Chestertown MD Real Estate & Homes for Sale


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Type:
Single Family-Detached
Sq.Ft.:
7,505
Status:
Active
Beds:
5
Lot size:
1.45 Acres
Year built:
1992
Baths:
7.00
MLS#:
MDKE115726
Subdivision:
Byford Court

ADDITIONAL INFORMATION

Impressive custom built brick waterfront home thoughtfully designed on the Chester River that combines classic elegance with modern open space living. Situated on a 1.45 acre lot just 2 blocks from downtown historic Chestertown , it is perfect for kayaking and canoeing! Main floor master suite, 4 bedrooms with baths, an in-law area, 3 car garage, and screened porch and deck both overlooking the river. The interior features high ceilings, built in shelving, and custom mouldings. Includes a pier with electric and water. Owner is a licensed real estate agent.

Type:
Single Family-Detached
Sq.Ft.:
3,246
Status:
Active
Beds:
5
Lot size:
0.08 Acres
Year built:
1730
Baths:
1.00
MLS#:
MDKE115820
Subdivision:
Historic Chestertown

ADDITIONAL INFORMATION

GEDDES PIPER HOUSE. Most unusual opportunity. Fine brick, Federal house in heart of Chestertown Historic District. Nine fireplaces, graceful stair hall, original details abount PLUS central AC. Private garden. MD Hist. Trust Easements. One block to Fountain Park, two blocks to Chester River and Marina, shops, live theatre, galleries. Four blocks to Washington College.

Type:
Single Family-Detached
Sq.Ft.:
2,642
Status:
Active
Beds:
4
Lot size:
0.08 Acres
Year built:
1995
Baths:
4.00
MLS#:
MDKE115728
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Gorgeous Victorian replica, 1995 build in the Historic District. Seller is offering a $4,000 appliance credit! BRAND NEW windows and siding; refinished mahogany hardwood flooring; elevator access from the basement to the 2nd floor; 3rd floor artists studio; spa room for ultimate relaxation; off street parking lot; only 1 block from the new marina and all that Downtown Chestertown has to offer.

Type:
Single Family-Detached
Sq.Ft.:
1,486
Status:
Active
Beds:
3
Lot size:
0.58 Acres
Year built:
1944
Baths:
3.00
MLS#:
MDQA141672
Subdivision:
Kingstown

ADDITIONAL INFORMATION

Eastern Shore waterfront compound with two separately deeded cottages on the Chester River offers coveted views looking across to the historic Chestertown waterfront, Wide Hall and the Chester River bridge. The main house has sweeping views of the river and is perfectly poised to see Sultana under sail, the Washington College boathouse, visiting Tall Ships and fireworks. Another cottage is set behind the main house with a pathway and in-ground pool between the two. Both houses have 1st floor bedrooms and 2 bedrooms upstairs. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants and pubs. Outdoor enthusiasts can enjoy the Chester River Walk and trails, or embark on a river cruise. Located in Queen Anne~s County, the property has 100-feet of shoreline, a 110-foot dock with 3-1/2 feet MLW and stunning sunsets.

Type:
Single Family-Detached
Sq.Ft.:
3,485
Status:
Active
Beds:
3
Lot size:
3.13 Acres
Year built:
1999
Baths:
4.00
MLS#:
MDKE115704
Subdivision:
Fairgale

ADDITIONAL INFORMATION

Eastern Shore waterfront cottage on Fairlee Creek offers a boat slip with lift at the community pier. Elevated, secluded setting offers sweeping water views. A large deck overlooks the backyard leading to a wood stairway going down to the waterfront. Cedar panelling, wood floors and large brick fireplace create a welcoming cottage ambiance. The Master Suite upstairs opens to a deck with stunning views, and on the first floor is another convenient master suite. Other features include a finished basement with flexible space, a separate garage, workshop and potting shed. A quick walk away is the Fairgale community pond, picnic area and dock. The property is located just 15-minutes from Chestertown. Founded in 1706, Chestertown is a lovely walking town with 18th century homes, shops, restaurants, galleries and pubs. Outdoor enthusiasts can use the Chester River Walk, parks and trails, or embark on a river cruise.

