
GREAT OAK ESTATES Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
117 WATER STREET N 1A CHESTERTOWN MD 21620
1 / 46
$685,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
3,000
SQFT
117 WATER STREET N 1A
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
118 LITTLE HARBOR WAY 202 CHESTERTOWN MD 21620
Open House Sat, Apr 4, 10 AM
1 / 56
$675,000
Condominium For Sale
Active
3
BEDS
2
TOTAL BATHS
1,600
SQFT
118 LITTLE HARBOR WAY 202
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Benson & Mangold, LLC
11040 KYLIE LANE CHESTERTOWN MD 21620
1 / 70
$649,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
3,684
SQFT
11040 KYLIE LANE
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
108 LITTLE HARBOR WAY CHESTERTOWN MD 21620
1 / 5
$635,000
Land For Sale
Active
0.09
ACRES
KENT
COUNTY
108 LITTLE HARBOR WAY
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Gunther-McClary Real Estate
204 DOUBLE CREEK ROAD CHESTERTOWN MD 21620
1 / 46
$612,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,927
SQFT
204 DOUBLE CREEK ROAD
CHESTERTOWN, MD 21620
DOUBLE CREEK WOODS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
216 BLAKEFIELD DRIVE CHESTERTOWN MD 21620
1 / 49
$559,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
2,400
SQFT
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD 21620
BLAKEFIELD Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
103 SUTTON WAY CHESTERTOWN MD 21620
New Listing - 14 hours on site
1 / 53
$550,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,816
SQFT
103 SUTTON WAY
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of TTR Sotheby's International Realty
206 S WATER STREET CHESTERTOWN MD 21620
1 / 45
$549,000
Single Family Residence For Sale
Pending
4
BEDS
4
TOTAL BATHS
2,008
SQFT
206 S WATER STREET
CHESTERTOWN, MD 21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of TTR Sotheby's International Realty
311 DEVON DRIVE CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 40
$525,000
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
3,504
SQFT
311 DEVON DRIVE
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
218 CAMELOT DRIVE CHESTERTOWN MD 21620
1 / 45
$525,000
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
3,932
SQFT
218 CAMELOT DRIVE
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of Coldwell Banker Realty
101 COLEMAN DRIVE CHESTERTOWN MD 21620
New Listing - a week on site
1 / 56
$524,900
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,268
SQFT
101 COLEMAN DRIVE
CHESTERTOWN, MD 21620
KINGS COURT Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
103 LANDING LANE CHESTERTOWN MD 21620
Open House Sat, Apr 25, 10 AM
1 / 70
$519,999
Townhouse For Sale
Active
2
BEDS
3
TOTAL BATHS
2,100
SQFT
103 LANDING LANE
CHESTERTOWN, MD 21620
CHESTER RIVER LANDING Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
116 HARLAN LOOP CHESTERTOWN MD 21620
1 / 21
$509,000
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
4,067
SQFT
116 HARLAN LOOP
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of Samson Properties
8620 PARK DRIVE CHESTERTOWN MD 21620
1 / 53
$499,900
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,524
SQFT
8620 PARK DRIVE
CHESTERTOWN, MD 21620
TOLCHESTER Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
206 FLYWAY LANE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 25
$499,900
Single Family Residence For Sale
Pending
4
BEDS
4
TOTAL BATHS
3,000
SQFT
206 FLYWAY LANE
CHESTERTOWN, MD 21620
THE FLYWAY Subdivision
Listing courtesy of Integrity Real Estate
206 CAMELOT DRIVE CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 65
$499,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
2,186
SQFT
206 CAMELOT DRIVE
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
100 ADELA WAY CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 67
$498,500
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
3,799
SQFT
100 ADELA WAY
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty
515 N KENT STREET CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 36
$495,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
2,220
SQFT
515 N KENT STREET
CHESTERTOWN, MD 21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of Cross Street Realtors LLC
201 GREENWOOD AVENUE CHESTERTOWN MD 21620
1 / 62
$495,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
3,984
SQFT
201 GREENWOOD AVENUE
CHESTERTOWN, MD 21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
101 PINE TREE ROAD CHESTERTOWN MD 21620
1 / 1
$480,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
2
TOTAL BATHS
1,848
SQFT
101 PINE TREE ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Rosendale Realty
110 TRAFFORD DRIVE CHESTERTOWN MD 21620
Open House Sun, Apr 12, 2 PM
1 / 26
$465,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,880
SQFT
110 TRAFFORD DRIVE
CHESTERTOWN, MD 21620
COVENTRY FARMS Subdivision
Listing courtesy of RE/MAX Advantage Realty
222 MOUNT VERNON AVENUE CHESTERTOWN MD 21620
Price Change - 3 weeks ago
1 / 29
$444,999
Single Family Residence For Sale
Active
4
BEDS
2
TOTAL BATHS
1,656
SQFT
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD 21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Long & Foster Real Estate, Inc.
104 GARLAND AVENUE CHESTERTOWN MD 21620
1 / 34
$440,000
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,734
SQFT
104 GARLAND AVENUE
CHESTERTOWN, MD 21620
EVERGREEN MANOR Subdivision
Listing courtesy of Cross Street Realtors LLC
704 TRUSLOW ROAD CHESTERTOWN MD 21620
New Listing - a week on site
1 / 43
$440,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,060
SQFT
704 TRUSLOW ROAD
CHESTERTOWN, MD 21620
KINGS COURT Subdivision
Listing courtesy of RE/MAX Executive
201 BIRCH RUN ROAD CHESTERTOWN MD 21620
New Listing - 5 days on site
1 / 24
$435,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,588
SQFT
201 BIRCH RUN ROAD
CHESTERTOWN, MD 21620
MILE TREE VILLAGE Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
109 S COLLEGE AVENUE CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 24
$419,900
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,216
SQFT
109 S COLLEGE AVENUE
CHESTERTOWN, MD 21620
CHESTERTOWN HISTORIC DISTRICT Subdivision
Listing courtesy of Taylor Properties
104 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 31
$399,900
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
2,535
SQFT
104 FLYING CLOUD DRIVE
CHESTERTOWN, MD 21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of Real Broker, LLC
349 & 351 HIGH STREET CHESTERTOWN MD 21620
1 / 47
$395,000
Duplex For Sale
Active Under Contract
6
BEDS
3,664
SQFT
349 & 351 HIGH STREET
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
349 HIGH STREET CHESTERTOWN MD 21620
1 / 33
$395,000
Townhouse For Sale
Active Under Contract
7
BEDS
4
TOTAL BATHS
3,664
SQFT
349 HIGH STREET
CHESTERTOWN, MD 21620
HISTORIC DISTRICT CHESTERTOWN Subdivision
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
202 WALDO DRIVE CHESTERTOWN MD 21620
New Listing - a week on site
1 / 3
$389,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,055
SQFT
202 WALDO DRIVE
CHESTERTOWN, MD 21620
BYFORD DEVELOPMENT Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
6746 QUAKER ROAD CHESTERTOWN MD 21620
Price Change - 3 days ago
1 / 49
$384,000
Mixed Use For Sale
Active
3
TOTAL BATHS
3,371
SQFT
6746 QUAKER ROAD
CHESTERTOWN, MD 21620
QUAKER NECK Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
6746 QUAKER NECK ROAD CHESTERTOWN MD 21620
Price Change - 3 days ago
1 / 50
$384,000
Single Family Residence For Sale
Active
5
BEDS
3
TOTAL BATHS
3,371
SQFT
6746 QUAKER NECK ROAD
CHESTERTOWN, MD 21620
QUAKER NECK Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
117 WATER STREET N 2A CHESTERTOWN MD 21620
1 / 24
$375,000
Condominium For Sale
Active
2
BEDS
1
TOTAL BATH
787
SQFT
117 WATER STREET N 2A
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
720 DEEP LANDING ROAD CHESTERTOWN MD 21620
0 / 0
$369,999
Single Family Residence For Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,271
SQFT
720 DEEP LANDING ROAD
CHESTERTOWN, MD 21620
PINE COVE Subdivision
Listing courtesy of Coldwell Banker Waterman Realty
148 STEP ROAD CHESTERTOWN MD 21620
Price Change - 4 weeks ago
1 / 46
$369,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
2
TOTAL BATHS
1,400
SQFT
148 STEP ROAD
CHESTERTOWN, MD 21620
CHAR NOR MANOR Subdivision
Listing courtesy of Anne Arundel Properties, Inc.
117 WATER STREET N 2B CHESTERTOWN MD 21620
1 / 23
$350,000
Condominium For Sale
Active
7
BEDS
6
TOTAL BATHS
850
SQFT
117 WATER STREET N 2B
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
109 WILTON ROAD CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 31
$344,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,392
SQFT
109 WILTON ROAD
CHESTERTOWN, MD 21620
CHESTER HARBOR Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
23110 OLD FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 29
$339,900
Single Family Residence For Sale
Pending
3
BEDS
1
TOTAL BATH
1,805
SQFT
23110 OLD FAIRLEE ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Real Broker LLC
21125 IOWA AVENUE CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 26
$339,900
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
1,294
SQFT
21125 IOWA AVENUE
CHESTERTOWN, MD 21620
 
