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Karen Flowers

Chestertown MD Real Estate & Homes for Sale

27 Properties Found

The median home value in Chestertown, MD is $380,000. This is higher than the county median home value of $249,900. The national median home value is $308,980. The average price of homes sold in Chestertown, MD is $380,000. 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.


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Beds:
4
Baths:
2 Full
Sq.Ft.:
2,568
Status:
NEW LISTING
MLS#:
MDQA2012546
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1976
Courtesy: Berkshire Hathaway HomeServices PenFed Realty
View additional info

Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting. Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall-crafted from the familys 1930s farm in Kennedyville. Just beyond, a spacious two-car garage provides convenience, while the backyard invites endless enjoyment with an above-ground pool, a deck, and a cozy fire pit. Inside, the galley kitchen boasts white cabinetry, granite countertops, and stainless steel appliances. Adjacent to the kitchen, a warm and inviting den features a wood stove, abundant natural light, and a spiral staircase leading to the private owners suite. The front of the home offers a welcoming sitting room, along with three comfortable bedrooms, a full hall bath, and a convenient laundry closet-all on the first floor. Upstairs, the expansive owners suite is a true sanctuary. Enter through a charming foyer into a space filled with natural light from grand portrait windows. Enjoy the oversized walk-in closet, vaulted ceilings, and a private balcony, plus a versatile nook ideal for a desk, workout space, or cozy reading corner. The ensuite bath is a spa-like retreat, featuring a jacuzzi tub, separate shower, dual sinks, and soaring ceilings. This Eastern Shore gem offers a lifestyle of comfort, character, and unforgettable moments. Dont miss your chance to make it yours! Walk to the water, spend weekends in downtown Chestertown at the famous farmers market, shops or restaurants. Watch a game at Washington College, take a kayak out on the river or make a day trip to Easton, St. Michaels, Chesapeake City or Delaware. This property has everything you could want and No HOA. Join us for an Open House 3/23 12-1:30pm. Seller is motivated and ready to pass this well maintained home to the next owners just in time for summer!

Open House:

Saturday, 3/29 11:00-1:00PM

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,420
Status:
NEW LISTING
MLS#:
MDKE2004946
Type:
Single Family, Single Family-Detached
Subdivision:
COVENTRY FARMS
Lot size:
0.24 Acres
Year built:
2010
Courtesy: The Parker Group
View additional info

Welcome to 314 Devon Dr, Chestertown, MD 21620-an elegant 4-bedroom, 3.5-bath home offering spacious living areas and thoughtful upgrades. The grand foyer leads to a beautifully designed kitchen with a large island, perfect for cooking and entertaining. The expansive master suite features a spa-like bath with a soaking tub, separate shower, and double vanity. The fully finished basement provides additional living space, complete with a full bathroom, making it ideal for guests, a recreation area, or a home theater. Select furnishings in basement are available to convey. Outside, enjoy a fenced-in backyard with a deck leading to a patio, ideal for outdoor gatherings. Conveniently located near downtown Chestertown, this home offers easy access to shopping, dining, and waterfront activities. Schedule your showing today!

Beds:
2
Baths:
2 Full/2 Half
Sq.Ft.:
1,867
Status:
NEW LISTING
MLS#:
MDKE2004942
Type:
Townhouse
Subdivision:
OAK HOLLOW
Lot size:
0.1 Acres
Year built:
2004
Courtesy: Doug Ashley Realtors, LLC
View additional info

Charming & Move-In Ready Discover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come. The spacious master suite features vaulted ceilings, a stall shower and a soaking tub. Additional roomy bedroom on this level with washer and dryer in between Primary bedrooms. Enjoy 10-foot ceilings on the second floor, Living room, dining and Kitchen area with a walk-out second-story deck, Main level as you can enter into the oversized garage with a workshop, perfect for storage or projects. On the ground level, you find a bonus room which is the perfect study /office all ready for you to decide. Powder room on each level. For relaxing and fresh air you have both a deck and patio, this home is again move-in ready. Updatd HVAC unit is another positive and reflection of how the home has been maintained and cared . As an end-unit, it benefits from an abundance of natural light, enhancing its warmth and charm. Conveniently located near shopping, dining, and entertainment, this home is perfect for both weekend getaways and year-round living. Don't miss out on this incredible opportunity-schedule your showing today!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDKE2004940
Type:
Townhouse
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Lot size:
0.09 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,056
Status:
Active
MLS#:
MDQA2012402
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1975
Courtesy: Doug Ashley Realtors, LLC
View additional info

Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

Beds:
2
Baths:
1 Full
Sq.Ft.:
912
Status:
Active
MLS#:
MDKE2004902
Type:
Single Family, Single Family-Detached
Subdivision:
TOLCHESTER ESTATES
Lot size:
0.37 Acres
Year built:
1952
Courtesy: RE/MAX Leading Edge
View additional info

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar. just a very quick trip to entertainment, dining or boating. Great location, just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,560
Status:
Active
MLS#:
MDQA2012102
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1987
Courtesy: RE/MAX Executive
View additional info

Welcome to this beautiful 3-level Colonial in the sought-after Chester Harbor community on the Queen Annes County side! Nestled on a private lot, this home offers timeless charm, modern updates, and access to the water. Inside, you'll find three spacious bedrooms with newer carpeten upstairs with a full bathroom, while the main level features a large kitchen, dining room, and a cozy sitting area with a wood-burning fireplace. A second full bathroom on the main level adds convenience, and the home boasts gleaming hardwood floors and fresh paint throughout. The full basement provides ample storage or the potential for additional living space, and the 2-car garage offers plenty of room for vehicles and gear. Located in the water-oriented Chester Harbor community, this neighborhood surrounds the Chester River and offers fantastic amenities, including boat ramps for easy water access, a community pier for fishing and relaxation, and a park with picnic tables. Enjoy the peaceful setting while remaining just minutes from major routes, shopping, and dining. Dont miss out on this incredible home-schedule your tour today!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
4,023
Status:
Active
MLS#:
MDKE2004906
Type:
Single Family, Single Family-Detached
Subdivision:
BROAD NECK
Lot size:
5 Acres
Year built:
1989
Courtesy: Maryland Heritage Properties
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HIGHFIELD, has been home to the renown architectural historian Michael Bourne and his family for almost forty-years. Mr. Bourne who authored the important Historic Houses of Kent County and guided the restorations of over 400 historic structures in the mid-Atlantic, together with his wife, Ann, created a home that reflects their deep appreciation for the refined beauty of historic architecture and preservation. HIGHFIELD, reflects the Bournes sophisticated taste and serious attention to every detail. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, HIGHFIELD is definitely reminiscent of the vernacular farmhouses of Suffolk County, England where they visited often. Outstanding historic architectural details have been incorporated throughout the house. From the Hamstone fireplace surround and hearth (actually imported from Somerset, England) in the formal Living Room, to the use of antique doors to many of the rooms fitted with both original antique and fine reproduction hardware, HIGHFIELD is a rare find! These most important details create an inviting warmth and add to its unique character. The handsome two-story, many-paned window of the Great Room faces SSE. While looking out over a stone patio and well-established perennial beds, it provides a significant amount of passive solar gain keeping energy costs low - a compliment to the six-zone heating system. As a design and practical feature, a blue enameled Lange wood stove stands proudly in the Great Room. A more formal Living Room offers windows on the west gable that afford views of the surrounding fields, expansive grounds and woods. French doors on the south side lead to an ample screened flagstone-floored porch. Additionally, the first floor includes the large open Chefs Kitchen, Den/Office, Mudroom, and half-bath. At the top of the stair, a balcony leads across the Great Room to the Master Suite where design details include a tray ceiling, built-in cupboards, dressing room, and spacious bath with separate vanities, shower, soaking tub, and Portuguese tile accents. The second bedroom with full bath is located at the east end of the balcony where a stair leads to the third-floor bedroom with walk-in closets. Access to the attic is found here. Accessible from the mudroom, the full basement includes, a large ante-space, laundry room, playroom, and workshop. An unusual â??bakeryâ? building with wood-fired brick oven, walk-in refrigerator, and half-bath stands nearby. An additional utility shed is included. See summary of features in Documents Folder. The private 5-acre property is located only 3 miles from Chestertown which uniquely offers swift access to this historic, vibrant town. Chestertown, located in the County of Kent on Marylands Eastern Shore, is home to Washington College, tenth oldest college in America, the Schooner Sultana, a strong arts community, and live theater. This area is known worldwide for its beautiful Chester River, sailing, wildfowl, and agriculture. All, a short drive to four major airports, New York, Annapolis, Baltimore and Philadelphia.

