Chestertown MD Real Estate & Homes for Sale


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Type:
Single Family-Detached
Sq.Ft.:
1,584
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE116036
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the home, including original windows, beams, hardwood floors, bookcases, and more. 3 spacious bedrooms, all with restored hardwoods, master with ensuite bathroom (a rare find in a historic home)! Further family bathroom offering double vanities and tub/shower. Laundry and half bath on main level. Large great room addition on the back of the house, with sliders to deck, overlooking private back yard. Home was just completely renovated in 2019 including new 2 x Zone heat pump with central A/C, tankless hot water (propane), complete new wiring, new kitchen and baths, new windows, new stainless appliances, new/restored floors, and more!

Type:
Townhouse
Sq.Ft.:
1,876
Status:
Active
Beds:
3
Lot size:
0.05 Acres
Year built:
2005
Baths:
3.00
MLS#:
MDKE116012
Subdivision:
Oak Hollow

ADDITIONAL INFORMATION

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!

Type:
Single Family-Detached
Sq.Ft.:
3,204
Status:
Active
Beds:
4
Lot size:
2.05 Acres
Year built:
1990
Baths:
3.00
MLS#:
MDKE116014
Subdivision:
Orchard Hill

ADDITIONAL INFORMATION

Spacious multilevel home with 2 story entrance foyer. Recently updated kitchen with Quartz counters, newer looking cabinets and new stainless steel appliances. New flooring in the family room with wood burning fireplace. There is also a living room with a wood burning fireplace. There is a formal dining room and a rear screened porch. The laundry room is huge and has an additional refrigerator. The HVAC is all new as well!! Property backs to woods and farm land. The garage has space for a small workshop. One of the best locations in Orchard Hill!

Open House:

Sunday, 2/23 1:00-3:00PM

Type:
Townhouse
Sq.Ft.:
2,200
Status:
Active
Beds:
3
Year built:
2007
Baths:
3.00
MLS#:
MDKE116006
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

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!

Type:
Single Family-Detached
Sq.Ft.:
2,186
Status:
Active
Beds:
4
Lot size:
0.69 Acres
Year built:
1971
Baths:
2.00
MLS#:
MDKE116022
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

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.

Type:
Single Family-Detached
Sq.Ft.:
3,248
Status:
Active
Beds:
3
Lot size:
213 Acres
Year built:
1856
Baths:
3.00
MLS#:
MDKE115982
Subdivision:
None Available

ADDITIONAL INFORMATION

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.

Type:
Single Family-Detached
Sq.Ft.:
1,190
Status:
Active
Beds:
2
Lot size:
0.13 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE115990
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

This in town location is perfect - walk to shops and restaurants and enjoy all the activities that Chestertown has to offer. The home is in good condition with new carpet on the first floor. Updated kitchen as well. Come take a look!

Type:
Single Family-Detached
Sq.Ft.:
1,296
Status:
Active
Beds:
3
Lot size:
0.5 Acres
Year built:
1968
Baths:
2.00
MLS#:
MDKE115922
Subdivision:
Kent Acres

ADDITIONAL INFORMATION

This property checks all the boxes! Fantastic location, convenient to Chestertown, with a private, partially wooded lot backing to trees, with no HOA! The 3 bedroom, 2 bathroom ranch-style home offers an updated kitchen with durable composite tile floors, wood cabinets, Corian counters, stainless steel appliances, and a large kitchen island with wood top. The kitchen and dining areas open to the huge living room with beautiful hardwood floors and a wood burning fireplace. Refinished hardwood floors continue down the hall and into each of the bedrooms. The master suite offers an updated bathroom with ceramic tile flooring, double vanity with quartz counters, and a tiled shower with marble floor. A full, unfinished basement adds additional storage and usable space, while the carport offers covered parking. Freshly painted and landscaped, this property is move-in ready!

Type:
Single Family-Detached
Sq.Ft.:
6,105
Status:
Active
Beds:
5
Lot size:
0.97 Acres
Year built:
2002
Baths:
6.00
MLS#:
MDKE115970
Subdivision:
Tolchester

ADDITIONAL INFORMATION

An exceptional architect-designed 6,105 square foot home perched 100 feet-high on a bluff overlooking 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. Floors throughout are finished in quarter-sawn red oak. Bluestone surrounds the house and continues into the entryway that provides a dramatic dining space with a 17-foot ceiling and a waterview as the backdrop. Sweeping open floor plan is graceful and elegant in its simplicity - 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, complete with a Thermador gas cooktop and electric double oven, two Subzero refrigerators, a Subzero freezer, under-counter Subzero refrigerator drawers, granite counters, and adjoining butler's pantry and many more custom features. A must see. First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Nationally known artisan-designed cherry stair rail leads to the guest floor with four bedrooms, three full baths and a huge bonus room, which could make a wonderful studio or game room. There are never-ending bay views from almost every room in the house. Heating and cooling is provided by a geothermal system. A three-car garage continues the house exterior design with matching trim and cedar shingles. 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. By appointment only. This is one of the finest designed homes on the Eastern Shore. Be sure to allow plenty of time for your tour.

