Luxury Homes for Sale & Real Estate

contract signed

Chandelier, Interior, Living room, Wood Texture Flooring

Chandelier, Dining room, Interior, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring, Wooden Walls

Interior, Piano, Recessed Lighting, Water, Wood Texture Flooring, Wooden Walls

Home Office, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring, Wooden Walls

Chandelier, Dining room, Fireplace, Interior

Chandelier, Dining room, Fireplace, Interior, Wood Texture Flooring

Chandelier, Dining room, Interior, Wood Texture Flooring

Interior, Living room, Recessed Lighting

Dining room, Interior, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Wood Texture Flooring

Bedroom, Fireplace, Interior, Recessed Lighting

Chandelier, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Fireplace, Home Office, Interior

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Recessed Lighting

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Fireplace, Interior, Wood Texture Flooring

Bedroom, Interior, Wood Texture Flooring

Interior, Living room, Wood Texture Flooring

$4,850,000

23620 LANDS END Rd, Chestertown, MD

5 br6 BA, 2 HALF BA9,852 sf

virtual tour

Listing Courtesy of CROSS STREET REALTORS LLC, RICHARD KEAVENEY - 410-708-6470

contract signed

$3,000,000

CROMWELL CLARK Rd, Chestertown, MD

Listing Courtesy of THE LAND GROUP, BRIAN MORRIS - 410-708-1984

Attached, Exterior, Facade, Raised Ranch

Dining room, Interior, Living room, Water, Wood Texture Flooring

Fireplace, Interior, Living room, Wood Texture Flooring, Wooden Walls

Fireplace, Interior, Living room, Wooden Walls

Dining room, Fireplace, Interior, Living room, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Wood Texture Flooring

Bedroom, Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wood Texture Flooring

Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Fireplace, Free Standing Baths, Glass Shower, Interior, Marble Walls, Recessed Lighting, Stone Walls, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Chandelier, Dining room, Interior, Wooden Beams, Wood Texture Flooring

Chandelier, Dining room, Interior, Living room, Wooden Beams, Wood Texture Flooring

Chandelier, Dining room, Fireplace, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Chandelier, Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wooden Beams, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble Walls, Recessed Lighting

Interior, Recessed Lighting, Utility Closets, Washer

$2,750,000

7989 QUAKER NECK Rd, Chestertown, MD

5 br4 BA, 1 HALF BA4,305 sf

virtual tour

Listing Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY, PETER D HELLER - 410-708-3301

Attached, Exterior, Facade, Queen Anne Victorian

$1,800,000

LITTLE HARBOR WAY 1, Chestertown, MD

4 br3 BA, 1 HALF BA3,540 sf

virtual tour

Listing Courtesy of GUNTHER-MCCLARY REAL ESTATE, JOHN J BURKE - 443-206-3727

contract signed

Fireplace, Interior, Living room, Recessed Lighting, Water, Wood Texture Flooring

Fireplace, Interior, Living room, Recessed Lighting

Fireplace, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Living room, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Water, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Water, Wood Texture Flooring

Fireplace, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Billiard Table, Game Room, Interior, Water

Game Room, Interior, Recessed Lighting, Wood Texture Flooring

Billiard Table, Game Room, Interior, Recessed Lighting, Wood Texture Flooring

Game Room, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Water, Wood Texture Flooring

Interior, Piano, Water, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Water, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

$1,550,000

7961 QUAKER NECK Rd, Chestertown, MD

5 br4 BA4,167 sf

virtual tour

Listing Courtesy of COMPASS, GRETCHEN V WICHLINSKI - 410-490-7779

Exterior, Facade, Brick Facade, Queen Anne Victorian

Empty room, Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Empty room, Interior, Wood Texture Flooring

Bathroom, Empty room, Interior, Recessed Lighting

Bathroom, Empty room, Interior, Wood Texture Flooring

$1,395,500

105 HIGH St, Chestertown, MD

5 br4 BA, 1 HALF BA3,243 sf

Listing Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY, MICHAEL ONEILL - 443-480-4275

$1,250,000

120 SPEER Rd, Chestertown, MD

Listing Courtesy of MACKENZIE COMMERCIAL R E SVCS, LLC, JOHN SCOTT WIMBROW - 410-821-8585

Exterior, Facade, Brick Facade, Rowhouse

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

$1,250,000

329 HIGH St, Chestertown, MD

Listing Courtesy of CROSS STREET REALTORS LLC, RICHARD KEAVENEY - 410-708-6470

contract signed

Fireplace, Interior, Wood Texture Flooring

Interior, Sun Room, Wood Texture Flooring

Dining room, Interior, Living room, Sun Room

Chandelier, Dining room, Fireplace, Interior, Piano, Wood Texture Flooring

Dining room, Fireplace, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Dining room, Interior, Piano

