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Chestertown MD Real Estate & Homes for Sale

44 Properties Found

The median home value in Chestertown, MD is $385,000. 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 $385,000. 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.


1–25 of 44 properties displayed
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Beds:
2
Baths:
1 Full
Sq.Ft.:
910
Status:
NEW LISTING
MLS#:
MDKE2005444
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.06 Acres
Year built:
1949
Courtesy: ANR Realty, LLC
View additional info

Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,325
Status:
NEW LISTING
MLS#:
MDKE2005430
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.41 Acres
Year built:
1960
Courtesy: Cummings & Co. Realtors
View additional info

It doesnt get any more hometown than this new offering right smack in the heart of hometown Chestertown! Its peaceful, its rural and it looks like a Norman Rockwell this town. This is the Eastern Shore at its finest with plenty amenities close to town and countless activities for those sportsman who like to hunt fish and crab. Thats what we do out here and you have the Chester River right in your backyard. Inside this modern style home youll find spacious rooms, a large kitchen and a perfect palette to bring your final details to make this one a shining star in the neighborhood. Its just about move in ready and its right in town so dont drag your feet, get over here, take a look and send us an offer!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,258
Status:
NEW LISTING
MLS#:
MDQA2013956
Type:
Single Family, Single Family-Detached
Subdivision:
CHAR NOR MANOR
Lot size:
0.35 Acres
Year built:
2006
Courtesy: RE/MAX Executive
View additional info

Chester River Views from Every Angle! Welcome to this stunning Colonial located on the Queen Annes County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living. This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy entertaining in the massive kitchen, which boasts a large eat-in area and picture-perfect views of the river and backyard. The main level also includes a huge laundry room and a 2-car attached garage for convenience. Step outside to your beautiful back deck and large yard, where you can relax, entertain, and soak in the breathtaking water views that make this home truly special. If you're looking for space, charm, and waterfront serenity, this Chester River gem is it!

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,401
Status:
NEW LISTING
MLS#:
MDKE2005366
Type:
Single Family, Single Family-Detached
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.84 Acres
Year built:
2005
Courtesy: Cross Street Realtors LLC
View additional info

Private waterfront retreat on Mill Creek offering beautiful views, spacious living, and all the peace and quiet you have been looking for. This custom-built Cape-style home is nestled on a serene, protected stretch of water and offers the ideal blend of comfort and tranquility. With 4 bedrooms and 3 full baths, the home features a flexible floor plan designed for both everyday living and entertaining. A cozy wood-burning fireplace anchors the open-concept great room, while large windows frame tranquil water views and flood the home with natural light. Beautiful hardwood floors flow throughout the main living areas, while two main-level bedrooms offer convenience and flexibility, including the Primary Suite with direct deck access. Step outside to a wraparound composite deck and enjoy your morning coffee overlooking the water-or take in the peaceful views from the bright breakfast area. Upstairs, you will find two additional bedrooms, and a spacious bonus room that could serve as a game room, media space, or guest bedroom. The full unfinished basement offers high ceilings and is ready for your vision-whether you're dreaming of a workshop, home gym, or additional living space. An oversized, climate-controlled two-car garage offers plenty of room for storage and projects. Outside, a private dock with 3 ft MLW includes an 8,000 lb boat lift, additional slip, a swim platform, and direct access to Mill Creek for boating, fishing, and crabbing. Spacious, private, and designed for comfort and connection-this is Eastern Shore waterfront living at its finest. Do not enter the property without an appointment.

Beds:
n/a
Baths:
Sq.Ft.:
1,600
Status:
NEW LISTING
MLS#:
MDKE2005422
Type:
Single Family, Single Family-Detached
Subdivision:
CHESMAR
Lot size:
0.63 Acres
Year built:
1956
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Open House:

Saturday, 7/12 10:00-12:00PM

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,056
Status:
NEW LISTING
MLS#:
MDQA2013930
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1975
Courtesy: RE/MAX Executive
View additional info