Type:
Single Family-Detached
Sq.Ft.:
1,008
Status:
Active
Beds:
3
Lot size:
1.27 Acres
Year built:
1961
Baths:
1.00
MLS#:
MDKE115964
Subdivision:
None Available

ADDITIONAL INFORMATION

All new inside and out, freshly finished and ready for you to move in. New roof, windows, siding, gutters, crawl space encapsulated. Original hardwood flooring sanded and stained. New all-wood construction cherry kitchen cabinets. New HVAC, new well, and a HUGE Garage with an attached workshop. Beautifully situated in a peaceful, park-like setting.

Type:
Single Family-Detached
Sq.Ft.:
1,128
Status:
Active
Beds:
3
Lot size:
1.66 Acres
Year built:
1970
Baths:
1.00
MLS#:
MDKE115936
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Near Rock Hall, MD. Great 3 bedroom, bath Ranch home on 1.66 acres in Chestertown, MD. This home is a great starter home or for downsizing. It has a large living room and dining room off the kitchen. Hardwood floors. The yard is flat with open space that backs to woods. The front of the house faces farm fields. If you are looking for peace and quiet you will find it here. It is definitely worth a look. All HUD homes are sold "As Is".

Type:
Single Family-Detached
Sq.Ft.:
1,658
Status:
Active
Beds:
3
Lot size:
0.58 Acres
Year built:
1999
Baths:
2.00
MLS#:
MDQA141974
Subdivision:
Kingstowne Manor

ADDITIONAL INFORMATION

Very nice rancher in QA Co just minutes from downtown Chestertown. This home features a large LR with gas FP, wood floors, vaulted ceiling & skylights. Separate DR also has wood floors. Spacious kitchen has corian counters and a sunny bay window. A sunroom was added off the LR which leads to a deck. Fully fenced back yard. There is a new heat pump with propane backup and water heater. Pack your bags - this home is move in ready! Photos coming next week.

Type:
Single Family-Detached
Sq.Ft.:
2,076
Status:
Active
Beds:
6
Lot size:
0.07 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE115928
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Investment opportunity! Multi unit in Downtown Chestertown offers 3 units, 1st floor (largest) is a 3 bedroom 1 bath, washer/dryer & has rented for $950/month, 2nd floor is a 2 bedroom 1 bath and has rented for $850 but currently empty & 3rd floor (attic) is a studio (needs work) but can be rented at $450/month. Second floor unit was recently updated in 2018 with a new kitchen, mahogany porch, floors sanded and re-stained, windows sanded down and painted to make lead testing easier, new ceiling and so much more. All units are separately metered and have a great rental history. Make your money back in less then 10 years! If that doesn't interest you, convert it back into a single family home!

Type:
Single Family-Detached
Sq.Ft.:
1,456
Status:
Active
Beds:
3
Lot size:
0.8 Acres
Year built:
1986
Baths:
2.00
MLS#:
MDKE115894
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

Great rancher in Heather Heights. Easy one floor living. Attached garage. 3 bedrooms, 2 bath. Nice rear deck over looking a great back yard. New carpeting, updated bathrooms, new stainless steal appliances, fresh paint. Close to town.

Type:
Single Family-Detached
Sq.Ft.:
1,152
Status:
Active
Beds:
3
Lot size:
0.02 Acres
Year built:
1920
Baths:
1.00
MLS#:
MDKE115906
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Enjoy living in Historic Chestertown, short distance to downtown, shopping, and restaurants and the Chester River. Well maintained 3 BR, 1 BA home, enclosed front porch with heat. Nice cozy home for first time homebuyers or investors.

Type:
Single Family-Detached
Sq.Ft.:
3,500
Status:
Active
Beds:
3
Lot size:
1.8 Acres
Year built:
1996
Baths:
2.00
MLS#:
MDKE115874
Subdivision:
Fairlee Cove

ADDITIONAL INFORMATION

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, 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!

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
3
Lot size:
1 Acres
Baths:
2.00
MLS#:
MDQA141960
Subdivision:
Blakefield

ADDITIONAL INFORMATION

NEW CONSTRUCTION GETTING READY TO GET STARTED. 8 LOTS TO PICK FROM. 3 BED 2 BATH RANCHER WITH GARAGE. OR BRING THE BUILDER YOUR PLANS FOR A PRICE.

