Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $283,000. This is higher than the county median home value of $195,300. The national median home value is $219,700. The average price of homes sold in Chestertown, MD is $283,000. Approximately 41.52% of Chestertown homes are owned, compared to 45.26% rented, while 13.22% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!


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Type:
Single Family
Sq.Ft.:
3,457
Status:
NEW LISTING
Beds:
6
Lot size:
0.24 Acres
Year built:
1920
Baths:
3.00
MLS#:
MDKE2000036
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

As-is Victorian with lots of potential. The attached apartment in the rear of the house can be used for rental, in-laws, or adult kids. The main house has wood floors in need of refinishing, some new lament flooring, high ceilings, and large rooms. Previously rented to College Kids.

Type:
Single Family
Sq.Ft.:
1,411
Status:
NEW LISTING
Beds:
3
Lot size:
0.34 Acres
Year built:
1975
Baths:
2.00
MLS#:
MDQA147894
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Completely renovated 3 bed, 2 bath home with 1 car attached garage. Brand new BAT system. New roof, new HVAC, new siding. Nothing left undone. Laminate flooring throughout. Gorgeous kitchen with concrete countertops, backsplash and stainless steal appliances. Den or family room on the back of the house leading out to a nice deck. Fenced in back yard. Storage shed. Primary bedroom is very spacious. Pull down stairs to the attic. Nice landscaping. Attached one car garage., encapsulated crawlspace. The whole house shows like a model. Come check it out before it's gone!

Type:
Single Family
Sq.Ft.:
1,658
Status:
NEW LISTING
Beds:
3
Lot size:
0.44 Acres
Year built:
1987
Baths:
2.00
MLS#:
MDKE118256
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Enjoy a creek side BBQ on the deck or the cozy living room fireplace on those cool autumn evenings in this charming Waterfront 3 bed 2 full bath home on the lovely Mill Creek. This must see Beautifully maintained 1987 Home is the ideal vacation or year round home. Enjoy the newly dredged Mill Creek for its serene beauty, wildlife and its close proximity to the Chesapeake Bay. This lovely home is privately situated at the end of a dead end street affording a peaceful setting among mountain laurels

Type:
Single Family
Sq.Ft.:
1,277
Status:
NEW LISTING
Beds:
3
Lot size:
0.34 Acres
Year built:
1965
Baths:
1.00
MLS#:
MDKE118258
Subdivision:
Byford Development

ADDITIONAL INFORMATION

Investment Opportunity in desirable Byford Development in downtown Chestertown! Brick Rancher, 3 Bedroom, 1 Bathroom with Screened in Porch, in need of renovation. Hardwood floors throughout the bulk of the home, under the carpet. Lovely yard and location. Bring this home back to its glory! Sold As-Is. Perfect location within walking distance to downtown, so you can enjoy everything historic Chestertown has to offer-from local artists, shops and waterfront dining, to the famous Farmer's Market, and more! *Sellers are requesting all offers to be submitted no later than 5pm on Sunday, June 20th.*

Type:
Single Family
Sq.Ft.:
1,416
Status:
NEW LISTING
Beds:
3
Lot size:
0.35 Acres
Year built:
1991
Baths:
2.00
MLS#:
MDKE118214
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
3,578
Status:
NEW LISTING
Beds:
4
Lot size:
1.34 Acres
Year built:
1975
Baths:
4.00
MLS#:
MDKE118226
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
1,008
Status:
NEW LISTING
Beds:
3
Lot size:
0.14 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE118190
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
2,465
Status:
Active
Beds:
4
Lot size:
1.03 Acres
Year built:
2021
Baths:
4.00
MLS#:
MDQA148132
Subdivision:
The Grove

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
1,248
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1960
Baths:
1.00
MLS#:
MDQA148074
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
776
Status:
Active
Beds:
2
Lot size:
1.75 Acres
Year built:
1980
Baths:
1.00
MLS#:
MDKE118212
Subdivision:
None Available

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,840
Status:
Active
Beds:
3
Lot size:
0.23 Acres
Year built:
1930
Baths:
2.00
MLS#:
MDKE118234
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

Welcome to 9035 Queen Anne Ave located in the beach community of Tolchester. This house is only a few short blocks from the Chesapeake Bay, Tolchester Marina and The Shanty. Huge sun room that wraps the front and side of the house, back deck, cozy living room with fireplace. 9035 Queen Anne Ave offers 3 bedrooms with1.5 bathrooms, a bonus room now used as an office and an oversized laundry room. Property is being sold with the front lot totaling .46 acres!!!!

