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Chestertown Real Estate — Homes For Sale in Chestertown, MD

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$3,900,000

22607 Handy Point Rd

Chestertown, MD 21620
Kent County Public Schools
7bed 7bath 10,328sq ft $378 / sq ft SFR
Lot Size21.0acre Built1785 On ZipRealty78 days
Magnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This Georgian Colonial was beautifully renovated & expanded, preserving its historic grandeur. Majestically... more
Magnificent 18th century estate w/1000' waterfront on Chesapeake Bay! This Georgian Colonial was beautifully renovated & expanded, preserving its historic grandeur. Majestically sited on a tranquil point surrounded by 2000-acre environmental trust w/spectacular bay views, sandy beach & formal gardens. Granary converted to recreation rooms + indoor pool, 4-stall stable, pastures & 3BR guest house less
Listing Provided Courtesy of Long & Foster Real Estate, Inc.
Popularity N/A
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$189,000

604 Cannon St

Chestertown, MD 21620
Kent County Public Schools
3bed 1bath 1,416sq ft $133 / sq ft SFR
Lot Size8,039sq ft Built1942 On ZipRealty78 days
House on Cannon Street, needs some cosmetic work. In historic part of Town. Full basement, attic, 3 bedrooms, front porch. Lot of potential. Deep lot.
House on Cannon Street, needs some cosmetic work. In historic part of Town. Full basement, attic, 3 bedrooms, front porch. Lot of potential. Deep lot. less
Listing Provided Courtesy of The Hogans Agency Inc.
Popularity N/A
$495,000

7800 Quaker Neck Rd

Chestertown, MD 21620
Kent County Public Schools
3bed 3bath 3,265sq ft $152 / sq ft SFR
Lot Size42,613sq ft Built1940 On ZipRealty78 days
Wow! All the benefits of waterfront without waterfront prices or taxes. Well built home with wide view of the Chester River. Within walking distance to Yacht Club. Stunning... more
Wow! All the benefits of waterfront without waterfront prices or taxes. Well built home with wide view of the Chester River. Within walking distance to Yacht Club. Stunning setting less than a mile from downtown! less
Listing Provided Courtesy of Benson & Mangold, Llc
Popularity N/A
$249,000

507 High St

Chestertown, MD 21620
Kent County Public Schools
3bed 2bath 1,465sq ft $170 / sq ft TWN
Lot Size3,036sq ft Built1900 On ZipRealty80 days
Absolutely Adorable! This downtown Colonial is one of character and charm that preserves the historic beauty of its time. If you are looking for a quality home in an amazing... more
Absolutely Adorable! This downtown Colonial is one of character and charm that preserves the historic beauty of its time. If you are looking for a quality home in an amazing in-town location - this is it. Central air, rear patio with fenced rear yard, deep front porch, wood floors throughout the interior. 1,465 Sq.ft. A must see! less
Listing Provided Courtesy of Cross Street Realtors Llc
Popularity N/A
$198,000

24731 Langford Rd

Chestertown, MD 21620
Kent County Public Schools
3bed 2bath 1,704sq ft $116 / sq ft SFR
Lot Size2.4acre Built2002 On ZipRealty80 days
Recently renovated 3 Bedroom rancher, located on the very upper reaches of the East Fork of Langford Creek. Great location just minutes from Chestertown, with 2+ acres for a... more
Recently renovated 3 Bedroom rancher, located on the very upper reaches of the East Fork of Langford Creek. Great location just minutes from Chestertown, with 2+ acres for a quite little retreat, perfect for the first home or downsizing. less
Listing Provided Courtesy of Gunther-mcclary Real Estate
Popularity N/A
$339,900

806 Meadowview Dr

Chestertown, MD 21620
Kent County Public Schools
4bed 4bath 2,162sq ft $157 / sq ft SFR
Lot Size26,440sq ft Built1994 On ZipRealty81 days
This truly is a beautiful home! The Florida/sun porch(added in 2011) or the rear deck is where you will spend most of your time overlooking your private backyard. There are... more
This truly is a beautiful home! The Florida/sun porch(added in 2011) or the rear deck is where you will spend most of your time overlooking your private backyard. There are owners suites on each level and 2 other bedrooms as well. The kitchen has been updated and has a breakfast area but also has a formal dining room for entertaining. Heat pumps were replaced in 2007. Oversized 2 car garage! less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
Impeccably maintained home with more upgrades than can be listed!Open floor plan is perfect for entertaining.Beautiful landscaping, gourmet kitchen with granite countertops,... more
Impeccably maintained home with more upgrades than can be listed!Open floor plan is perfect for entertaining.Beautiful landscaping, gourmet kitchen with granite countertops, hard wood floors, master bath with soaking tub & ceramic tile floor, high efficiency systems, fully finished basement with outside entrance, kitchenette & sauna could be in-law quarters. Optional furniture package available. less
Listing Provided Courtesy of Coldwell Banker Chesapeake Real Estate Co
Popularity N/A
This charming cottage in Chestertown's Historic District offers you a front row seat to all that our town has to offer...Tea Party Festivities, Farmer's Market, The Chester... more
This charming cottage in Chestertown's Historic District offers you a front row seat to all that our town has to offer...Tea Party Festivities, Farmer's Market, The Chester River, Washington College, dining and shopping to name a few. If you are looking to own a piece of history for an affordable price ~ this is your chance. less
Listing Provided Courtesy of Cross Street Realtors Llc
Popularity N/A
Historic home c.1852 has been renovated to preserve the original historic character but decorated with provincial charm. Brick pavers lead to a private low maintenance, fenced,... more
Historic home c.1852 has been renovated to preserve the original historic character but decorated with provincial charm. Brick pavers lead to a private low maintenance, fenced, courtyard garden. All major systems have been replaced and updated to include 2 zone HVAC, slate and pine flooring, Soapstone countertops, fully tiled baths and more! Just a few blocks from downtown and the Chester River! less
Listing Provided Courtesy of Doug Ashley Realtors, Llc
Popularity N/A
First time offered in decades. Every detail has been meticulously considered & executed! One is struck by the sophistication of style and design. Chester River is integral... more
First time offered in decades. Every detail has been meticulously considered & executed! One is struck by the sophistication of style and design. Chester River is integral feature of life-style that includes sun room, dock, boat lift, graceful lawn, willows & peaceful gardens. "Chef's" kitchen, exercise room, 300 bottle wine cellar, bookcases, contemporary lighting. Situated in Historic District. less
Listing Provided Courtesy of Maryland Heritage Properties
Popularity N/A
Immaculate cape cod located on pristine 1.89 acre lot in one of Chestertowns most sought after communities. Interior boasts vaulted ceilings, ground floor master bedroom w/super... more
Immaculate cape cod located on pristine 1.89 acre lot in one of Chestertowns most sought after communities. Interior boasts vaulted ceilings, ground floor master bedroom w/super bath, upgraded kitchen offering granite counter tops, stainless appliances, bread warmer and wine cellar. 3rd bedroom doubles as an office. The screened porch & elevated deck are private and perfect for cookouts. less
Listing Provided Courtesy of Kevin Dey Realty
Popularity N/A
Casual elegance describes this immaculate home with a well designed floor plan and spacious rooms throughout - great for entertaining. Recent upgrades and renovations include... more
Casual elegance describes this immaculate home with a well designed floor plan and spacious rooms throughout - great for entertaining. Recent upgrades and renovations include the kitchen and master bath. Relax on the deck and enjoy the private back yard setting, complete with charming garden areas & a picturesque fish pond. Near Chester River. Contingent on Seller finding home of choice. less
Listing Provided Courtesy of Gunther-mcclary Real Estate
Popularity N/A
Stunning views of the Chesapeake Bay & abundant wildlife are enjoyed by this secluded 23 acre waterfront retreat. Situated within the critical area buffer, the home was rebuilt... more
Stunning views of the Chesapeake Bay & abundant wildlife are enjoyed by this secluded 23 acre waterfront retreat. Situated within the critical area buffer, the home was rebuilt in 2007 & custom designed to maximize water views. Hickory hardwood flooring and cabinetry, an open floor plan & a loft style upper level den - great for entertaining! 1000 ft beachfront, wooded trails and open fields. less
Listing Provided Courtesy of Cross Street Realtors Llc
Popularity N/A
$1,250,000

300 Water St

Chestertown, MD 21620
Kent County Public Schools
7bed 6bath 4,274sq ft $292 / sq ft SFR
Lot Size23,958sq ft Built1910 On ZipRealty105 days
Currently 3 apartments, could be 5, actual acreage is 0.55. In Chestertown's Historic District, but private. Could be one home, many, many possibilities, live on one floor and... more
Currently 3 apartments, could be 5, actual acreage is 0.55. In Chestertown's Historic District, but private. Could be one home, many, many possibilities, live on one floor and rent the rest, etc. less
Listing Provided Courtesy of Gunther-mcclary Real Estate
Popularity N/A
Currently 3 apartments, could be 5, actual acreage is 0.55. In Chestertown's Historic District, but private. Could be one home, many, many possibilities, live on one floor and... more
Currently 3 apartments, could be 5, actual acreage is 0.55. In Chestertown's Historic District, but private. Could be one home, many, many possibilities, live on one floor and rent the rest, etc. less
Listing Provided Courtesy of Gunther-mcclary Real Estate
Popularity N/A
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Data last updated: Wednesday, August 20, 2014 at 5:54 AM