Search Kent County, MD Homes for Sale

Kent County, MD Homes for Sale and Living Guide

Kent County is where I grew up and where I live today. Tucked between the Chesapeake Bay, the Chester River and the Sassafras River on Maryland's Upper Eastern Shore, it is the least populous county in Maryland, with about 19,000 residents, and that is exactly its appeal: open farmland, small historic towns and more than 200 miles of shoreline. Below is a local's guide to Kent County, followed by the newest Kent County homes, farms and land for sale, updated daily from the MLS.

Kent County real estate at a glance

As of November 2026, about 240 properties are listed for sale in Kent County, including roughly 105 single-family homes with an average asking price near $555,000. The rest is a mix that is hard to find anywhere else on the Bay: working farms and acreage, building lots, Chester River, Sassafras River and Bay waterfront, and historic homes in town. Ask me for current numbers on the area or property type you are interested in.

Towns and communities

  • Chestertown: the county seat on the Chester River, with a historic downtown, Washington College and a busy calendar of festivals.
  • Rock Hall: a working harbor town on the Bay, close to Eastern Neck National Wildlife Refuge.
  • Betterton: a small town on the Sassafras River near the head of the Bay.
  • Galena and Millington: small towns in the northern and eastern parts of the county, surrounded by farmland.
  • The countryside: rural roads, farms and waterfront necks around Chestertown, Worton, Tolchester and Quaker Neck.

Waterfront living

Water covers about a third of Kent County's total area, and its shoreline runs along the Chesapeake Bay to the west, the Sassafras River to the north and the Chester River to the south, including Eastern Neck Island. That means waterfront options from wide Bay views to quiet creeks with private piers. Before you buy, it helps to understand Maryland's Critical Area law and to read my tips for buying waterfront on the Chester River.

Farms, land and historic homes

Kent County's farmland is a big part of its character, and much of it is protected by conservation easements that keep the countryside open for generations. If you are looking at a farm or acreage, read why land conservation matters on the Shore and what to check before you buy. For lovers of older homes, see my post on historic farmhouses in Kent County.

A little history

Kent County was established in 1642, making it one of the oldest counties in Maryland. St. Paul's Church near Chestertown, with its earliest section built in 1711, is described as the oldest Episcopal church in Maryland in continuous use. Washington College in Chestertown, founded in 1782 with George Washington's support, is the oldest college in Maryland.

Schools

Kent County Public Schools serves the whole county, with Henry Highland Garnett Elementary School in Chestertown, Galena Elementary School and Rock Hall Elementary School, plus Kent County Middle School in Chestertown and Kent County High School near Worton. School assignments depend on the address, so confirm with the district for any home you are considering.

Buying or selling in Kent County?

As a lifelong Kent County resident and a licensed attorney, I know the towns, the waterways and the details that matter on farms and waterfront property here. Learn how I work with buyers or sellers, see homes I have sold, get a free home valuation, or contact me and call (410) 708-3924.

Newest Kent County Listings

7570 Muirfield Dr, Chestertown
$895,000
4 Beds ⋅ 3 Baths
Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence overlooking the 10th tee and fairway of the Chester River Yacht & Country Club. Set on 1.45 acres of thoughtfully landscaped grounds in the desirable Prestwick community, this exceptional property offers privacy, timeless craftsmanship, and the ease of single-level living. Custom-built by Alton Darling, the approximately 2,500-square-foot home features an inviting, open floor plan with hardwood floors, elegant crown molding, and generously proportioned rooms designed for comfortable everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully appointed bath featuring dual vanities with quartz countertops, an oversized walk-in shower. Two additional bedrooms, thoughtfully situated in a separate wing, offer privacy for family and guests. A formal dining room, breakfast room, and versatile office or 4th bedroom space provide flexibility for today’s lifestyles. The kitchen features granite countertops, updated appliances, and convenient access to the home’s gathering spaces. Freshly painted interiors and numerous system improvements further enhance the property’s appeal. Beyond the interiors, the home’s setting truly distinguishes it. A screened porch overlooks mature landscaping and the picturesque golf course, creating an inviting place to enjoy morning coffee, entertain friends, or simply appreciate the peaceful surroundings. A new hot tub and outdoor gathering area offer additional opportunities for relaxation. An attached two-car garage, generous storage, and extensive mechanical and safety improvements complete this thoughtfully maintained residence. Appliances 2024, washer/dryer 2025 More upgrades in the document section.

7570 Muirfield Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

818 High St, Chestertown
$3,300,000
Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versatile space perfectly situated on High Street. Known locally as the home of the premier Aqua Fit Health Center, this highly functional multi-floor building features an excellent mix of large-scale operational facilities and multiple private office suites. The ground level boasts extensive infrastructure, including a custom-built aquatic center with a heated saltwater pool, expansive weight/cardio rooms, and physical therapy areas. The upper floors offer a flexible layout of professional office spaces, ideal for medical practices, wellness professionals, or traditional corporate tenants. Complete with an elevator, high-visibility street presence, and a dedicated customer/tenant parking lot, this unique asset is a turnkey opportunity for an investor or an owner-user looking to establish a major presence in Kent County.

818 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

4020 Eastern Neck Rd, Rock Hall
$799,000
4 Beds ⋅ 2 Baths
This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at the rear of the property could remain in ag use as tilled land and/or be used for hunting or as a horse farm. With ample room to customize, this home is a canvas for your personal touch. Located in Kent County, you'll enjoy a peaceful retreat while still being close to local amenities. This property is not just a house; it's a place where you can truly feel at home. Don't miss the opportunity to make this inviting space your own! This property is being sold as-is.

