Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Come and be amazed!!

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is move in readyIt is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2 car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the Conservatory. It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for a master suite. Two sets of French doors open to either the front lawn or side yard for entertaining. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the sunrises and sunsets.With the lowest price per square foot for a Luxury, Waterview, in town home, it is also a comparatively excellent value.

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House.Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.

The Sally Harris Mill House was once part of the Bloomingdale Estate is one of the remaining 18th Century masterpieces on the Eastern Shore. This peaceful farmette boasts over 31 acres with a blend of open pasture and wooded seclusion. The property sits on the Western banks of Madam Alices Branch, a tributary of the Wye River. Mature evergreens line the entrance creating a dramatic feel and historic charm is displayed throughout the home with 5 fireplaces, Flemish bond brickwork, and a gambrel roof. Modern amenities have been incorporated with the 2 story North wing which was completed around 2000 to include a first floor primary suite with en suite bathroom, makeup room, and 2 separate walk-in closets on the first floor and 2nd floor family room. The updated kitchen, partially finished basement with kitchenette, and heated pool are also highlighted upgrades. Outdoor living is celebrated here with a screened in rear porch for dinners in nature, a front porch to sit and watch the wildlife, and pool deck for making memories. Bring your machines and toys because there is plenty of storage in the outbuildings. The 2 story machine shop has been impeccably maintained and is perfect for any type of project. The open pasture would be perfect for horses and though they haven't been maintained in a few years, the forest contains nature trails for disconnecting from the hustle and bustle or hunting opportunities. This is your chance to make a piece of Eastern Shore's history your own peaceful retreat.

Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Much more info and professional photos coming soon. Stay tuned!

Perfectly situated on over an acre, this custom-built masterpiece offers over 4,000 SF with three fully finished levels thoughtfully designed for luxurious living and effortless entertaining. From the moment you arrive, you'll appreciate the meticulous care, craftsmanship, and extensive upgrades this home has to offer. Step inside to find a spacious formal dining room framed by elegant segmental archways, setting a warm and inviting tone. The main level flows seamlessly into the heart of the home — the gourmet kitchen — featuring soft-close cabinetry, a large center island, dual ovens, under-cabinet lighting, an induction cooktop, a spacious walk-in pantry, and a reverse osmosis water filtration system connected to both the kitchen sink and refrigerator. Adjacent to the kitchen, a cozy breakfast nook provides the perfect space for everyday meals. The expansive family room offers the ideal gathering place, complete with a pellet stove, a beautiful wet bar perfect for entertaining, and oversized sliders that fill the space with natural light. These sliders open directly to the screened-in porch — newly updated with pet-resistant screens — and lead to an attached deck, creating even more space for outdoor relaxation. Upstairs, the second level is designed for ultimate comfort. The luxurious oversized primary suite features a private propane fireplace, dual walk-in closets, and a spa-like en-suite bathroom with a luxury stone jacuzzi tub, rainfall shower, abundant natural and overhead lighting, and separate his-and-hers vanities. Two additional bedrooms with spacious closets, a large bonus room with a pellet stove (ideal for a recreation room or optional sixth bedroom), and a second full bathroom complete this floor. For added convenience, a second-floor laundry room makes everyday living even easier. The third level offers two more versatile bedrooms, a full bathroom, and access to the HVAC system — perfect for home offices, guest suites, or teen retreats. The solar panels will be paid off before closing The outdoor space is just as impressive. Enjoy a partially fenced yard, ideal for children and pets to safely roam, an oversized attached 2-car garage with access to the crawl space, a detached 2-car garage that makes an excellent workshop, storage space, or man cave, plus an additional storage shed. A partial whole-house generator provides added peace of mind. And the best part? No HOA! Located just minutes from downtown Centreville's charming shops, restaurants, marina, and parks, with easy access to Route 301 and only 13 miles from the Bay Bridge, this property truly leaves no comfort feature overlooked. Welcome to a home where luxury, privacy, and convenience meet — your Eastern Shore dream awaits.

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one bedroom in the walk out basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, kayaking and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Welcome home!