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Chestertown Real Estate

A Colonial Town on the Chester River

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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: 87
Average Price: $422,553
Highest Price: $2,999,500
Lowest Price: $14,000

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

Residential, Detached
  • 6 Beds
  • Baths
  • 49 DOM
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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 ...

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

Residential, Detached
  • 4 Beds
  • Baths
  • 17 DOM
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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...

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

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 2,236 SQFT
  • 364 DOM
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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
  • 225 DOM
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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
  • 136 DOM
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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
  • 223 DOM
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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
  • 86 DOM
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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
  • 220 DOM
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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...

8415 Rock Hall Rd Rd, Chestertown, MD - $895,000

Residential, Detached
  • 2 Beds
  • 1 Baths
  • 1,582 SQFT
  • 24 DOM
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166 +/- Total Acre Farm With 66 Tillable Acres, 75 Wooded Acres And The Remaining In Home Site, Barns, And Active Gravel Pit. The Farm Offers Excellent Deer, Turkey And Waterfowl Hunting And Has Several Potential Pond Sites. Located Near Remington...

114 Little Harbor Way #4, Chestertown, MD - $850,000

Residential, End of Row/Townhouse
  • 4 Beds
  • 4 Baths
  • 25 DOM
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Experience True Luxury In This Magnificent Chestertown Waterfront Residence. Gleeming Hardwood Floors, High Ceilings And Well-appointed Architectural Detail Accent The Main Level Open Floor Plan Outfitted With A Great Room That Includes A Grand ...

Photo of Listing #1000083761

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

Residential, Detached
  • 3 Beds
  • 3 Baths
  • 3,085 SQFT
  • 779 DOM
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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 ...

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

Residential, Detached
  • 3 Beds
  • 1 Baths
  • 120 DOM
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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
  • 163 DOM
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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...

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

Residential, Detached
  • 5 Beds
  • Baths
  • 5,563 SQFT
  • 56 DOM
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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
  • 812 DOM
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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...

121 Lyons Ln, Chestertown, MD - $669,000

Residential, Detached
  • 4 Beds
  • Baths
  • 101 DOM
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Premium Materials And Finishes,including Yellow Pine Floors Reclaimed From Camden Yards,really Set This Waterfront Cape Apart.crown Moulding,wainscoting,panel Doors,fireplace,sun Room And Master On First Floor Are Among The Many Amenities.studio W...

Photo of Listing #1001511428

303 Queen St N, Chestertown, MD - $625,000

Residential, Detached
  • 4 Beds
  • Baths
  • 216 DOM
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This Lovely Four-bedroom Home Has The Best Of Everything: Walk-to-town Neighborhood, Chester River Views, Water Access For Kayaks, Canoes, And Mini Sailboats. Features A Beautifully Landscaped, Easy To Maintain Yard. Patio And Gardens. The First F...

Photo of Listing #1005560717

7689 Waterview Ln, Chestertown, MD - $625,000

Residential, Detached
  • 4 Beds
  • Baths
  • 4,138 SQFT
  • 325 DOM
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Beautiful Home Placed Along The 13th Fairway Of The Chester River Yacht & Country Club. Sit In The Pool, Porch, Hot Tub, Enjoy The Manicured Golf Course With Views Of The Chester River In The Distance.1st & 2nd Floor Masters Sitting Room,washer/dr...

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.

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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 December 19th, 2018 at 5:30am EST.