Charming Updated and Well Maintained Rancher in the Chester Harbor Community of Queen Anne's County Chestertown! This house is the definition of "move-in ready" as the owner has taken tremendous pride in keeping the property updated. Over the years, they've installed new windows, new HVAC unit, new hot water heater, remodeled the kitchen, installed new appliances, painted the interior, added new flooring , and given the bathroom a refresh. The fully fenced backyard includes an oversized detached shed, upgraded BAT septic system, concrete patio and mature trees for additional privacy and shade. Plus, a brand new roof!! Conveniently located close to Church Hill, Centreville, Wye Mills and Kent Island. Or head across the Chester River (moments away) into Kent County Chestertown, Worton, Galena or Kennedyville!! Community of Chester Harbor also features a neighborhood playground, basketball hoop, pier and small boat launch with voluntary fee.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,008
Status:
NEW LISTING
MLS#:
MDKE2005362
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Lot size:
0.04 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

See your boat from your house! This historic home located at Chestertown marina has been remodeled as recently as 2021. Gorgeous Heartland appliances compliment the hand crafted free-standing cabinetry in the kitchen. A first floor guest suite addition includes a sitting room connected to the house via a mudroom/porch. Above the mudroom is a second story deck that was built to hold a hot tub (with double 2x8 joists according to the owner!) This private water-view deck leads to walk in attic space above the new guest/au-pair suite. Anderson composite dual pane windows custom fitted with planation shutters were installed throughout the home- all easy to open & energy efficient. The mudroom is fully insulated to allow open doors between the house and the rooms of the guest suite for complete versatility. This home is adaptable to many ways of living! With bedrooms on every floor to be used as you like, the 3rd floor could just as easily be a large family room or a bunk room. Explore the possibilities at 206 S Water St and enjoy complete walkability to parks, restaurants, farmers market, groceries, art galleries, festival activities, and shops!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,128
Status:
NEW LISTING
MLS#:
MDQA2013988
Type:
Single Family, Single Family-Detached
Subdivision:
CHAR NOR MANOR
Lot size:
0.2 Acres
Year built:
1954
Courtesy: Meredith Fine Properties
View additional info

Chester River Charm: Your Gateway to Eastern Shore Living Completely Renovated Cottage with River Views & Endless Possibilities Discover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifully transformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristine Chester River. Whether you're seeking a weekend escape, investment opportunity, or year-round retreat, this property delivers on every front. The Perfect Package Step into a home that's been thoughtfully reimagined from top to bottom. The open, light-filled interior showcases luxury vinyl plank flooring, fresh paint throughout, and new lighting that creates an inviting atmosphere perfect for both relaxation and entertaining. The updated kitchen features brand-new stainless steel Frigidaire appliances, while plantation shutters and custom window treatments add elegant touches throughout. Every comfort has been considered with new Mitsubishi mini-split heating and cooling systems ensuring year-round efficiency, plus a cutting-edge Stiebel Eltron tankless water heater and energy-saving solar panels that make this home as smart as it is beautiful. Outdoor Living at Its Finest The real magic happens outside, where mature gardens tell the story of seasons past and future. Dogwoods and cherry blossoms frame slate walkways and stone borders, creating a landscape that's both sophisticated and naturally beautiful. The 12x16 treated lumber deck provides the perfect spot for morning coffee with river glimpses, while the 10x12 shed offers excellent storage with its updated siding and metal roof. Location Advantages Position yourself in one of Maryland's most coveted regions, where the Chester River's calm waters offer world-class fishing, kayaking, and boating just 2 miles away at Deep Landing Boat Ramp. Historic Chestertown brings year-round culture with festivals like the famous Tea Party celebration, Saturday farmers markets, vibrant arts scenes, and waterfront dining that draws visitors from across the region. The strategic location offers quick access to major corridors-25 minutes to the Chesapeake Bay Bridge opens up Baltimore and Washington DC markets, while Delaware's beaches and Middletown are equally close.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,588
Status:
NEW LISTING
MLS#:
MDKE2005380
Type:
Single Family, Single Family-Detached
Subdivision:
MILE TREE VILLAGE
Lot size:
0.41 Acres
Year built:
1980
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much of the interior as well. The primary suite includes an en suite bathroom, make up parlor, and walk in closet. Outdoor living is a plus here with a partially shaded, fully fenced rear yard which includes a deck and a front private courtyard perfect for dinner parties. The detached 2 car garage allows for storing all of the toys that come along with the Eastern Shore lifestyle. This is the perfect balance with walkability, a spacious yard and the tranquility of living on a quiet cul de sac.

