Chestertown MD Real Estate & Homes for Sale


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Type:
Single Family
Sq.Ft.:
1,029
Status:
Active
Beds:
2
Lot size:
0.16 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE2000170
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Home needs some updating but very live able. Being sold AS-IS. (As-is addendum required) Lots of potential, close to downtown Chestertown, Washington College and the Chester River. Listing is about location and lot. Seller is a licensed Real Estate Agent.

Type:
Other
Sq.Ft.:
950
Status:
Active
Beds:
1
Lot size:
0.04 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDKE2000112
Subdivision:
Historic District Chestertown

ADDITIONAL INFORMATION

This property would benefit from TLC, but the potential is there and the structure is solid. Owner owns the other side of the duplex and rehabbed it and has used it as a rental. Owner prefers to sell both units at one time.

Type:
Other
Sq.Ft.:
884
Status:
Active
Beds:
1
Lot size:
0.05 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDKE2000110
Subdivision:
Historic District Chestertown

ADDITIONAL INFORMATION

Life in Historic downtown Chestertown is a life of charm and ease. Easy proximity to stores, including a health food stores, restaurants, library, art galleries, adorable boutiques and the Chester River! There is so much to enjoy in Chestertown, it's almost a life on permanent vacation. This property is part of a duplex, and the owner would prefer to sell both units at one time. Live in this one, and rehab the other one. This unit has been a rental for years, is in great condition, and shows well. Call us for more information.

Type:
Single Family
Sq.Ft.:
2,518
Status:
Active
Beds:
4
Lot size:
0.08 Acres
Year built:
1881
Baths:
3.00
MLS#:
MDKE118062
Subdivision:
Chestertown Historic District

ADDITIONAL INFORMATION

Hirons House is a beautifully restored historic home, located on Cannon Street in the heart of Chestertown. No detail was overlooked in the renovation of the original 19th century structure and construction of a new addition, both of which were completed in 2015. The original pine flooring and plaster walls were carefully restored. Iron radiators, radiant floor heat, and central AC were installed, as well as new plumbing and electric. The fireplace was restored and is functional. The roof was replaced with long-lasting Vermont white cedar shingles; the porch roofs were replaced with standing seam copper. A brand-new kitchen with granite countertops, stainless steel appliances, and an island was added as well as a master bedroom suite with cathedral ceilings, a loft, a walk-in-closet and a bathroom that includes a walk-in shower and double sinks. The guest bathroom includes a walk-in shower and an original clawfoot tub. The backyard includes a long side porch overlooking a garden, a brick walkway and patio, and a landscaped lawn. Hirons House is located in the middle of the newly revitalized Cannon Street neighborhood. Just steps away is Fountain Park, shopping, restaurants, the Chestertown rail trail, and the new marina. Within walking distance is both Washington College and the Chester River waterfront. This carefully maintained home has many unique details, historic charm, and modern amenities that perfectly complement its ideal Chestertown location

Type:
Single Family
Sq.Ft.:
600
Status:
Active
Beds:
1
Lot size:
0.34 Acres
Year built:
1945
Baths:
1.00
MLS#:
MDQA2000234
Subdivision:
Kingstown

ADDITIONAL INFORMATION

Waterfront Lot with dilapidated residence. Existing well and septic.

Open House:

Friday, 7/30 6:00-8:00PM

Type:
Single Family
Sq.Ft.:
2,861
Status:
Active
Beds:
4
Lot size:
0.46 Acres
Year built:
2004
Baths:
4.00
MLS#:
MDQA148184
Subdivision:
Evergreen Manor