Listing courtesy of Doug Ashley Realtors, LLC
103 FLYING CLOUD DRIVE CHESTERTOWN MD 21620
New Listing - a week on site
1 / 1
$339,900
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
1,724
SQFT
103 FLYING CLOUD DRIVE
CHESTERTOWN, MD 21620
THE VILLAGE AT CHESTERTOWN Subdivision
Listing courtesy of American Premier Realty, LLC
304 HADAWAY DRIVE CHESTERTOWN MD 21620
Price Change - 16 hours ago
1 / 44
$339,000
Single Family Residence For Sale
Active
4
BEDS
2
TOTAL BATHS
1,325
SQFT
304 HADAWAY DRIVE
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of Cummings & Co. Realtors
8750 GEORGETOWN ROAD CHESTERTOWN MD 21620
1 / 25
$334,000
Manufactured Home For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,900
SQFT
8750 GEORGETOWN ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Chesapeake Real Estate Associates, LLC
23055 OLD FAIRLEE ROAD CHESTERTOWN MD 21620
1 / 26
$330,000
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,628
SQFT
23055 OLD FAIRLEE ROAD
CHESTERTOWN, MD 21620
FAIRLEE Subdivision
Listing courtesy of Benson & Mangold, LLC
2032 PONDTOWN ROAD CHESTERTOWN MD 21620
0 / 0
$325,000
Single Family Residence For Sale
Coming Soon
3
BEDS
2
TOTAL BATHS
1,120
SQFT
2032 PONDTOWN ROAD
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of Northrop Realty
23043 BAY SHORE SPUR CHESTERTOWN MD 21620
1 / 27
$325,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
3
TOTAL BATHS
2,630
SQFT
23043 BAY SHORE SPUR
CHESTERTOWN, MD 21620
FAIRLEE Subdivision
Listing courtesy of Rock Hall Properties Real Estate
217 PHILOSOPHERS TERRACE CHESTERTOWN MD 21620
New Listing - 2 days on site
1 / 25
$325,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,404
SQFT
217 PHILOSOPHERS TERRACE
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
222 DUTCHESS ROAD CHESTERTOWN MD 21620
1 / 24
$320,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,096
SQFT
222 DUTCHESS ROAD
CHESTERTOWN, MD 21620
CHESTER HARBOR Subdivision
Listing courtesy of Gunther-McClary Real Estate
24775 LANGFORD ROAD CHESTERTOWN MD 21620
1 / 37
$319,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,008
SQFT
24775 LANGFORD ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of RE/MAX Advantage Realty
10584 KLAMATH ROAD CHESTERTOWN MD 21620
1 / 1
$319,900
Residential For Sale
Coming Soon
2
BEDS
2
TOTAL BATHS
10584 KLAMATH ROAD
CHESTERTOWN, MD 21620
CHESAPEAKE LANDING Subdivision
Listing courtesy of Real Broker, LLC
154 LONGFELLOW DRIVE CHESTERTOWN MD 21620
1 / 26
$315,000
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
1,408
SQFT
154 LONGFELLOW DRIVE
CHESTERTOWN, MD 21620
CHESTER HARBOR Subdivision
Listing courtesy of Cross Street Realtors LLC
301 LINCOLN DRIVE CHESTERTOWN MD 21620
1 / 40
$309,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,152
SQFT
301 LINCOLN DRIVE
CHESTERTOWN, MD 21620
WASHINGTON PARK Subdivision
Listing courtesy of Chesapeake Real Estate Associates, LLC
107 LONGFELLOW DRIVE CHESTERTOWN MD 21620
New Listing - 19 hours on site
1 / 37
$295,000
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
107 LONGFELLOW DRIVE
CHESTERTOWN, MD 21620
CHESTER HARBOR Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
611 CANNON STREET CHESTERTOWN MD 21620
1 / 18
$275,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
920
SQFT
611 CANNON STREET
CHESTERTOWN, MD 21620
 
