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  4. Doug Ashley Realtors, Llc

Doug Ashley Realtors, Llc

2271/2 High St

Chestertown, MD

Team Members

Elisabeth Ostrander

Carlton Felty

Douglas Ashley

Vincenzo Assante Di Cupillo

Michele Palmer

Debra Meikle

Grace Crockett

Retha Arrabal

Vincent Raimond

Richard King

Frances Miller

Helen Mcadory

William Brockschmidt

Abigail Powell

Andrew Meikle

Elizabeth Green

Debbie Meikle

Beth Green

Doug Ashley

Beth Ostrander

Bud Felty

Abby Powell

Rick King

Abigail Usilton

Disclaimer: This page displays real estate agents and offices generated from active and closed MLS listings affiliated with this office. While we make every effort to provide accurate information, there may be inaccuracies due to factors such as fluctuating staff, office name changes, changes of address, and other varying circumstances. If you are the owner of the office or an agent listed here and would like to advertise, please fill out the form at https://www.realty.com/advertise.

Listings & Recent Sales (34)

Active Rental Sold

For Sale (16)

Address Bed / Bath Listing Price
Picture of 26670-26680 MAPLE AVENUE
26670-26680 MAPLE AVENUE STILL POND, MD
Living Area: 2024 Sqft.
3 Beds, 2 Baths
$230,000
Picture of GEORGETOWN RD
GEORGETOWN RD CHESTERTOWN, MD
-, 0 Baths
$60,000
Picture of 8620 PARK DRIVE
8620 PARK DRIVE CHESTERTOWN, MD
Living Area: 2524 Sqft.
4 Beds, 3 Baths
$499,900
Picture of 311 DEVON DRIVE
311 DEVON DRIVE CHESTERTOWN, MD
Living Area: 3504 Sqft.
4 Beds, 3 Baths
$499,000
Picture of 6746 QUAKER NECK ROAD
6746 QUAKER NECK ROAD CHESTERTOWN, MD
Living Area: 3371 Sqft.
5 Beds, 3 Baths
$384,000
Picture of 6746 QUAKER ROAD
6746 QUAKER ROAD CHESTERTOWN, MD
Living Area: 3371 Sqft.
-, 3 Baths
$384,000
Picture of 204 DOUBLE CREEK ROAD
204 DOUBLE CREEK ROAD CHESTERTOWN, MD
Living Area: 2927 Sqft.
3 Beds, 3 Baths
$565,000
Picture of 21125 IOWA AVENUE
21125 IOWA AVENUE CHESTERTOWN, MD
Living Area: 1294 Sqft.
2 Beds, 1 Bath
$339,900
Picture of 113 PEAR TREE POINT ROAD
113 PEAR TREE POINT ROAD CHESTERTOWN, MD
Living Area: 1296 Sqft.
3 Beds, 1 Bath
$250,000
Picture of 202 WALDO DRIVE
202 WALDO DRIVE CHESTERTOWN, MD
Living Area: 2055 Sqft.
3 Beds, 2 Baths
$340,000
Picture of 8706 ELM ROAD
8706 ELM ROAD CHESTERTOWN, MD
Living Area: 1232 Sqft.
3 Beds, 2 Baths
$320,000
Picture of MAP 36 PARCEL 80 WATERTOWER ROAD
MAP 36 PARCEL 80 WATERTOWER ROAD CHESTERTOWN, MD
-, 0 Baths
$55,000
Picture of 5989 N MAIN STREET
5989 N MAIN STREET ROCK HALL, MD
Living Area: 1386 Sqft.
3 Beds, 2 Baths
$390,000
Picture of 31673 W EDGE ROAD
31673 W EDGE ROAD MILLINGTON, MD
Living Area: 832 Sqft.
2 Beds, 1 Bath
$395,000
Picture of 11106 PLUM DRIVE
11106 PLUM DRIVE WORTON, MD
Living Area: 1008 Sqft.
3 Beds, 1 Bath
$279,000
Picture of 10790 WORTON ROAD
10790 WORTON ROAD WORTON, MD
Living Area: 1484 Sqft.
3 Beds, 2 Baths
$410,000

