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Chestertown MD Real Estate & Homes for Sale

37 Properties Found

The median home value in Chestertown, MD is $283,000. This is higher than the county median home value of $178,000. The national median home value is $277,796. The average price of homes sold in Chestertown, MD is $283,000. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1–25 of 37 properties displayed
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Beds:
3
Baths:
2 Full
Sq.Ft.:
1,416
Status:
NEW LISTING
MLS#:
MDKE118214
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.35 Acres
Year built:
1991
Courtesy: Gunther-McClary Real Estate
View additional info

Reach out and touch the water, 2+ feet mlw at the dock with privately maintained channel that is just minutes to the Chesapeake Bay. Park like setting just waiting for you to stop by and relax. Well maintained 2/3 bedroom home, very close to Historic Chestertown. .47 acre waterfront parcel included. Separate parcels provide very low overall property tax relative to other waterfronts. Perfect getaway or looking to downsize and live on the water.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,578
Status:
NEW LISTING
MLS#:
MDKE118226
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
1.34 Acres
Year built:
1975
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Chestertown Waterfront home! Dock with 2 boat lifts and deep water! Bring your sailboat 4' at the dock and 20' a short distance out from the dock on the Chester River! Home has everything you could want plus more! Lovely flow floor plan taking advantage of the water views! Gourmet kitchen with gorgeous Slate backsplash and granite counters. Large Kitchen Island to share all your yummy food. Waiting for guests? Pop the food in the plate warmer. Lots of room for entertaining. The primary suite has a Huge Bedroom, 2 Balconies, one for 3 seasons with beautiful views of the water. And the other Balcony is open. Large sitting area and the biggest walk-in closet I've seen! Laundry room with plenty of space. One room is used as a Study but has a closet, so it could easily be turned into a 5th Bedroom. Bamboo and Hardwood floors. Large deck and slate patio, great for relaxing and entertaining. So many amenities, you'll just have to come and check it out!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,008
Status:
NEW LISTING
MLS#:
MDKE118190
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.14 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

New to the market! 3 bedroom 2 bath Victorian in downtown Chestertown. Large front porch, rear deck and large fenced in backyard. Off street parking in rear. Current access thru alley with potential for front driveway access. Original wood floors throughout, in great condition. Both baths have been updated. Newer furnace, hot water heater, oil tank and upgraded electric. Double staircase. Window unit AC. This has been a very popular college rental for many years - but would make a wonderful single family home. Potential rental income of $2,000/month Walk to everything Chestertown has to offer. Large home on a rare oversized lot in town is priced to sell!

Beds:
4
Baths:
3 Full
Sq.Ft.:
1,831
Status:
NEW LISTING
MLS#:
MDKE118218
Type:
Single Family, Single Family-Detached
Subdivision:
Fannell's Meadow
Lot size:
2.02 Acres
Year built:
2000
Courtesy: Cross Street Realtors LLC
View additional info

This Chesapeake Architect's original is thoughtfully set among a variety of hand-selected landscaping, which has matured into a private and serene park-like setting that overlooks a pond and farm field. Trust me, this is a special place. The interior is just as pleasing aesthetically as the exterior - one of a kind open floor plan with main level living, gourmet kitchen, a multitude of built-ins, vaulted ceilings, second story loft overlook⦠all of which is bathed in natural light. Generous storage capacity, full basement, detached garage⦠this isnât just another residential property for sale, itâs an experience to tour and one you will want to live everyday. WHAT YOU DON'T SEE: highest speed fiber wifi service through Talkie, refrigerator 2017, dishwasher 2016, roof installed 2019 has a 50-year life with transferrable warrant, french drain system around the perimeter, dual zoned heating & cooling (electric with propane backup), wired speaker system, heated tile flooring in master bathroom. MATURE LANDSCAPE INCLUDES: apple, plum, pear, fig, and Why Oak trees, fresh herb and vegetable gardens, decorative landscape, and more... **ALL OFFERS NEED TO BE SUBMITTED BY 5:00PM MONDAY, JUNE 14, 2021.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,465
Status:
NEW LISTING
MLS#:
MDQA148132
Type:
Single Family, Single Family-Detached
Subdivision:
The Grove
Lot size:
1.03 Acres
Year built:
2021
Courtesy: Clark & Co Realty, LLC
View additional info

Under Construction, end of May completion...Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre features 4 bedrooms, 3.5 baths, 1st floor primary bedroom with trayed ceiling, walk-in closet, lavish bath with tiled shower and double vanity, gorgeous designer kitchen with island, SS appliances, quartz countertops, farm sink and a custom pantry by California Closets, open dining area and living room with cathedral ceiling. Other highlights of the home include extra wide foyer, custom bench/locker area, Jack & Jill bath, separate laundry room, powder room, wrap around porch, LED designer lighting throughout, paddle fans, recessed lighting, black windows, flat screen TV setup and USB outlets in living room & primary bedroom, This home will be love at first sight

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,248
Status:
NEW LISTING
MLS#:
MDQA148074
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.52 Acres
Year built:
1960
Courtesy: Rosendale Realty
View additional info

WELCOME TO CHESTER HARBOR'S NEWEST LISTING. DON'T LET THE AGE FOOL YOU.... VINTAGE RANCH STYLE HOME HAS NEW METAL ROOF IN 2017 AND NEW WELL IN 2019. PLENTY OF LIVING SPACE WITH HARDWOOD FLOORS AND COZY OIL HEAT, PLUS CAC. ...FAMILY ROOM CURRENTLY USED AS BEDROOM HAS BRICK HEARTH AND FLUE FOR WOODSTOVE OR PELLET STOVE. STORAGE SHED AND CAR PORT. LARGE HALF ACRE LOT WITH FARMLAND VIEWS ACROSS THE STREET, SHOULD ALLOW FOR FUTURE ADDITIONS OR A GARAGE. (VERIFY WITH QAC P/Z AND HEALTH DEPT.) LARGE FRONT AND BACK YARD SPACES FOR RELAXING , GARDENS, OR PETS. CLOSE TO HISTORIC CHESTERTOWN, COUNTY PARK, AND EASY COMMUTE TO TAX FREE DE SHOPPING. COMMUNITY HAS VOLUNTARY HOA

Beds:
2
Baths:
1 Full
Sq.Ft.:
776
Status:
NEW LISTING
MLS#:
MDKE118212
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.75 Acres
Year built:
1980
Courtesy: Hartman Realty, LLC.
View additional info

2 Bedroom bungalow on 1.75 acres just outside Fairlee. House needs some TLC but could be a good starter home or potential investment property. Property has public water and sewer services and a 12'x15' block storage building. The property is being offered for sale as part of an Estate settlement.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,944
Status:
NEW LISTING
MLS#:
MDKE118228
Type:
Manufactured Home
Subdivision:
Chestertown
Lot size:
1.14 Acres
Year built:
1996
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Coming Soon! Welcome home to your very own country oasis located on 1.14 acres that backs up to beautiful farm land. Just a short drive to access 301 or the great town of Chestertown and all things Kent County. This country charmer has 3 bedrooms and two full baths that have been completely renovated. NEW flooring, roof, tankless water heater, dry wall, HVAC, siding.... the list goes on and on. 27824 Morgnec Road offers a modern open floor plan where the newly renovated kitchen flows into the formal living room and the dining space. Did I mention the dreamy barn doors to access your pantry?! Very private master suite located at the opposite end of the other bedrooms includes a NEW on suite bathroom. Large bonus room with access to your spacious backyard which includes a new back deck and patio and shed for storage. This one checks all of the boxes! Call today!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
4,434
Status:
NEW LISTING
MLS#:
MDKE118174
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.25 Acres
Year built:
2006
Courtesy: RE/MAX Eagle Realty
View additional info

