91 properties for sale in Washington Park, Chestertown town District 4 Chestertown Kent County Maryland

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs youll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertowns most historic locations

Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life. Inside, the home is designed for comfort and easy living, featuring a desirable first-floor primary suite that provides both privacy and convenience. The spacious family room, anchored by a cozy gas fireplace, creates the perfect gathering space, while the rear screened-in porch invites you to unwind and enjoy the tranquil surroundings. Upstairs, you’ll find two additional bedrooms along with a versatile bonus room—ideal as a home office, playroom, or craft space—plus walk-in attic storage for added functionality. Outdoor living shines with a brand new deck complete with a hot tub, perfect for relaxing or entertaining under th

Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the homes Clean, Contemporary Feel. Major Updates Include a Brand New HVAC System (2026) and New Windows (2026) for Energy Efficiency, Much More! Relax on the Inviting Covered Front Porch and Enjoy a Truly Move-In Ready Home Designed to Impress

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

Charming and inviting! Welcome to 139 Prospect St. A delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available fo

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCAblending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deckthe perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It wo

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This property presents an excellent opportunity for first-time homebuyers looking to build equity or investors seeking their next investment property! Opportunities at this price point in Chestertown don't come along often! Schedule your showing today and discover the potential this home has to offer! Property is being sold AS-IS

Price Reduction! VERY motivated selleropen to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer constructionmajor systems like the roof, HVAC, and water heater are all just a few years old, giving you confidence and low maintenance for years to come. Located in a desirable community with an affordable HOA that includes lawn mowing, youll appreciate easy, low-maintenance living. Conveniently situated just minutes from shopping centers, restaurants, and everyday amenities. This move-in ready home is truly a must-see!

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after locatio

A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home thats been well-loved. The layout flows with ease a bright formal living room for gathering, three cozy bedrooms, and a cheerful kitchen with space for morning coffee at a small table. Downstairs, a partial unfinished basement offers room for storage, hobbies, or future projects waiting to take shape. Outside, a detached two-car garage sits beside a wide yard with plenty of room to play, garden, or simply relax on the patio. The home does call for some updating, but thats part of its charm a chance to create something thats uniquely yours. Come see the potential and picture how youll make this lovely Byford property your own a home w

Fully Renovated Rancher in the Heart of Chestertown Walk to Everything. Most homes in this price range make you choose: updated systems or a great location. This one delivers both. Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the Eastern Shore's most walkable town right outside your front door without the noise or traffic. The home has been completely overhauled from the outside in. New metal roof, gutters, downspouts, vinyl siding, and windows protect your investment from the elements before you ever step inside. Inside, a new HVAC system, updated 200-amp electrical panel, new hot water heater, and fully replaced water main and plumbing mean zero deferred maintenance just move in and live. Refinished hardwood floors and new vinyl flooring run throughout open, light-filled spaces. The updated bathroom features a new vanity, and th

Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. This home brings modern comfort and a bright, inviting feel to every space. Perfectly positioned to enjoy the best of summer on the Shore, youre just a short drive (approximately 12 minutes) from the charm of historic Chestertown, the sandy shoreline at Betterton Beach, or waterfront dining and boating at Great Oak Landing. Whether your weekends are spent on the water, exploring local shops, or relaxing by the bay, this location puts it all within easy reach. If youve been searching for a low-maintenance home with modern updates and unbeatable access to the Shores favorite destinations, this one checks all the boxes

Investor Alert. Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This Home is Ready for Your Personal Touches. A Little Cosmetic Love will go a Long Way in Unlocking Serious Equity and Making this Property Truly Shine. Whether you're an Investor, Flipper, or Savvy First-Time Buyer Looking to Build Sweat Equity, This is the Opportunity You've Been Waiting For. Sold As-Is

This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing outdoors. Located within walking distance to Downtown Chestertown’s restaurants, shops, farmers market, and waterfront, this property is a great opportunity to enjoy convenient in-town living

ONLINE AUCTION: Bidding begins 07/20/2026 @ 10:00 AM. Bidding ends 07/24/2026 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $25,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Marylands Eastern Shore in Kent County, this single-family home offers approximately 1,896 square feet of living area on a 0.51 acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property

Absolutely Stunning Custom-Built Home! A Rare Opportunity You Won't Want to Miss! Welcome to this exceptional home offering nearly 3,000 square feet of beautifully designed living space, where luxury, comfort, and style come together effortlessly. Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you’ll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantryu002Fworkstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spac

Built in 1780/1-, Highcroft' is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient'green' house

Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. This home brings modern comfort and a bright, inviting feel to every space. Perfectly positioned to enjoy the best of summer on the Shore, you’re just a short drive (approximately 12 minutes) from the charm of historic Chestertown, the sandy shoreline at Betterton Beach, or waterfront dining and boating at Great Oak Landing. Whether your weekends are spent on the water, exploring local shops, or relaxing by the bay, this location puts it all within easy reach. If you’ve been searching for a low-maintenance home with modern updates and unbeatable access to the Shore’s favorite destinations, this one checks all the boxes

Charming and inviting! Welcome to 139 Prospect St. A delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchenperfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertowns shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for

Welcome to 11029 Brindley Drive that is move-in ready with new flooring, heat/air and has been freshly painted. The open floor plan offers great family time and the back yard backs to trees which now offers privacy and shade for picnics and play. Convenient to Parks and Recreation with a public beach only minutes away

Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnish