- Home
- SELL
- BUY
- The Chesapeake Reserve
- Luxury
- Communities
- New Construction Homes
- Annapolis Overview
- Arnold Overview
- Cambridge Overview
- Centreville Overview
- Chester Overview
- Chestertown Overview
- Denton Overview
- Easton Overview
- Glen Burnie Overview
- Grasonville Overview
- Odenton Overview
- Oxford Overview
- Pasadena Overview
- Queenstown Overview
- Rock Hall Overview
- Saint Michaels Overview
- Severn Overview
- Severna Park Overview
- Stevensville Overview
- Local Home Prices Report
- About
- Resources
-
- Register
- Sign In
MD
Chestertown
LISTINGS
- 1/31 31
Active$ 399,900
5 Beds4 Baths2,535 SqFt104 FLYING CLOUD DR, Chestertown, MD 21620
Single Family Home
MLS# MDKE2006212
Listed by Real Broker, LLC

Open 5/2 11AM-1PM$ 296,000
2 Beds3 Baths1,864 SqFt115 ACORN DR, Chestertown, MD 21620
Townhouse
MLS# MDKE2006360
Listed by Chesapeake Real Estate Associates, LLC

- 1/39 39
Open Sat 11AM-1PM$ 299,500
2 Beds3 Baths1,867 SqFt108 OAK LEAF DR, Chestertown, MD 21620
Townhouse
MLS# MDKE2006224
Listed by Doug Ashley Realtors, LLC

RECENTLY SOLD
Image
Address
Sold Date
Property Type
Configuration
Price

101 METCALF RD, Chestertown, MD 21620
Townhouse
3 Beds2 Baths1,280 SqFt
$ 264,900 $ 264,900
MLS# MDKE2005882
Listed by Real Broker, LLC


10578 TONOPAH RD, Chestertown, MD 21620
Single Family Home
3 Beds3 Baths1,500 SqFt
$ 335,000 $ 335,000
MLS# MDKE2005352
Listed by RE/MAX Executive


473 PEAR TREE POINT RD, Chestertown, MD 21620
Single Family Home
3 Beds3 Baths1,512 SqFt
$ 359,900 $ 349,900 2.9%
MLS# MDQA2012050
Listed by RE/MAX Executive

MARKET TRENDS
- Average Sold Price
- Median Sold Price
- Highest Sold Price
- Lowest Sold Price
Market Trends are calculated using MLS® sold listing data
housing detail
Coming Soon
Listing Detail
Nearby Locations
104 FLYING CLOUD DR, Chestertown, MD 21620
5 Beds 4 Baths 2,535 SqFt
Single Family Home
MLS# MDKE2006212
Listed by Real Broker, LLC
115 ACORN DR, Chestertown, MD 21620
2 Beds 3 Baths 1,864 SqFt
Townhouse
MLS# MDKE2006360
Listed by Chesapeake Real Estate Associates, LLC
108 OAK LEAF DR, Chestertown, MD 21620
2 Beds 3 Baths 1,867 SqFt
Townhouse
MLS# MDKE2006224
Listed by Doug Ashley Realtors, LLC
106 QUEEN ST S, Chestertown, MD 21620
3 Beds 4 Baths 2,472 SqFt
Single Family Home
MLS# MDKE2006152
Listed by Chesapeake Real Estate Associates, LLC
101 COLEMAN DR, Chestertown, MD 21620
3 Beds 3 Baths 2,268 SqFt
Single Family Home
MLS# MDQA2016624
Listed by Coldwell Banker Chesapeake Real Estate Company
7989 QUAKER NECK RD, Chestertown, MD 21620
5 Beds 5 Baths 4,305 SqFt
Single Family Home
MLS# MDKE2005590
Listed by Coldwell Banker Chesapeake Real Estate Company
103 LANDING LN, Chestertown, MD 21620
2 Beds 3 Baths 2,100 SqFt
Condo
MLS# MDKE2005670
Listed by Coldwell Banker Chesapeake Real Estate Company
25475 TURNBERRY CT, Chestertown, MD 21620
4 Beds 4 Baths 4,145 SqFt
Single Family Home
MLS# MDKE2006350
Listed by Taylor Properties
136 HILLTOP DR, Chestertown, MD 21620
3 Beds 2 Baths 1,432 SqFt
Single Family Home
MLS# MDQA2016782
Listed by Northrop Realty