Beautiful 4 Bedroom 3.5 bath brick front executive home on an oversized corner lot. This 3500 sq ft home was built to be shown off. The open style home has Gleaming hardwood floors on the first and second floor, split staircase, first floor laundry and an office that anyone would be proud of. This home has a formal living room and dining room, Gourmet country kitchen with granite counters, upgraded 42â cabinets, recessed lighting, center island with breakfast bar and a morning room addition. From the kitchen you can be a part of everything going on in the large family room with gas fireplace. The second floor has 4 total bedrooms with a huge master bedroom with a 5 piece ensuite bath including tile shower and soaking tub. The hallway is open to the first floor family room and foyer making this a totally open concept home. The partially finished walkout basement is set up for entertaining with its pool table, family room and sitting area and not to forget the full bath if entertaining guests. The front of the home welcomes everyone with mature landscaping and paver walkways leading to the garage and the main street. The back yard is a slice of paradise with the oversized paver patio mature plantings and white vinyl privacy fence. Put this home on your tour today.

Beds:
5
Baths:
2 Full/1 Half
Sq.Ft.:
2,976
Status:
NEW LISTING
MLS#:
MDKE118142
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.24 Acres
Year built:
2009
Courtesy: RE/MAX Executive
View additional info

Welcome to Coventry Farms! Community living at it's best. Enjoy the country feel with all the town amenities. Need rooms or room to grow? This home offers 4/5 bedrooms including a large FROG (finished room over garage) that can be that 5th bedroom or family room on the upper level. Living room, dining room as well as everyday dining area of the large kitchen and powder room all on the main level. New carpet installed in living room and formal dining room. Kitchen, dining area off kitchen and foyer all have new luxury vinyl flooring. Main level has a great entertaining flow. If you need additional space, the partially finished basement will fill that need. Game room, workout space, office or playroom, so many possibilities for this finished space, there's even a plumbed lower level bathroom area if you choose to finish. Fenced rear yard with patio. Relax on the beautiful front porch....perfect spot to meet and greet your neighbors. Stop dreaming and start living your American dream.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,294
Status:
NEW LISTING
MLS#:
MDKE118204
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.65 Acres
Year built:
1927
Courtesy: Century 21 Downtown
View additional info

The sought after Chestertown introduces you to this spacious solid brick home. This home offers over 2294 square feet living area, crown moldings, recessed lighting, relaxing living room with wood burning fireplace and wood beam ceilings, formal dining room with wide windows, lovely kitchen with island and granite counters, large master suite with built-in closets, master bath with whirlpool tub and dual vanity, and full basement with plenty of room for storage. Enjoy the balcony with great view of the front yard or have an outdoor fun in the rear porch. The detached garage makes this home complete. Just a few minutes away from historic Chestertown!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,948
Status:
NEW LISTING
MLS#:
MDKE118210
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.99 Acres
Year built:
1965
Courtesy: Doug Ashley Realtors, LLC
View additional info

Waterfront.. sunsets are gorgeous... and the house has hardwood flooring pretty much throughout. Two sided wrap screened porch, open porch facing the water, full basement, unfinished. Roof is six years old. All on one level living. There is an additional lot with sewer allocation on the property which makes the possibility of a family compound very feasible. Three bedrooms, 1 bath and beautiful mature landscaping. Just a gorgeous setting. Professional photographs to come

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,997
Status:
Active
MLS#:
MDKE118182
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.72 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful Cape Cod reproduction in Country Club Estates, quality build by Tom Yetman. Gorgeous random width wood floors, Detailed Fireplace mantel, crown moldings, and chair rail moldings. Large windows in the Living room add lots of light and french doors open to the large deck, perfect for entertaining and viewing the lovely gardens. Cozy up by the fireplace in the living room or enjoy a book in the sunroom. The formal Dining room is a delight for the holidays. The kitchen is open with an island and an easy flow floor plan for cooking your favorite dishes!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,200
Status:
Active
MLS#:
MDQA147968
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.43 Acres
Year built:
1997
Courtesy: Long & Foster Real Estate, Inc.
View additional info

PRICE REDUCTION! OPEN HOUSE SAT 6/12 12-2 Beautiful 3 Bedroom 2 Bath Rancher in Chester Harbor! Located in Queen Anne's County, Recently updated and move-in ready! Huge fenced in backyard with screened in porch and firepit, Perfect for outdoor get togethers! Stainless steel appliances, Beautiful accent walls, Must see, Shows well! Minutes from downtown Chestertown and 20 minutes from Centreville, Easy access to 301. Don't miss out on the home!