ADDITIONAL INFORMATION

Rare find on the Queen Anne's County side of Chestertown! You 'll be delighted with this beautiful spacious light filled home! Located on a quiet Cul-de-sac with over 3,000 square feet of finished living space. Tax records do not reflect the correct finished square feet of space!! Open concept Living features soaring vaulted ceilings and a gorgeous stacked stone fireplace in the Living room. Fireplace has been outfitted with a wood burning stove for efficiency and added heat for the house. Hardwood floors bring warmth and beauty to the main level. Kitchen is spacious and outfitted with stainless steel appliances , all appliances are less than four years old and stove is brand new! Granite counters, under cabinet lighting and decorative tile backsplash. There is a separate Wine bar with Granite counter, seating and storage! The laundry is just off the Kitchen and provides additional pantry storage, cabinets and wine racks! An eat in breakfast area holds a table large enough for six! This is an entertaining dream! Open floor plan flows into the Living room and through to the Den or can be a Formal dining area... Make it suit your needs! The Large cabinet bookcase is included in the sale! Main Level Primary Bedroom suite! Primary bedroom is filled with light and has door out to the rear deck and hot tub for your enjoyment! Spacious primary bath has separate tub and shower stall. Large walk in closet holds all your clothes with ease! Upstairs find 3 large bedrooms with spacious closets and ceiling fans. Upper level bonus room /office with vaulted ceilings, fan and attached 3 piece bathroom! All new carpet on the entire upper level and Fresh paint in most rooms! Jack and Jill bath for convenience serves the upper bedrooms. Dramatic catwalk balcony overlooks the main living area! Did I mention the basement? Also a rare find, there is an additional 1300 square feet of room down below! Walls in basement are sealed , A large workshop with storage and cabinets will be included and has stairs and bulkhead doors to the backyard! a few extra bits... House has been wired for "Smart Home " use! Rough in plumbing exists in the basement for a bathroom! Washer and dryer only 3 years young! Home has on demand tankless hot water system! Central Vacuum system! Brand new Water Softener system! Outdoors you will find a spectacular summer paradise featuring a large above ground pool, spacious deck and hot tub! The .46 Acres has a fully fenced backyard and mature landscaping across the front yard. Plenty of pictures here for you to enjoy and see how this spacious home can fulfill all your needs! A home warranty will be provided to the buyers of this well loved home to ensure it's next owners are well cared for! Call for your showing today!

Type:
Single Family
Sq.Ft.:
1,792
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1990
Baths:
2.00
MLS#:
MDQA148194
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

This 3 bedroom 2 bath rancher with a spacious yard has a lot to offer in the water-oriented community of Chester Harbor. The home features a large living room with a pellet stove that was updated in 2019 with a shiplap accent wall and new flooring, Kitchen / Dining combo with an all-season room off the dining area. separate laundry area and detached garage, Updated hallway bath in 2019, and New Roof in 2021, Home is conveniently located on Queen Anne's County side of Chestertown.

Type:
Single Family
Sq.Ft.:
2,444
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1967
Baths:
2.00
MLS#:
MDKE2000120
Subdivision:
Foxley Manor

ADDITIONAL INFORMATION

Very spacious split level home sited on a corner lot in Foxley Manor offers open dining/family room pleasure with a galley kitchen. The family room accesses to a patio in the side yard offering privacy with the border of trees. The home offers large windows for natural lighting and views. There is an additional family room that is quite large offering exterior access to the rear yard. This home is located within the town limits of Historic Chestertown with great convenience to shopping, the library and restaurants.

Type:
Single Family
Sq.Ft.:
2,564
Status:
Active
Beds:
4
Lot size:
0.46 Acres
Year built:
1985
Baths:
3.00
MLS#:
MDQA2000036
Subdivision:
Kingstowne Manor

ADDITIONAL INFORMATION

Oversized ranch home located in well sought after community, Kingstowne Manor. This home has had many upgrades including granite countertops, stainless steel appliances & more. In 2015 a new roof, HVAC, floors, garage door, and bathrooms were all updated. It has a 3 season room off the rear of the home, where you can enjoy the beauty of the fenced in back yard that backs up to farmland. Walk to the Chester River or a short drive to historic downtown Chestertown, where you can enjoy waterfront dining and shopping. Schedule your private showing today, because you are going to want to see this one.

Type:
Single Family
Sq.Ft.:
960
Status:
Active
Beds:
3
Lot size:
0.49 Acres
Year built:
1966
Baths:
2.00
MLS#:
MDKE2000100
Subdivision:
Washington Park

ADDITIONAL INFORMATION

Why rent when you can buy? This affordable rancher within town limits provides you with public utilities and amenities on a large .49 acre lot. Room to expand. Room to add a garage, outbuilding, garden or more. If you enjoy shooting hoops, you will be thrilled to find this community has a great park area waiting for you to come play or host a party in the picnic pavilion . If you are looking for a updated home that is move in ready, this is it. Central air and heat new roof and kitchen cabinets. Tankless water heater, new appliances and two baths ( nicely done ) make this home complete. Outdoor space galore with just shy of 1/2 acre, fire pit, shed for all the gardening tools and mature shade trees make having outdoor gatherings a must. All this within minutes of downtown Chestertown.

