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!

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 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers move-in ready. The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank views and no houses on the opposite shoreline. Upon walking into the home, this same goal is achieved with large windows along the water side providing sweeping views. The river room has glass all of the way around flooding the space with light and perfect for reflection or entertaining. Hardwood floors bring serious charm and warmth to the home. The primary bedroom is spacious and includes an ensuite bathroom while the other two bedrooms provide river views. An oversized 2 car garage allows extra space to mess around on your workbench and store those beloved kayaks. The large and cleared yard has a split rail fence and trees that along with the meandering paved driveway provide a sense of privacy. The community itself is very quiet and has the Jim and Mary B. Lynch Preserve adjacent which provides roughly 2 miles of walking trails and is currently managed by the Eastern Shore Land Conservancy. Make this your own tranquil Eastern Shore retreat.

This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.

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!

Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!