4,712 properties for sale in 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

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

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

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

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

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

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

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 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

Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. Theres room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedrooms expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. Theres plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sun

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A Listed for $375,000: a two bedroom, one bath su

Offer deadline tomorrow Sunday, October 18 at 2pm*. Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a. 37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. Theres so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertaining alike! Perfectly perched above the creek, this home offers an outdoor wonderland! It showcases a long dock with 2 lifts perfect for boating or kayaking or canoeing, an inground pool, 2 decks and magical water views! A bird lover paradise, Swantown Creek and the connecting Sassafras River sit on the upper Chesapeake Bay watershed, making it a thoroughfare for resident species and migratory birds traveling the Atlantic Flyway! You will see Bald Eagles all year long! Inside this completely renovated Masterpiece, the fine details will fascinate even the most discerning buyers, from the gorgeous hardwood flooring to the gourmet kitchen to the double sided fireplace! The very spacious open floor plan is ideal for entertaining with multiple living and dining areas that simultaneously offer those lovely views! The luxurious k

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen upgrades n unit 2 including new counter tops and flooring

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on. 31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Halls restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall

Update. New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location

Welcome to 21191 West Sharp Street. Conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant ho

This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, five bedrooms, an office and four and a half baths, there is abundant space for family, guests, and effortless entertaining. The ground level welcomes you with a spacious game room, sitting area, exercise space, and an oversized two-car garage. A split-level entry foyer leads to the main living area, where an open-concept layout seamlessly connects the living and dining rooms. The expansive kitchen with two sinks and wine fridge is designed for both function and gathering, featuring generous cabinetry and ample countertop space. Just off the kitchen, the family room with vaulted ceiling, opens to a screened porchperfect for enjoying cool breezes and waterfront views. A deck spanning the width of the home provides additional outdoor living space and includes an electric hoist for firewood or groceries. A living room with

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

To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, can

Nice old home in Rock Hall located on Main Street that needs some TLC. 4 bedrooms, 2 1/2 baths, upgraded kitchen, bath, Florida room and rear deck. Maintenance free exterior (new shingles 2022) and fenced yard. Short walking distance to downtown, shopping, Churches. A short drive to the Chesapeake Bay, Public Landings and Eastern Neck Wildlife Refuge

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Che

Open Every Tuesday and Thursday from 6 to 7pm. 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

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of the road where you can launch a kayak or just enjoy the water views. Just outside the quaint town of Rock Hall, this charming cottage would make a great vacation or retirement home

The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and. 5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed Reference 249/96. Both homes are in need of major repair however the parcels are lovely. These residentially zoned properties present a great investment opportunity. The parcels are of a generous size, featuring front and side yards that offers great outdoor space. Still Pond is just minutes from Betterton Beach. Total size of three parcels is 1.66 +/. Acre

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Marylands Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome gues

Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that invites tranquility and privacy. Built in 2005, this meticulously maintained home boasts 2,748 square feet of thoughtfully designed living space, perfect for those who appreciate both style and functionality. The upgraded countertops and stainless steel appliances in the kitchen elevate the culinary experience, while the formal dining room, adorned with crown moldings and exposed beams, adds a touch of sophistication. Natural light floods the interior through casement windows, enhancing the warmth of the hardwood floors that flow throughout the home. The main level features a convenient entry-level bedroom, perfect for guests or as the primary bedroom. The luxurious bathrooms include a walk-in shower and claw foot soaking tub providing a spa-like retreat at home. For those who appreciate the finer details, the home is

New path to water for your gator or utv*. 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 w