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Chestertown Real Estate — Homes For Sale in Chestertown, MD

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$299,000

854 High St

Chestertown, MD 21620
Kent County Public Schools
3bed 3bath 2,274sq ft $131 / sq ft SFR
Lot Size27,000sq ft Built1926 On Site319days
Three bedrooms, 2.5 baths, built in, country kitchen, large enclosed porch and screened in porch off back of house. Hardwood floors seperate dining room, living room, den and... more
Three bedrooms, 2.5 baths, built in, country kitchen, large enclosed porch and screened in porch off back of house. Hardwood floors seperate dining room, living room, den and enclosed porch operated as an insurance agency in the past. Also zoned C1. Call for more information regarding this very functional home! less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
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$2,000,000

10568 Cliff Rd

Chestertown, MD 21620
Kent County Public Schools
12bed 13bath 13,851sq ft $144 / sq ft SFR
Lot Size8.5acre Built1938 On Site324days
Eastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great Oak Manor operates as a B&B offering 12 rooms with private baths, and an owner's quarters. Guests... more
Eastern Shore waterfront manor on the Chesapeake Bay. Recently renovated, Great Oak Manor operates as a B&B offering 12 rooms with private baths, and an owner's quarters. Guests enjoy the tranquil waterfront setting, library, bar, conservatory and other spaces. The Manor is a unique venue for weddings, parties and meetings. 15-min. from Historic Chestertown. Waterfront Building Lot also available. less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
$205,000

201 Maple Ave

Chestertown, MD 21620
Kent County Public Schools
3bed 2bath 1,428sq ft $144 / sq ft SFR
Lot Size1,936sq ft Built1880 On Site325days
Charming 1880's Victorian has a prime location in historic Chestertown only 2 blocks from the Chester River and within walking distance of shops and restaurants. With 3 bedrooms... more
Charming 1880's Victorian has a prime location in historic Chestertown only 2 blocks from the Chester River and within walking distance of shops and restaurants. With 3 bedrooms and 1 1/2 baths and R-3 zoning the commercial or residential possibilities are endless. Partially renovated with lots of original details. A 10' deeded right of way enables off-street parking in rear. Great opportunity! less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
$109,000

108 Conley Dr

Chestertown, MD 21620
Kent County Public Schools
3bed 2bath 1,280sq ft $85 / sq ft TWN
Lot Size2,000sq ft Built1983 On Site335days
Great investment property, or first time home buyer, convenient location close to college, shopping, restaurants, and churches. The home is nicely kept. Patio in rear, attached... more
Great investment property, or first time home buyer, convenient location close to college, shopping, restaurants, and churches. The home is nicely kept. Patio in rear, attached storage shed. Call for an appointment today. less
Listing Provided Courtesy of Champion Realty, Inc.
Popularity N/A
$189,900

23315 Sandpiper Rd

Chestertown, MD 21620
Kent County Public Schools
3bed 1bath 1,392sq ft $136 / sq ft SFR
Lot Size15,000sq ft Built1973 On Site343days
Striking contemporary Cottage in the woods, move-in condition, fully updated & beautifully appointed. The sleek interior boasts a remodeled kitchen and bath with gorgeous... more
Striking contemporary Cottage in the woods, move-in condition, fully updated & beautifully appointed. The sleek interior boasts a remodeled kitchen and bath with gorgeous finishes and a spiral staircase leading to 2 spacious, light-filled bedrooms. Airy first floor art studio/ den/ or utility room. Enjoy the woods in this water access community by relaxing on the deck or covered front porch. less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
$255,000

25750 Collins Ave

Chestertown, MD 21620
Kent County Public Schools
3bed 2bath 1,901sq ft $134 / sq ft SFR
Lot Size33,000sq ft Built1954 On Site350days
Country Club Estates home is conveniently located near the golf course and is just 1.5-miles from downtown Chestertown. The brick home with public sewer features hardwood... more
Country Club Estates home is conveniently located near the golf course and is just 1.5-miles from downtown Chestertown. The brick home with public sewer features hardwood floors, screened porch, full basement and 2-car garage with workshop area. Historic Chestertown on the banks of the Chester River is 90-minutes from Washington, D.C. and Philadellphia. less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
Great investment property! Turn key opportunity with this wonderful property that can be occupied by you or rented as an investment. This house was remodeled in 2011 and has a... more
Great investment property! Turn key opportunity with this wonderful property that can be occupied by you or rented as an investment. This house was remodeled in 2011 and has a good rental history. As a bonus there is a commercial takeout restaurant adjacent to the home that is an additional investment opportunity. Live in this house and run your business next door. Two parcels 827 & 829 High St. less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
Darling Georgian Colonial, well maintained and ready for a new family. Great location between Rock Hall and Chestertown. Property fronts on two roads and may be subdividable,... more
Darling Georgian Colonial, well maintained and ready for a new family. Great location between Rock Hall and Chestertown. Property fronts on two roads and may be subdividable, but check with county. Large lot with additional building and large screened porch, fireplace in living room, wood floors throughout. Whether you are looking for a comfy home or an investment property this one's a winner! less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Waterfront on the Chesapeake - this well constructed Cottage offers 1,995 SF of finished living space with detached guest house. Unobstructed views of the bay are appreciated... more
Waterfront on the Chesapeake - this well constructed Cottage offers 1,995 SF of finished living space with detached guest house. Unobstructed views of the bay are appreciated from every room whether you are entertaining, vacationing or simply relaxing. Appreciate the natural privacy in this peaceful setting suited for telecommuting, reading, writing, reflection....... less
Listing Provided Courtesy of Cross Street Realtors Llc
Popularity N/A
Don't miss out on this great property in the quiet neighborhood of Fairlee. This house has been remodeled inside and is in great shape! Call today to schedule your showing.
Don't miss out on this great property in the quiet neighborhood of Fairlee. This house has been remodeled inside and is in great shape! Call today to schedule your showing. less
Listing Provided Courtesy of The Hogans Agency
Popularity N/A
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful... more
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful Lot #12 Within a few minute's drive to historic Chestertown, home of Washington College. less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful... more
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful Lot #10 Within a few minute's drive to historic Chestertown less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. This lot borders the Chester River Yacht and Country Club's golf course. Mature trees,... more
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. This lot borders the Chester River Yacht and Country Club's golf course. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful Lot #8. Within a few minute's drive to historic Chestertown. less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. This lot borders the Chester River Yacht and Country Club's golf course. Mature trees,... more
Presenting Prestwick! Beautiful new subdivision developed by Alton Darling Construction. This lot borders the Chester River Yacht and Country Club's golf course. Mature trees, amazing views! Let Alton help you build your dream home on this beautiful Lot #9. Within a few minute's drive to historic Chestertown. Beautiful pond view less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Beautiful new subdivision of Prestwick that offer some lots that border the golf course at Chester River Yacht and Country Club. This property has been developed by Alton... more
Beautiful new subdivision of Prestwick that offer some lots that border the golf course at Chester River Yacht and Country Club. This property has been developed by Alton Darling Construction and the model home is being built at present. Gorgeous location. Let Alton Darling Construction help you build your dream home. No builder tie-in. less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
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Local real estate services provided by:
Coldwell Banker Residential Brokerage
Coldwell Banker Residential Brokerage
6031 Univeristy Blvd., Ste 140
Ellicott City, MD 21043
1.844.662.5642
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Data last updated: Thursday, October 2, 2014 at 5:13 AM