Kathy Christensen
410-924-4814

Chestertown MD Real Estate & Homes for Sale

90 Properties Found


Sort Results:
51–75 of 90 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 of 4    Prev | Next
Beds:
3
Baths:
1 Full
Sq.Ft.:
993
Status:
Active
MLS#:
MDKE116152
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.69 Acres
Year built:
1962
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Nice investment property, tenant occupied. Tenant would like to stay.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE116136
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
168.77 Acres
Year built:
2002
Courtesy: Maryland Heritage Properties
View additional info

Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound.

Beds:
n/a
Baths:
Sq.Ft.:
1,503
Status:
Active
MLS#:
MDKE116074
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.09 Acres
Year built:
1939
Courtesy: Doug Ashley Realtors, LLC
View additional info

Great opportunity for someone wanting professional office space or would like to convert into a residence! RB professional zoning permits both! Was used as a law office for many years and would be ideal for the lawyer who is ready to branch out on their own. Recently has had mold remediation, documentation is available. The off street parking included is a premium in this location with 4+/- spaces available. Conveniently located in downtown Historic Chestertown and within the historic district. Formal appraisal completed in fall of 2019 and is currently listed under the appraised value.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,876
Status:
Active
MLS#:
MDKE116012
Type:
Townhouse
Subdivision:
Oak Hollow
Lot size:
0.05 Acres
Year built:
2005
Courtesy: Doug Ashley Realtors, LLC
View additional info

Town-home located in Oak Hollow, a well managed town-home community. This unit is brick fronted with a one car garage. The master bedroom has a cathedral ceiling with large bath with separate shower and tub. There are 2 additional bedrooms on the upper level. The middle level has kitchen with sliders to a rear deck and a living room. The lower level has the garage and an additional room ready for you to finish the way you want it. Close to shopping and restaurants!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE116006
Type:
Condo, Townhouse
Subdivision:
Chester River Landing
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim in the lovely pool, walk the shell walking paths throughout the community and along the shoreline, go kayaking from the community launching area, or take a bike ride or walk into town. Lots of ways to enjoy the care-free Eastern Shore lifestyle! Boat slip available.

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,186
Status:
Active
MLS#:
MDKE116022
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.69 Acres
Year built:
1971
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Just on the market, two story contemporary home located in water community area. Over 2,000 sq. ft., walk to beach and launching area and waterview. 4 BR, 2 BA with dining room and kitchen area, over a half an acre of ground, has a 40 X 24 ft. workshop with electric, and deck on the back of house, seller is offering new buyer's a home warranty.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,248
Status:
Active
MLS#:
MDKE115982
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
213 Acres
Year built:
1856
Courtesy: Cross Street Realtors LLC
View additional info

Middle Plantation Circa 1856, better known as Running Fox Farm, is one of the finest hunting farms in Kent County, Maryland - abundant deer, Canada and Snow geese, dove and turkey. The residence has been meticulously renovated, an extensive, well-documented project that includes upgrades such as 400 amp electric service and wiring, updated plumbing, custom restorations true to the period, and more. 213 acres with 166.6 prime soils, 60.5acres in CRP... all on FIVE 30+ acre subdivided, perc-approved lots.

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
6,105
Status:
Active
MLS#:
MDKE115970
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
0.97 Acres
Year built:
2002
Courtesy: Gunther-McClary Real Estate
View additional info

An exceptional architect-designed 6,105 square foot home perched out of the flood zone on the Chesapeake Bay - the Chesapeake/Delaware shipping channel in full view. Included in the sale is the adjacent .66 acre parcel, "LOT PAR 1-2 ON A PL S/S MONTGOMERY AVE." You'll never tire of watching the ships and daily sunsets through the floor to ceiling windows. Full of light, angles, white walls and stunning views from every window. Plenty of gallery-like spaces to display your art. A chef-designed gourmet kitchen is a cook's dream, with an adjacent butler's panty of equal size.First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Heating and cooling is provided by a geothermal system. Attached three-car garage. Dock your boat at the premier marina just a three minute drive away. Nearby is Rock Hall with more marinas, shops, restaurants, and a world-class jazz venue called the Mainstay. Twelve miles away is historic Chestertown with Washington College and more shops and restaurants. Within two hours to Philadelphia, Baltimore and DC. This is one of the finest designed homes on the Eastern Shore.

Beds:
3
Baths:
2 Full
Sq.Ft.:
3,500
Status:
Active
MLS#:
MDKE115874
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Cove
Lot size:
1.8 Acres
Year built:
1996
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Exceptional architect designed Contemporary residence sited on a 1.8 acre private wooded lot enjoys 190' of protected waterfront, a 110' private dock and 3.5' MLW on Fairlee Creek; one of the prettiest bodies of navigable water in Kent County situated within just 1 nautical mile of the Chesapeake Bay. The property includes three separate living structures: the main house, an office/guest house. and a heated workshop/storage shed that, together, include approximately 3500 square feet of finished living space. The open floor plan interior of the main house features vaulted beaded board ceilings, strategically placed nooks and ledges to showcase art and collectibles, a double sided free standing fireplace between the kitchen and dining area, over sized windows and full-view glass doors overlooking the waterfront and easy care radiant heated tile floors. The cooks delight eat-in kitchen features stainless appliances, granite counter-tops, maple Brookhaven cabinetry, above and under-cabinet lighting, a large walk-in pantry, a built-in maple breakfast table, lovely views of surrounding gardens and the waterfront from the sink area through large space-enhancing corner windows and a double sided wood burning fireplace located between the kitchen and the dining area. A spacious private master bedroom and bath area includes a walk-in closet and a master bath with a tiled walk-in shower and Pearl brand whirlpool bathtub. Generously sized windows in the bedroom frame a serene verdant view through the trees to the water . The open living room features large windows and a brick wood-burning fireplace and opens to a screened porch that spans the waterfront side of the house. A 2011 addition includes a spacious cork floored Great Room with an outdoor deck seating area and a separate outdoor entrance. A discreet stairway leads from the Great Room to a bright and airy 2nd level studio that can, alternatively, serve as a third bedroom. A ships ladder stairway leads from the studio/bedroom up into a delightful tower space that offers birds-eye views of Fairlee Creek. An ingenious arrangement of a hallway and hide-away doors connects the Great Room and studio/bedroom to the first floor guest bedroom and bath; enabling use of this whole wing of the house as private guest or live-in quarters with its own private outdoor entrance. Additional main house rooms include a cozy den adjacent to the kitchen, a bright office area with water views and a separate laundry/utility room. The two outbuildings and carport connect to the main house via raised treated-wood walkways. The heated/air conditioned office/guest house includes a large main room, kitchenette, full bathroom and sleeping loft. The workshop includes a large built-in workbench and storage shelving. Rounding out this unique residential compound are a bluestone central courtyard patio, a roofed 2 car carport and a large outdoor equipment storage shed with sliding doors. Lush native and ornamental plant gardens watered with an automated in-ground irrigation system surround the house and point the way to steps leading down to the dock which has electric service. As if all of this isn't more than enough to support a great lifestyle, the property is located in easy walking distance to the Fairlee Creek Public Landing where area residents can easily off-load trailored boats, canoes and kayaks into Fairlee Creek and just a 15 minute drive to both historic downtown Chestertown and the lively waterfront town of Rock Hall. Plus, this property comes with a one year Home Warranty and has just been reduced $25K! Won't last long at this price!

Beds:
5
Baths:
2 Full/1 Half
Sq.Ft.:
3,850
Status:
Active
MLS#:
MDKE115886
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.73 Acres
Year built:
1990
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located in Country Club Estates, new carpet and fresh paint, this home offers so much. There is a detached 2 car garage, an attached 2 car garage 4/5 bedrooms, a media room, upstairs playroom area, storage galore. The living spaces on the first floor offer loads of space!. A double sided wood burning fireplace, large country kitchen, screened porch, first floor master, a second bathroom on the first floor, you could have three bedrooms on the first floor and 2 on the second. Shows great. Professionally landscaped, the lawn is manicured nicely!. Great curb appeal!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,460
Status:
Active
MLS#:
MDQA141818
Type:
Single Family, Single Family-Detached
Subdivision:
Pearl Creek Estates
Lot size:
1.25 Acres
Year built:
2019
Courtesy: Coldwell Banker Waterman Realty
View additional info

Modern Split Level home To Be Built. Pick your own colors and finishes. Stick built, quality construction. Cathedral ceilings, hardwood floors, granite counter tops, Master Bedroom with attached bath. 2 car garage. Huge lower level for extra living space or bedroom. Peaceful setting. Large lot. Customize to your taste! Stock photos shown, may include upgrades.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,080
Status:
Active
MLS#:
MDQA141822
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
6.51 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