Type:
Single Family-Detached
Sq.Ft.:
1,400
Status:
Active
Beds:
3
Lot size:
0.17 Acres
Year built:
1926
Baths:
2.00
MLS#:
MDKE115678
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

This renovated, meticulously maintained, & upgraded home is MOVE-IN READY! Refinished hardwood floors throughout, updated baths, modern kitchen with stainless steel appliances, ample back porch & private master deck, large & beautiful fully fenced backyard, full basement with storage & laundry, central A/C, & fully foam insulated. This highly sought after street is just a few blocks from downtown, neighbors the Washington College campus, & is convenient to the shopping centers. Chestertown, MD is Eastern Shore Life at its best... come experience it for yourself!

Type:
Single Family-Detached
Sq.Ft.:
5,190
Status:
Active
Beds:
5
Lot size:
76.07 Acres
Year built:
1781
Baths:
6.00
MLS#:
MDKE115772
Subdivision:
None Available

ADDITIONAL INFORMATION

Sellers offering creative financing for sale of this Beautifully Restored Historic Waterfront Farm plus Guest House, Inground Pool, Dock with lift and Tree lined drive. Exquisite restoration features magnificent 1st floor Master Suite with His and Hers baths and Walk-In Closets. A Sportsman Paradise with Hunting, Crabbinig and Boating in a vibrant college town on the Eastern Shore. Owner is a licensed Realtor.

Type:
Single Family-Detached
Sq.Ft.:
1,653
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1975
Baths:
2.00
MLS#:
MDKE115764
Subdivision:
Byford Development

ADDITIONAL INFORMATION

Situated on a corner lot within blocks of Historic Downtown Chestertown and the Chester River, this home is filled with possibilities. Featuring a large kitchen with wood cabinets, tile floor and fireplace, formal dining room, 3 bedrooms and 2 full baths, and a great rear addition. The rear yard is completely fenced and offers mature landscaping and extensive hardscaping. With great bones and a great location, this property is the perfect opportunity!

Type:
Single Family-Detached
Sq.Ft.:
2,656
Status:
Active
Beds:
4
Lot size:
51.55 Acres
Year built:
1900
Baths:
5.00
MLS#:
MDKE115756
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Picture this ~ you drive past the crops, down the tree lined lane, past the barns and there is the river. You have arrived at your own piece of paradise ~ Grassymeade Farm. Situated on 51.55 picturesque acres with expansive views of the Chester River this charming waterfront compound offers something for everyone. Whether you~re looking for hunting, fishing, boating, equine activities and/or a private waterfront getaway you will find it in this special setting. There is a main farm style house with 4BR~s as well as 3 cottages perched on the banks of the Chester River. You will also find a private dock, a sandy beach, a hot tub and an in ground pool with pool house. Then there are the barns! The main barn has 8 stalls, a tack room, hay loft and a large workshop area. There are two more barns one with living space above. Plus 8 acres of fenced pasture with 2 run in sheds. Don~t miss this opportunity to own a unique property in the sought after Quaker Neck area.

Type:
Single Family-Detached
Sq.Ft.:
2,656
Status:
Active
Beds:
4
Lot size:
51.55 Acres
Year built:
1900
Baths:
5.00
MLS#:
MDKE115694
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Picture this ~ you drive past the crops, down the tree lined lane, past the barns and there is the river. You have arrived at your own piece of paradise ~ Grassymeade Farm. Situated on 51.55 picturesque acres with expansive views of the Chester River this charming waterfront compound offers something for everyone. Whether you~re looking for hunting, fishing, boating, equine activities and/or a private waterfront getaway you will find it in this special setting. There is a main farm style house with 4BR~s as well as 3 cottages perched on the banks of the Chester River. You will also find a private dock, a sandy beach, a hot tub and an in ground pool with pool house. Then there are the barns! The main barn has 8 stalls, a tack room, hay loft and a large workshop area. There are two more barns one with living space above. Plus 8 acres of fenced pasture with 2 run in sheds. Don~t miss this opportunity to own a unique property in the sought after Quaker Neck area.

Type:
Single Family-Detached
Sq.Ft.:
3,590
Status:
Active
Beds:
3
Lot size:
0.82 Acres
Year built:
1990
Baths:
4.00
MLS#:
MDKE115752
Subdivision:
Country Club Estates Add

ADDITIONAL INFORMATION

Bright, beautiful and spacious! Lovely home in Country Club Estates with numerous amenities. Wood floors, 3 fireplaces, wainscotting, crown molding, generous sized rooms, artist studio, bonus room over garage and wonderful screened in porch overlooking pool, patio and landscaped grounds. Handsome fence offers privacy. Close to historic Chestertown, Washington College and Chester River Yacht and Country Club.

Type:
Single Family-Detached
Sq.Ft.:
640
Status:
Active
Beds:
2
Lot size:
0.14 Acres
Year built:
1950
Baths:
1.00
MLS#:
MDKE115750
Subdivision:
Chestertown

ADDITIONAL INFORMATION

This could be the perfect investment for you!!! Fix it up and make it your own! Just a few blocks to downtown and the waterfront area! FANTASTIC PRICE!

Type:
Single Family-Detached
Sq.Ft.:
1,460
Status:
Active
Beds:
3
Lot size:
0.38 Acres
Year built:
1965
Baths:
1.00
MLS#:
MDKE115696
Subdivision:
College Heights

ADDITIONAL INFORMATION

Family home time on the market. Handsome home on the corner of Elm and Hadaway in College Heights needs a little bit of loving care to bring it back to its prime. Wood floors under carpet. Large Living Room with Brick wood-burning fireplace. 3 Bedrooms with split Heat-AC units. Kitchen has lots of cabinets. Breakfast area has sliding doors to the backyard. Full basement has play/family room with wood stove.

Type:
Single Family-Detached
Sq.Ft.:
1,404
Status:
Active
Beds:
3
Lot size:
0.38 Acres
Year built:
1994
Baths:
2.00
MLS#:
MDKE115662
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Welcome home in the water access community Chesapeake Landing. This home offers a newly installed "Best Available Technology" septic system, and brand new heating and air conditioning system. The detached shed will convey with the home sale. Inside the home you find carpeted floors with newer floating floor in the kitchen and downstairs bathroom. This home offers 3 beds (one on main level), and two full bathrooms. Home is freshly painted with a deck that looks towards back yard and wooded areas.

Type:
Single Family-Detached
Sq.Ft.:
2,524
Status:
Active
Beds:
4
Lot size:
9.71 Acres
Year built:
1920
Baths:
3.00
MLS#:
MDKE115646
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Outstanding Waterfront property, with excellent deer, turkey, and waterfowl hunting with two impoundment ponds, an irrigation well, and 4.5 +/- tillable acres, on 9.75 acres nestled along Phillips Creek. The restored and renovated farmhouse features hardwood floors and exposed wood beams, as well as 4 bedrooms, 3 full bathrooms, separate living, dining and kitchen spaces and a wood burning fireplace. The partially wooded property offers a secluded respite, as well as a detached oversize garage, a concrete in-ground pool, floating dock, and abundant wildlife. Enjoy private Eastern Shore living within a few minutes of the Historic town of Chestertown.

Type:
Single Family-Detached
Sq.Ft.:
2,152
Status:
Active
Beds:
3
Lot size:
0.12 Acres
Year built:
1920
Baths:
3.00
MLS#:
MDKE115642
Subdivision:
Historic Chestertown

ADDITIONAL INFORMATION

Splendid restoration of this variant four square on Mount Vernon Avenue. Many amenities like tumbled stone floor in shower, heated towel racks. Huge master bath with his and her walk in closets. Upgraded kitchen overlooking family room. Large rooms, stone driveway, Comfortable living close to college and restaurants.