8706 ELM RD, Chestertown, MD 21620
3 Beds 2 Baths 1,232 SqFt
Single Family Home
MLS# MDKE2006390
Listed by Doug Ashley Realtors, LLC
10594 MILLBROOK DR, Chestertown, MD 21620
3 Beds 2 Baths 1,499 SqFt
Single Family Home
MLS# MDKE2006378
Listed by Chesapeake Real Estate Associates, LLC
208 CENTRAL DR, Chestertown, MD 21620
3 Beds 1 Bath 1,120 SqFt
Single Family Home
MLS# MDQA2016836
Listed by Redfin Corp
21217 TEXAS AVE, Chestertown, MD 21620
2 Beds 1 Bath 912 SqFt
Single Family Home
MLS# MDKE2006364
Listed by RE/MAX Leading Edge
226 S WATER ST, Chestertown, MD 21620
3 Beds 4 Baths 2,172 SqFt
Townhouse
MLS# MDKE2006354
Listed by Gunther-McClary Real Estate
103 SUTTON WAY, Chestertown, MD 21620
5 Beds 4 Baths 3,816 SqFt
Single Family Home
MLS# MDKE2006344
Listed by TTR Sotheby's International Realty
704 TRUSLOW RD, Chestertown, MD 21620
3 Beds 3 Baths 2,060 SqFt
Single Family Home
MLS# MDQA2016632
Listed by RE/MAX Executive
201 BIRCH RUN RD, Chestertown, MD 21620
3 Beds 2 Baths 1,588 SqFt
Single Family Home
MLS# MDKE2006316
Listed by Coldwell Banker Chesapeake Real Estate Company
139 PROSPECT ST, Chestertown, MD 21620
3 Beds 1 Bath 1,200 SqFt
Single Family Home
MLS# MDKE2006250
Listed by Redfin Corp
202 WALDO DR, Chestertown, MD 21620
3 Beds 2 Baths 2,055 SqFt
Single Family Home
MLS# MDKE2006260
Listed by Doug Ashley Realtors, LLC
109 S COLLEGE AVE, Chestertown, MD 21620
3 Beds 3 Baths 1,216 SqFt
Single Family Home
MLS# MDKE2006040
Listed by Taylor Properties
- 5
Kent County Middle School
Public | 6 - 8
- 0
Kent School
Private | PK - 8
- 0
Chestertown Christian Academy
Private | PK - 12
- 0
Radcliffe Creek School
Private | PK - 8
- 0
Chester River Adventist School
Private | 2 - 8
- 5
H. H. Garnett Elementary School
Public | PK - 5
- 0
Kent School
Private | PK - 8
- 0
Chestertown Christian Academy
Private | PK - 12
- 0
Radcliffe Creek School
Private | PK - 8
- 0
Chester River Adventist School
Private | 2 - 8
- 0
Chestertown Christian Academy
Private | PK - 12
Lemon Leaf Cafe
443-282-0004 Cafes
Great Oak Landing Lodge & Restaurant
410-778-2100 Hotels
Ellen’s Coffee Shop & Family Restaurant
410-810-1992 Breakfast & Brunch
McDonald’s
410-810-0163 Fast Food
Arby’s
410-810-8955 Fast Food
Plaza Tapatia
410-810-1952 Mexican
Kent Agricultural Center Kitchen
The Freeze
410-778-2128 Fast Food
Pizza Hut
410-778-1070 Italian
Luisa’s Cucina Italiana
410-778-5360 Seafood
China House
410-778-3939 Chinese
Domino’s Pizza
410-810-3811 Pizza
Jj’s Deli and Liquors
443-282-0091 Delis
Happy Grass Lawn Care & Property Maintenancece
410-490-2324 Landscaping
Eastern Shore Homes & Realty
410-778-6654 Contractors
Anthony Tree Experts
410-778-3385 Tree Services
Green Home Spaces
410-778-2095 Contractors
Deep Landing Workshop
410-778-4042 Lighting Fixtures & Equipment
Montgomery Heating and Cooling
410-778-1212 Heating & Air Conditioning/HVAC
Men on the Move
443-480-2615 Movers
Roy Kirby & Sons
410-810-3113 Contractors
Bramble David A
410-778-3023 Contractors
Langford Constrctn
410-778-6130 Contractors
Water Wizard
410-778-6323 Plumbing
Everett Jerry
