Chestertown MD Real Estate & Homes for Sale


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Type:
Single Family-Detached
Sq.Ft.:
1,200
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1959
Baths:
1.00
MLS#:
MDKE115430
Subdivision:
Chesmar

ADDITIONAL INFORMATION

Just bring your food and clothes for this one! This property is fully furnished and stocked for immediate use. Located on Morgan creek with a 40' dock w/ "L" head. 20 feet deep at the end of the dock. The property has two additional waterfront lots to add to the privacy. Making the total acres around 2.5. The out building has been converted to a game room equipped with windows, sliding door & ceiling fans. The kitchen & bath have been updated. The basement is unfinished, but has been waterproofed. Has been approved and currently in the process of getting a new BAT septic. Well is 2 yrs old. The property is currently being used as a vacation rental. The rental income for 2018 was nearly $18k. It is presently listed on VRBO. No showings will be permitted when property is rented. Agent is Seller.

Type:
Single Family-Detached
Sq.Ft.:
1,128
Status:
Active
Beds:
3
Lot size:
0.2 Acres
Year built:
1954
Baths:
1.00
MLS#:
MDQA140736
Subdivision:
Char Nor Manor

ADDITIONAL INFORMATION

Quiet property located off the scenic Chester River in Queen Anne's County with water view. Perfect for the nature lover who enjoys birdwatching and wildlife, very near to the Foreman's Branch Bird Observatory. Home also has a large variety of perennial flowers and a sitting garden off the deck with shade trees. The Home has a newly renovated bathroom, stainless steel appliances, and solar panels are installed on the roof.Needs a central heating and cooling system.Great for a starter home or retired family.

Type:
Single Family-Detached
Sq.Ft.:
1,524
Status:
Active
Beds:
3
Lot size:
0.04 Acres
Year built:
1920
Baths:
3.00
MLS#:
MDKE115388
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Meticulously renovated with stunning details. One of Chestertown~s finest historic renovations. Professionally designed features preserving its original historic charm. A perfect example of what careful planning and style achieves. Close distance to the river, bakery, local coffee shop, waterfront dining, Washington College and the soon to be completed Chestertown Marina. Perfect haven for weekends of year round lifestyle. One must experience to fully appreciate.

Type:
Single Family-Detached
Sq.Ft.:
1,694
Status:
Active
Beds:
3
Lot size:
0.6 Acres
Year built:
1995
Baths:
2.00
MLS#:
MDKE115348
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

Looking for a cottage in the woods? This .60-acre private haven, centrally located 10 minutes from Chestertown and Rock Hall, is quite the secluded spot. Bordered by mature landscape, the property welcomes local wildlife, which is perfect for nature lovers. Enjoy scenic views from the 500 sqft wrap around Trex deck, including from every room in the home. Consisting of 1,694 square feet of finished living space and filled with an abundance of natural light, this energy efficient A-Frame residence was constructed with quality and thoughtfully designed for the modern homeowner with an energetic lifestyle... The Chesapeake Bay can be accessed at the community beach and boat ramp. If you're looking for entertainment, there may be live music at The Shanty Bar at Tolchester Marina less than 1 mile away.

Type:
Single Family-Detached
Sq.Ft.:
1,976
Status:
Active
Beds:
3
Lot size:
0.08 Acres
Year built:
2003
Baths:
3.00
MLS#:
MDKE115366
Subdivision:
Oakstreet

ADDITIONAL INFORMATION

Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living. A MUST SEE!!

Type:
Single Family-Detached
Sq.Ft.:
1,440
Status:
Active
Beds:
2
Lot size:
0.53 Acres
Year built:
1920
Baths:
1.00
MLS#:
MDKE115284
Subdivision:
Fairlee

ADDITIONAL INFORMATION

Handyman special, needs work, lots of potential. Rt. 20, to right in Fairlee to Bayshore Road, property on the right.

Type:
Single Family-Detached
Sq.Ft.:
1,344
Status:
Active
Beds:
3
Lot size:
0.85 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE115216
Subdivision:
Fairlee Cove

ADDITIONAL INFORMATION

Welcome to 'Knot Now Boat House', which has been a very tastefully remodeled home located on Fairlee Creek. This can be a full time residence or your Holiday retreat or week-end get away. Fully updated kitchen with new counter tops, cabinets, and stainless appliances, Wonderful color choices with paint,decorating and flooring. New HVAC system and tankless water heater. Has own private dock with power lift and jet ski ramps. Plenty of room for all your water toys. Detached garage with extra storage area. A must see if your seeking waterfront property with your own private dock.

Type:
Single Family-Detached
Sq.Ft.:
2,464
Status:
Active
Beds:
4
Lot size:
1.19 Acres
Year built:
1987
Baths:
3.00
MLS#:
MDKE115148
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

Opportunity is knocking!! This beautiful home is located in Heather Heights conveniently situated between The Chester River Yacht and Country Club and Historic Chestertown. The home is turn key and well maintained with spacious rooms, wood floors, corian counters, large florida room overlooking the back yard, with attached garage. There are currently 4 bedrooms with the option to take the smallest bedroom and make it an office like the current owners have. Call to schedule your showing!!

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
3
Lot size:
1.18 Acres
Baths:
3.00
MLS#:
MDKE115074
Subdivision:
Prestwick

ADDITIONAL INFORMATION

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders

Type:
Single Family-Detached
Sq.Ft.:
3,031
Status:
Active
Beds:
5
Lot size:
0.21 Acres
Year built:
1925
Baths:
4.00
MLS#:
MDKE115048
Subdivision:
Chestertown

ADDITIONAL INFORMATION

This stately colonial is located on the famed Water Street in the historic district of Chestertown. The home features 1 off street parking space and one on street parking space, high-end upgrades including Wolf appliances, Sub Zero refrigerator, Granite counters, Rinnai instant hot water, radiant floor heating in the kitchen, Generac whole house generator, Honeywell commercial dehumidifier in the basement, slate roof and extensive landscaping with a sprinkler system. The owners have done a great job preserving features from the original era. With the large flowing rooms downstairs and the added porches and patio, this home is perfect for entertaining. A classic Chestertown beauty! Call to schedule your showing today.

Type:
Single Family-Detached
Sq.Ft.:
2,928
Status:
Active
Beds:
3
Lot size:
1.38 Acres
Year built:
1955
Baths:
2.00
MLS#:
MDKE115054
Subdivision:
Country Club Estates

ADDITIONAL INFORMATION

Water views of the Chester River are a visual delight from this outstanding property on the Eastern Shore. Set on 1.3-acres in a highly-desirable residential area, the meticulously cared for home is just a walk away from Chester River Yacht & Country Club and is 1-mile from historic Chestertown. The open design creates generously sized, bright rooms with lovely views inviting outdoor living. Notable highlights such as wood detail, built in bookcases and a fireplace create a warm ambiance. The terrace overlooking gardens and the pond offers a serene setting, while the screened porch offers a lovely spot to enjoy the river views. Visitors and residents alike stroll around downtown Chestertown with its picturesque 18th century homes, brick walkways, Chester River Walk and marina. Enjoy the cafes, galleries, pubs, shops, live theater, farmers market, trails, First Friday, or take a river cruise on the Chester River Packet. There is a vibrant arts community and the town~s annual events include the Chestertown Tea Party, Harry Potter Festival and the Tall Ship Downrigging Weekend. Chestertown is home to Washington College and is located about 90-minutes from Washington and Philadelphia.

Type:
Single Family-Detached
Sq.Ft.:
1,260
Status:
Active
Beds:
3
Lot size:
0.48 Acres
Year built:
1994
Baths:
2.00
MLS#:
MDQA139446
Subdivision:
Char Nor Manor

ADDITIONAL INFORMATION

Three bedroom cottage with wonderful water views of the Chester River. Settle today.. entertain tonight. House is turn key, move in condition with furniture conveying with house. Must see, located in Queen Anne's County with lots of charm! Perfect size and in immaculate condition! Sellers are offering a one year home warranty plan

Type:
Other
Sq.Ft.:
1,849
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE114134
Subdivision:
None Available

ADDITIONAL INFORMATION

Lovely, low-maintenance 3-bedroom, 2-bath Victorian features a charming interior with beautifully restored original pine floors and updated kitchen. The home also offers a third floor studio/loft space and a private, fenced rear yard, plus off-street parking for two cars! Ideally located a few blocks from the town waterfront and right in the heart of the Historic District, it doesn't get any better than this!

Type:
Single Family-Detached
Sq.Ft.:
2,530
Status:
Active
Beds:
4
Lot size:
0.1 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE113968
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

PRICE IMPROVEMENT! Historic Downtown beauty with numerous recent upgrades has a potential FIRST FLOOR MASTER, sought after off street/driveway parking, within ONE block of the new & improved Chestertown Marina, and in the HEART of everything Chestertown has to offer. Totaling four bedrooms - with the possibility for two more, two bathrooms, gorgeous hardwood floors, huge kitchen with stainless steel appliances, the perfect front porch, and a cozy, low maintenance backyard full of raised bed gardens and entertaining space! What more can you ask for in a Downtown home? A must see.