Type:
Single Family-Detached
Sq.Ft.:
1,504
Status:
Active
Beds:
3
Lot size:
1.33 Acres
Year built:
1937
Baths:
1.00
MLS#:
MDKE115596
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

Eastern Shore Chesapeake Bay cottage with sweeping westerly views is set on 1.3 acres in Tolchester Estates. Built in 1930 and offering 200~ of waterfront with beach, the home captures stunning water views of the Chesapeake Bay. Tolchester Marina, a full service marina located just 1-mile away, has a private beach, restaurant, pool, and beach bar. Just 20 minutes away is downtown Chestertown set on the banks of the Chester River. The lovely walking town with 18th century homes offers a river walk, cafes, pubs, shops, theater and waterfront dining. Chestertown is also home to Washington College.

Type:
Single Family-Detached
Sq.Ft.:
2,060
Status:
Active
Beds:
4
Lot size:
1.17 Acres
Year built:
1870
Baths:
2.00
MLS#:
MDKE115586
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Circa 1870 home with Chester River views situated on an acre-plus just blocks from downtown Chestertown and Washington College. Enjoy the private, park-like setting of this hilltop property located in a quiet riverfront neighborhood. The 3-story, 3-4 bdrm/2 bath house recently underwent extensive renovations; updates include a new high-efficiency electric heat pump and AC, new duct work, new hot water heater, new electric service line and panel, new floor system and hardwood floors, and fresh paint throughout. The first floor master offers the option of single-story living while the finished 3rd floor may be used as 4th bedroom or play room. Property includes a separate 32'x16' workshop and office space for your home business and/or studio. The large lot provides ample off-street parking for your vehicles, RV, boat, etc.

Type:
Single Family-Detached
Sq.Ft.:
3,088
Status:
Active
Beds:
3
Lot size:
0.65 Acres
Year built:
1996
Baths:
3.00
MLS#:
MDKE115624
Subdivision:
Crestview

ADDITIONAL INFORMATION

Contemporary Home with hardwood floors, gas fireplace, a Florida Room, deck overlooks beautiful back yard with pond view. First floor master/mother in law suite, which has a second kitchen. Nice flow to this home with a formal living room, dining room, kitchen and family room are open, with the Florida Room . Upstairs has two large bedrooms, a walk in attic, full bath & a balcony with an overlook to the foyer and den. The basement is a full basement with another "lawn" garage for your mowers and equipment, 15' x 21' Amazing storage space in this home! Basement is 24' x 44' in one section, and 28' x 22' in the other section.

Type:
Single Family-Detached
Sq.Ft.:
1,296
Status:
Active
Beds:
4
Lot size:
0.51 Acres
Year built:
1950
Baths:
2.00
MLS#:
MDKE115588
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Buy this home for no money down $1075 est: per month. This home is what you've been waiting for. Completely renovated rancher on over .5 acre lot 100x220 at an affordable price. 4 bedroom/2 full baths with new flooring, recessed lighting, ceramic tile, fixtures. New paint, carpet, exterior siding, windows, roofing. Everything in this kitchen is sparkling and new, appliances, cabinets, granite counters. All new plumbing, electrical, HVAC. Lot is partially wooded for privacy but plenty of space to add shed or garage. Public water & sewer. Preview the photos and call me for a showing.

Type:
Single Family-Detached
Sq.Ft.:
1,640
Status:
Active
Beds:
2
Lot size:
0.79 Acres
Year built:
1981
Baths:
2.00
MLS#:
MDKE115590
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

This beautiful, totally renovated property located in Heather Heights just a short walk to Chestertown , the marina and the Chester River Yacht and Country Club. Set on a large lot , the home offers views of fields and church steeples through oversized windows that ensure plenty of light in every room . The house has a spacious one car garage with plenty of storage space available above it. While the house is currently configured as a two bedroom home with two renovated full baths , the home can be easily converted into a three bedroom house. A family room with working brick fireplace, dining area and very large living room boasts hardwood flooring .The bedrooms , master bath and laundry room have brand new simulated hardwood floors. The kitchen has been completely renovated with new stainless steel appliances and cabinetry. A fully glass enclosed sunroom completes this handsome offering.

