Kathy Christensen
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Chestertown MD Real Estate & Homes for Sale

129 Properties Found


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Beds:
3
Baths:
2 Full
Sq.Ft.:
2,928
Status:
Active
MLS#:
MDKE115054
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
1.38 Acres
Year built:
1955
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Water views of the Chester River are a visual delight from this outstanding property on the Eastern Shore. Set on 1.3-acres in a highly-desirable residential area, the meticulously cared for home is just a walk away from Chester River Yacht & Country Club and is 1-mile from historic Chestertown. The open design creates generously sized, bright rooms with lovely views inviting outdoor living. Notable highlights such as wood detail, built in bookcases and a fireplace create a warm ambiance. The terrace overlooking gardens and the pond offers a serene setting, while the screened porch offers a lovely spot to enjoy the river views. Visitors and residents alike stroll around downtown Chestertown with its picturesque 18th century homes, brick walkways, Chester River Walk and marina. Enjoy the cafes, galleries, pubs, shops, live theater, farmers market, trails, First Friday, or take a river cruise on the Chester River Packet. There is a vibrant arts community and the town~s annual events include the Chestertown Tea Party, Harry Potter Festival and the Tall Ship Downrigging Weekend. Chestertown is home to Washington College and is located about 90-minutes from Washington and Philadelphia.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,138
Status:
Active
MLS#:
1001973778
Type:
Single Family, Single Family-Detached
Subdivision:
Long Cove Court
Lot size:
3.28 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Nature's paradise on Lovely Cove-enjoy a short and peaceful boat/kayak ride from your private dock to the East Fork of Langford Creek. This comfortable waterfront home celebrates 180 degrees water views, available from virtually all rooms. Outbuildings include garage area, workshop, storage, and potting shed. Over 3 1/4 acres of woods, cleared and privacy. Your own dock and 9 Ft. wide concrete launching ramp.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE114994
Type:
Single Family, Single Family-Detached
Subdivision:
Prestwick
Lot size:
1.6 Acres
Courtesy: Gunther-McClary Real Estate
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Spec home located on corner lot located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area~s finest builders.

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,064
Status:
Active
MLS#:
1006633640
Type:
Single Family
Subdivision:
None Available
Lot size:
0.06 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Live in the heart of Historic Chestertown, Water views of the Chester River from the back of the house. Historic Water Street in front. Charming Colonial Revival house overlooking Washington College's Presidents gardens. A great place to sit on back or front porch and watch the world go by. Off street parking on the river side, on street parking in front. Easy to show, come and see.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,745
Status:
Active
MLS#:
MDKE115614
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
2.34 Acres
Year built:
1986
Courtesy: Doug Ashley Realtors, LLC
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This 3 bedroom, 3-1/2 bath waterfront home is located in a beautiful spot overlooking Morgan Creek, just off of the Chester River. Secluded and private but only 5 miles from all the charm and events in historic Chestertown. There are views of the water and salt marsh of the creek, the gardens, or the rolling hills of the surrounding farms from almost every room in the house. This is a great home for entertaining family and friends with generous, light filled rooms, a spacious kitchen with an island, enclosed creekside sunroom, large outside deck and a stone patio. Perfect for creating memories with plenty of room for holiday gatherings, crab feasts and outdoor barbecues. The house has a first-floor master bedroom with double closets, separate bathroom and heart wood pine floors. The two bedrooms upstairs each have their own private full baths with a bonus sitting room in between on the landing. Outside, the two-car detached garage has plenty of storage for all your yard toys and kayaks and could easily be converted to a workshop. Wake up in a peaceful spot-teeming with wildlife. Bring your kayak or your boat to launch at the public landing and fish and paddle to your hearts content. Enjoy being surrounded by nature as you watch the seasons change and the eagles, osprey, herons and geese fly by. Sit on the deck, relax, and look over the creek and your own private paradise. A great home to have as a full time resident or as a week-end getaway!!

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

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,972
Status:
Active
MLS#:
MDKE115602
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Bay Estates
Lot size:
1.84 Acres
Year built:
1986
Courtesy: Doug Ashley Realtors, LLC
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Beautiful and Unique, 3 bdr, 3 level, waterfront home. Located in Langford Bay Estates and Nestled back on the West Fork of Langford Creek on Long Cove. This property offers 300ft of bulkheaded shoreline, a private dock with water and electric access for fishing and crabbing year round! 2 large detached garages, carport w/shed for tool storage and a gazebo for relaxing and enjoying the beautiful private surroundings. Adorned with handmade, stained glass, transom windows, a finished basement as a 2nd living area, w/ den (or office) and 1/2 bath, utility room w/workbench and tons of storage area as well as a whole house generator. Open, wrap around deck offers perfect water view and the enclosed sun porch for enjoying the views year round!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE107934
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District Chestertown
Lot size:
0.14 Acres
Year built:
2015
Courtesy: Doug Ashley Realtors, LLC
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Located in historic Chestertown, this home was built in 2015 and is gorgeous. Offers upgrades such as wood floors, gas fireplace, open living room/dining room, with an open kitchen. There is a first floor master suite, a laundry room, a screened porch, semi private picket fenced back yard. So much to love about this home! Detached garage with additional storage. There are three bedrooms all today, with two large rooms upstairs and a large bath. Just a short jaunt to all the fun in downtown Chestertown.