Type:
Manufactured Home
Sq.Ft.:
1,944
Status:
Active
Beds:
3
Lot size:
1.14 Acres
Year built:
1996
Baths:
2.00
MLS#:
MDKE118228
Subdivision:
Chestertown

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
4,434
Status:
Active
Beds:
4
Lot size:
0.25 Acres
Year built:
2006
Baths:
4.00
MLS#:
MDKE118174
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
2,976
Status:
Active
Beds:
5
Lot size:
0.24 Acres
Year built:
2009
Baths:
3.00
MLS#:
MDKE118142
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,147
Status:
Active
Beds:
3
Lot size:
0.69 Acres
Year built:
1949
Baths:
1.00
MLS#:
MDQA147980
Subdivision:
Kingstown

ADDITIONAL INFORMATION

The CUTEST bungalow cottage has a Chestertown address on the Queen Anne's County side of the River! Carpet, paint, appliances, water heater, and water conditioner are only 2 years young. Spacious bathroom has a dual vanity and a large closet. And the backyard is HUGE... plenty of room to play and relax. Schedule quickly!

Type:
Single Family
Sq.Ft.:
1,392
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1967
Baths:
2.00
MLS#:
MDKE118180
Subdivision:
Foxley Manor

ADDITIONAL INFORMATION

IF YOU WANT IT, THIS ALMOST 1400 SQFT BRICK RANCHER HAS IT. SUPER UPGRADED KITCHEN, GOT IT! (LIGHTED CABINETS, SOLID SURFACE COUNTERS, STAINLESS APPLIANCES, AND TILE FLOOR) BEAUTIFUL HARDWOOD FLOORS THROUGHOUT, CHECK! AWESOME PRIMARY BATH, YOU GUESSED IT. GOT IT! SCREENED PORCH, FRESH PAINT, HUGE STORAGE SHED, PAVED DRIVEWAY. FIRE PIT, SHADE TREES, BEAUTIFUL GARDENS, AND GREAT LOCATION. SMALL CINDERBLOCK SHED/BUILDING, "AS IS" CLOSE TO SHOPPING AND QUICK ACCESS TO ALL POINTS OF INTEREST. YOU WILL NOT BE DISAPPOINTED ,UNLESS YOU MISS OUT ON THIS ONE. DO NOT WAIT. LOOK FOR OPEN HOUSE ON JUNE 5TH 11-1 PICS COMING SHORLTY

Type:
Single Family
Sq.Ft.:
2,294
Status:
Active
Beds:
3
Lot size:
0.65 Acres
Year built:
1927
Baths:
3.00
MLS#:
MDKE118204
Subdivision:
Chestertown

ADDITIONAL INFORMATION

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!

Open House:

Tuesday, 6/22 11:00-2:00PM

Type:
Single Family
Sq.Ft.:
1,948
Status:
Active
Beds:
3
Lot size:
0.99 Acres
Year built:
1965
Baths:
1.00
MLS#:
MDKE118210
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
1,536
Status:
Active
Beds:
2
Lot size:
0.07 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE118202
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Updated home.. fenced back yard with a storage shed, zoned heat pumps. There is a patio and a third floor deck overlooking the semi private back yard. Brand new carpet throughout. Tiled floors in kitchen and Florida room, and fresh paint, inside and out. This home is adorable, just a couple of blocks from the wonderful historic Chestertown Shopping Area, and Washington College. One of the rooms upstairs has "cut outs" overlooking the stairway and owner will close those off to make another bedroom if desired. Shows well. For an acceptable to seller offer he will provide a credit for appliances

Type:
Single Family
Sq.Ft.:
1,840
Status:
Active
Beds:
3
Lot size:
0.05 Acres
Year built:
2005
Baths:
3.00
MLS#:
MDKE118194
Subdivision:
Oak Hollow

ADDITIONAL INFORMATION

COMING SOON! Impeccably maintained town home with updated flooring, newer roof, a fresh coat of paint, and a finished bonus room. And did you see that kitchen?! Just steps away from the new business campus on Warner Drive and within one block of the almost complete YMCA! Convenient to the shopping centers, restaurants, and downtown Chestertown. Showings start on June 1st!

