Chestertown | Luxury Homes for Sale & Real Estate

Dining room, Interior, Wooden Beams, Wooden Ceilings, Wood Texture Flooring, Wooden Walls

Dining room, Interior, Wooden Beams, Wood Texture Flooring

Dining room, Interior, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Wooden Beams, Wood Texture Flooring, Wooden Walls

Home Office, Interior, Wood Texture Flooring

Home Office, Interior, Wooden Beams, Wood Texture Flooring, Wooden Walls

Bathroom, Interior, Wood Texture Flooring, Wooden Walls

Elevator, Interior, Wood Texture Flooring

Interior, Kitchen, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Wooden Beams, Wood Texture Flooring

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

Dining room, Interior, Wood Texture Flooring, Wooden Walls

Interior, Kitchen, Pendant Lights, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances

Empty room, Interior, Pendant Lights, Wooden Beams, Wood Texture Flooring

Interior, Pendant Lights, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Recessed Lighting, Wood Texture Flooring

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

$2,400,000

860 & 870 HIGH St, Chestertown, MD

virtual tour

Listing Courtesy of TAYLOR PROPERTIES, JULIE H SANTOBONI - 202-607-6762

$1,870,000

870 HIGH St, Chestertown, MD

virtual tour

Listing Courtesy of TAYLOR PROPERTIES, JULIE H SANTOBONI - 202-607-6762

$1,459,000

LITTLE HARBOR WAY 1, Chestertown, MD

3 br2 ba, 1 half ba2,315 sf

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

open house

Exterior, Facade, Brick Facade, Queen Anne Victorian

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

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, 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

Bathroom, Interior, Wood Texture Flooring

$1,395,000

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

Dining room, Interior, Recessed Lighting, Wood Texture Flooring

$1,250,000

120 SPEER Rd, Chestertown, MD

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

$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

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

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

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, 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

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

Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

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

$950,000

228 S WATER St, Chestertown, MD

3 br3 ba, 1 half ba

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

$895,000

515 WASHINGTON Ave, Chestertown, MD

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

$860,000

860 HIGH St, Chestertown, MD

virtual tour

Listing Courtesy of TAYLOR PROPERTIES, JULIE H SANTOBONI - 202-607-6762

contract signed

Attached, Backyard, Exterior, Facade, Brick Facade, Georgian

Exterior, Facade, Brick Facade, Georgian

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

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

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

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

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

Chandelier, Dining room, Interior, Wood Texture Flooring

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

Interior, Living room, Recessed Lighting, Sun Room

Fireplace, Interior, Living room, Wood Texture Flooring

Bathroom, Bedroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Interior, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting

Fitness Equipment, Interior, Wooden Beams, Wooden Ceilings

Attached, Exterior, Facade, Brick Facade, Cape Cod

Backyard, Exterior, Facade, Brick Facade, Georgian

$795,000

211 DAVID Dr, Chestertown, MD

4 br4 ba4,401 sf

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

contract signed

Interior, Living room, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Wood Texture Flooring

Home Office, Interior, Utility Closets, Washer, Wood Texture Flooring

Attached, Exterior, Facade, Brick Facade, Georgian

$789,000

308 LANDING Ln, Chestertown, MD

3 br2 ba, 1 half ba2,204 sf

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

open house

Interior, Living room, Pendant Lights, Wood Texture Flooring

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

$779,000

212 LANDING Ln, Chestertown, MD

3 br3 ba, 1 half ba

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

contract signed

Attached, Backyard, Exterior, Facade, Farmhouse

Chandelier, Interior, Wood Texture Flooring

Chandelier, Interior, Kitchen, Wood Texture Flooring

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

Chandelier, Interior, Living room, Piano, Wood Texture Flooring

Fireplace, Interior, Living room, Recessed Lighting

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

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

Chandelier, Interior, Sun Room, Wooden Ceilings, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Wooden Ceilings

Bathroom, Glass Shower, Interior, Tile Countertops

Home Office, Interior, Recessed Lighting, Wooden Ceilings, Wood Texture Flooring, Wooden Walls

Interior, Living room, Recessed Lighting, Wooden Ceilings, Wood Texture Flooring, Wooden Walls

Bathroom, Dual Sink Vanities, Glass Shower, Interior

Interior, Wooden Beams, Wooden Ceilings, Wood Texture Flooring, Wooden Walls

$749,900

7988 ALDAN Dr, Chestertown, MD

5 br3 ba3,394 sf

virtual tour

Listing Courtesy of DOUG ASHLEY REALTORS, LLC, DOUGLAS J ASHLEY - 410-708-0480

Exterior, Water, Wooden Beams, Wooden Ceilings

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

Fireplace, Interior, Living room, Pendant Lights, Wood Texture Flooring

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

Bedroom, Fireplace, Interior, Wood Texture Flooring

Fireplace, Fitness Equipment, Home Office, Interior, Wood Texture Flooring

$725,000

117 N WATER St 1A, Chestertown, MD

3 br3 ba

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

open house

Attached, Exterior, Facade, Queen Anne Victorian

Backyard, Exterior, Facade, Queen Anne Victorian

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

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

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

$725,000

100 LITTLE HARBOR Way, Chestertown, MD

2 br2 ba, 1 half ba2,204 sf

Listing Courtesy of KELLER WILLIAMS REALTY CENTRE, JEANNETTE A WESTCOTT - 410-336-6585

Interior, Living room, Recessed Lighting

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

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

Interior, Utility Closets, Washer, Wood Texture Flooring

Fitness Equipment, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Wooden Beams, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble Walls

$649,000

129 N QUEEN St N, Chestertown, MD

3 br2 ba, 1 half ba2,296 sf

Listing Courtesy of SELECT LAND & HOMES, LLC, WILLIAM H NORRIS III - 410-708-0956

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Luxury listings for sale in Chestertown

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860 & 870 HIGH St, Chestertown, MD

870 HIGH St, Chestertown, MD

LITTLE HARBOR WAY 1, Chestertown, MD

105 HIGH St, Chestertown, MD

120 SPEER Rd, Chestertown, MD

206 CANNON St, Chestertown, MD

206 CANNON St, Chestertown, MD

226 S WATER St, Chestertown, MD

228 S WATER St, Chestertown, MD

515 WASHINGTON Ave, Chestertown, MD

860 HIGH St, Chestertown, MD

211 DAVID Dr, Chestertown, MD

308 LANDING Ln, Chestertown, MD

212 LANDING Ln, Chestertown, MD

7988 ALDAN Dr, Chestertown, MD

117 N WATER St 1A, Chestertown, MD

100 LITTLE HARBOR Way, Chestertown, MD

129 N QUEEN St N, Chestertown, MD