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

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,107
Status:
Active
MLS#:
1000479984
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.81 Acres
Year built:
1976
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Eastern Shore waterfront retreat is privately sited on Mill Creek. Designed with cedar exterior and interior, the single floor home offers a casual ambiance with great room and large windows with water views. A new roof was installed in 2013. The dock, new deck, hot tub and floating dock invite outdoor living. Enjoy historic Chestertown with its River Walk, Washington College, shops and dining.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,378
Status:
Active
MLS#:
MDKE115248
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.42 Acres
Year built:
1963
Courtesy: Sommers Enterprises, Inc.
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This offering of one & 1/4 waterfront acres at the end of a cul de sac sits in a private, park-like setting on Worton Creek. The improved lot is fully bulkheaded with a dock. The well maintained three bedroom, two bath ranch with a waterside three season room has had periodic upgrades during its current ownership

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,268
Status:
Active
MLS#:
MDKE115490
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.47 Acres
Year built:
2004
Courtesy: Doug Ashley Realtors, LLC
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The pictures tell the story. Amazing remodel on this incredible home, with formal living room, dining room, den, family room, Florida Room, full deck, private fenced in back yard. Five bedrooms in all, with a wonderful master suite. The basement has been completely finished, with an incredible media area, play room, wet/dry bar, full bath and bedroom. Come and see this in person.

Open House:

Tuesday, 10/1 11:00-1:00PM

Beds:
3
Baths:
3 Full
Sq.Ft.:
3,088
Status:
Active
MLS#:
MDKE115624
Type:
Single Family, Single Family-Detached
Subdivision:
Crestview
Lot size:
0.65 Acres
Year built:
1996
Courtesy: Doug Ashley Realtors, LLC
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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. Amazing storage space in this home!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDQA140474
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.47 Acres
Year built:
1984
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Affordable waterfront home on Rosin Creek is a wonderful place to relax and unwind. Custom woodwork features include a spiral staircase and walnut kitchen cabinets. The floors are 2x6 tongue and groove pine. First floor bedroom with full bath as well as two bedrooms upstairs that share closets and a full bath. Full unfinished basement with outside entrance - it's dry too! Energy efficient heat pump has oil back up. There is also a wood stove. Relax and enjoy the views of Rosin Creek from your deck! HOA is not mandatory but $20/yr provides access to the community waterfront areas.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,660
Status:
Active
MLS#:
MDKE107896
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District
Lot size:
0.11 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Charm and character abound in this home, renovated and updated inside and out in 2008. Nice layout on main level includes gracious kitchen with wet bar, pantry, powder room, wood stove fireplace insert in family room, open dining room and separate craft room. Second floor offers nice master bedroom with private tiled shower and soaking tub plus two additional bedrooms, ceramic tile bath and bedroom level laundry. Third floor includes an additional finished 500 sq ft with 2 rooms, one of which could be 4th bedroom. Hardwood floors throughout. Privacy fenced back yard with deck overlooks space that will not be developed and includes a cute and functional shed. Off street parking included. Property is ideally located on a desirable street one block from college and an easy walk to downtown. Currently rented but available immediately subject to lease. Leased for $2400/month. Good investment opportunity. Agent related to owners.

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,776
Status:
Active
MLS#:
MDKE114136
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District Chestertown
Lot size:
0.19 Acres
Year built:
2004
Courtesy: Cross Street Realtors, LLC
View additional info

A sanctuary in Downtown Chestertown, this contemporary Craftsman home offers the best of both worlds...a private rear yard and garden retreat, and easy, walk-able access to enjoy all this charming town has to offer! Architectural details and an open design, with a stunning array of high-quality windows to invite an abundance of natural light, custom shades, new appliances, gas fireplace, radiant heat and tankless water heaters. Move in ready!

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,344
Status:
Active
MLS#:
MDKE115216
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Cove
Lot size:
0.85 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Welcome to 'Knot Now Boat House', which has been a very tastefully remodeled home located on Fairlee Creek. This can be a full time residence or your Holiday retreat or week-end get away. Fully updated kitchen with new counter tops, cabinets, and stainless appliances, Wonderful color choices with paint,decorating and flooring. New HVAC system and tankless water heater. Has own private dock with power lift and jet ski ramps. Plenty of room for all your water toys. Detached garage with extra storage area. A must see if your seeking waterfront property with your own private dock.

