70 houses for sale in Pear Tree Point

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there's a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District

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

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

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

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

Sellers willing to contribute seller help to fund a buyers 2-1 interest rate buydown! Buyers get the benefit of a lower mortgage payment the first 2 years! Dependant upon offer amount and or an'as-is' offer. Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style. Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest

Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This room could also be used as an office, or second living area. The huge plus is the conveniently located laundry room located on the first floor. Upstairs, find three spacious bedrooms, two full baths, and a bonus room over the garage that can serve as a fifth bedroom, media room, or office. The unfinished

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

Get settled in before cooler weather. Renovated from top to bottom. Pictures say it all. 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. The quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

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