410-778-0198 Painters
Eastern Shore Landscaping Co
410-758-2267 Landscaping
Nicholson Doug Electric Heating & Plumbing Repair
410-778-0838 Plumbing
Village House
410-778-5766 Interior Design
Ryan Homes
410-778-4795 Contractors
J & M Builders
410-810-1508 Contractors
Williams Marine & Cabinetry
410-778-5594 Cabinetry
Jj Deluca Company
410-778-5945 Contractors
University of Maryland Shore Nursing and Rehab
410-778-4550 Rehabilitation Center
Chestertown Vision Center
410-778-6764 Optometrists
Moorman Anthony J MD
410-810-0767 Doctors
Fisher Bonnie Michaelson PHD
410-778-7289 Doctors
Eastern Shore Family Footcare
410-778-1801 Podiatrists
Real Life Prosthetics
410-810-1370 Prosthetics
Health Street
888-378-2499 Laboratory Testing
Buckel Tamy MD
410-778-0003 Dermatologists
Ross Harry Paul MD
410-778-3300 Doctors
Diagnostic Radiology Associates PA
410-778-7073 Radiologists
Internal Medicine Associates
410-778-0200 Internal Medicine
Chesapeake Pain and Balance
410-885-1988 Anesthesiologists
Shanahan Patrick J MD
410-778-9300 Doctors
Araujo Freddy MD
410-778-5505 Doctors
Grant John A Dr
410-778-0414 Doctors
Aquilla Joseph B MD
410-778-1150 Ophthalmologists
Crossroads Community
410-778-9200 Medical Centers
Julio A. Ramirez, MD, PC
410-778-5255 Pediatricians
Noble Helen A MD
410-778-0200 Internal Medicine
Chester River Hospital Center
410-778-5135 Hospitals
Wun Kin K MD
410-778-5312 Doctors
Ross Susan MD
410-778-1878 Doctors
Womens Health Care
410-778-9152 Obstetricians & Gynecologists
Kent & Queen Anne’s Hospital
410-778-3300 Hospitals
Tobey Gail Y Dr
410-778-1112 Doctors
Delboy Frederick MD
410-778-0300 Doctors
Dansky Roy S DPM
410-778-1801 Podiatrists
Thomas Velotti DPM
410-810-3133 Sports Medicine
Lacey James MD
410-778-1878 Doctors
Pagano Lisa MD
410-810-0767 Doctors
Fanning Patricia A DC
410-810-0530 Chiropractors
Acupuncture Center of Chestertown
410-778-8111 Acupuncture
Sieffert William J
410-778-2811 General Dentistry
Hearing Center of Chestertown
410-778-5170 Doctors
Loringer Richard L Dr
410-778-6495 Doctors
Chestertown Physical Therapy and Rehabilitation
410-778-6565 Speech Therapists
Nicholson J Laurence
410-778-2646 Couriers & Delivery Services
Chester River Association
410-810-7556 Community Service/Non-Profit
Graham Perry Award Foundation
410-778-2998 Community Service/Non-Profit
Dependable Pest Management
410-778-5658 Pest Control
Marie’s Sewing
410-810-0475 Sewing & Alterations
WIldlife Damage Control
410-708-1228 Pest Control
Computer User Services
410-810-1560 IT Services & Computer Repair
Little Lights
410-778-6505 Child Care & Day Care
Kent Sanitation Septic Tank Cleaning & Repair
410-778-2288 Septic Services
Mid-Atlantic Border Collie Rescue
410-778-4669 Community Service/Non-Profit
Kent County Day Care
410-778-6680 Child Care & Day Care
Ehrman Tapestry
410-810-3119 Home Decor
Fine Arts Conservation Center
410-778-5252 Antiques
Stenger Gas Appliances
410-778-3456 Appliances
Chestertown Vision Center
410-778-6764 Optometrists
Chestertown Used Book Store
410-778-5777 Used Bookstore
The Carla Massoni Gallery