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,015
Status:
Active
MLS#:
MDKE115210
Type:
Condo, Townhouse
Subdivision:
Historic District Chestertown
Lot size:
0.02 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
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Wonderful Water Street Condo with elevated views, a private balcony, and a boat slip to enjoy the Chester River. Large eat-in kitchen, beautifully renovated with stainless steel appliances, farmhouse sink and custom cabinets. The property also offers an open living room with gas fireplace and views of Chestertown's Historic District, in addition to a Master bedroom, two full bathrooms, and a second bedroom/office space. Perfectly situated to enjoy all the Chester River AND Chestertown's Historic District has to offer!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,087
Status:
Active
MLS#:
MDKE114878
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District
Lot size:
0.09 Acres
Year built:
1753
Courtesy: Cross Street Realtors LLC
View additional info

This wonderful historic home sits only one block from the Chestertown waterfront. It has period details throughout the house and the charm of being in the historic district. The Harris (Malloy) House is a registered Historic Home which offers "in town" lifestyle with an appreciation for historic properties. Convenient to all town amenities and many updated features throughout the home.

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,530
Status:
Active
MLS#:
MDKE113968
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

PRICE IMPROVEMENT! Historic Downtown beauty with numerous recent upgrades has a potential FIRST FLOOR MASTER, sought after off street/driveway parking, within ONE block of the new & improved Chestertown Marina, and in the HEART of everything Chestertown has to offer. Totaling four bedrooms - with the possibility for two more, two bathrooms, gorgeous hardwood floors, huge kitchen with stainless steel appliances, the perfect front porch, and a cozy, low maintenance backyard full of raised bed gardens and entertaining space! What more can you ask for in a Downtown home? A must see.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,023
Status:
Active
MLS#:
MDQA136926
Type:
Single Family, Single Family-Detached
Subdivision:
Pear Tree Point
Lot size:
0.41 Acres
Courtesy: The Hogans Agency Inc.
View additional info

Unique 2,208 square foot home to be built in the water privileged community of Pear Tree Point. 3 BR, 2.5 baths, granite counter tops, wood, carpet and tile floors. This home provides a very functional split-floor plan, an open kitchen layout with plenty of counter space for a growing family and a bonus room over the garage. The plan features an expansive master bedroom / bath with a trayed ceiling and plenty of storage space in his and her walk-in closets. The large great room also includes a trayed ceiling. Front and rear covered porches make the evenings enjoyable. This home is a great value with a wide variety of innovative features. Home to be finished within 120 days of Contract. Water access for $30 annual fee. Water access for $30 annual fee.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,524
Status:
Active
MLS#:
MDKE115388
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.04 Acres
Year built:
1920
Courtesy: Benson & Mangold, LLC
View additional info

Meticulously renovated with stunning details. One of Chestertown~s finest historic renovations. Professionally designed features preserving its original historic charm. A perfect example of what careful planning and style achieves. Close distance to the river, bakery, local coffee shop, waterfront dining, Washington College and the soon to be completed Chestertown Marina. Perfect haven for weekends of year round lifestyle. One must experience to fully appreciate.

Beds:
2
Baths:
1 Full
Sq.Ft.:
800
Status:
Active
MLS#:
MDKE113992
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
0.54 Acres
Year built:
1943
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Location! Location! Location! Cozy 1940's Bay front cottage on .54 acre lot with spacious screened porch & detached 2 bay garage offers incomparable panoramic year round views of the Chesapeake Bay. distant shores & passing ships. In addition, there's access to waterfront on a quiet water inlet on the other side of the property. Rehab the cottage as a cozy get away or tear it down and build your dream house on the Bay. Flood insurance not required. Grandfathered over-sized lot affords lots of options for new home siting and sizing. Public sewer. Community beach access. Down the road from a full service Marina. A rare find!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,600
Status:
Active
MLS#:
MDKE115520
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.05 Acres
Year built:
1852
Courtesy: Select Land & Homes, LLC
View additional info

A charming colonial on S Kent Street. This tasteful renovation features 3 bedrooms, 2 full updated bathrooms, pine and slate floors, updated HVAC,a new roof, and modern kitchen. Enjoy the open floor plan which leads out to a brick patio and gardens. Located on a quiet street this home has the conveniences of walking to the downtown waterfront, shops and restaurants. The historical charm and move in condition truly make this home a must see!

Open House:

Saturday, 10/5 10:00-12:00PM

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
1,476
Status:
Active
MLS#:
MDKE115456
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

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