Type:
Single Family-Detached
Sq.Ft.:
1,348
Status:
Active
Beds:
3
Lot size:
0.26 Acres
Year built:
1944
Baths:
2.00
MLS#:
MDQA141104
Subdivision:
Kingstown

ADDITIONAL INFORMATION

Cute Cape Cod that was updated 8+/- years ago with replacement windows, heat pump and more. Living room is carpeted but has wood flooring underneath. Dining has wood floors. There is a sitting area/possible office area off the living room. The partial basement is neat and tidy. The rear deck overlooks the private backyard. There is even a one car garage. Property is zoned Suburban Commercial so it allows for uses other than residential. Just a short drive over the Chester River Bridge to Historic Chestertown.

Type:
Single Family-Detached
Sq.Ft.:
2,004
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
1992
Baths:
3.00
MLS#:
MDQA141026
Subdivision:
None Available

ADDITIONAL INFORMATION

AMAZING CONTEMPORARY HOME! Pristine condition following a through renovation from top to bottom including all new roof, skylights, hardwood flooring, carpet, brand new central heating and air conditioning, new wiring, new plumbing, new lighting, and a fully encapsulated crawlspace. The stylish new kitchen has an awesome layout for cooking and entertaining with updgraded stainless appliances, granite countertops, subway tile backsplash, and barnwood accents. The first floor master bedroom features a HUMONGOUS walk in closet and a luxurious private bathroom with tiled shower. The home also boasts a large deck for entertaining and a 1 car attached garage and all of this one just over an acre. At a price like this, it's too good to be true! SELLER NOW OFFERING $5,000 CLOSING HELP!

Type:
Other
Sq.Ft.:
1,476
Status:
Active
Beds:
2
Lot size:
0.08 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE115456
Subdivision:
Historic Chestertown

ADDITIONAL INFORMATION

Quiet Mill St with historic charm. A contemporary open floor plan for this classic Victorian. Original wood floors, East Lake style mantle, bulls eye molding, plantation shutters, wood stove, upgraded kitchen. Large rear yard has a patio, gardens, and paths. Living roof on the shed. Enjoy the church bells. A stone's throw from the library, gym, college, dining and shops. Store your bikes in the side yard.

Type:
Single Family-Detached
Sq.Ft.:
1,200
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1959
Baths:
1.00
MLS#:
MDKE115430
Subdivision:
Chesmar

ADDITIONAL INFORMATION

Just bring your food and clothes for this one! This property is fully furnished and stocked for immediate use. Located on Morgan creek with a 40' dock w/ "L" head. 20 feet deep at the end of the dock. The property has two additional waterfront lots to add to the privacy. Making the total acres around 2.5. The out building has been converted to a game room equipped with windows, sliding door & ceiling fans. The kitchen & bath have been updated. The basement is unfinished, but has been waterproofed. Has been approved and currently in the process of getting a new BAT septic. Well is 2 yrs old. The property is currently being used as a vacation rental. The rental income for 2018 was nearly $18k. It is presently listed on VRBO. No showings will be permitted when property is rented. Agent is Seller.

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51–75 of 103 properties displayed
Thomas H. O’Leary, Maryland License 665968, Xome Inc., License 665968, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Thomas H. O’Leary, D.C. License BR98378780, Xome Inc., License CO98372739, ThomasH.OLeary@Xome.com, 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Thomas H. O’Leary, PA License #RM423918, Xome Inc., PA License #RB067821, ThomasH.OLeary@Xome.com, 844-400-XOME (9663) 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626
Thomas H. O'Leary, NJ License # 1754747, Xome Inc. NJ License # 1861285, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

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