Sold (18)

Address Sold date Last List Price Represented
Picture of 21217 TEXAS AVENUE
21217 TEXAS AVENUE CHESTERTOWN, MD
Living Area: 912 Sqft.
06/05/2026 $99,900 Listing
Picture of 23069 RALEIGH ROAD
23069 RALEIGH ROAD CHESTERTOWN, MD
Living Area: 1160 Sqft.
06/05/2026 $175,000 Selling
Picture of 25209 WYMONT PARK ROAD
25209 WYMONT PARK ROAD WORTON, MD
Living Area: 2874 Sqft.
06/05/2026 $1,150,000 Listing
Picture of 21316 PERSIMMON DRIVE
21316 PERSIMMON DRIVE CHESTERTOWN, MD
Living Area: 1232 Sqft.
06/05/2026 $169,000 Listing
Picture of 23110 OLD FAIRLEE ROAD
23110 OLD FAIRLEE ROAD CHESTERTOWN, MD
Living Area: 1805 Sqft.
06/05/2026 $339,900 Selling
Picture of 11969 AUGUSTINE HERMAN HIGHWAY
11969 AUGUSTINE HERMAN HIGHWAY KENNEDYVILLE, MD
Living Area: 2520 Sqft.
06/05/2026 $319,000 Listing
Picture of 206 VIRGINIA AVENUE
206 VIRGINIA AVENUE GALENA, MD
Living Area: 1406 Sqft.
06/05/2026 $250,000 Listing
Picture of 327 CYPRESS STREET
327 CYPRESS STREET MILLINGTON, MD
Living Area: 1404 Sqft.
06/05/2026 $199,700 Listing
Picture of 201 GREENWOOD AVENUE
201 GREENWOOD AVENUE CHESTERTOWN, MD
Living Area: 3984 Sqft.
06/05/2026 $495,000 Listing
Picture of 224 MAIN STREET
224 MAIN STREET CHURCH HILL, MD
Living Area: 2668 Sqft.
06/05/2026 $99,900 Selling
Picture of 11029 BRINDLEY DRIVE
11029 BRINDLEY DRIVE WORTON, MD
Living Area: 844 Sqft.
06/05/2026 $239,000 Listing
Picture of 1807 PRICE STATION ROAD
1807 PRICE STATION ROAD CHURCH HILL, MD
Living Area: 1605 Sqft.
06/05/2026 $400,000 Selling
Picture of 11350 LYNCH ROAD
11350 LYNCH ROAD WORTON, MD
Living Area: 1215 Sqft.
06/05/2026 $345,000 Listing
Picture of 5188 SKINNERS NECK ROAD
5188 SKINNERS NECK ROAD ROCK HALL, MD
Living Area: 1628 Sqft.
06/05/2026 $299,000 Selling
Picture of 107 CONLEY DRIVE
107 CONLEY DRIVE CHESTERTOWN, MD
Living Area: 1140 Sqft.
06/05/2026 $170,000 Listing
Picture of 107 LONGFELLOW DRIVE
107 LONGFELLOW DRIVE CHESTERTOWN, MD
Living Area: Sqft.
06/05/2026 $295,000 Listing
Picture of 108 OAK LEAF DRIVE
108 OAK LEAF DRIVE CHESTERTOWN, MD
Living Area: 1867 Sqft.
06/05/2026 $299,500 Listing
Picture of 22360 GREAT OAK LANDING ROAD
22360 GREAT OAK LANDING ROAD CHESTERTOWN, MD
Living Area: 2688 Sqft.
06/05/2026 $525,000 Listing

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Service Areas

STILL POND, MD
CHESTERTOWN, MD
ROCK HALL, MD
MILLINGTON, MD
WORTON, MD
KENNEDYVILLE, MD
GALENA, MD
CHURCH HILL, MD

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