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: 121
Average Price: $458,861
Highest Price: $6,900,000
Lowest Price: $695

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

6798 Broad Neck Rd, Chestertown, MD - $6,900,000

Residential, Detached
  • 5 Beds
  • Baths
  • 10,870 SQFT
  • 27 DOM
View details More Photos Save

300+/- Acre Waterfront Estate With Exceptional Amenities. Main House With 7,500+/- Sq Ft, With A Retreat Feel And Open Floor Plan. Indoor And Outdoor Pools, High Elevation And Expansive Southern And Western Views Down Coveted West Fork Langford Cr...

4845 Cliffs City Rd, Chestertown, MD - $3,950,000

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

Bachelors Hope Farm, Available For The First Time In 50+ Years, Is A Once-in-a-lifetime Waterfront & Hunting Farm. 9,600 Square Foot, 7 Bed Main Home Is Situated Within Feet Of The Chester River. 420 Foot Dock Has 8 Feet Mlw, Water & Electric, Wit...

24091 Providence Plantation Ln, Chestertown, MD - $2,999,500

Residential, Detached
  • 6 Beds
  • Baths
  • 12 DOM
View details More Photos Save

A Quintessential 76-acre Eastern Shore Waterfront Estate Built In 1781 & 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 ...

6320 Quaker Neck Rd, Chestertown, MD - $1,600,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 2,236 SQFT
  • 327 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 ...

6870 Pentridge Ct, Chestertown, MD - $1,195,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 188 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 - $1,100,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 4,402 SQFT
  • 99 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
  • 186 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...

22470 Fairgale Farm Ln, Chestertown, MD - $979,500

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 4,257 SQFT
  • 49 DOM
View details More Photos Save

Fairlee Creek Waterfront Haven Is Set On A Private 3.5-acres With Water Views Throughout The Home. Built In 2002 With A 2005 Addition, The Open Design With Great Room, Large Kitchen, Loft And Deck Invites Outdoor Living And Entertaining. Features ...

Photo of Listing #1001205824

406 River Rd, Chestertown, MD - $899,000

Residential, Detached
  • 3 Beds
  • Baths
  • 183 DOM
View details More Photos Save

Great Opportunity!! This Beautifully Built Brick Home Has Stunning Water Views From Almost Every Room. The Property Boasts 3 Bedrooms W/ 4.5 Baths, Slate Roof, Bulkhead, Swimming Pool, Hot Tub, Back Patio Area, 2nd Floor Deck Overlooking The River...

Photo of Listing #1000083761

22460 Fairgale Farm Ln, Chestertown, MD - $845,000

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 3,085 SQFT
  • 742 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 ...

8020 Airy Hill Rd, Chestertown, MD - $810,000

Residential, Detached
  • 4 Beds
  • Baths
  • 3,128 SQFT
  • 32 DOM
View details More Photos Save

Eastern Shore Georgian Style Home Is Situated On A Serene, Rural 10-acres, Yet Is Conveniently Located Just 2 Miles From The Colonial Town Of Chestertown. Designed By The Architect, Andrea Lombardini, And Built In 2005, The Thoughtfully Designed I...

9784 White Swan Ct, Chestertown, MD - $799,000

Residential, Detached
  • 5 Beds
  • Baths
  • 4,000 SQFT
  • 207 DOM
View details More Photos Save

Easy Access To The Chesapeake Bay, Waterfront House Designed To Be Compatible With Its Surroundings, Water Views In Each Room. Vaulted Ceilings, Main Floor Living, 3 Master Suites. Almost 5,000 Sq.ft. Of Living Space. Indoor Heated Endless Pool. D...

21175 Georgia Ave, Chestertown, MD - $795,000

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 83 DOM
View details More Photos Save

Seller Assumes Buyer Will Be Tearing Down (or Completely Rebuilding) Existing Structures. Value Is Based On 200' Of Chesapeake Bayfront, A "c" Shaped Assemblage Of 3 Parcels, 8 Lots Which Includes One Allocation For Water/sewer. Several Nearby Ne...

Photo of Listing #1001989080

9840 White Swan Ct, Chestertown, MD - $729,500

Residential, Detached
  • 4 Beds
  • 5 Baths
  • 4,682 SQFT
  • 126 DOM
View details More Photos Save

Located In An Exclusive Water-oriented Community, This Magnificent Home Offers An Open Plan Design For Those Who Enjoy Entertaining And Being Active. The Prominent Eye-catching Architectural Style Of The Interior Accents A Classic Paint Scheme Thr...

8601 Chestertown Rd, Chestertown, MD - $729,000

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

Open Sat, 27th, 12-2 Pm! Amazing Custom-built Estate Sited On Almost 14 Acres W/every Luxury & Upgrade + 2500 Sf Basement. First Floor Master, 4 Addtnl Brs, Phenomenal Kitchen Includes 3 Ovens, Double Dishwasher, Granite Counters, Custom Amish Li...

265 Pear Tree Point Rd, Chestertown, MD - $699,000

Residential, Detached
  • 5 Beds
  • Baths
  • 5,563 SQFT
  • 19 DOM
View details More Photos Save

Over 21 Acres Ready For Your Horses & Existing Vineyard- Possible B&b! Entertainer's Delight- Nearly 5600 Sq Ft, 5 Bedrooms, 3.5 Baths. In-ground Pool, Large Patio. Fenced Pasture. Large Outbuilding With 2 Stalls, Main-level Master Suite W/ Additi...

111 Queen St, Chestertown, MD - $695,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,086 SQFT
  • 775 DOM
View details More Photos Save

Fine Landmark Property Rarely Available. Brick W All Refinements Of 1788 C. Maintained W Great Care. Grand Stair Hall Flows To All Social Rooms. Perfect "stage" For Fine Collections. Quiet Setting In Chestertown Hist. Dist. Handsome Glass Sunporch...

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

Residential, Detached
  • 4 Beds
  • Baths
  • 2,866 SQFT
  • 788 DOM
View details More Photos Save

A Classic American Victorian ,wrap-around Porch With Balustrade. Many New Appointments, Including A New Kitchen & New Baths, While Retaining The Victorian Signatures Of High Ceilings, Spacious Rooms, Fine Wood Floors, Detailed Wood Trim, Long Wind...

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 2018.

Listing information last updated on November 12th, 2018 at 8:31pm EST.