Type:
Single Family-Detached
Sq.Ft.:
1,848
Status:
Active
Beds:
4
Lot size:
0.69 Acres
Year built:
1989
Baths:
2.00
MLS#:
MDQA141902
Subdivision:
Pear Tree Point

ADDITIONAL INFORMATION

SUMMER FUN AWAITS! GET IN NOW AND BE READY TO LIVE LIFE ON THE EASTERN SHORE. PEACE AND QUIET ABOUND AT THIS BEAUTIFUL CAPE COD. ACROSS THE STREET FROM THE CHESTER RIVER, CLOSE TO CHESTERTOWN, COUNTY PARK AND LOCAL POINTS OF INTEREST. (DEEDED R-O-W TO CHESTER RIVER, SUITABLE FOR LAUNCHING KAYAK, CANOE, OR SMALL CRAFT) HOME FEATURES LARGE BEDROOMS, BRAND NEW UPGRADED KITCHEN COUNTER TOP, FRESH PAINT AND NEW CARPET UPSTAIRS. LARGE, LIGHTED DECK FOR RELAXING AND 24 X 32 DETACHED GARAGE BUILT ON 6IN CONCRETE SLAB AND INCLUDES 220 OUTLET FOR THE HOME WORKSHOP, PLUS ADDITIONAL STORAGE SHED.

Type:
Single Family-Detached
Sq.Ft.:
3,850
Status:
Active
Beds:
5
Lot size:
0.73 Acres
Year built:
1990
Baths:
3.00
MLS#:
MDKE115886
Subdivision:
Country Club Estates

ADDITIONAL INFORMATION

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!

Type:
Single Family-Detached
Sq.Ft.:
1,800
Status:
Active
Beds:
3
Lot size:
0.18 Acres
Year built:
1948
Baths:
2.00
MLS#:
MDKE115880
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

A must see charming renovation in a private setting! The home features 3 bedrooms, 2 full bathrooms, hardwood and ceramic tile floors, efficient geothermal HVAC, a new roof, and hardiplank siding. Improved with a 4 zone home stereo system, horseshoe pit, outdoor shower and detached garage, this home is great for entertainment. Tolchester Marina and the Shanty Tiki Bar are within walking distance making this move in condition property is the perfect full time residence or weekend getaway. The sale includes 3 neighboring lots for a total of .459 acre to secure the private setting.

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
3
Lot size:
1.25 Acres
Year built:
2019
Baths:
3.00
MLS#:
MDQA141818
Subdivision:
Pearl Creek Estates

ADDITIONAL INFORMATION

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.

Type:
Single Family-Detached
Sq.Ft.:
5,794
Status:
Active
Beds:
5
Lot size:
24.83 Acres
Year built:
1975
Baths:
5.00
MLS#:
MDKE115864
Subdivision:
None Available

ADDITIONAL INFORMATION

Rare (for Kent County) and exceptionally exciting, ultra-contemporary residence is situated on a promontory above twenty-five private pastoral acres. The combination of the position of the main house above the open natural grounds below featuring a breathtaking view of a pond with a "mile-high" fountain, a stream, woods and wildlife. You are on the level of the flight of birds. "Sophistication", "alluring" and extremely "comfortable" are the words that come to mind. The owner has thought of even the most minor detail. One is part of nature and yet is able to enjoy all the amenities of today. This property satisfies the desire for privacy and nature while also offering a lap pool, sauna, exercise area, whirlpool tub, hot tub, expansive windows and multiple level deck. There is an apartment adjacent to carport/garage where caretaker lives but could also be additional guest quarters. After passing through the entrance gates one is enveloped by a feeling of privacy and a sense that you are entering a "very special place".

Type:
Single Family-Detached
Sq.Ft.:
1,080
Status:
Active
Beds:
3
Lot size:
6.51 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDQA141822
Subdivision:
None Available

ADDITIONAL INFORMATION

12.34 TOTAL ACRES, Includes 2 Parcels in Queen Anne's County. 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

Type:
Single Family-Detached
Sq.Ft.:
1,720
Status:
Active
Beds:
3
Lot size:
0.93 Acres
Year built:
1979
Baths:
2.00
MLS#:
MDKE115862
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

Great single family ranch located in Heather Heights. Loads of outdoor living space with nearly 1 acre lot, detached 2 car garage and shady enclosed porch ! Many recent updates to baths, flooring, and kitchen. MBR features private MBA with shower. Convenient location to downtown shopping and restaurants as well as the Chester River Yacht and Country Club. Bring the boat and move in !

Type:
Single Family-Detached
Sq.Ft.:
800
Status:
Active
Beds:
2
Lot size:
0.54 Acres
Year built:
1943
Baths:
1.00
MLS#:
MDKE115846
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

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

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26–50 of 104 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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