Beds:
5
Baths:
6 Full/2 Half
Sq.Ft.:
9,852
Status:
Active
MLS#:
MDKE2004760
Type:
Single Family, Single Family-Detached
Subdivision:
QUAKER NECK
Lot size:
80.51 Acres
Year built:
2001
Courtesy: Cross Street Realtors LLC
View additional info

Beautifully situated on the east fork of Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. Sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The residence succeeds as a home for family comfort, entertaining, relaxing and being one with nature. Its east/west orientation highlights sunrises and sunsets that can be enjoyed from every room in the house. A real retreat. The five bedroom and 7 fireplace (woodburning) home was designed with 12-foot ceilings on the first floor to accentuate the views and the light. A main floor primary suite includes two separate en-suite dressing rooms and bathrooms along with a wood burning fireplace. The second floor has four bedrooms, three with fireplaces, and all with en-suite bathrooms. One bedroom has a separate sitting room. A wide hall runs along the width of the house providing access to all of the rooms. The exterior property of this 80-acre estate features the landscape design of acclaimed D.C. based Oehme, van Sweden. Hardscapes and plantings were strategically orchestrated and include a walled garden filled with flowering trees and shrubs along with a sweep of peonies in the spring. Three ponds invite active wildlife, including a beautiful blue heron. The farm fields are being organically farmed by a neighboring farmer. Two structures in the garden provide a relaxing reading or meditation venue. Bluestone and brick terraces along the entire river facing side of the house lead to a pool and pool pagoda. The property is uniquely designed to capture the feeling of the land while being welcoming and inviting to all who live there or visit. Caretaker house with barns and silo are situated at property entry. Family hunting and fishing are exceptional. Rock Fish is plentiful. The main residence has recently benefited from a new cedar shake roof and updated energy efficient French doors and windows throughout. The unfinished basement is approx. 2900 square feet with 9' ceilings, inviting the next steward to introduce additional lifestyle enhancements. (Property access is prohibited without a scheduled showing with licensed broker/agent. Thank you.)

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,106
Status:
Active
MLS#:
MDKE2004846
Type:
Single Family, Single Family-Detached
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.95 Acres
Year built:
1988
Courtesy: EXP Realty, LLC
View additional info

Welcome to 10705 Millbrook Drive, a charming Cape Cod-style home located in the desirable Chesapeake Landing community. This 3-bedroom, 2-bathroom residence offers comfortable living with modern updates, including bamboo flooring and a high-efficiency water heater. The open floor plan is perfect for entertaining, with a spacious living area and well-appointed kitchen featuring Meganite countertops. Enjoy the tranquility of the surrounding area from the private deck, or take advantage of the community amenities, including a boat ramp, dock, and water privileges. The home also features a basement with a sump pump, a gravel driveway for off-street parking, and a private well and septic system. Just minutes from the heart of Chestertown, this home is a perfect blend of convenience, comfort, and nature. To help visualize this homes floorplan and to highlight its potential, virtual furnishings may have been added to photos found in this listing

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,224
Status:
Active
MLS#:
MDKE2004840
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HEIGHTS-RT 213 N
Lot size:
0.21 Acres
Year built:
1949
Courtesy: Cross Street Realtors LLC
View additional info

Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use functionality .Excellent potential for a home business, in-law suite, or rental income from one or both units! With a prime location, countless upgrades, and flexibility, this diamond in the rough is ready to shine. Don't miss the opportunity to make it yours! Unit A: Bright & Spacious 2 Bed / 1 Bath This well-appointed 2-bedroom unit offers a comfortable and inviting living space. Large Living Room Area Updated kitchen with new Vinyl flooring and fixtures, perfect for cooking and separate Dining area. Convenient in-unit laundry with a stackable washer/dryer to simplify daily life. Refinished oak floors complemented by new ceiling fans, faucets, lights, receptacles and Freshly Painted for a polished look. Recently upgraded bathroom featuring Vinyl floor and a fresh design. Dedicated front parking for convenient and private access. Unit B: Modern 1 Bath Studio with Private Access This updated studio unit is ideal for a tenant seeking comfort, privacy, and convenience. With thoughtful renovations and modern upgrades. Private parking area with a safety light for added security and convenience. Dedicated side entrance featuring a new porch with safety rails and a durable cement base. Vinyl flooring throughout for a fresh and modern feel. Fully renovated kitchenette and bathroom, providing all the essentials in a sleek design. Exterior Highlights Newly installed apron driveway allows for seamless in-and-out access and parking around the house. Regraded landscaping with underground drainage ensures quick water management. New siding, trim, and gutter-guard gutters offer low-maintenance protection. Dependable pest/termite policy transferable to the new owner. Shed for additional storage Septic pumped and Well sealed in January 2025 for peace of mind. Registered with separate addresses for county emergency services. A wall divides the units but includes an existing door for easy conversion back to a single-family home if desired. Excellent potential for a home business, in-law suite, or rental income from one or both units!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2004782
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Year built:
2024
Courtesy: Gunther-McClary Real Estate
View additional info

