Discover a haven of exquisite living with this magnificent property set over 5 acres of prime waterfront, just 15 minutes from St. Michaels. Designed for multi-generational families, large families, or entertaining, the property includes a main residence and a recently renovated guest house, both featuring ground-floor primary suites. The main residence offers breathtaking water vistas, spacious en-suite bedrooms, a versatile third-floor space, an extra-large pantry, and an extra-large laundry room. The guest house includes a modern kitchen, dining and lounging space, a ground-level master suite, a screened porch, and a separate laundry room. Six bathrooms are modern, tiled, and feature quartz finishes, adding to the home's elegant and contemporary design.The property also boasts over 300 feet of pristine shoreline, beautiful views of the bay, a deep-water dock that can host multiple boats and jet skis with its own ramp, an outdoor saltwater pool with an inbuilt jacuzzi, and an indoor Endless Pool Swim/Spa with 3 hydromassage seats. Sustainable amenities include geothermal heating, cooling, and a solar energy system.The second floor of the main residence features an additional primary suite plus another bedroom, both with renovated bathrooms and large walk-in closets. A versatile third-floor space is ideal for a home office or creative studio. An interior corridor past the 3-car garage leads to a dedicated indoor pool zone, fitness area, and cozy family lounge with fireplace and media abilities.The guest house's second floor has two bedrooms, a common area, and a renovated bathroom. With ample space to host family and friends for long periods of time, this property offers both comfort and sustainability in a picturesque setting near St. Michaels and Easton.

W A T E R F R O N T!!! Breathtaking Panoramic Views – Renovated Waterfront HomeExperience the beauty of waterfront living in this meticulously maintained, renovated (2024) home in Earleville, offering over 3,500 sq. ft. of living space. Designed to capture unparalleled panoramic views from every room in the rear of the home, this 4-bedroom, 2.5-bath home features an open floor plan.Step inside and be captivated by the breathtaking water views. The spacious living room boasts a floor-to-ceiling stone wall with an electric fireplace, seamlessly flowing into the stunning new kitchen with quartz countertops, brand-new appliances, a coffee bar, and a dry bar—perfect for entertaining. A sunroom and dining area provide the ideal setting to take in the serene surroundings, while custom blinds throughout the home enhance privacy and style. The main level also includes a luxurious owner’s suite and an additional bedroom or office space, both with spectacular water views.A beautiful open staircase leads to the bright and spacious lower level, where a large family room with another floor-to-ceiling stone wall featuring an electric fireplace awaits. This level also features two generously sized bedrooms, a kitchenette, and direct access to the covered lower deck, offering even more stunning waterfront views. The layout makes this space ideal for guests or an in-law suite.Extensive updates completed in 2024 include fresh interior and exterior paint, new landscaping, gutter replacement, two new HVAC systems, and brand-new kitchens and baths with high-end finishes. Outdoor living is enhanced with a spacious main-level deck featuring a retractable awning, providing comfort and shade, while the covered lower deck offers another perfect space to relax and enjoy the waterfront setting. The expansive lot offers plenty of room for an inground pool, making it ideal for entertaining and outdoor enjoyment.Additional features of this exceptional home include custom blinds, central vacuum, a 3-car garage, a deeded boat slip with lift, and private beach access. Don’t miss this rare opportunity to own a turnkey waterfront retreat where luxury meets tranquility!

Comfort. Nature. Luxury. All are expressed in this Contemporary waterfront home on Southeast Creek. Listen to Ospreys from your screened porch or private second floor balcony. Cool off in the pool or practice yoga in the poolside studio space. Friends from far away can come use your detached guest cottage as a tranquil retreat. Walk down your dock and go sailing with easy access to the Chester River and beyond. Gather with the ones you care about most on the central open floor plan on the main floor. Upstairs has everything you need to decompress and take in the fine Eastern Shore lifestyle. The home is less than 15 minutes from Historic Downtown Chestertown by boat or car and less than 2 hours from Washington D.C., Philadelphia, or Baltimore.

This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on finishes such as countertops, floor stains, wall colors, and fixtures to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.

