61 properties for sale in Deep Landing, District 7 Crumpton Queen Anne's County Maryland

Welcome to Mile Tree Village, one of Chestertowns most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. Inside, the open kitchencomplete with breakfast areaflows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranq

From the moment you arrive, this charming Cape Cod feels like home. Built in 2002 with 2x6 construction and beautifully updated in 2021, it offers the perfect mix of comfortable living and thoughtful upgrades. Inside, youll find 4 spacious bedrooms and 3.5 baths, 9' ceilings, along with a warm, welcoming interior featuring hardwood floors, recessed lighting, and touches of stained glass that add just the right amount of character. The kitchen truly is the heart of the home, with upgraded countertops, stainless steel appliances, and a center island thats perfect for everything from quick breakfasts to gathering with friends and family. The living room invites you to slow down and relax, centered around a beautiful marble fireplace that makes chilly evenings feel extra cozy. Youll also appreciate the convenience of main-level laundry, plus an additional hookup in the basement. Downstairs, the partially finished basement creates a fun and flexible space to enjoycomplete with a home theate

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

Welcome to 329 Union Church Road in Chestertown, located in Queen Annes Countya home with plenty of space, useful updates, and room to truly make it your own! Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loftproviding plenty of room for storage, hobbies, a workshop, or all the extras. Inside, youll find a spacious and functional layout ready for its next owners to settle in and make it feel like home. The kitchen features updated appliances, including a new stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. Outside, the 1.03-acre property gives you room to spread out, enjoy the outdoors, and create a space that fits the way you want to live. The detached pole barn adds even more versatility

Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether youre looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional potential. The generous layout includes four bedrooms, one full bath, one half bath, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, youll enjoy access to the community boat ramp and the Chester Ri

Open House: Thursday September 3 from 3:00pm. 6:30pm One-Level Living in a Quiet Cul-de-Sac with Amazing Outdoor Space! Welcome to 226 Lakeside Drive, a beautifully maintained 3-bedroom, 2-full-bath Alton E Darling Construction. Built home offering timeless charm, quality craftsmanship, and 1,914 sq. Ft. of comfortable one-level living in the Springview community. Situated at the end of a quiet cul-de-sac, this home features beautiful hardwood floors, crown molding, two fireplaces, and custom built-ins. The dining room is filled with natural light and features a large picture window overlooking the beautifully landscaped backyard. The spacious sunroom offers the perfect spot to relax and enjoy views of the outdoors throughout the seasons. Outside, enjoy an impressive combination of deck, brick patio with pergola, fully fenced yard, and established landscapingproviding plenty of space for entertaining, gardening, or simply enjoying the peaceful setting. Recent improvements include profe

Welcome home. Spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little TLC and updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, youll enjoy charming boutiques, local restaurants, seasona

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater, art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertowns shops and restaurants just one block away, 117 N Water Street, Unit 3B is a maintenance-free escape within 90 minutes of Washington, D. C. and Philadelphia

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D. C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafr

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or add

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy

Also available for lease: please reach out to agent for details. This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, youll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room. Perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway h

Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to f

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For

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

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. 1A Listed for $685,000: three bedrooms and three b

Listing price is for FOUR units for sale as an investment package! 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 addr

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H. M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown ha

Experience waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining guests, or simply enjoying spectacular sunset views over the water. Boating enthusiasts will love the private dock with electric power providing direct access to the Chester River for boating, kayaking, fishing, swimming, and paddleboarding. Your private escape just steps from home. The river truly becomes an extension of your backyard. Inside, the light-filled two-bedroom layout offers comfortable and easy living, making it perfect as a primary residence, weekend getaway, or waterfront investment property. Additional highlights include: New roof Public water and sewer No HOA enjoy privacy and flexi

Investor Special Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertowns shops, restaurants, and waterfront, the location cant be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Marylands most beloved small towns. Sold as-is. Cash or renovation loans preferred

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a homeit's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the propertyfrom the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths, and mature trees that create a peaceful retreat just steps from town. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a tradition

Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with todays conveniences. From the moment you arrive, youll be drawn to the inviting wraparound front porchperfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the homes historic charm. Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible