Old Town Single Family Homes for Sale - Chestertown, Maryland

Name: 3D View Available
Start: 2026-09-26
End: 2026-09-26

Real Estate & Homes For Sale Near Old Town, Chestertown, MD

We found 30 more homes matching your filters just outside Old Town

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NEW CONSTRUCTION
BUILDABLE PLAN
3D VIEW
$654,990+
4 Beds
2.5 Baths
3,335 sqft
Preston Plan in Greenleigh,
Middle River, MD 21220
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NEW
OPEN SUN, 12-2PM
NEW CONSTRUCTION
$699,900
4 Beds
3.5 Baths
2,610 sqft
3734 3rd Ave,
Edgewater, MD 21037
RE/MAX Executive
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NEW
3D VIEW
$799,900
4 Beds
2 Baths
2,784 sqft
356 Severn Rd,
Annapolis, MD 21401
EXP Realty, LLC
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NEW - 45 MIN AGO
0.53 ACRES
$525,000
4 Beds
2 Baths
1,798 sqft
911 Blue Ridge Dr,
Annapolis, MD 21409
HomeSource Pro Real Estate
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NEW - 7 HRS AGO
$480,000
1 Bed
1 Bath
725 sqft
7678 Berry Dr,
Pasadena, MD 21122
Keller Williams Flagship
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OPEN SAT, 12-2PM
3D VIEW
$350,000
4 Beds
2 Baths
1,404 sqft
9215 Orbitan Rd,
Baltimore, MD 21234
Long & Foster Real Estate, Inc.
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NEW - 1 HR AGO
3D VIEW
0.47 ACRES
$699,000
4 Beds
2.5 Baths
2,111 sqft
407 Five Farms Dr,
Stevensville, MD 21666
RE/MAX Executive
NEW - 17 HRS AGO
3D VIEW
$683,500
5 Beds
4 Baths
4,525 sqft
646 Swansea Dr,
Middletown, DE 19709
Century 21 Gold Key Realty
1.7 ACRES
$1,250,000
6 Beds
4.5 Baths
6,128 sqft
12115 Manor Rd,
Glen Arm, MD 21057
Perticone Properties, Inc.
OPEN SAT, 12-2PM
3D VIEW
$585,000
3 Beds
3.5 Baths
3,170 sqft
1910 Waters Landing Dr,
Essex, MD 21221
RE/MAX Leading Edge
NEW - 1 DAY AGO
0.98 ACRES
$1,795,000
2 Beds
2 Baths
3,377 sqft
4852 & 4850 Church Ln,
Galesville, MD 20765
Long & Foster Real Estate, Inc.
NEW CONSTRUCTION
BUILDABLE PLAN
3D VIEW
$479,990+
4 Beds
2.5 Baths
2,148 sqft
Penwell Plan in Ridgely's Reserve,
Joppa, MD 21085
NEW CONSTRUCTION
BUILDABLE PLAN
$492,990+
3 Beds
2.5 Baths
1,440 sqft
Opal Plan in Trimble Hills,
Joppa, MD 21085
NEW
COMING SOON 10/9
0.26 ACRES
$740,000
4 Beds
3.5 Baths
2,340 sqft
3146 Stonehenge Dr,
Riva, MD 21140
Atlantic Shores Sotheby's International Realty
NEW - 9 HRS AGO
$489,909
3 Beds
2 Baths
1,242 sqft
3458 Newport Ave,
Annapolis, MD 21403
RE/MAX Galaxy
NEW
OPEN SAT, 1-3PM
3D VIEW
0.55 ACRES
$949,000
3 Beds
2.5 Baths
2,208 sqft
1130 Mainsail Dr,
Annapolis, MD 21403
Coldwell Banker Realty
NEW - 21 HRS AGO
3D VIEW
0.34 ACRES
$1,650,000
4 Beds
3 Baths
2,890 sqft
1739 Vineyard Trl,
Annapolis, MD 21401
Berkshire Hathaway HomeServices PenFed Realty
NEW
OPEN SAT, 1-3PM
3D VIEW
0.25 ACRES
$1,085,000
4 Beds
5.5 Baths
5,854 sqft
2700 Windswept Ln,
Annapolis, MD 21401
Berkshire Hathaway HomeServices PenFed Realty
3D VIEW
1.69 ACRES
$2,995,000
3 Beds
3.5 Baths
4,223 sqft
1800 River Watch Ln,
Annapolis, MD 21401
TTR Sotheby's International Realty
NEW
COMING SOON 9/30
NEW CONSTRUCTION
0.47 ACRES
$1,295,000
4 Beds
3 Baths
2,720 sqft
1546 Shipsview Rd,
Annapolis, MD 21409
Long & Foster Real Estate, Inc.
OPEN SAT, 1-3PM
0.27 ACRES
$599,000
4 Beds
2 Baths
1,754 sqft
626 Edwards Rd,
Annapolis, MD 21409
Monument Sotheby's International Realty
NEW
COMING SOON 10/1
0.27 ACRES
$499,000
3 Beds
2.5 Baths
2,299 sqft
7931 Wooded Glen Ct,
Pasadena, MD 21122
Douglas Realty, LLC
$700,000
5 Beds
3 Baths
2,238 sqft
530 Saint Martins Ln,
Severna Park, MD 21146
Douglas Realty, LLC
0.39 ACRES
$749,000
5 Beds
3 Baths
2,800 sqft
239 Kennedy Dr,
Severna Park, MD 21146
Long & Foster Real Estate, Inc.
NEW
COMING SOON 9/28
3D VIEW
$2,650,000
5 Beds
5 Baths
4,435 sqft
8 Brooke Ave,
Annapolis, MD 21401
EXP Realty, LLC
NEW
3D VIEW
$539,000
3 Beds
3.5 Baths
2,280 sqft
237 Chatham Ln,
Annapolis, MD 21403
Coldwell Banker Realty
OPEN SAT, 12-2PM
3D VIEW
$525,000
4 Beds
2.5 Baths
1,985 sqft
2 Silopanna Ct,
Annapolis, MD 21403
Compass
NEW - 1 DAY AGO
NEW CONSTRUCTION
1.41 ACRES
$1,850,000
6 Beds
5.5 Baths
4,875 sqft
13707 Jarrettsville Pike,
Phoenix, MD 21131
LPT Realty, LLC
NEW - 2 DAYS AGO
1.21 ACRES
$529,900
3 Beds
2 Baths
1,587 sqft
4111 Halifax Ct,
Glen Arm, MD 21057
Samson Properties
NEW - 16 HRS AGO
3D VIEW
$279,900
3 Beds
2.5 Baths
1,689 sqft
116 Williams Ave,
Baltimore, MD 21222
Real Estate Professionals, Inc.