410-778-7330 Art Galleries
Boyer’s Jewelers
410-778-1966 Jewelry
Rachel’s Flower Power
410-778-1025 Florists
Chester River Lawn & Garden
410-778-4150 Nurseries & Gardening
Tractor Supply
410-778-2047 Hardware Stores
Hidden Treasures
410-778-1219 Antiques
Empty Hangers
410-778-1300 Used, Vintage & Consignment
Chestertown Old Book Company
410-810-3880 Bookstores
The Finishing Touch
410-778-5292 Art Galleries
Houston’s Dockside Emporium
410-778-9079 Sports Wear
David Ferguson Oriental Rugs & Jewelry
410-810-0603 Jewelry
Second Chance
410-778-2493 Antiques
The Vape Shop
410-778-4377 Vape Shops
Sherwin-Williams Paint Store
410-778-2500 Paint Stores
Village House
410-778-5766 Interior Design
Chestertown Arts League
410-778-5789 Art Galleries
Riverside Vape
443-480-6718 Vape Shops
Clovelly Nurseries
410-778-9686 Nurseries & Gardening
Antiques On Cannon
410-778-1138 Antiques
Bloomin’ Wild
410-778-5300 Florists
River Arts Chestertown
410-778-6300 Art Galleries
Rolph’s Wharf Marina & Boat Sales
410-778-6375 Boating
Fine Arts Conservation Center
410-778-5252 Antiques
Chester 5 Theatres
410-778-2227 Cinema
The Carla Massoni Gallery
410-778-7330 Art Galleries
The Finishing Touch
410-778-5292 Art Galleries
Chester River Yacht & Country Club
410-778-1369 Country Clubs
Chestertown Arts League
410-778-5789 Art Galleries
River Arts Chestertown
410-778-6300 Art Galleries
Pomona General Store
410-778-0932 Grocery
Ellen’s Coffee Shop & Family Restaurant
410-810-1992 Breakfast & Brunch
Tracy’s Smoothie Place
410-778-2203 Juice Bars & Smoothies
Pip’s Liquors
410-778-0123 Beer, Wine & Spirits
M J K Products
410-810-2888 Meat Shops
Lockbriar Farms
410-778-9112 Fruits & Veggies
ACME Markets
410-778-5641 Grocery
The Black Burro
Food Trucks
Chester River Wine & Cheese
443-282-0220 Wine Bars
Super Fresh
410-778-9535 Grocery
Jj’s Deli and Liquors
443-282-0091 Delis
The Hot Spot
410-778-1588 Tanning
P Nails
410-810-7277 Nail Salons
Leaverton Louise
410-778-2686 Hair Removal
Show N Tell Salon & Day Spa
410-778-5200 Hair Salons
Nail Garden
410-778-5105 Nail Salons
Hair We Are
410-778-2635 Nail Salons
Images Salon
410-778-4432 Hair Salons
Olde Towne Barber & Stylists
410-778-4771 Barbers
Luisa’s Cucina Italiana
410-778-5360 Seafood
Chester River Wine & Cheese
443-282-0220 Wine Bars
Chesapeake Inns
410-778-4667 Bed & Breakfast
Great Oak Landing Lodge & Restaurant
410-778-2100 Hotels
Eastern Shore Tents & Events
410-810-0686 Party & Event Planning
Court Yard Inn
410-778-2755 Hotels
Laurentum Inn
410-778-3236 Bed & Breakfast
The DJ Price
410-739-7718 DJs
Widow’s Walk Inn B&B
410-778-6864 Bed & Breakfast
Great Oak Lodge
410-778-5943 Hotels
Colonial Chevy-Buick
443-282-1290 Auto Repair
Napa Auto Parts
410-758-2449 Auto Parts & Supplies
Geno’s Automotive Services
410-778-4341 Auto Repair
K & L Automotive Service & Repairs
410-778-2639 Towing
Joey’s Auto Repair & Used Cars
410-778-4144 Car Dealers
Rolph ‘s Warf Marina
410-778-6389 Marinas
Ramsey GMC
443-282-1376 Auto Repair
Colonial Chevy & Buick
410-776-6018 Car Dealers
Chuck’s Body & Fender Inc.
