Discover the unparalleled beauty and serenity of Kelly’s Bank, an extraordinary 31.99-acre waterfront estate offered for the first time. Nestled along over 4,400 feet of shoreline on Langford Bay and a protected cove, this completely renovated home offers breathtaking water views from every room. Sitting high on a bank outside the flood zone, this meticulously updated residence features 5 bedrooms, 3.5 bathrooms, and timeless craftsmanship throughout. The primary suite is a luxurious retreat with a spacious en-suite bathroom, walk-in closet, sitting area, and gas fireplace. At the heart of the home is the chef’s kitchen, designed for entertaining, with an oversized island and walk-in pantry. The living and dining areas feature original hardwood floors, a wood-burning fireplace, and exquisite paneling, adding warmth and character. A sunroom with a wall of windows showcases panoramic views of Langford Bay and the Chester River.The four guest bedrooms are thoughtfully connected by Jack and Jill bathrooms. A partially finished basement features a gas fireplace, wet bar, and rough-in plumbing for an additional half bath, offering endless possibilities. Ample storage and a whole-house generator ensure convenience and peace of mind.Beyond the home, the property offers 16 tillable acres, a pond, a multi-slip dock, and abundant wildlife, making it a prime location for deer and waterfowl hunting. The detached two-car garage and shed/workshop provide additional space, with the potential to transform the workshop into a future poolside cabana. Kelly's Bank is conveniently located for boating to Rock Hall, Chestertown, Kent Island, and other points on the Bay.Don’t miss the opportunity to own this one-of-a-kind private waterfront retreat. Schedule your private tour today!

Built on a 40-foot bluff overlooking the Chesapeake Bay facing west for nightly sunsets, this is a tour-de-force of design and luxury on the Eastern Shore of Maryland, with truly stunning views from every room. Follow your dreams with this resort-like property as a primary or secondary home. Drive along the maple-lined lighted drive to 1.5 acres of award-winning, irrigated, landscaped grounds designed by South Fork Studio. Walk through the mahogany gate into the courtyard with fountain along the bluestone path around the Gunite pool. The main house on the water (c. 2011 and updated in 2018) has 3 bedrooms and 2 and 1/2 baths, and a wall of large windows with an automatic shade system that follows the sun's path. Open floor plan living with private first-floor owner's suite (double shower, Toto washlet, and custom walk-in closet). Wake up to views of the Bay and Bald Eagles fishing. Custom hand-crafted hardwood flooring, millwork, cabinetry, and New Zealand wool carpeting. Built-in Sub-Zero and Wolf appliances and top-of-the line luxury materials throughout. Automated control for whole-home media and sound, lighting, HVAC, irrigation, swimming pool, alarm system, and window shades. Gas-started wood-burning fireplace in the living room. Ipe decking, 3 outdoor showers, and numerous spaces to entertain friends and family. A custom-lighted staircase and brand-new dock (2023) with boat lift and large Ipe dining table sit above the rip-wrapped shoreline.The guest house and three-car garage, designed by Purple Cherry Architects and built by the acclaimed Taylor-Loughry partnership in 2019, cleverly create the privacy, mystery and architectural stature of the entire four-parcel domain. Currently, the guest house presents 1 bedroom, 1 full bathroom with laundry, a kitchenette and a very large multi-purpose room with cathedral ceiling that overlooks the center core of the gardens, saltwater and heated pool, custom cedar pergola, and Chesapeake Bay.The pool building contains the latest technology in pool filtration, whole-property water filtration system, well pump, irrigation system, pool heater, and storage. There is also on-demand hot water throughout the property and radiant heated flooring in all full bathrooms.This property awaits a most discerning and capable buyer yearning for a discreet and well-designed lifestyle. Only 15 minutes from historic downtown Chestertown.

Here is your chance to own a stunning one-year-old property in one of Middletown’s only custom home luxury communities! This gorgeous 5000 square foot custom built ranch completed in April 2023 features 5 bedrooms, 4 bathrooms, a finished basement, a pool house with a 5th bathroom, a 3-car attached garage with a vehicle lift, an additional detached garage, an in-ground fiberglass saltwater pool & spa with pool grotto and waterfall feature- what a dream! Walk through the front door into a large open layout surrounded by neutral tones & warm white oak hardwood wide width flooring. A dining room greets you on your right & flows seamlessly into the great room. A beautiful fireplace with stone up to the ceiling highlights the space- you can imagine just how cozy it will be in the winter months! A custom shelving unit adjoins the fireplace! Steps away from the great room is a dream kitchen! The oversized accent colored island is a perfect entertainment space & is truly the centerpiece of the home. Luxurious and modern white cabinetry, contrasting hardware, curved range vent hood, tile backsplash, quartz countertops, Blanco farmhouse sink, high end appliances- no detail has been overlooked! A window nook provides the perfect area for a small table, and there is plenty of space under the island for breakfast barstools! Off the great room, the left wing of the home features 2 generously sized bedrooms and the owner’s suite! The owner's bedroom has two large walk-in closets with closet systems by Elfa. The owner’s bathroom has two separate sinks and cabinets as well as an oversized shower with body sprayers! All of the bedrooms have been painted with rich warm tones to create a peaceful place to sleep. On the other side of the kitchen in the right wing is a princess suite bedroom and attached bath. This large room would be a great in-law suite or guest space! A mudroom with built-in cabinetry & a laundry room completes the first floor. Heading down into the basement- WOW!! A huge recreation space, a beautiful built-in wet bar with basement bar beverage cooler, a 5th bedroom and attached full bath, and another flex room that could easily be used for a home theatre! There is also ample storage & a double well English walkout staircase which leads to the backyard paradise. The home features built-in audio throughout, with six zones (including the backyard and garage!) that are controllable wirelessly via Sonos. This smart home also features 2 server racks mounted in the basement, a UniFi network controller with ceiling-mounted access points to blanket the property in fast Wi-Fi, a UniFi network video recorder with exterior mounted PoE UniFi cameras, and recessed iPad mounts to access smart home controls. The backyard oasis is amazing! The owners spared no expense! Not only is there a fiberglass saltwater pool & spa with pool grotto & waterfall feature, there is also a 475 square foot pool house with its own full bath, mini split system and space that could be used as a guest house! The pool house includes a stainless-steel refrigerator, microwave, sink, dishwasher & also has quartz countertops! The large flip out window overlooking the pool opens to a 90 angle to make serving food and drinks for parties a breeze! Outside speakers by the pool & pool house make it a perfect outdoor entertaining space. Extensive stone paver patio around the pool area is enclosed by a wrought iron black fence. Attached to the home is a three-car oversized garage with mini split climate control, a vaulted ceiling, and a Backyard Buddy Side by Side B-SXS-10000 Double 4-post lift- allowing an automotive enthusiast to safely store a collection of 5 vehicles! A separate detached garage with service door compliments the space and keeps a 6th vehicle out of the elements. Both garages are finished with professional concrete floor coating and feature app-controllable openers. Don't miss your chance to see this incredible home!