Type:
Single Family
Sq.Ft.:
1,499
Status:
Active
Beds:
3
Lot size:
0.47 Acres
Year built:
2001
Baths:
2.00
MLS#:
MDQA2000198
Subdivision:
Kingstowne Manor

ADDITIONAL INFORMATION

Come check out this open spacious rancher! You won't want to miss out on this home with 1,500 +/- SQFT 3 large bedrooms 2 full bath, cathedral ceilings, large kitchen with lots of cabinets, fresh paint, upgraded HVAC, Deck overlooking private backyard, Paved driveway, two car garage, and so much more. All located just outside of historic Chestertown where you will find waterfront and downtown dining at its finest, local art galleries, bakery, stores, parks, schools and hospital. Call today before this charmer says SOLD!

Type:
Single Family
Sq.Ft.:
1,344
Status:
Active
Beds:
3
Lot size:
0.87 Acres
Year built:
1992
Baths:
2.00
MLS#:
MDQA2000026
Subdivision:
Leonard Caldwell Lands

ADDITIONAL INFORMATION

Well maintained rancher with 3 bedrooms and 2 baths. Many upgrades including new wood stove, instant hot water heater, laminate flooring. Sliding doors from the kitchen lead to a nice rear deck with remote control Sunsetter awning for shade. Separate laundry room. Part of the back yard is fenced. Nicely landscaped. 2 sheds plus a 3rd shed that is large enough to be used as a 1 car garage. The owner does park his vehicle inside. The woodstove is only a few years old and is cleaned and maintained yearly and basically heats the whole house! Truly a nice home on a lovely lot in a quiet, cul de sac neighborhood.

Type:
Single Family
Sq.Ft.:
3,724
Status:
Active
Beds:
3
Lot size:
4.09 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE2000034
Subdivision:
None Available

ADDITIONAL INFORMATION

Investment opportunity! Property consists of 4 acres with a main house and a guest house that is separated into 2 apartments. The main house features 3 bedrooms, 1.5 baths. Large living room and dining room. The guest house has two units that are side by side with screened in porches, 3 bedrooms and one bath each. Both houses need major rehab. The main house was clearly a beauty in its day. Easy to show. Guest house with 2 units would make a great rental.

Type:
Single Family
Sq.Ft.:
944
Status:
Active
Beds:
3
Lot size:
2.77 Acres
Year built:
1956
Baths:
1.00
MLS#:
MDKE2000080
Subdivision:
None Available

ADDITIONAL INFORMATION

Investment opportunity! Over 2.5 acres close to downtown Chestertown. House is in need of rehab and the value is in the land. Existing house is occupied detached garage has additional storage, or keep its current use as a chicken coop. The house can be renovated., or take advantage of R4 zoning, which allows for construction of multi-family dwellings to fulfill the demand for rental housing. R4 zoning allows for the conditional use for mobile homes. A plan is included in the available documents. See documents for further information on allowable uses. Do not enter property without a confirmed appointment. Tenant occupied and 24 hour notice needed.

Type:
Single Family
Sq.Ft.:
2,691
Status:
Active
Beds:
4
Lot size:
1.5 Acres
Year built:
1950
Baths:
2.00
MLS#:
MDKE2000068
Subdivision:
Cliffs City

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
1,408
Status:
Active
Beds:
2
Lot size:
0.69 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDQA2000078
Subdivision:
Queen Annes County

ADDITIONAL INFORMATION

Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek. Private location but convenient distance to shops, restaurants and park just over the Chester River. Nice side screened porch with removable winter panels. Recent upgrades include: New tilt-in insulated double pane windows, storm doors, new carpet throughout. Updated Kitchen with new vinyl flooring, countertops and Stainless Steel Appliances. Bathroom updated with new tub/shower and vinyl flooring. BAT septic system and drain field installed approximately 2011 and will allow for a 3rd bedroom to be added. Newer well. Dual zone central air, dual zone hot water baseboard heat converted to LP gas. New water softener system. 1-car attached garage with workshop, remote garage door and entrance to kitchen. Garage had new roof installed 2018. Fresh paint throughout home in 2020. Full RV hookup with water, sewer & electric in back yard.