Listing courtesy of Select Land & Homes, LLC
112 ELM STREET CHESTERTOWN MD 21620
New Listing - 4 weeks on site
1 / 19
$269,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,356
SQFT
112 ELM STREET
CHESTERTOWN, MD 21620
COLLEGE HEIGHTS Subdivision
Listing courtesy of Coldwell Banker Waterman Realty
109 METCALF ROAD CHESTERTOWN MD 21620
Open House Sat, Apr 4, 11 AM
1 / 28
$264,900
Townhouse For Sale
Active
3
BEDS
2
TOTAL BATHS
1,280
SQFT
109 METCALF ROAD
CHESTERTOWN, MD 21620
CHESTER ARMS Subdivision
Listing courtesy of Real Broker, LLC
107 METCALF ROAD CHESTERTOWN MD 21620
1 / 17
$259,900
Townhouse For Sale
Active
3
BEDS
2
TOTAL BATHS
1,200
SQFT
107 METCALF ROAD
CHESTERTOWN, MD 21620
CHESTER ARMS Subdivision
Listing courtesy of Real Broker, LLC
SCHEELER ROAD LOT 2 CHESTERTOWN MD 21620
New Listing - a week on site
1 / 4
$250,000
Commercial Sale For Sale
Active
0.0
SQFT
SCHEELER ROAD LOT 2
CHESTERTOWN, MD 21620
 