This beloved waterfront property has been a treasured family gathering place for over twenty four years. There have been numerous updates throughout that time, including the spectacular shoreline area which offers a private dock with about 5 feet MLW, bulk-headed shoreline, several boat lifts, water slide and sandy beach. From the homesite, you can walk down the well constructed stairs or you can take a golf cart down the convenient ramp area beside the steps.This home was designed for entertaining family and friends inside and out with an outdoor covered deck, expansive lawn and amazing sunset views. The large updated Gourmet kitchen opens into a spacious dining and sitting area overlooking the water and adjoins a media/entertainment room. There are 5 bedrooms, a large laundry and storage room, recent BAT upgraded septic system, and an oversized double plus garage.This location affords you protected water on Fairlee Creek for your boat but easy access to the Chesapeake Bay. With membership in GOCA, the volunteer Civic association, for $100 per year the Marina has graciously granted certain privileges that have been enjoyed by the membership, dating back to the 1980's. They include access to the marina grounds and facilities, swimming pool, golf course, boat ramp, and beaches. There is no other community like Great Oak!

Discover your dream home in this perfectly maintained 4-bedroom, 3.5-bath gem resting on a generous half-acre in the highly coveted Cooke’s Hope community. Tucked away in a serene cul-de-sac, this residence offers the tranquility you’ve been searching for, with no drive-by traffic to disturb your peace.As you enter, you’ll be greeted by a spacious haven that has been thoughtfully updated for modern living. The heart of the home, a beautifully redesigned kitchen, features sleek marble backsplash, a Newport Brass faucet, premium Cambria countertops, and top-of-the-line appliances from Wolf, Sub-zero, Bosch, and KitchenAid. Custom cabinetry and elegant lighting elevate the space, making it perfect for culinary enthusiasts and family gatherings alike.The interior is adorned with custom carpeting, new interior lighting, and freshly painted walls in soft Benjamin Moore tones. The primary bath and powder room have been expertly redesigned, featuring luxurious finishes and impresses with tasteful wall coverings.Step outside to your own oasis! A meticulously landscaped backyard—with over $45,000 invested—boasts vibrant seasonal blooms, a charming rock waterfall, and multiple patio spaces for outdoor entertaining. Relax on the large outdoor brick patio or flagstone terrace, surrounded by flourishing plantings enhanced by an efficient sprinkling system.For hobbies and entertainment, the detached oversized garage includes a spacious upper-level finished room, perfect for hosting guests or indulging in your favorite pastimes! Equipped with a golf simulator, movie screen, and comfortable theater seating, it’s an entertainer’s dream.Beyond your front door, Cooke’s Hope offers fantastic amenities including a secure community post office, tennis courts, scenic walking paths, a community room, and a dog park! With boat and kayak slips available on a first-come basis, you’ll have endless opportunities for outdoor adventure, all while enjoying the peaceful backdrop of the adjacent farm with rare cows that adds to the charm of the area. Plus, an onsite gym is available for a minimal monthly fee.Don’t miss your chance to own this slice of paradise in Cooke’s Hope—where comfort meets community living. Schedule your private tour today!

Waterfront property on the Chester River on Queen Anne's side of Chestertown.

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!

Welcome to this mid-century waterfront home, nestled on a high elevation along the serene Miles River. This charming property boasts three bedrooms and three full bathrooms, providing ample space and comfort for you and your family. The home features a timeless mid-century design, blending classic architecture with the potential for modern updates. Recently, new roof, siding and windows have been added, enhancing the home's durability and aesthetic appeal. One of the standout features of this property is the private dock, ideal for boating enthusiasts or simply enjoying the scenic waterfront. Whether you’re looking to relax by the water, entertain guests, or embark on river adventures, this home offers it all. Situated between the charming towns of Easton and Saint Michaels, this location offers the perfect balance of tranquility and accessibility. Enjoy the convenience of nearby shops, dining, and recreational activities while relishing the peace and privacy of waterfront living. Don't miss the opportunity to own this exceptional waterfront home on the Miles River. With some updates, it can become your dream retreat. Schedule a viewing today and experience the unique blend of mid-century charm and waterfront living for yourself.

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 (2022), 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.