Luxury Smart Home, High-End Upgrades & Off-Grid Solar. Prime Location with Waterviews and Water Access!Nestled on a 2.4-acre lot in the scenic Ingleton community, this custom-built smart homeoffers breathtaking water views and shared waterfront access, perfect for kayaking,paddleboarding, or simply enjoying the tranquil setting. Ideally located between Easton andSt. Michaels, you get the perfect balance of privacy and convenience.Smart, Sustainable, and Built for Comfort:This modern, high-tech home is designed for energy efficiency, luxury, and security.Featuring off-grid solar panels on the shed and a dual Eco-Flow in-house generator setup(Batteries not included), You will enjoy peace of mind during outages.With 3,500+ sq. ft. of finished space plus an additional 1,400+ sq. ft. of unfinished potential,this home offers room to grow and customize.Gourmet Kitchen with High-End Appliances, a dream for home chefs, boasts:✔ Viking stainless steel appliances, including a six-burner gas range with a Miele hood✔ Pot filler for added convenience✔ Quartz countertops and two functional center islands✔ Walk-in pantry for ample storage✔ Instant hot water faucet for quick meal prep✔ USB-C outlets for modern charging needsPrivate Suites & Expansive Living Spaces:✔ First-floor primary suite with a sitting area, dual walk-in closets, and spa-like en-suitebath featuring a jetted tub, separate shower, and dual vanities✔ First-floor in-law suite with a living area, kitchenette, large full bath, and direct access toA brand-new screened porch overlooking the backyard✔ Upstairs features a large bedroom, full bath, and a versatile bonus/game roomSmart Technology & Modern Upgrade:✔ 1GB wired Ethernet to every room + pre-wired connectivity to unfinished spaces✔ pre-wired outdoor security system, including shed solar-powered cameras and woodsnear the cornfield embedded with security wiring✔ New outdoor smart lighting system (including mailbox and vertical garage lights)✔ Built-in smart speaker system throughout the home✔ Upstairs 7.2 surround sound system for an immersive entertainment experience✔ Three Ecobee Smart Thermostats for energy-efficient climate control✔ Eufy Smart Security Door Locks on bedroom and garage side doorsBrand-New Mudroom & High-Performance Laundry:✔ Brand-new mudroom built off the garage for extra storage and easy entry✔ New Speed Queen dryer & Maytag washer✔ Samsung refrigerator in the garage for additional cold storage✔ GE refrigerator in the in-law suite for added convenienceUltimate Garage Setup for Car Enthusiasts:✔ Side-mount garage door openers allow space for up to six cars (lifts not included)✔ Utility sink for convenienceAdditional Highlights:✔ Finished crawl space with two new sump pumps✔ Recently sealed driveway (2024)✔ Brand-new tankless water heater (installed 3 months ago)✔ Bidets installed in bathrooms✔ Added landscaping in the rear and side of the home✔ 2023-2024 dead trees removed from property✔ All fans, lights, and blinds are brand new and were replaced in 2022✔ Brand new outdoor playsetThis one-of-a-kind smart home offers the perfect mix of luxury, energy efficiency, and state-of-the-art technology. Don’t miss this rare opportunity to own a high-tech, water viewretreat with modern upgrades and security features already in place!Schedule your private showing today!

This Waterfront Contemporary home is nestled on a bluff with sweeping views of Still Pond Creek. The property checks all of the boxes for your retreat including a well maintained deck, screened river room for crab feasts, private sandy beach and dock with several boat lifts. The living room has a cathedral ceiling, wood burning fireplace, and glass sliders leading you to the deck with incredible views of nature and wildlife. One of the 3 main floor bedrooms, the primary suite has an ensuite bathroom, walk-in closet, and full length windows to celebrate the property's connection with the water. On the lower level you will find another bedroom, den, workshop, and garage. Upgrades include New Heating and Cooling (2024&2025), New Roof (2024), Garage Door (2024), Plumbing and Electrical Updates (2022), Generator, Rinnai Tankless hot water heater, and Reverse Osmosis water treatment. Still Pond Creek provides direct access to the open waters of the Chesapeake Bay for prime boating opportunities however is a protected tributary making it great for water sports. The property is located in the rolling farmlands of Worton, only 15 minutes from the shops, restaurants, and galleries of downtown historic Chestertown. Philadelphia, Washington D.C., and Baltimore are all less than a 2 hour drive making this perfect for a weekend getaway or year round residence.