Dining room, Interior, Kitchen, Pendant Lights, Wood Texture Flooring

Dining room, Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Home Office, Interior, Wood Texture Flooring

Backyard, Exterior, Facade, Queen Anne Victorian

Fireplace, Interior, Living room, Wood Texture Flooring

$1,250,000

119 HIGH St, Chestertown, MD

5 br4 BA, 1 HALF BA4,409 sf

Listing Courtesy of CROSS STREET REALTORS LLC, RICHARD KEAVENEY - 410-708-6470

Dining room, Interior, Recessed Lighting

Chandelier, Dining room, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Empty room, Interior, Wooden Beams, Wooden Ceilings, Wooden Walls

Attached, Backyard, Exterior, Facade, None

$1,198,000

300 HICKORY Ln, Chestertown, MD

5 br3 BA, 1 HALF BA3,640 sf

Listing Courtesy of GUNTHER-MCCLARY REAL ESTATE, JOHN J BURKE - 443-206-3727

contract signed

Dining room, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Dining room, Fireplace, Interior, Living room, Recessed Lighting, Wood Texture Flooring

$1,195,000

23393 CACAWAY FARM Ln, Chestertown, MD

3 br3 BA, 1 HALF BA4,446 sf

virtual tour

Listing Courtesy of GUNTHER-MCCLARY REAL ESTATE, ASHTON M KELLEY - 410-708-8144

$1,150,000

206 CANNON St, Chestertown, MD

Listing Courtesy of BENSON & MANGOLD, LLC, BRIAN K GEARHART - 410-310-5179

$1,150,000

206 CANNON St, Chestertown, MD

Listing Courtesy of BENSON & MANGOLD, LLC, BRIAN K GEARHART - 410-310-5179

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

$998,000

226 S WATER St, Chestertown, MD

3 br3 BA, 1 HALF BA

Listing Courtesy of GUNTHER-MCCLARY REAL ESTATE, JOHN J BURKE - 443-206-3727

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances, Wooden Ceilings, Wood Texture Flooring

Attached, Backyard, Exterior, Facade, Cape Cod

Empty room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Empty room, Interior, Kitchen, Recessed Lighting, Wooden Ceilings, Wood Texture Flooring

Empty room, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Wooden Ceilings, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wooden Ceilings, Wood Texture Flooring

Empty room, Interior, Recessed Lighting, Wooden Beams

Fireplace, Interior, Stone Walls, Wooden Walls

Empty room, Fireplace, Interior, Stone Walls

$920,000

492 PEAR TREE POINT Rd, Chestertown, MD

3 br2 BA2,632 sf

Listing Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY, JOSEPH S. CIGANEK - 410-708-3924

$899,000

515 WASHINGTON Ave, Chestertown, MD

Listing Courtesy of ESHORE, FRANKLIN T HOGANS JR. - 410-778-7070

contract signed

Dining room, Interior, Wooden Beams, Wood Texture Flooring

Dining room, Interior, Wood Texture Flooring

Dining room, Interior, Kitchen, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances

$899,000

10050 FORREST Ln, Chestertown, MD

4 br2 BA1,820 sf

Listing Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY, TERRI L KULP - 301-462-9976

Interior, Sun Room, Wooden Beams, Wooden Ceilings

Fireplace, Interior, Wooden Beams, Wooden Ceilings

Empty room, Fireplace, Interior, Kitchen, Recessed Lighting

Interior, Recessed Lighting, Wooden Beams, Wooden Ceilings

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Interior, Kitchen, Pendant Lights, Recessed Lighting

Empty room, Interior, Wooden Beams, Wooden Ceilings

$895,000

10761 KASOTA Rd, Chestertown, MD

3 br3 BA2,582 sf

Listing Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY, MICHAEL ONEILL - 443-480-4275

YOUR NEXT HOME IS WAITING

FOR SALE

VIEW: MAP AND LIST

Luxury listings for sale in 21620

FEATURED IMAGE: DEFAULT

SORT BY: DE EXCLUSIVES

23620 LANDS END Rd, Chestertown, MD

CROMWELL CLARK Rd, Chestertown, MD

7989 QUAKER NECK Rd, Chestertown, MD

LITTLE HARBOR WAY 1, Chestertown, MD

7961 QUAKER NECK Rd, Chestertown, MD

105 HIGH St, Chestertown, MD

120 SPEER Rd, Chestertown, MD

329 HIGH St, Chestertown, MD

119 HIGH St, Chestertown, MD

300 HICKORY Ln, Chestertown, MD

23393 CACAWAY FARM Ln, Chestertown, MD

206 CANNON St, Chestertown, MD

206 CANNON St, Chestertown, MD

226 S WATER St, Chestertown, MD

492 PEAR TREE POINT Rd, Chestertown, MD

515 WASHINGTON Ave, Chestertown, MD

10050 FORREST Ln, Chestertown, MD

10761 KASOTA Rd, Chestertown, MD