12.34 TOTAL ACRES, Includes 2 Parcels in Queen Anne's County. BOTH PARCELS FOR $175,000! Build your own home, hunting, fishing in private stocked pond, opportunities abound. Parcels must be sold together. Value is in the land, home structure is not safe but electric, well, and septic is on-site. Property sold strictly as-is. Second parcel listed separately, see MDQA141824

Beds:
2
Baths:
1 Full
Sq.Ft.:
800
Status:
Active
MLS#:
MDKE115846
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.54 Acres
Year built:
1943
Courtesy: Gunther-McClary Real Estate
View additional info

What's your pleasure? I cozy little getaway with spectacular views and 24/7 Sunsets or the perfect spot to start your retirement dreams with plenty of options available for future growth. How about both? This two bedroom cottage offer sweeping views of the Chesapeake and all the bay has to offer, with ships passing day and night and on clear days you can see as far as the Bay and Key bridges. This gem in the rough, is less than two hours from Philadelphia and Washington, DC making it the perfect location for a weekend of relaxing and regenerating on the screened in porch. The property also offers a large two car garage to keep all the water toys, kayaks, boats ect

Beds:
5
Baths:
5 Full/2 Half
Sq.Ft.:
7,505
Status:
Active
MLS#:
MDKE115726
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Court
Lot size:
1.45 Acres
Year built:
1992
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
5
Baths:
1 Full
Sq.Ft.:
3,246
Status:
Active
MLS#:
MDKE115820
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.08 Acres
Year built:
1730
Courtesy: Maryland Heritage Properties
View additional info

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.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,642
Status:
Active
MLS#:
MDKE115728
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.08 Acres
Year built:
1995
Courtesy: Cross Street Realtors LLC
View additional info

Gorgeous Victorian replica, 1995 build in the Historic District. 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.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,485
Status:
Active
MLS#:
MDKE115704
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale
Lot size:
3.13 Acres
Year built:
1999
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore waterfront home 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 paneling, wood floors and large brick fireplace create a welcoming cottage ambiance. Recent upgrades include a brand new architectural shingled roof and a new Septic System with B.A.T. (Best Available Technology ) system providing for clean ground water entering the Aqua-fir in the" Critical Area "buffer. 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.

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
5,190
Status:
Active
MLS#:
MDKE115772
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
76.07 Acres
Year built:
1781
Courtesy: Brandywine Fine Properties Sotheby's International
View additional info

SELF SUSTAINING WATERFRONT RESTORED HISTORIC GEM. Looking for separation and the ability to support yourself? Look no further than this 76 acre farm on the quiet Eastern Shore with on- site well and septic, underground utilities, rich soil for gardening, fruit trees, dairy barn, crabbing, stocked fishing pond and abundant waterfowl or deer hunting. Add the in-ground heated swimming pool, private dock with electric boat lift, sandy beach in low tide and charming 3BR 2 B guest house for family use or a successful source of Airbnb income. A tenant farmer tills 30 acres of corn or soybeans for more rent with more acreage possible. You can grow or obtain most of life's necessities and be self reliant! 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.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,590
Status:
Active
MLS#:
MDKE115752
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates Add
Lot size:
0.82 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,524
Status:
Active
MLS#:
MDKE115646
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
9.71 Acres
Year built:
1920
Courtesy: Cross Street Realtors LLC
View additional info

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. Check out the video tour: https://www.youtube.com/watch?v=vQTnaS0indc&feature=youtu.be

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,152
Status:
Active
MLS#:
MDKE115642
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.12 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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. High speed internet available on site.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,504
Status:
Active
MLS#:
MDKE115596
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
1.33 Acres
Year built:
1937
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
3
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. High speed internet available on site.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,160
Status:
Active
MLS#:
MDKE115422
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1969
Courtesy: Rock Hall Properties Real Estate
View additional info

Very unique home in Tolchester Estates with breath taking views of the Chesapeake Bay. This home has ceramic tile floors, lots of stone and tile work throughout. Stainless Steel appliances and whirl pool tub in the Master bedroom. Like I said, very unique and beautiful. Definitely a "Must See".

Beds:
2
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.

Refine Property Search
Page 1 | 2 | 3 | 4 of 4    Prev | Next
51–75 of 90 properties displayed

How may I help you?

Get property information, schedule a showing or find an agent






We respect your privacy