Open House:

Saturday, 7/31 1:00-3:00PM

Type:
Single Family
Sq.Ft.:
1,872
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1973
Baths:
2.00
MLS#:
MDQA148094
Subdivision:
Sarah Skipper Lands

ADDITIONAL INFORMATION

Well kept and cared for rancher is located on .345 acres only a couple blocks from the water. 129 Primrose Road offers 3 bedrooms and 2 bathrooms with beautiful hardwoods flowing throughout. Very private fenced in back yard with small patio. Gas fireplace in oversized family room and a bonus room off the back for even more space. Call today for your private showing.

Type:
Single Family
Sq.Ft.:
1,590
Status:
Active
Beds:
4
Lot size:
0.33 Acres
Year built:
1973
Baths:
2.00
MLS#:
MDKE2000094
Subdivision:
College Heights

ADDITIONAL INFORMATION

4 bedrooms, 1.5 bathrooms, extra large eat-in kitchen, screened in porch, mature trees add privacy in this College Heights community - walking distance to the College, Downtown, the Waterfront, Shopping Center - doesn't get more convenient than this!

Open House:

Sunday, 8/1 11:00-1:00PM

Type:
Single Family
Sq.Ft.:
1,376
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1974
Baths:
2.00
MLS#:
MDQA2000086
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

GREAT CHESTER HARBOR RANCHER, ALMOST 1400 SQFT. NICE LOT BACKING TO FARMLAND COME ENJOY SHADY YARD. LARGE KITCHEN AND LIVING ROOM WITH AMPLE BEDROOM SPACE, FIREPLACE, DECK AND LARGE STORAGE SHED. COMMUNITY HAS VOLUNTARY HOA AND WATER PRIV. FOR HOA MEMBERS. CLOSE TO CHESTERTOWN YET QAC SCHOOLS, EASY COMMUTE TO TAX FREE DE SHOPPING AND OTHER POINTS OF INTEREST. Voluntary HOA HOME IS UNDERGOING MAJOR FACELIFT IN THE NEXT 2 WEEKS. FRESH PAINT, CARPET, AND SIDING AND GUTTERS. STAY TUNED FOR UPDATED PICS AND OPEN HOUSE DETAILS.

Open House:

Saturday, 8/7 11:00-1:00PM

Type:
Single Family
Sq.Ft.:
1,440
Status:
Active
Beds:
4
Lot size:
0.4 Acres
Year built:
1989
Baths:
2.00
MLS#:
MDKE2000056
Subdivision:
Fairlee

ADDITIONAL INFORMATION

Such a delightfully well kept home. Truly Move in Ready! This four bedroom home is near a public landing, about five minutes away. Four bedrooms and 2 baths, with 2 of the bedrooms and full bath on the main level. The deck is quite large, with built in seating. Leave the hustle and bustle behind, and come relax in this beautiful spot! Floors have just been redone and are gorgeous. Leading to deck are French Doors, and the deck wraps around one side of the home. Come see! Owner has contracted to have some work done on the shed, and they are going to start that either in September or October. She will cover the cost

Type:
Single Family
Sq.Ft.:
1,269
Status:
Active
Beds:
2
Lot size:
0.07 Acres
Year built:
1955
Baths:
1.00
MLS#:
MDKE2000052
Subdivision:
Tolchester

ADDITIONAL INFORMATION

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?

Type:
Single Family
Sq.Ft.:
1,747
Status:
Active
Beds:
4
Lot size:
0.13 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE2000050
Subdivision:
Historic District Chestertown

ADDITIONAL INFORMATION

Ideally located in Chestertown's Historic District, and within walking distance of all Chestertown has to offer, this home offers 3 bedrooms and a full bath upstairs and a fourth bedroom or office with a full bath on the main level. The property features off street parking, a fenced rear yard with a patio, and a shed with electric. With updated kitchen and baths, beautiful hardwood floors, and a fresh coat of paint - this house is move-in ready!