410-778-9777 Auto Repair
Chestertown Auto Plus & Goodyear
443-282-0049 Auto Repair
Penn Jersey Auto
410-778-2566 Auto Repair
Mike’s Auto Service
410-810-3980 Auto Repair
Todd’s Body Shop
410-778-5868 Body Shops
First Baptist Church of Chestertown
410-778-0390 Churches
Calvary Chapel of Chestertown
Gospel Church of God
First United Methodist Church
410-778-2977 Churches
Liberty Lighthouse
410-778-6521 Churches
St Paul’s Kent
Mercantile Eastern Shore Bank
410-778-6110 Banks & Credit Unions
Pnc Bank
410-778-7520 Banks & Credit Unions
Chesapeake Bank and Trust Company
410-778-1600 Banks & Credit Unions
Invest Financial Corporation
410-778-3500 Banks & Credit Unions
Raymond James Financial Services
410-810-0800 Investing
Chesapeake Farm Credit Aca
Hank Starkey - State Farm Insurance Agent
410-778-0647 Insurance
Kent Insurance Agency Inc- Nationwide Insurance
410-778-5700 Insurance
Crestar Bank
410-810-0483 Banks & Credit Unions
Heller Peter D
410-778-6666 Banks & Credit Unions
Allstate Insurance: Andrew Rengarts
410-810-2600 Insurance
SunTrust
443-282-3243 Banks & Credit Unions
Rasin Alex P
410-778-3515 Lawyers
Wright & Meehan
410-778-0266 Bankruptcy Law
Law Office of Thomas N Yeager
410-810-0428 Personal Injury Law
Meehan Stephen Z Attny At Law
410-778-7941 Lawyers
Karns M CPA
410-778-0382 Accountants
Wadkovsky & Mowell
410-778-1630 Lawyers
O’Dell Valuation Consulting, LLC - CPA
443-480-5800 Accountants
Job Service-Maryland State
410-778-3525 Employment Agencies
Bowman Paul M
410-778-5171 Lawyers
Barroll R Stewart
410-778-2112 Lawyers
Johnson Offices
410-778-6965 Accountants
Flannagan Joseph C Jr
410-778-2380 Lawyers
Judge James A CPA
410-758-0179 Accountants
Wright David Craig Atty
410-758-3360 Lawyers
Cookerly Ernest S Lwyr
410-778-2112 Lawyers
Wright Arthur M Lawyers
410-778-3515 Lawyers
Cookerly & Barroll
410-778-2112 Lawyers
Chesapeake Architects
410-778-4899 Architects
Chester Valley Community Mediation Srvs
410-810-9188 Mediators
Chesapeake Inns
410-778-4667 Bed & Breakfast
Great Oak Landing Lodge & Restaurant
410-778-2100 Hotels
Court Yard Inn
410-778-2755 Hotels
Laurentum Inn
410-778-3236 Bed & Breakfast
Whitehair Hunting & Fishing Travel
410-778-3592 Travel Services
Widow’s Walk Inn B&B
410-778-6864 Bed & Breakfast
Great Oak Lodge
410-778-5943 Hotels
Townshend Albert S
410-778-1200 Veterinarians
Running W Kennel
410-778-2887 Pet Boarding/Pet Sitting
Eastern Shore Animal Hospital
410-778-1200 Veterinarians
Mid-Atlantic Border Collie Rescue
410-778-4669 Community Service/Non-Profit
Tidewater Trader
410-778-1262 Print Media
Chesapeake Times
410-810-1525 Print Media
Chestertown Christian Academy
Religious Schools
Washington College Alumni House
410-778-7846 Colleges & Universities
H. H. Garnett Elementary School
410-778-6890 Middle Schools & High Schools
Kent County Public Library - Chestertown Branch
410-778-3636 Libraries
Commute Score
Coming Soon
demographics
Coming Soon
Population
Density
Households
Gender
Coming Soon
Education
Coming Soon
Coming Soon
Coming Soon

GET MORE INFORMATION
