30 properties for sale in Great Oak Estates, District 6 Fairlee Kent County Maryland

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

Situated on. 97 acres in Worton, this versatile property offers plenty of space and possibilities with two utility buildings, public water, and public sewer. The main home features an open floor plan highlighted by a custom wooden kitchen bar that provides generous counter space and creates a natural gathering spot for entertaining. A separate shop building adds even more functionality and is equipped with an oil furnace and air conditioning, making it comfortable for year-round use. Whether youre looking for workshop space, storage, a hobby area, or room for your next project, this property offers flexibility that's hard to find. Conveniently located in Worton with nearly an acre of land, public utilities, and multiple buildings, this property is ready for its next owner to make it their own

Move-in ready and packed with updates, this 3-bedroom, 1-bath home offers an affordable opportunity to enjoy Eastern Shore living without a long list of projects waiting for you. Major improvements include a newer roof, HVAC system, water heater, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, plus a vapor barrier and insulation in the crawlspace. Inside, the home feels bright, clean, and refreshed, making it an easy choice for buyers looking for comfort, convenience, and low-maintenance living. The location makes it even better. In approximately 12 minutes, you can be exploring historic Chestertown, spending the day at Betterton Beach, or enjoying waterfront dining, boating, and sunsets at Great Oak Landing. With its extensive updates, convenient location, and newly improved price, this home offers a lot of value for buyers

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $15,000. 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 o

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Marylands Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home o

Welcome to 25133 Smithville Rd. This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and moreall while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity to make it your own. Come see all that 25133 Smithville Rd. Has to offer and make this home yours!

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:45 PM. The list price is the suggested opening bid. Deposit: $15,000. 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 1,056 square feet of living area on a 0.46 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 o

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this bea

Seller is offering a 1 year home warranty with acceptable offer. Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lotperfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, youll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living

Brand new construction in Chesapeake Landing, and the primary suite is on the main level full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association

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

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on3.5 acres in a private, peaceful setting and thoughtfully designed for both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Cre

Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single-family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy quartz counters, SS appliances, and a neutral color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5' baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. The expansive deck offers views of a private, level lot backing to woods. Chestertown is a quaint, historic district on the Eastern Shore with an avid art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $12,000

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless t

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5' baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. All on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provi

This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an

The one youve been waiting for! This extensively updated 3 bedroom, 2 full bath ranch boasts 1,376 square feet of open living space and a roomy 2 car garage. The property sits at the end of a quiet street and lies adjacent to farm land and a pond with a seasonal view. Enjoy serene privacy from your spacious 20 x 16 deck! The home is beautifully remodeled and updated with a new stone driveway and landscaping, HVAC, hot water heater, waterproof LVP flooring, fresh paint, and new lighting and fixtures throughout. The custom kitchen features a large walk in pantry, new stainless steel appliance package, high quality 36 soft close cabinetry, and gorgeous quartz countertops paired with a custom tile backsplash. The Primary bedroom is bright and spacious with a walk-in closet and Primary bath that impresses with a custom tiled walk-in shower. The 2nd and 3rd bedrooms are a generous size and offer easy access to a full bathroom with a tub/shower surround. This home is 10 minutes from Chesterto

Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding. Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house. You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. All of the quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

103 Sutton is perfectly situated just a stones throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of todays Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. Originally built as the community model home and meticulously maintained since it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. As you step inside, youll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chefs paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effor

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, youll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs youll find two waterfront bedrooms, one