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Samantha Grimes
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Chestertown MD Real Estate & Homes for Sale

41 Properties Found


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Beds:
1
Baths:
1 Full
Sq.Ft.:
652
Status:
Active
MLS#:
MDKE2003722
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
4,804
Status:
Active
MLS#:
MDQA2009012
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
9.58 Acres
Year built:
2010
Courtesy: TTR Sotheby's International Realty, (410) 673-3344
View additional info

Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,512
Status:
Active
MLS#:
MDQA2009262
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.39 Acres
Year built:
2024
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

This BRAND NEW 3-bedroom, 2.5-bathroom Cape Cod home is move-in ready! It boasts water views of the Chester River and an open-concept layout. The kitchen has stainless steel appliances, and the main-level master suite has a walk-in closet and ensuite. Upstairs, you'll find two more generously sized bedrooms and an additional full bathroom. High speed internet is available. The home is located at the end of a quiet, private street. Queen Anne's County Impact Fees have been paid by the Seller.

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,459
Status:
Active
MLS#:
MDKE2003704
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
3.95 Acres
Year built:
2000
Courtesy: Doug Ashley Realtors, LLC
View additional info

Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip with a lift onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood.

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
2,210
Status:
Active
MLS#:
MDKE2003556
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
1.89 Acres
Year built:
1992
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds and located just minutes from Historic downtown Chestertown. Community living without any HOA restrictions. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. Property provides ample space to expand with additions to the current floor plan or adding a detached garage/shop, pool or add to the expensive landscaping. As you step inside, you're greeted by the grandeur of vaulted ceilings that create an open and airy atmosphere. The ground floor primary bedroom provides convenience and luxury. Complete with a upgraded kitchen featuring granite countertops, quality stainless steel appliances, an island with a gas cooktop, and a built-in wine refrigerator centers the home. The main level's open layout is perfect for entertaining, with the added convenience of a bar with a sink. The primary bedroom is a true sanctuary, featuring a luxury primary bath with a jetted tub and a stylish tile shower with glass doors. The second floor offers a guest bedroom, a full bath, and a loft that could easily be converted into a third bedroom or utilized as a versatile space according to your needs. Outdoor living is equally impressive, with a screened porch, large composite deck with a retractable canopy, a gazebo, and beautiful English cottage gardens featuring many native plants. The expansive outdoor space is perfect for gardening, outdoor activities, or simply enjoying the serene surroundings. Backing to trees and farmland, this property provides a peaceful backdrop and ample privacy. It's truly a must-see for those seeking a blend of modern luxury and peaceful countryside living. Schedule a showing today to experience the beauty and serenity of this exceptional property at Orchard Hill.

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,150
Status:
Active
MLS#:
MDKE2003374
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.46 Acres
Year built:
1949
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty Beach Bar and the Tolchester Marina. A great place to enjoy live music, great food and drinks. Each unit has new mini-split systems for heating and cooling. These would be a perfect vacation home or you could live in one and rent out the other. These would also make good airbnb or vrbo properties. The front cottage is approximately 400 sq ft. The back cottage is approximately 750 sq ft. Come check them out!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,454
Status:
Active
MLS#:
MDKE2003384
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, 4434803453
View additional info

Prime Location Alert! Nestled along one of Chestertown's bustling thoroughfares, this delightful 3-bedroom, 1-bathroom bungalow exudes charm and possibility. Boasting a coveted Intense Village zoning, this property opens doors to a myriad of opportunities, whether for residential bliss or a variety of commercial endeavors. Step inside to find a generous family room seamlessly connected to the galley kitchen, offering a cozy yet functional layout. Relax and unwind in the screened-in porch or take advantage of the detached 2-car garage, complete with abundant off-street parking. Recent upgrades add to the allure, including a new heat pump with central air in 2021, a fresh roof installment 2022, and plush new carpetingâeach enhancing both comfort and aesthetics. Location-wise, convenience reigns supreme, with proximity to Chestertown's treasures such as Washington College, the hospital, local boutiques, the newest marina, eclectic dining options, and much moreâall just a stone's throw away, promising a lifestyle of ease and accessibility. Overflowing with potential, this property beckons for visionaries and dreamers alike. Please take note, there's an existing lease in place, expiring on December 31, 2024. Don't miss out on this golden opportunity!

Beds:
2
Baths:
1 Full
Sq.Ft.:
826
Status:
Active
MLS#:
MDQA2007694
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.81 Acres
Year built:
1961
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main floor, and beautiful windows to let in an abundance of natural light. Enjoy almost an acre of land with plenty of room to enjoy the quiet outdoors. This home is located in Queen Anneâs County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake Bay Bridge, and lots of local amenities near by.

Beds:
4
Baths:
4 Full/1 Half
Sq.Ft.:
5,195
Status:
Active
MLS#:
MDKE2002790
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.39 Acres
Year built:
1760
Courtesy: Maryland Heritage Properties, (443) 480-7342
View additional info

SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchantâs home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chefâs kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a âsecretâ staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the homeâs original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artistâs studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian âpainted ladies.â With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleriesâbut no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
Active
MLS#:
MDKE2002800
Type:
Single Family, Single Family-Detached
Subdivision:
Chester River Landing
Lot size:
0.06 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,315
Status:
Active
MLS#:
MDKE2002724
Type:
Single Family, Single Family-Detached
Subdivision:
Chester River Landing
Lot size:
0.03 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,784
Status:
Active
MLS#:
MDKE2002704
Type:
Single Family, Single Family-Detached
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE2002650
Type:
Townhouse
Subdivision:
Chester River Landing
Lot size:
0.03 Acres
Year built:
2024
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2001612
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.06 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,490
Status:
Active
MLS#:
MDKE2001598
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.09 Acres
Year built:
2022
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2001618
Type:
Townhouse
Subdivision:
Chestertown Historic District
Lot size:
0.09 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

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