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,392
Status:
Active
MLS#:
MDQA2011782
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.76 Acres
Year built:
1976
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large primary bedroom with its own private bath and an impressive walk-in closet, which includes a cedar section for added storage and warmth. The kitchen and dining area, featuring newer flooring (installed just two years ago), create a modern, inviting space for meals and family gatherings. The kitchen is equipped with updated appliances, ensuring a functional and stylish area for cooking. Outside, the fenced yardâ??perfect for both kids (two- or four-legged)â??provides a safe and spacious environment to play and explore. The fence, installed just four years ago, adds a secure touch to the property. Additionally, the detached two-car garage offers ample storage for vehicles, tools, or water toys.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,698
Status:
Active
MLS#:
MDQA2011970
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1977
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 238 X 184 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to have a daycare! A voluntary HOA allows access to the communities private beach, dock and playground all located on Rosin Creek with access to the Chester River! Va loan has an assemble low interest rate for those who qualify for VA!

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,272
Status:
Active
MLS#:
MDKE2004728
Type:
Single Family, Single Family-Detached
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.34 Acres
Year built:
1973
Courtesy: Doug Ashley Realtors, LLC
View additional info

Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax on the easterly front porch or open side deck, surrounded by nature's beauty and wildlife. With a fully encapsulated crawlspace, tankless hot water heater, and a well-equipped kitchen, this home is truly move-in ready for your peaceful Eastern Shore retreat.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,114
Status:
Active
MLS#:
MDQA2011266
Type:
Single Family, Single Family-Detached
Subdivision:
CHAR NOR MANOR
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your boat and the Deep Landing Boat Ramp is just minutes away . Very affordable home in our area, don't wait on this one! Back on the market at no fault of the seller! Schedule your showing today!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,380
Status:
Active
MLS#:
MDQA2011746
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.35 Acres
Year built:
2005
Courtesy: The Hogans Agency
View additional info

Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen Annes County Schools! Comfortable serene and convenient - this well cared for home has hardwood floors and a new hot water heater and water tank on 3/11/2023 and an attached workshop!

Beds:
5
Baths:
3 Full
Sq.Ft.:
3,355
Status:
Active
MLS#:
MDKE2004550
Type:
Single Family, Single Family-Detached
Subdivision:
CHESMAR
Lot size:
0.91 Acres
Year built:
1963
Courtesy: TTR Sotheby's International Realty
View additional info

A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles, and storage. All situated on almost one full acre. Brand new upgrades since Sept '24 include central AC, roof, refinished hardwood floors, and paint throughout. With easy access to Morgnec Rd, Rt. 301 is only 12 minutes away... which leaves you only an hour's drive from Wilmington, DE or Philadelphia, PA. And into the heart of NYC in less than three hours. Escape to the Eastern Shore lifestyle!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
4,446
Status:
Active
MLS#:
MDKE2004002
Type:
Single Family, Single Family-Detached
Subdivision:
KENT COUNTY
Year built:
1990
Courtesy: Gunther-McClary Real Estate
View additional info

**Exclusive Waterfront Craftsman Home with Sandy Beach - A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water slip at the community dock provides the perfect spot for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above-complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether youre lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. Its the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
2,767
Status:
Active
MLS#:
MDQA2010882
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.46 Acres
Year built:
1970
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Dont let the outside fool you-this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm. Step inside to discover a stunning custom kitchen, a true chefs dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving-perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout. Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath. Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities-whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality. Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed-ideal for hobbies, storage, or workshop space. This home is completely move-in ready and packed with upgrades-all it needs is you! Dont miss your chance to see this hidden gem-schedule your private showing today!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2004262
Type:
Single Family, Single Family-Detached
Subdivision:
PRESTWICK
Lot size:
1.18 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

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

Beds:
3
Baths:
3 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2004206
Type:
Condo
Subdivision:
HISTORIC CHESTERTOWN
Year built:
1885
Courtesy: Gunther-McClary Real Estate
View additional info

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This condominium embodies the ideal waterfront living experience. Located in the heart of historic Chestertown, this unique property includes off-street parking and provides the convenience of walking into town for dining and shopping. Situated on Maryland's scenic Eastern Shore, it's less than 85 miles from Washington D.C. and Philadelphia, making it a perfect meeting spot for those in the Mid-Atlantic region.

Beds:
7
Baths:
3 Full/1 Half
Sq.Ft.:
3,664
Status:
Active
MLS#:
MDKE2004076
Type:
Townhouse
Subdivision:
HISTORIC DISTRICT CHESTERTOWN
Lot size:
0.13 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

Beds:
2
Baths:
1 Full
Sq.Ft.:
787
Status:
Active
MLS#:
MDKE2003742
Type:
Condo
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. Deeded slips are also available for purchase, with boat lifts! 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 Marylands 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.

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 1800s 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 Marylands 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.

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