Connect

Find us on...

Dashboard

Login using...

Chestertown Real Estate

A Colonial Town on the Chester River

View All Communities

Overview

Historic Chestertown is set on the banks of the Chester River on the Eastern Shore of Maryland. From quaint cottages to stunning waterfront homes, condos and farms, you’ll find boundless choices of Chestertown properties for sale. Stroll along the River and brick walkways lined with 18th century homes, shops, cafes, theater and Washington College. Located in Kent County about 90-minutes from Washington, D.C. and Philadelphia. Chestertown is a great location for year round living or second homes.

Chestertown Real Estate Statistics

Total Listings: 147
Average Price: $417,151
Highest Price: $3,499,000
Lowest Price: $19,500

Chestertown Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
Map Save this Search
Sort listings by:Price, High to Low
Photo of Listing #1008176730

4845 Cliffs City Rd, Chestertown, MD - $3,499,000

Residential, Detached
  • 7 Beds
  • 8 Baths
  • 292 DOM
View details More Photos Save

Bachelors Hope Farm, Available For The First Time In Over 50 Years, Is A Once-in-a-lifetime Waterfront And Hunting Farm. The 9,600 Square Foot, Seven Bedroom Main Home Is Situated Within Feet Of The Chester River. With Three Master Suites, An In-l...

Photo of Listing #MDKE100016

24091 Providence Plantation Ln, Chestertown, MD - $2,795,000

Residential, Detached
  • 5 Beds
  • Baths
  • 5,250 SQFT
  • 262 DOM
View details More Photos Save

Owners Will Be Creative In Financing This1781 Eastern Shore Beauty Fully Restored In The 90's. Providence Plantation Defines Country Elegance With A Fabulous 1st Floor Master Bedroom Suite, A New 3 Br Tenant House, Dock With Lift And An In-ground ...

7250 Pentridge Ln, Chestertown, MD - $1,850,000

Residential, Detached
  • 4 Beds
  • Baths
  • 230 DOM
View details More Photos Save

Rarely Do You Find A True Contemporary Residence In This Traditional Area In Kent County On Maryland's Eastern Shore. This Architecturally Designed House Is Surrounded By 168 Private Acres Of Open Fields, Virgin Woods & Ponds. The 3000+ Square Foo...

Photo of Listing #MDKE115298

5240 Johnsontown Road, Chestertown, MD - $1,850,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 2,656 SQFT
  • 34 DOM
View details More Photos Save

The Location Of The Main House, 3 Cottages, In-ground Pool & Pool House In The Critical Area Buffer Make This Waterfront Compound Offering One That Is Extraordinary And Extremely Rare. Situated On The Banks Of Comegys Bight Roughly 7.5 Miles From ...

6970 Pomona Rd, Chestertown, MD - $1,750,000

Residential, Detached
  • 5 Beds
  • 2 Baths
  • 3,008 SQFT
  • 44 DOM
View details More Photos Save

Hilltop Farm C. 1810 In Historic Chestertown Includes 113 Acres With Waterfront On Langford Creek Off The Chester River. Property Includes Large 8 Feet Deep Fresh Water Pond And Impoundment.perc Test Done In 2019 For New Construction 3500 +sf On...

Photo of Listing #1004147827

6320 Quaker Neck Rd, Chestertown, MD - $1,380,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 2,236 SQFT
  • 577 DOM
View details More Photos Save

Amazing Sense Of Peace Emphasized By The Quiet Of Authentic 18th C.brick Architecture. Methodically Restored Honoring Its Origins And Yet Made Comfortable With 21st C. Amenities. Lovely Wf Cove On Lankford Creek. Minutes From Chestertown On Highy ...

10718 Tilden Ln, Chestertown, MD - $1,250,000

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 4,715 SQFT
  • 12 DOM
View details More Photos Save

Enjoy Sweeping Water Views From Three Sides Of This Spectacular Property. The Custom Built Sprawling Ranch Home Offers First Floor Living, Is Ideally Situated On A Point Of Land That Provides Broad Water Views, A Private Dock With Protected Water...

Photo of Listing #1000869440

6870 Pentridge Ct, Chestertown, MD - $1,150,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 3,848 SQFT
  • 421 DOM
View details More Photos Save

Impressive Brick Colonial Waterfront Home On The East Fork Of Langford Creek, With Its Own Private Dock. Detached 4 Car Garage With Copious Storage. Interior Features Include A First Floor Master Bedroom, Theater, Bar And Game Room, And Gourmet K...

Photo of Listing #1005951739

7999 Quaker Neck Rd, Chestertown, MD - $1,025,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 4,402 SQFT
  • 349 DOM
View details More Photos Save

One Of Chestertown's Most Prestigious Addresses. Located On The River Halfway Between Town And "the Club". 1.48 Acres Of Privacy. Professionally Maintained And Landscaped. The House Has Had One Addition And Two Remodels. Large Open Floor Plan,po...

Photo of Listing #1001160002

6910 Pentridge Ln, Chestertown, MD - $998,000

Residential, Detached
  • 3 Beds
  • Baths
  • 3,440 SQFT
  • 436 DOM
View details More Photos Save

Peaceful,tranquil,beautiful And Private Just Begin To Describe This Waterfront Property On The East Fork Of Langford.the Grounds Were Designed By A Landscape Architect And Are Filled With Indigenous Plants And Trees.the Home Is Impeccably Maintain...

Photo of Listing #MDKE114086

9326 N Bayview Ave, Chestertown, MD - $995,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,133 SQFT
  • 112 DOM
View details More Photos Save

Expansive Frontage On The Bay. Private, End Of Road Lot. Large Fenced Pool With Breathtaking Bay View. House Completely Renovated Thru 2004 Including Infrastructure. 1st And 2nd Floor Master Suites. Open Den/study On Second Floor. Maintained Steps...

Photo of Listing #MDKE115382

21124 Texas Ave, Chestertown, MD - $899,000

Residential, Detached
  • 3 Beds
  • 2 Baths
  • 2,425 SQFT
  • 2 DOM
View details More Photos Save

From The Time You Enter This Property, It Exceeds All Expectations. Custom Built, Designed By Owner, No Space Is Without Purpose. Great Entertainment Areas, Efficient, Energy Smart, Wood & Tile Flooring, Top Of The Line Materials From The Constr...

108 N Water St, Chestertown, MD - $874,000

Residential, Detached
  • 5 Beds
  • Baths
  • 3,031 SQFT
  • 70 DOM
View details More Photos Save

This Stately Colonial Is Located On The Famed Water Street In The Historic District Of Chestertown. The Home Features 1 Off Street Parking Space And One On Street Parking Space, High-end Upgrades Including Wolf Appliances, Sub Zero Refrigerator, G...

Photo of Listing #1000083761

22460 Fairgale Farm Ln, Chestertown, MD - $795,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 3,085 SQFT
  • 993 DOM
View details More Photos Save

Lovely Home Nestled Amongst Mature Trees Along The Shoreline Of Fairlee Creek. Built By The Current Owner, Many Well Thought Out Features Throughout. Currently First Floor Bedroom Is Used As A Den With Connected Bath, Gas Fireplace. Cedar Closets ...

Photo of Listing #MDKE114924

10800 Cliff Rd, Chestertown, MD - $749,900

Residential, Detached
  • 5 Beds
  • Baths
  • 4,866 SQFT
  • 93 DOM
View details More Photos Save

Custom Built Water Front 5 Bedroom 3.5 Bath Dream House In Great Oak Community Of Chestertown, Md! This Property Is Perfectly Situated On An Elevated Bluff With Absolutely Breath Taken Water Views And Sunsets From Almost Every Room In The House! ...

8601 Pippin Hill Ln, Chestertown, MD - $729,000

Residential, Detached
  • 5 Beds
  • Baths
  • 281 DOM
View details More Photos Save

Open 5/18, 12-2pm Amazing Custom-built Estate Sited On Almost 14 Acres W/stream & Every Luxury & Upgrade + 2500 Sf Basement. First Floor Master, 4 Addtnl Brs, Phenomenal Kitchen Includes 3 Ovens, Double Dishwasher, Granite Counters, Custom Amish L...

244 River Rd, Chestertown, MD - $699,990

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 2,182 SQFT
  • 69 DOM
View details More Photos Save

Enjoy The Best Of Chestertown Waterfront Living! This Beautifully Updated Home Nestles On The Shoreline Of The Chester River With Breathtaking Views Across The Bridge From Historic Chestertown. Meticulously Renovated In 2015, This Property Is Ope...

102 N Water St, Chestertown, MD - $695,000

Residential, Detached
  • 4 Beds
  • Baths
  • 3,960 SQFT
  • 139 DOM
View details More Photos Save

A Classic American Victorian, Wrap Around Porch With Balustrade. Many New Appointments, Including A New Kitchen And New Baths, While Retaining The Victorian Signatures Of High Ceilings, Spacious Rooms, Fine Wood Floors, Detailed Wood Trim, Long Wi...

CHESTERTOWN INFORMATION

Chestertown dates back to 1706 when it served as a port of entry for colonial settlers arriving to Maryland.  It was a prosperous trading and shipbuilding center.  It's shipbuilding past has been revived by the Schooner Sultana Project.  The Sultana is a replica of a traditional 18th century schooner.  It was constructed locally by a non-profit organization, and serves as a floating classroom.  Children and adults enjoy hands on educational experiences that focus on history and the study of the natural environmentChestertown Memorial Day Weekend is a big event as Chestertown kicks off each summer with the Chestertown Tea Party Festival - a weekend of fun for the whole family including a tea toss reenactment in the Chester River on the Sultana, a raft race, re-enactor street performances, colonial crafts, strolling musicians, local fare, and 5k & 10 mile run as well as other activities.

The annual Chestertown Historic House Tour is held in September.  Peek in and visit many of the area's historic homes owned by wealthy merchants in the 18th and 19th centuries.  Chestertown is also home to Washington College - the tenth oldest college in the United States.  The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college.  Washington served as a trustee and received an honorary degree. For more information about local activities and events, use this link Town of Chestertown or visit the Visitor Center located at 122 North Cross Street, Chestertown.  

For more information about the Chestertown area or real estate properties,
please feel free to call me at: (443) 480-1181 or send an email using the form below. Thank you - Richard.

Please provide a valid email address.

 

The listing content relating to real estate for sale on this web site is courtesy of MRIS. Listing information comes from various brokers who participate in the MRIS IDX.Properties listed with brokerage firms other than Coldwell Banker Chesapeake are marked with the MRIS Logo and detailed information about them includes the name of the listing brokers.The properties displayed may not be all the properties available. All information provided is deemed reliable but is not guaranteed and should be independently verified.All listing information copyright MRIS 2019.

Listing information last updated on July 20th, 2019 at 9:15pm EDT.