Welcome to 1600 Liberty Road: the perfect home for a growing family in a great location. Quality craftsmanship in this new construction truly shows while the list of features goes on and on: Brazilian Cherry hardwood floors, 9 foot tray ceilings, bay windows, ceramic tile kitchen and baths, brushed nickel fixtures, a electric fireplace, oversized back deck and so much more. This home has so much natural light and really celebrates the views of the surrounding farmland. The gourmet kitchen features quartz countertops with overhanging bar, stainless steel appliances, double sink, quiet-close drawers and more. The kitchen / breakfast area flow seamlessly into the expansive open concept living and formal dining rooms. Easily step out of the living room and onto the oversized back deck. The main floor also features a second living room / family room or an office space. Continuing upstairs, the luxurious owner's suite has great views of the surrounding farmland. The 3 additional comfortably sized bedrooms with large closets and another full bath complete the second floor. The fully finished basement has another bedroom with full bath and laundry room with separate exterior entrance. This completely separate space could easily be turned into a rental for extra income. Private backyard features a tall privacy fence: perfect for entertaining and plenty of space for the kids and pets. Plenty of parking with an oversized 2-car garage and concrete paved driveway. All systems and appliances come with a one-year manufacturer's warranty. Minutes away from shopping, dining, and entertainment: this property is ideally situated for an easy commuting lifestyle. Schedule an appointment today!

Welcome to the Johnson-Lindsey House, a rare opportunity to own a piece of Chesapeake City’s history. Located in the heart of the Historic District, this Federal-style home was built around 1850 by Joseph W. Lindsey, the town’s sawmill and lumber yard owner. Zoned Village Center (VC), the property offers incredible flexibility for residential or commercial use, making it ideal for those looking to blend history with modern living or business potential. Situated along the route of Chesapeake City’s beloved parades and festivals, it’s just a short walk to waterfront dining, boutique shopping, and local attractions.This charming home exudes character with its classic wood-sided Federal-style architecture and distinctive bump-out picture windows on the south side. The original cast and wrought iron fence still encloses the front courtyard, a space once adorned with a porch. With historic approval already granted, a new owner has the option to restore this feature. The front entrance welcomes you with intact stained glass and an old-style door ringer, setting the tone for the timeless beauty within.Inside, the home showcases original hardwood flooring, tall wood windows with storm covers, and six-inch floor moldings. The light-filled foyer leads into a spacious family room with floor-to-ceiling windows and an electric fireplace wired for propane. From there, the dining room offers built-in cabinetry and access to a covered side porch. The remodeled kitchen seamlessly blends old-world charm with modern updates, featuring Quartz Silestone countertops, Italian subway tile, luxury vinyl plank flooring, a new sink, stainless steel appliances, and professionally painted cabinets. Off the kitchen, a remodeled powder room and an enclosed laundry room with an antique sink provide added convenience.The second level offers a generously sized primary suite with a fully remodeled bath, including a tile walk-in shower and luxury vinyl plank flooring. Two additional bedrooms on this floor provide space for guests, family, or a potential additional full bath if desired. The third level features two more bedrooms, one currently used as storage, with ample space to add a third full bath.The backyard is a hidden retreat, offering a courtyard-style space with a side porch, a brick side patio, and a rear brick patio leading to the detached two-car garage. Very few homes in town offer garage parking, making this a rare and valuable feature. With electricity, a concrete floor, and a propane heating element, the garage could easily be transformed into a carriage house, Airbnb rental, or business space. A parking pad allows for two additional vehicles, making this property one of the few in the historic district with a backyard backing to woods and extra off-street parking.This home has been meticulously maintained with a series of updates, including five new mini-split heating and cooling units installed in 2024, along with a new storm door, professionally painted kitchen cabinets, and new ceiling fans. Recent improvements also include luxury vinyl plank flooring in the kitchen and primary bath, updated carpeting on the stairs and upper hallway, a new furnace, oil tank, and hot water heater, as well as professional interior painting. The main architectural shingle roof was replaced in 2019 with a 30-year warranty.The Johnson-Lindsey House has been featured on the Candlelight Tour and is prominently displayed on the cover of the Chesapeake City town map. Annual grant opportunities through the Maryland Historic Trust provide additional incentives for restoration and improvements. Whether you're looking for a distinctive home, a commercial opportunity, or a combination of both, this historic gem is truly one of a kind.

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 Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller offering $7,000 credit at closing to repair the Air Conditioning units.

Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout.Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath.Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality.Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space.This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!