Listing courtesy of Select Land & Homes, LLC
SCHEELER ROAD LOT 2 CHESTERTOWN MD 21620
New Listing - a week on site
1 / 4
$250,000
Land For Sale
Active
0.85
ACRES
KENT
COUNTY
SCHEELER ROAD LOT 2
CHESTERTOWN, MD 21620
 
Listing courtesy of Select Land & Homes, LLC
112 METCALF ROAD CHESTERTOWN MD 21620
1 / 54
$249,500
Townhouse For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,280
SQFT
112 METCALF ROAD
CHESTERTOWN, MD 21620
CHESTER ARMS Subdivision
Listing courtesy of Rosendale Realty
HAACKE DRIVE LOT 3 CHESTERTOWN MD 21620
New Listing - a week on site
1 / 7
$225,000
Land For Sale
Active
0.87
ACRES
KENT
COUNTY
HAACKE DRIVE LOT 3
CHESTERTOWN, MD 21620
 
Listing courtesy of Select Land & Homes, LLC
HAACKE DRIVE LOT 3 CHESTERTOWN MD 21620
New Listing - a week on site
1 / 4
$225,000
Commercial Sale For Sale
Active
0.0
SQFT
HAACKE DRIVE LOT 3
CHESTERTOWN, MD 21620
 
Listing courtesy of Select Land & Homes, LLC
513 ROUND TOP ROAD CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 18
$225,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
1
TOTAL BATH
1,248
SQFT
513 ROUND TOP ROAD
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of Cummings & Co. Realtors
139 PROSPECT STREET CHESTERTOWN MD 21620
Open House Sat, Apr 4, 11 AM
1 / 28
$225,000
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
1,200
SQFT
139 PROSPECT STREET
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of Redfin Corp
117 WATER STREET N 1B CHESTERTOWN MD 21620
1 / 20
$200,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
700
SQFT
117 WATER STREET N 1B
CHESTERTOWN, MD 21620
 