Type:
Townhouse
Sq.Ft.:
3,350
Status:
Active
Beds:
4
Year built:
2013
Baths:
4.00
MLS#:
MDKE118162
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

Exquisite Chestertown waterfront with 2 deep water boat slips and spacious garage. The Flemish bond brick facade sets the stage for the well appointed details throughout the home - i.e. eye-level wainscoting, gleaming hardwood floors, French provincial gourmet kitchen, surround sound, 9' high ceilings, master bedroom suite with waterfront balcony, second story ensuite, elevator, 3 heating and cooling zones, 2 tankless water heaters, and more. Community amenities include BBQ grill/picnic area, fire pit, outdoor pool, marina, and sandy beach area. **ANY CONTRACT OF SALE SHALL BE CONTINGENT UPON SETTLEMENT OF SELLER'S PROPERTY, currently under contract, JUNE 24, 2021.

Type:
Single Family
Sq.Ft.:
1,997
Status:
Active
Beds:
3
Lot size:
0.72 Acres
Year built:
1990
Baths:
3.00
MLS#:
MDKE118182
Subdivision:
Country Club Estates

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
1,200
Status:
Active
Beds:
3
Lot size:
0.35 Acres
Year built:
1962
Baths:
1.00
MLS#:
MDKE118168
Subdivision:
Foxley Manor

ADDITIONAL INFORMATION

Adorable updated rancher in Foxley Manor featuring 3 bedrooms , 1 full bath, paved driveway with carport and attached shed. Hardwood floors in living room area and bedrooms. Nice layout with large kitchen and separate utility room. Great location close to schools, restaurants, Washington College, and Historic downtown Chestertown. Don't miss out! Come and take a look.

Type:
Single Family
Sq.Ft.:
2,679
Status:
Active
Beds:
3
Lot size:
1.63 Acres
Year built:
1978
Baths:
3.00
MLS#:
MDKE118156
Subdivision:
Tolchester

ADDITIONAL INFORMATION

Donât miss out on this impeccably maintained, custom built home on 1.63 acres in Tolchester Heights, just steps from the Bay. This home has 3 oversized bedrooms and 2 1/2 bathrooms plus a partially finished basement. Outstanding features include recently refinished hardwood floors, kitchen with breakfast area, wood-burning fireplace, and an amazing screened-in porch. Working from home? Use the formal living room on the main level or basement recreation room for your office. Large, sunny family room connects to the screened-in porch. Primary bedroom with walk in closet and en-suite bathroom. Tons of storage throughout the house. Check out the floor plans! Unfinished workshop space in the basement with access to the garage. Low-maintenance landscaping provides ample, curb appeal. Expansive yard makes outdoor entertaining a breeze. Keep your boat one block away at Tolchester Marina, home of The Shanty Beach Bar. Make this place your home!

Type:
Single Family
Sq.Ft.:
2,016
Status:
Active
Beds:
4
Lot size:
0.39 Acres
Year built:
1987
Baths:
2.00
MLS#:
MDKE118124
Subdivision:
Byford Development

ADDITIONAL INFORMATION

What do you get when a renown "botanical inspired" artist and former subcontractor for Viking Yacht Company collaborates with one of the finest contractors in the industry to perform an 18th Century Cape renovation? You get 525 N. Kent Street - hand split cedar shake roof, french drain system, HardiePlank siding, hardwood floors, fireplace, granite countertops, High-Speed Internet through Talkie, sun room overlooking the in-ground pool with patio area bordered by mature landscape creating a private oasis within walking distance to downtown.

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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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