Type:
Single Family
Sq.Ft.:
2,570
Status:
Active
Beds:
4
Lot size:
0.38 Acres
Year built:
2000
Baths:
3.00
MLS#:
MDKE2000048
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Spacious home in water privileged Chesapeake Landing available. This well constructed home has features typically only found in homes priced much higher. Hardwood floors throughout, exposed axe hewn beams accent the soaring living room ceiling, wrap around mahogany porch, over sized garage- you can actually fit 2 real sized cars and still have room for work benches and storage. All rooms are generous in size and three bedroom have a walk in closets and the fourth has an oversized closet. The master is located on the main level with a serene view overlooking woods. The second level has 3 additional bedrooms with one being exceptionally large. Recently painted, the HVAC system is less than a year old, septic recently certified and so much more. Only a change in commute makes this gorgeous home available.

Type:
Single Family
Sq.Ft.:
6,334
Status:
Active
Beds:
6
Lot size:
6.02 Acres
Year built:
1881
Baths:
6.00
MLS#:
MDKE118230
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Lauretum, an 1881 country house built in the grand manner, defines a period of American history when architecture was at it more picturesque and exuberant. An exemplar of the Queen Anne style, Lauretum, Latin for "laurel grove". This unusual landmark building was designed by the renowned architect, Edmund George Lind, commissioned by the prominent Vickers family, is rich in 19th c. history. An accomplished builder of the time, R.K. Pippin was the local contractor. Fine Pippin buildings are scattered throughout Chestertown emphasizing his importance as a builder. Approached by a gravel driveway that winds rising from the County road. Other aspects of Lauretum indicate the tasteful and selective influence of a master architect. Details include pierced fretwork, Oriole window, granite sills, elaborately paned window lights, Jib-way doors that allow the interior to open to the extensive open porches. The extremely high ceilings, room transoms and the many windows speak to the importance to the late Victorian penchant for cooling rooms and fresh air in designs of that period. Lauretum has been a residence, a Bed & Breakfast and currently the cooperate offices of a national firm. The construction is stucco over solid thick brick walls. The current owners relocated the kitchen while bringing the kitchen into the very modern era. It features fine architectural details, fireplace and high-end appliances. Please call for an extensive brochure on the many details of this fine property located within Chestertown on six acres high on a prominent hill. A National Register property. Lauretum is site on the Civil Trail. Because of its size, location and architectural prominence one can envision Lauretum is so many ways. A tour will bring those used to light. Lauretum, an 1881 country house built in the grand manner, defines a period of American history when architecture was at it more picturesque and exuberant. An exemplar of the Queen Anne style, Lauretum, Latin for "laurel grove". This unusual landmark building was designed by the renowned architect, Edmund George Lind, commissioned by the prominent Vickers family is rich in 19th c. history. An accomplished builder of the time, R.K. Pippin was the local contractor. Fine Pippin buildings are scattered throughout Chestertown emphasizing his importance as a builder. Approached by a gravel driveway that winds rising from the County road. Other aspects of Lauretum indicate the tasteful and selective influence of a master architect. Details include pierced fretwork, Oriole window, granite sills, elaborately paned window lights, Jib-way doors that allow the interior to open to the extensive open porches. The extremely high ceilings, room transoms and the many windows speak to the importance to the late Victorian penchant for cooling rooms and fresh air in designs of that period. Lauretum has been a residence, a Bed & Breakfast and currently the cooperate offices of a national firm. The construction is stucco over solid thick brick walls. The current owners relocated the kitchen while bringing the kitchen into the very modern era. It features fine architectural details, fireplace and high-end appliances. Please call for an extensive brochure on the many details of this fine property located within Chestertown on six acres high on a prominent hill. A National Register property. Because of Lauretum's proximity to a well-known and admired Historic Town (home of Washington College - tenth oldest in America) one can envision the many ways Lauretum could be used including a lovely residence.

Type:
Single Family
Sq.Ft.:
1,408
Status:
Active
Beds:
3
Lot size:
0.06 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE2000040
Subdivision:
None Available

ADDITIONAL INFORMATION

Attention Investors! Charming in-town home offering hardwood floors in many rooms. The main level features a kitchen with separate dining room, living room, powder room and enclosed front porch. There are three bedrooms with hardwood floors on the second floor and a full bath. Quaint backyard and detached one-car garage. Located in the cozy Historic District and close to downtown and Washington College. Solid rental history. House being sold 'As Is'.

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26–50 of 85 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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