Listing courtesy of TTR Sotheby's International Realty
0 ROUND TOP ROAD CHESTERTOWN MD 21620
New Listing - 2 weeks on site
1 / 23
$200,000
Land For Sale
Active
5.81
ACRES
QUEEN ANNES
COUNTY
0 ROUND TOP ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
Lot 9 PRESTWICK DRIVE CHESTERTOWN MD 21620
1 / 20
$185,000
Land For Sale
Active Under Contract
1.95
ACRES
KENT
COUNTY
Lot 9 PRESTWICK DRIVE
CHESTERTOWN, MD 21620
 
Listing courtesy of Gunther-McClary Real Estate
127 WOOD DUCK LANE CHESTERTOWN MD 21620
1 / 26
$185,000
Mobile Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,666
SQFT
127 WOOD DUCK LANE
CHESTERTOWN, MD 21620
 
Listing courtesy of RE/MAX Point Realty
107 CONLEY DRIVE CHESTERTOWN MD 21620
New Listing - 3 weeks on site
1 / 16
$170,000
Townhouse For Sale
Active
3
BEDS
1
TOTAL BATH
1,140
SQFT
107 CONLEY DRIVE
CHESTERTOWN, MD 21620
CHESTER ARMS Subdivision
Listing courtesy of Doug Ashley Realtors, LLC
132 PROSPECT STREET CHESTERTOWN MD 21620
Price Change - 3 days ago
1 / 20
$159,900
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
910
SQFT
132 PROSPECT STREET
CHESTERTOWN, MD 21620
CHESTERTOWN Subdivision
Listing courtesy of ANR Realty, LLC
CAULKS FIELD ROAD CHESTERTOWN MD 21620
1 / 8
$150,000
Land For Sale
Active
2
ACRES
KENT
COUNTY
CAULKS FIELD ROAD
CHESTERTOWN, MD 21620
 
Listing courtesy of RE/MAX Allegiance
GEORGETOWN ROAD SE CHESTERTOWN MD 21620
1 / 3
$150,000
Land For Sale
Active
2
ACRES
KENT
COUNTY
GEORGETOWN ROAD SE
CHESTERTOWN, MD 21620
 
Listing courtesy of RE/MAX Allegiance
21324 PERSIMMON DRIVE CHESTERTOWN MD 21620
Real Estate Owned
1 / 17
$136,800
Townhouse For Sale
Active
2
BEDS
1
TOTAL BATH
1,232
SQFT
21324 PERSIMMON DRIVE
CHESTERTOWN, MD 21620
 
Listing courtesy of Coldwell Banker Realty - Washington
234 N COLLEGE AVENUE CHESTERTOWN MD 21620
Short Sale
1 / 3
$130,000
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
1,296
SQFT
234 N COLLEGE AVENUE
CHESTERTOWN, MD 21620
 
Listing courtesy of Cummings & Co Realtors
1 - 100 of 142 listings (142 total matches)


The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.


Share My QR
Success!
blue-therapy-plus-brokerage-footer
Contact

Phone
302-690-0245

Email
[email protected]

Address
4628 Benoni Point Rd,
Royal Oak, MD 21662

Quick Links
  • About us
  • Meet the Team
  • Testimonials
  • Thyme’s Heart Fund
  • Discover Blue Therapy
  • Contact
Real Estate
  • Featured Listings
  • Search Waterfront
  • Buyers
  • Sellers
  • Home Valuation
  • Perfect Home Finder
  • What’s My Home Worth?
  • Mortgage Calculator
Search Waterfront & Water View
  • Waterfront
  • Water View
  • Water Access
equal-housing-white

We are committed to providing an accessible website. If you have difficulty accessing content, have difficulty viewing a file on the website, or notice any accessibility problems, please contact us at 302-690-0245 to specify the nature of the accessibility issue and any assistive technology you use. We strive to provide the content you need in the format you require.

Copyright © 2026 | Privacy Policy. Admin. Sitemap. Accessibility. Data Powered by Home Junction. Created By AgentFire.