Open House:

Saturday, 6/19 12:00-2:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,126
Status:
Active
MLS#:
MDKE118158
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak
Lot size:
1.03 Acres
Year built:
2005
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous house in Great Oak Waterfront Community! Marina, restaurant, sandy beaches, lots of fishing and fun! One level living with an Open floor plan. Wood floors and Ceramic Tile. The Living Room wood-burning fireplace will warm you on those cool evenings. The master suite has a sitting area, 2 walk-in closets, and a large bedroom. The primary bath has a jacuzzi tub and stall shower. Florida room has lots of windows and just outside it is the gorgeous in-ground pool, 20x40 with a new liner. The extra-large garage has plenty of storage space and room for your workshop. Easy to show. Quick settlement is okay. Furniture can stay or not.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,344
Status:
Active
MLS#:
MDQA147808
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.48 Acres
Year built:
1962
Courtesy: Coldwell Banker Realty
View additional info

Exciting Opportunity to own this 3-bedroom 2 bath home with full basement on large lot with 40 x 60 Pole Barn. Nice, updated kitchen with tiled floors and granite countertop plus open dining area. Spacious sunny living room with brick fireplace, hardwood floors throughout living area and bedrooms. Primary bedroom offers a full updated bath, plus updated hall bath. Large mudroom off the kitchen with separate entrance and access to the pole building. The full basement with fireplace and rough in for 2 baths is ideal for multiple uses including in-law suite, apartment and home offices with private ground level entrance. The pole building has plenty of space for all your toys and great opportunity for contractors or another business that need storage and work area. Nice location close to Chestertown, local restaurants and Marinaâs. Tenant Occupied and must approve showing, must have at least 24 hour notice. Tenant Lease Expires on July 30,2021. Dogs on property please do not enter without appointment.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,420
Status:
Active
MLS#:
MDKE118114
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.65 Acres
Year built:
1960
Courtesy: Gunther-McClary Real Estate
View additional info

Welcome to Honeysuckle Haven, an enchanting artisan's cottage on the Chesapeake Bay. Watch ships go by and the most INCREDIBLE sunsets as you enjoy the fragrant gardens. Customized craftsman's touches throughout. Downstairs is open for entertaining, with a gourmet kitchen, dining and living area all open to views of the Chesapeake Bay, leading to a patio and deck beyond - and an outdoor shower! Back inside, there is also a half bath, and a bedroom with an en-suite bath on the first floor. There is a sweet screened porch off the side of this downstairs bedroom, the perfect spot for catching a nap and the Bay breezes. Primary bedroom and bath is on the second floor, as well as a guest room. But perhaps the most delightful suprise is a spiral staircase to the very top cupula "lookout" room - perfect as an office, or just a relaxing hideaway to watch the birds and the Bay. There is a ladder to the roof-top for the most spectacular birds-eye views of the Bay. The owners of this residence have maximized their bayfront location very nicely by installing rip-rap to control erosion, as well as a very easily-managed staircase to the waterfront, providing a gentle path to a lower deck at the water's edge. You can easily launch a canoe or kayak from this location, or just enjoy hanging out and listening to the bay lapping on the rocks. LOVE this house - you will too!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,040
Status:
Active
MLS#:
MDKE118128
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
1 Acres
Year built:
1920
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Remodel or tear down this home in the beautiful country of Quaker Neck outside of Chestertown. New electric has been installed by licensed electrician. Could be a great flip home or permanent residence with some carpentry know how. Will need new septic and well. Possible help with cost of septic from the county. Seller wants it sold, bring offers.

Beds:
3
Baths:
3 Full/2 Half
Sq.Ft.:
5,595
Status:
Active
MLS#:
MDKE118122
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
21.07 Acres
Year built:
2002
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Complete privacy surrounds this stunning waterfront farmette on the east fork of Langford Creek featuring 21 picturesque acres. Custom built home features 1 gigabyte high speed internet , grand entryway leading into a center hall, wide halls, arched doorways, formal living room, dining room, library, breakfast room, family room. Three fireplaces have been converted to propane but could easily be switched back to wood burning. First floor owners suite with sitting room, double walk in closets, fireplace, spacious bath. Two guest bedrooms on the second floor with en suite baths. Bonus room and office on second floor could be converted into bedrooms. Large gourmet kitchen with high end appliances. Many other amenities to include a screened in porch, 3 car attached garage, unfinished basement, large indoor pool, 3 zones for heat/AC, central vacuum, and whole house generator. Do not enter property without listing agent. No drive-bys. Video monitored. Please schedule appointment.

Beds:
3
Baths:
3 Full
Sq.Ft.:
2,160
Status:
Active
MLS#:
MDKE118118
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2 Acres
Year built:
1991
Courtesy: Benson & Mangold, LLC
View additional info

The Fannells Meadow community is like living in the country and being close to town at the same time. This home underwent an extensive renovation in 2021. Roof, HVAC, siding, kitchen, bathrooms, three seasons porch, custom built-ins, primary suite, flooring and paint all updated or replaced. One story living at its finest and a large corner lot. This home is a must see!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,300
Status:
Active
MLS#:
MDKE118082
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2013
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

PRICE REDUCTION! Live beautifully and comfortably in this waterfront community on the Chester River, just minutes from historic Chestertown. The elegant amenities of the home are complemented by the amenities of the community. View the abundant wildlife on the fresh-water pond from your deck or take a few steps to stand at the edge and watch up close. A pier on the Chester is great for crabbing, fishing, or launching your kayak for a cruise. Boat slips are available. Spend a warm afternoon sunbathing or cooling off in the community pool. 2nd story main living, with guest quarters on entry level. Third bedroom is being used as a family room. Delightfully different, unquestionably unique, and ready for you to move in.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE117998
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
7
Baths:
5 Full/2 Half
Sq.Ft.:
10,328
Status:
Active
MLS#:
MDKE117878
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
21.02 Acres
Year built:
1800
Courtesy: Select Land & Homes, LLC
View additional info

This Majestic stately residence is perched at a perfect elevation with incredible views of undeveloped, preserved farmland and gently sloping lawn to the 1000' of white sandy beach on the Upper Chesapeake Bay. This awesome property offers ultimate privacy with the convenience to several urban centers within 90 minutes away. Historic Chestertown and the bayside town of Rock Hall are only moments away as well! Property features include a restored Georgian Colonial main residence in great condition with many original features and numerous recent updates, a large enclosed pool with attached recreation play house, 4 stall barn with 4 acre fenced pasture, tenant house, detached garages, extensive patios and landscape features, gorgeous private beach with bath house and much, much more! Come take a look and take advantage of all the value at a very reasonable asking price! Subject to Maryland Environmental Trust Easement, see documents.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,454
Status:
Active
MLS#:
MDKE117962
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.21 Acres
Year built:
1956
Courtesy: Cross Street Realtors LLC
View additional info

PRIME LOCATION!!! This adorable 3 BR, 1 BA bungalow is located on one of the main thoroughfares in Chestertown. Zoned Intense Village which allows residential and/or a broad range of commercial uses. The living space includes a large family room off the galley kitchen, new heat-pump with central air, new carpet, screened in-porch and a detached 2-car garage with ample off street parking. Close to all Chestertown offers; Washington College, restaurants, hospital, local shops, new marina and much more. Lots of possibilities here!

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,050
Status:
Active
MLS#:
MDKE117956
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.37 Acres
Year built:
1969
Courtesy: The Hogans Agency Inc.
View additional info

Cozy ranch style lakefront cottage on large lot with beautiful hardwood floors - one half mile from Public Landing Marina. Scenic views and wildlife abound with outstanding fishing on the the lake. A must see - your enjoyment awaits!

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