Chestertown, MD Homes for Sale

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Home for sale: 24091 Providence Plantation Ln., Chestertown, MD 21620
  • 24 Photos

$3,950,000

Beds: 6 Baths: 5 Full, 1 Half

Single Family Home

Quintessential Eastern Shore waterfront gentleman's estate restored in 1990 to exacting standards with many...

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Brandywine Fine Properties Sothebys International Realty

Wendy Bunch

(877) 730-9377

Home for sale: 101 Water St., Chestertown, MD 21620
  • 19 Photos

$3,850,000

Beds: 6 Baths: 5 Full, 2 Half

Single Family Home

Widehall is one of the foremost examples of mid-Georgian architecture in Maryland and was placed on the register of...

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Brandywine Fine Properties Sothebys International Realty

Laird Bunch

(877) 730-9377

Home for sale: 6904 Pentridge Ln., Chestertown, MD 21620
  • 44 Photos

$1,675,000

Beds: 5 Baths: 4 Full, 1 Half

Single Family Home

"Poorman's Pointe" a dream come true for the original owners from the spectacular landscaping to the...

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Brandywine Fine Properties Sothebys International Realty

Ian Bunch

(877) 730-9377

$995,000

Beds: 3 Baths: 3 Full, 1 Half

Single Family Home

Unique waterfront Federal style brick home located on Upper Fairlee Creek. Private setting surrounded by trees and...

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Brandywine Fine Properties Sothebys International Realty

Laird Bunch

(877) 730-9377

Home for sale: 211 Garland Way, Chestertown, MD 21620
  • 20 Photos
  • Virtual Tour

$316,000

Beds: 5 Baths: 2 Full, 1 Half

Single Family Home

Located on a premium corner lot across from the community open space, this 5 bedroom home features over $40,000 in...

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Coldwell Banker Residential Brokerage-Annapolis Plaza

Charles Kraus

(877) 818-2874

We know your neighborhood and reach the world.

Home for sale: 106 Camelot Dr., Chestertown, MD 21620
  • 25 Photos
  • Virtual Tour

$230,000

Beds: 5 Baths: 3 Full, 1 Half

Single Family Home

Beautiful Colonial in Coventry Farms. Brick exterior, hardwood floors, gourmet kitchen, granite, the works....

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Coldwell Banker Residential Brokerage-Annapolis Plaza

Susannah Barnum

(877) 219-1705

We know your neighborhood and reach the world.

Home for sale: 22607 Handy Point Rd., Chestertown, MD 21620
  • 6 Photos

$4,900,000

Beds: 7 Baths: 5 Full, 2 Half

Single Family Home

Chesapeake Real Estate Associates, Llc

Diana Carlson

(800) 331-0901

$2,950,000

Commercial Building

Valuable property zoned, LI-1 within the town limits of Chestertown. Road frontage on both RT. 291 and Talbot BLVD....

NEW CONSTRUCTION

The Hogans Agency

Matthew Hogans

(800) 446-4267

Home for sale: 9425 Fairlee Rd., Chestertown, MD 21620
  • 2 Photos

$2,500,000

Farm

335+/- acre farm located between Chestertown and Rock Hall. 189+/- acres tillable and 146+/- acres wooded. Tillable...

Doug Ashley Realtors, Llc

Douglas Ashley

(410) 810-0010

Home for sale: 27349 Venaringham Ln., Chestertown, MD 21620
  • 6 Photos

$2,250,000

Beds: 5 Baths: 4 Full, 2 Half

Single Family Home

Waterfront farm on the Chester River with marvelous hunting off the marsh & on 2 ponds. House has 4 BR, 3 1/2...

Sassafras River Realty, Ltd.

William Leager

(410) 778-0238

Home for sale: 27349 Venaringham, Chestertown, MD 21620
  • 2 Photos

$2,250,000

Beds: 5

Building Lot

Waterfront farm on the Chester River with marvelous waterfowl hunting off the marsh and on 2 ponds. Conveniently...

Sassafras River Realty,Ltd./Land Source, Llc

Wm David Leager

(410) 778-0238

Home for sale: 7637 Quaker Neck Rd., Chestertown, MD 21620
  • 6 Photos

$1,595,000

Beds: 7 Baths: 4 Full

Single Family Home

Perched on 33 acres with 1200' of Chester River frontage and panoramic views, the traditional c. 1890 home takes...

Coldwell Banker Chesapeake Real Estate Co

Richard Budden

(410) 778-0330

$1,499,000

Commercial Building

For Sale: 337-337 1/2-339-341 High Street. Commercial location in Historic Downtown Chestertown, Maryland with...

The Hogans Agency

Matthew Hogans

(800) 446-4267

Home for sale: 9545 Chantilly Farm Ln., Chestertown, MD 21620
  • 6 Photos

$1,495,000 (Reduced 05/15/13)

Beds: 3 Baths: 3 Full, 1 Half

Single Family Home

Chesapeake Privacy 24+ acres, 700+ frontage with a nice beach and deep water not far off shore, approx 4,000 sq....

Lacaze Meredith Real Estate

Phil Riordan

(800) 331-0901

Home for sale: Chestertown, MD 21620
  • 6 Photos

$1,450,000

Beds: 5 Baths: 5 Full, 1 Half

Single Family Home

. Chestertown: Beautifully sited on 2. 44 acres, this spacious waterfront home provides sprawling views of Fairlee...

Lacaze Meredith Real Estate

Sheila C. Wheatley

(800) 331-0901

Home for sale: 500 Primrose Point Ln., Chestertown, MD 21620
  • 6 Photos

$1,400,000

Beds: 5 Baths: 5 Full, 2 Half

Single Family Home

Primrose Pt. a first time offering. 20 acres on a private point of land, convenient to Chestertown. Property...

The Hogans Agency Inc.

Lisa Raffetto

(800) 331-0901

Home for sale: 416 Pear Tree Point Rd., Chestertown, MD 21620
  • 6 Photos

$1,395,000

Beds: 5 Baths: 4 Full, 1 Half

Single Family Home

Charming waterfront 3 building compound sitting on 1 Ac. with expansive views over the Chester River. Extensive...

Coldwell Banker Chesapeake Real Estate Co

Lisa Hoon

(410) 778-0330

$1,250,000

Building Lot

Commercial property (3. 10 acres) centrally located at a busy intersection in Chestertown, Md. Extensive...

The Hogans Agency

Matthew Hogans

(800) 446-4267

Home for sale: 25498 Mary Morris Rd., Chestertown, MD 21620
  • 6 Photos

$1,200,000

Commercial Building

Industrial property w/15,000+/- sq. ft. in two buildings on 2. 02 acres near Chestertown. Main building has show...

Sassafras River Realty, Ltd.

William Leager

(410) 778-0238

Home for sale: 6520 Church Hill Rd., Chestertown, MD 21620
  • 6 Photos

$1,200,000

Commercial Building

Highly successful operation 3. 34 acres improved with 5029 SQ FT Gas'n Go Convenience beer and wine store, pizza...

Coldwell Banker Chesapeake Real Estate Co, Llc

Raymond Staats

(410) 822-9000

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Notify me when any of my Saved Properties have a price reduction or get photos added.

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  Chestertown, MD Community Information

Community Information for 21620

Population: 12,833

Median Age: 42

Median Household Income: $58,723

Households with Children: 38.98%

Median Travel Time to Work: 23 minutes

Real Estate Market Information

Median years in residence: 8

Homes Owned: 59.63%

Homes Rented: 29.96%

Homes Vacant: 10.41%

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