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
2
Lot size:
0.5 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE107850
Subdivision:
None Available

ADDITIONAL INFORMATION

Rehab potential value is in the land only

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
4
Lot size:
168.77 Acres
Year built:
2002
Baths:
3.00
MLS#:
MDKE104742
Subdivision:
None Available

ADDITIONAL INFORMATION

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

Type:
Single Family-Detached
Sq.Ft.:
5,250
Status:
Active
Beds:
5
Lot size:
76.07 Acres
Year built:
1781
Baths:
6.00
MLS#:
MDKE100016
Subdivision:
None Available

ADDITIONAL INFORMATION

Owners will be creative in financing this1781 Eastern Shore beauty fully restored in the 90's. Entered down a tree line drive Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite addition, a new 3 BR Tenant House, dock with lift and an in-ground pool. Tenant house is a successful Airbnb source of income. Tenant farmed on 27 acres with more available. Perfect for todays lifestyle for the Sportsman while enjoying peaceful Eastern Shore outdoor life in a vibrant college town. New 301 road around Middletown makes an easy drive from Philadelphia, Wilmington. Owner is Licensed Real Estate Agent.

Type:
Single Family-Detached
Sq.Ft.:
1,168
Status:
Active
Beds:
2
Lot size:
2 Acres
Year built:
1948
Baths:
1.00
MLS#:
1009918978
Subdivision:
Fairlee

ADDITIONAL INFORMATION

Type:
Single Family-Detached
Sq.Ft.:
n/a
Status:
Active
Beds:
7
Lot size:
164.13 Acres
Year built:
1965
Baths:
9.00
MLS#:
1008176730
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular.

Type:
Other
Sq.Ft.:
2,064
Status:
Active
Beds:
4
Lot size:
0.06 Acres
Year built:
1900
Baths:
2.00
MLS#:
1006633640
Subdivision:
None Available

ADDITIONAL INFORMATION

Live in the heart of Historic Chestertown, Water views of the Chester River from the back of the house. Historic Water Street in front. Charming Colonial Revival house overlooking Washington College's Presidents gardens. A great place to sit on back or front porch and watch the world go by. Off street parking on the river side, on street parking in front. Easy to show, come and see.

Type:
Single Family-Detached
Sq.Ft.:
2,327
Status:
Active
Beds:
4
Lot size:
1.9 Acres
Year built:
1990
Baths:
3.00
MLS#:
1002400784
Subdivision:
Reba Anthony

ADDITIONAL INFORMATION

Premium materials and finishes,including yellow pine floors reclaimed from Camden Yards,really set this waterfront cape apart.Crown moulding,wainscoting,panel doors,fireplace,sun room and master on first floor are among the many amenities.Studio with AC/Heat is surrounded by a Williamsburg Garden and a gazebo sits waterside.Very private. Adjacent .44 perc approved lot can be purchased separately. Walk to C-town.

Type:
Single Family-Detached
Sq.Ft.:
9,651
Status:
Active
Beds:
7
Lot size:
164.13 Acres
Year built:
1965
Baths:
9.00
MLS#:
1002149830
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular.

Type:
Single Family-Detached
Sq.Ft.:
2,934
Status:
Active
Beds:
4
Lot size:
20.18 Acres
Year built:
2018
Baths:
4.00
MLS#:
1001986560
Subdivision:
Fairgale Properties

ADDITIONAL INFORMATION

Build your waterfront dream home on this little slice of heaven, offering the best of both worlds with 20+ acre of farmland and fringe woodlands on Fairlee Creek, with deeded slip at the private community dock with deep water! Hunting, fishing, horses, waterfront homestead...there are so many possibilities to enjoy the Eastern Shore lifestyle! Pictures show options & upgrades that can be built.

Type:
Single Family-Detached
Sq.Ft.:
896
Status:
Active
Beds:
3
Lot size:
0.46 Acres
Year built:
1955
Baths:
1.00
MLS#:
1001536056
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

TOLCHESTER BEACH COTTAGE - cozy 3 bedroom, 1 bath cottage with public sewer on large lot with outbuilding and mature trees. Home needs some cosmetic TLC, but would be perfect for your weekend getaway. Community access to beach area and Chesapeake Bay just around the corner. Come check it out!

Type:
Single Family-Detached
Sq.Ft.:
1,107
Status:
Active
Beds:
3
Lot size:
0.81 Acres
Year built:
1976
Baths:
2.00
MLS#:
1000479984
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Eastern Shore waterfront retreat is privately sited on Mill Creek. Designed with cedar exterior and interior, the single floor home offers a casual ambiance with great room and large windows with water views. A new roof was installed in 2013. The dock, new deck, hot tub and floating dock invite outdoor living. Enjoy historic Chestertown with its River Walk, Washington College, shops and dining.

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76–100 of 103 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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