Open House:

Sunday, 7/13 1:00-3:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,350
Status:
NEW LISTING
MLS#:
MDKE2005402
Type:
Single Family, Single Family-Detached
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.6 Acres
Year built:
1977
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Welcome to 10674 Kasota Rd - Your Tranquil Masterpiece on the Chesapeake's Edge. Nestled in the serene enclave of Chesapeake Landing near Chestertown, this charming 2-bed, 1-bath ranch-style home invites you to reimagine rural living on nearly 0.6 acres of lush landscape. With 1,350 sq ft of one-level living, the brick exterior and detached 2-car garage offer timeless appeal and solid bones with breathtaking updates. Backing to a tranquil community recreation area and pond; Worton Creek access with optional HOA privileges means kayaking, fishing, or lakeside lounging are just steps away. Sprawling grounds offer plenty of room for gardening, play, or adding outbuildings-yet you're just minutes from Chestertowns antique charm, local eateries, and historic flair. Take a short drive to stroll historic High Streets boutiques or enjoy seasonal festivals like the Chestertown Tea Party. Boating, waterfront dining, and a strong sense of community make this more than a home-its a lifestyle. Thoughtfully Renovated: This gem is beautifully renovated and 100% move in ready, you can move in with confidence knowing that every detail was taken care of from the roof to the HVAC. Updates include: New Roof on both the house and the garage New Tankless Hot Water Heater New Windows New Updated Kitchen New Flooring New Updated Bathroom New Electrical Panel New AC New Heater New Trex Deck New Garage Doors New Siding Offered at $325,000. Schedule your tour today!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDKE2005398
Type:
Single Family, Single Family-Detached
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.45 Acres
Year built:
1988
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Charming One-Level Living Near the Chesapeake Bay! This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind. Enjoy your mornings on the shaded back deck, overlooking a large yard with a brand-new shed-perfect for storage or hobbies. Nestled on a quiet street, this property provides easy access to the Chesapeake Bay, and with optional HOA membership, you can unlock marina privileges for boating or kayaking adventures. Whether you're looking for a weekend retreat or a full-time residence close to town and proximity to water access, this home offers the perfect blend of convenience and tranquility.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,640
Status:
Active
MLS#:
MDQA2013388
Type:
Single Family, Single Family-Detached
Subdivision:
PHEASANTFIELD
Lot size:
21.23 Acres
Year built:
1940
Courtesy: Gunther-McClary Real Estate
View additional info

Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style home offers plenty of space for entertaining. Enjoy meals on the front porch, overlooking the Chester River. Additionally, there is a guesthouse with a kitchen, living area, bedroom and full bath. A short distance from the main home you will find the fully equipped horse barn. Completed in 2003, this barn has been exceptionally maintained. The barn offers 3 stalls, a tack room, sliding doors with glass windows, and a hayloft. The stalls open to the large fenced pastures, perfect for rotation. While not on the farm, enjoy exploring the Chester River! The private dock includes an electric boat lift, floating dock, and sun or swimming deck. Spend evenings watching the sunsets on the sundeck or easily launch a kayak off of the floating dock. Additional features include a 4-car garage with a loft, potting room or workshop, upstairs storage or office space and a pole barn to accommodate farm equipment. Discover the many possibilities of Pheasantfield Farm, an exceptional waterfront escape in Queen Anne's County!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,522
Status:
Active
MLS#:
MDKE2005370
Type:
Single Family, Single Family-Detached
Subdivision:
PRESTWICK
Lot size:
1.83 Acres
Year built:
2023
Courtesy: Gunther-McClary Real Estate
View additional info

Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless steel appliances, propane range and range hood, sizable island and countertop space, and a butler's pantry that adds functionality and organization. Enjoy summer meals and views of the trees on the spacious screened porch, or enjoy winter evenings inside by the fireplace. Two large guest bedrooms share a full bathroom, plus there is an extra room for an office, gym, or playroom. The primary bedroom has a massive walk-in closet and a beautifully finished bathroom with a walk-in shower. The spacious laundry area leads to the two-car garage with a walk-up attic space for extra storage. Prestwick offers the best of eastern shore living with small-town charm, yet it is only 1 to 2 hours from Wilmington, Philadelphia, Baltimore, and Washington, DC. Join the Chester River Yacht & Country Club and gain access to great golfing, club pool, marina (with boat slips), and boat a ramp. Located a short distance from the town marina or the many county-owned boat ramps. This property is a must-see; every aspect was thoughtfully considered to create a living space that is both functional and breathtaking.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,820
Status:
Active
MLS#:
MDKE2005094
Type:
Single Family, Single Family-Detached
Subdivision:
BYFORD DEVELOPMENT
Lot size:
0.34 Acres
Year built:
1986
Courtesy: Cross Street Realtors LLC
View additional info

Charming Rancher with Private Backyard Oasis in Byford Estates-Dont miss your opportunity to own this beautifully maintained ranch-style home tucked within the highly sought-after neighborhood of Byford Estates-just a short stroll to historic downtown Chestertown! With 3 spacious bedrooms, 2 full baths, and multiple living spaces, this property offers comfort, privacy, and the kind of charm thats hard to find. Inside you will discover sun-filled interiors, gleaming hardwood floors, and custom built-ins that add both character and functionality. The home flows effortlessly with a traditional yet open feel, featuring a formal dining area, a cozy breakfast room, and a welcoming living room. A bonus room off the primary suite is perfect for a home office, studio, or quiet reading nook. Enjoy the peaceful privacy of your professionally landscaped backyard, a true oasis with travertine pavers, lush native Maryland plantings, and an inground pool-ideal for entertaining or unwinding in solitude. The only known Katsura tree in Chestertown adds a touch of rarity and beauty to this one-of-a-kind property. The primary suite is your personal retreat with a walk-in closet, ensuite, and serene backyard views. On the opposite wing of the home, two additional bedrooms and a full bath offer separation and comfort for guests or family members. With three separate entrances to the rear patio, theres a natural indoor-outdoor flow perfect for gatherings. Upgrades include a 40-year architectural shingle roof, newer HVAC system with a 10 year warranty, a meticulously landscaped backyard custom designed to offer low maintenance for lasting appeal. Located within walking distance to downtown Chestertown where you can enjoy the nationally acclaimed Farmers Market, Walking Trails, Parks, Boutique Shops, Restaurants, Entertainment and of course the Chester River. Don't miss your opportunity, schedule a showing today!

Open House:

Saturday, 7/19 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE2005356
Type:
Townhouse
Subdivision:
TOLCHESTER
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Gently used 2 bedroom townhome in sought after Tolchester Village! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Thoughtfully remodeled and it shows like new! Common areas include a playground. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,056
Status:
Active
MLS#:
MDQA2013044
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1977
Courtesy: TTR Sotheby's International Realty
View additional info

Welcome to this cute-as-a-button home in the water-access community of Chester Harbor! Whether you're starting out, downsizing, or simply looking to simplify your lifestyle, this move-in ready gem offers the perfect balance of comfort, convenience, and charm. Set on a spacious third of an acre lot, this home offers just the right amount of space-three bedrooms, one full bath, and room to grow both inside and out. Recent updates over the past few years take the worry out of homeownership: enjoy low maintenance living with newer flooring throughout, a durable and stylish metal standing seam roof, a generously sized HVAC system for year-round comfort, and freshly sealed asphalt driveway. Step out back to a deck thats just calling for summer barbecues, crab feasts, or quiet evenings under the stars. A large two-bay shed with electric is the perfect place to store tools, bikes, or gear for all your hobbies. The manageable yard offers green space without hours of upkeep-ideal for pets, gardening, or a game of catch. Located just minutes from downtown Chestertown, shops, restaurants, and the water, this home blends quiet community living with everyday convenience. Best of all, there's no HOA-giving you flexibility and freedom without extra fees. Dont miss this opportunity to own your own home in a well-loved neighborhood at an approachable price point. Low maintenance, move-in ready, and full of potential-this is the one you've been waiting for!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,788
Status:
Active
MLS#:
MDKE2005230
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
3.22 Acres
Year built:
2003
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen / dining room combo behind with sun-room and back deck. Recent upgrades include: crawl space encapsulation, stainless steel kitchen appliances, downstairs heat pump, backyard fence, solid wood plantation shutters, automatic retractable blinds and more. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA. Enjoy easy country living on the Eastern Shore.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,290
Status:
Active
MLS#:
MDKE2005274
Type:
Single Family, Single Family-Detached
Subdivision:
VICKERS PARK
Lot size:
0.07 Acres
Year built:
1920
Courtesy: Tesla Realty Group, LLC
View additional info

Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or long-term rental. With some renovation, you can restore it's original character and create serious value in a highly walkable, waterfront community. Sold as-is. No repairs will be made by Seller. Bring your contractor and your imagination- historic opportunity awaits!

Open House:

Saturday, 7/26 10:00-12:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,294
Status:
Active
MLS#:
MDKE2005240
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.65 Acres
Year built:
1927
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds-proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island, gas cooktop, and a cozy breakfast nook. You'll also find a dedicated laundry room with a convenient side entrance. Flooring throughout the home includes a mix of wood, tile, and carpet, while the living room offers a comfortable gathering space anchored by a working fireplace. Step outside to enjoy the expansive backyard, perfect for entertaining or relaxing. The detached two-car garage includes an additional space ideal for a workshop or home office, plus a loft area with endless possibilities. Don't miss this opportunity to enjoy country-style living just minutes from downtown Chestertown!

Open House:

Saturday, 7/19 11:00-1:00PM

Beds:
5
Baths:
4 Full
Sq.Ft.:
4,167
Status:
Active
MLS#:
MDKE2005090
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.47 Acres
Year built:
1952
Courtesy: Compass
View additional info

**Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD - an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dream kitchen. This culinary masterpiece boasts an expansive island with seating for eight, upgraded cabinetry and countertops, a deep farmhouse sink, and top-of-the-line stainless steel appliances, including two dishwashers, two wall ovens, a gas range, microwave, refrigerator, and a wine fridge. Every detail has been meticulously crafted to showcase the stunning water views. The adjoining sunroom offers a serene space to unwind, while the recreation room provides ample space for entertainment and leisure. The main level also includes three spacious bedrooms, one with an ensuite, and an additional full bathroom. Upstairs, discover two more bedrooms, each with its own en suite, and a primary bedroom that features expansive windows and access to a private deck, perfect for savoring the tranquil water views. Outside, the peaceful backyard beckons you to relax and enjoy the serene beauty of the Chester River. A recently constructed dock, less than three years old, provides easy access to the water, while two outdoor showers offer convenience after a day of river adventures. The large detached garage ensures ample storage space for all your needs. This home is enhanced by a range of modern upgrades, including newer windows, skylights, and doors, all completed in 2022, along with freshly painted exteriors and a Rinnai water heater. Three working fireplaces, two wood-burning and one gas, create inviting spaces to gather on cool evenings. Additional amenities include a whole house generator, two whole house dehumidifiers, and a fully remodeled interior designed for ultimate relaxation and enjoyment. Located just minutes from Historic Chestertown, this property allows you to enjoy the charm of small-town living with access to a variety of shops, coffee houses, and bakeries. Experience the perfect blend of elegance and modern comfort in this meticulously curated waterfront retreat. Homes like this are truly a rare find.

Beds:
1
Baths:
1 Full
Sq.Ft.:
900
Status:
Active
MLS#:
MDQA2013084
Type:
Single Family, Single Family-Detached
Subdivision:
DUCKS NECK
Lot size:
0.51 Acres
Year built:
1973
Courtesy: Thurston Wyatt Real Estate, LLC
View additional info

Major price correction! Looking for that off the beaten path property, here it is! Property located in a water privileged community on the Chester River, access at end of road. Investors this property could possibly make a great Airbnb property to add to the portfolio. Home offers a 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Subject is sold in as is condition, seller nor buyer can make any repairs. Property is owned by the US Dept. of HUD, HUD Case #241-770004. Insurability Code: UI. Seller makes no representations or warranties as to property condition and HUD Homes are sold â??AS-ISâ? only. Seller may contribute up to 3% for buyers closing costs, upon buyer request. EHO

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,699
Status:
Active
MLS#:
MDKE2005016
Type:
Single Family, Single Family-Detached
Subdivision:
TOLCHESTER
Lot size:
0.99 Acres
Year built:
1965
Courtesy: Doug Ashley Realtors, LLC
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Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation in 2022-2023, this property continues to impress with ongoing enhancements. The large deck overlooking the pool is the latest improvement. Inside the main house, the open-concept design flows effortlessly from the expansive living room area, and dining area that has nonstop water views. Amazing renovation of the kitchen is a standout feature. The kitchen is equipped with stainless steel appliances, a spacious kitchen island, and ample storage, its perfect for culinary enthusiasts. The primary bedroom offers a luxurious retreat, complete with a large step-in shower and a two-person vanity, showcasing thoughtful design throughout. A charming book nook with access to the water views and landscaping provides an ideal spot for morning coffee. The design includes a walk-in closet, a custom designed ceiling and luxury vinyl tile continued. Throughout the home, the nautical theme is evident with lighting and ceiling fan fixtures. It just won't disappoint. The basement has even more storage and plenty of room for a workout area. Total square footage for the main level is 2569 and Unfinished basement area is 1948 sq. feet Guest House & Garage: Guests will appreciate the new two-car garage that includes a well-appointed guest house upstairs, featuring modern appliances and a balcony that showcases beautiful water views. This space combines privacy with luxury, ensuring a comfortable stay for visitors. Outdoor Oasis: Step onto the covered porch, designed for all-weather enjoyment, and take in the breathtaking vistas of the Chesapeake Bay. The outdoor space is further complemented by a brand-new custom-built deck that offers direct access from the bedrooms, perfect for entertaining. The Gunite pool, complete with a tanning ledge and seating, invites relaxation and fun and water views of the Chesapeake Bay. A convenient changing room and storage for pool toys are located in the garage of the guest house, which also features its own cozy covered porch area providing coverage from any inclement weather The guest house has a a kitchen/and full bath along with a combined living and sleeping area. Additional Features: This home also boasts a walk-in closet and exquisite landscaping that enhances its picturesque setting. Notable renovations include a geothermal well and HVAC system, Hardie Plank siding, and a 320-gallon propane tank that services both the main house and guest house which is leased through Dixie Land. Electric/plumbing/ New foam and spray insulation in exterior walls have all been updated, and a new grinder pump is in place. Additionally, an extra parcel with sewer allocation is included with sewer allocation billed quarterly-check with Kent County for further details. Footprint for a new build would possibly be 2000 SQ feet with the ability to build up. Verify with Planning and Zoning This home is a true gem, offering the perfect blend of luxury, comfort, and stunning natural beauty. Dont miss your chance to own a slice of paradise on the Chesapeake Bay! Whether you are looking for a second home to relax and enjoy or live here year around. It's an incredible home, not overwhelming in upkeep! Turnkey living with amazing water views and incredible sunsets!

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,496
Status:
Active
MLS#:
MDQA2012972
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.83 Acres
Year built:
1978
Courtesy: Taylor Properties
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Priced over $70,000 below recent appraised value! Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stones throw from historic Chestertown, the property combines seclusion with convenience-making it the perfect canvas for your vision. The large, wooded lot offers privacy, but still allows for beautiful views of Rosin Creek. The existing dock is in need to repair, but is a perfect spot to launch kayaks and paddle boards. With loads of potential, this home is being sold As Is. Information from the contractor retained by the previous owner on work previously performed on the house is available in the documents and a quote for a full remodel is available on request. In addition, a new well pump was installed in 2025. Please do not walk the property without an appointment.

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,966
Status:
Active
MLS#:
MDKE2005060
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
9.18 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,104
Status:
Active
MLS#:
MDKE2005020
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.46 Acres
Year built:
1972
Courtesy: Taylor Properties
View additional info

Are you ready to make this lovely well-maintained rancher home yours? It has new HVAC, a new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Three-bedroom, one full bath, large open kitchen/dining and cozy living room. Enjoy time in the large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes to Middletown's shopping, dining, and entertainment options. Don't miss the opportunity to make this delightful rancher your own. Schedule a private showing today and envision the possibilities of living on the Eastern Shore!

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