4020 Eastern Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

111 Kent St S, Chestertown
$450,000
2 Beds ⋅ 3 Baths
Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

403 Calvert St, Chestertown
$135,000
3 Beds ⋅ 2 Baths
INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly renovated bathrooms, light fixtures, fresh paint, trim, new wall to wall carpet, and LVP flooring. Buyers should independently verify achievable rents, however it should be noted recently rented townhomes in the area have ranged from $1,800-$2,000. Conveniently located near Washington College, Chestertown's shops, restaurants, and local amenities. Independent appraisal on file showing strong ARV potential. Property is being sold strictly as-is.

403 Calvert St, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

201 Garland Way, Chestertown
$375,000
4 Beds ⋅ 3 Baths
Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

201 Garland Way, Chestertown

Listing courtesy of ERA Martin Associates. Contact:

108 N Water St, Chestertown
$1,125,000
5 Beds ⋅ 4 Baths
This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

5705 Walnut St, Rock Hall
$425,000
3 Beds ⋅ 2 Baths
Close to the Beach, Restaurants, and Marinas in Rock Hall This well-loved and nicely cared-for solid brick rancher sits on a quiet street, offering the perfect blend of peaceful living and incredible convenience. The property features excellent curb appeal, mature landscaping, ample parking, and an oversized detached concrete garage built to match the house. It is completely ready for its next owner to move right in and make it their own. Comfortable Living & Layout • Open Kitchen & Dining: The heart of the home features a generous open kitchen and dining area, creating a wonderful space for meals and gathering. • All-Season Room: Located right off the dining area, the sun-filled all-season room expands your living space year-round. • Living Room: A cozy living room features a classic wood-burning fireplace that provides warmth and charm for the fall and winter seasons, along with a roomy bow window that lets in plenty of natural light and offers great space for plant lovers. • Bedrooms & Baths: The single-level floor plan includes three bedrooms, one full bathroom, and one half bath. • Den & Mudroom: A separate den offers flexible space, while a large utility room serves as a functional laundry, mudroom, and extra storage area. • Flooring: Beautiful hardwood floors run throughout most of the home, complemented by durable tile in select areas. Perfect Rock Hall Location Situated on a quiet, low-traffic street, this location is ideal for enjoying everything the area has to offer: • Walking distance to the beach, quaint shops, local restaurants, and marinas. Community pool is only minutes away if you choose to get a quick cool-down. • An easy, flat area for riding bikes and getting your daily walks in. • A spacious yard featuring mature landscaping. Whether you are looking for a full-time residence or a cozy, low-maintenance getaway for weekends and holidays, this solid brick home is a must-see. Additional Note Home is being sold as is. The backyard features an established concrete pool that has been in place for years and well-enjoyed. For informational purposes, the seller has a current estimate for you to repair the concrete pool or, if a pool isn't on your list, an estimate to fill it in.

5705 Walnut St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

7545 Quaker Neck Rd, Chestertown
$175,000
3 Beds ⋅ 1 Baths
Needs work. Sold as is

7545 Quaker Neck Rd, Chestertown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

12035 Galena Rd, Massey
$365,000
3 Beds ⋅ 2 Baths
Enjoy the charm of country living in this 3-bedroom, 2-bath rancher situated on just over an acre in Massey! Offering convenient one-level living, this home has a rustic, cozy feel with vaulted ceilings, distinctive Scotch Pine wood from Finland in the living room, and a pellet stove that creates a warm and inviting atmosphere. Step outside to enjoy the deck and above-ground pool, perfect for relaxing and making the most of your outdoor space. One of the property's standout features is the impressive 24' x 32' insulated pole building/shop, complete with 100-amp electric, a car lift, and built-in office space—ideal for automotive enthusiasts, hobbyists, contractors, or anyone needing extra workspace and storage. The 75-inch TV in the shop and car lift convey with the sale. Additional peace of mind comes from the fully encapsulated crawlspace with a dehumidifier. The living room couches also convey. With room to enjoy the outdoors, a functional workshop, and the convenience of one-level living, this property offers plenty of possibilities. Home also has Starlink for Internet and equipment stays with property/Talkie is also available. Well pump and pressure tank replaced September, 2026. Property is being sold strictly AS IS. Shared driveway and existing right-of-way access for the farm.

12035 Galena Rd, Massey

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

501 High St, Chestertown
$349,900
Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen upgrades n unit 2 including new counter tops and flooring

501 High St, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

8668 Elm Rd, Chestertown
$349,900
4 Beds ⋅ 2 Baths
Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

7655 James Ln, Chestertown
$519,900
3 Beds ⋅ 3 Baths
Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,475 square feet of living space, three bedrooms, and two-and-a-half bathrooms, complemented by mature landscaping and a scenic farmland backdrop. A cozy front porch welcomes you inside to a spacious layout featuring separate living and family rooms, a formal dining area, and an eat-in country-style kitchen with rich wood cabinetry and stainless steel appliances. Flowing through the main living area are hardwood floors leading to a large and bright sunroom. The sunroom, complete with skylights offers an inviting space to relax and enjoy the surroundings, with a dedicated mini-split providing heating and cooling for year-round comfort. Just off the sunroom, a deck extends the living space outdoors, while a fenced portion of the yard offers additional flexibility for outdoor enjoyment. The attached two-car garage provides convenient parking and storage. A standout feature of this property is the large pole building, measuring approximately 40' by 22', with a heated shop and two tall doors—one at the front and another on the side—for RV or boat storage. This versatile building offers valuable space for projects, equipment, and recreational vehicles, along with a mezzanine storage loft above the shop. The rear of the building provides additional unfinished storage space with separate access. Located approximately 10 minutes from Chestertown, Rock Hall, and the public boat launch at Broadneck Landing, this property pairs a peaceful rural setting with convenient access to nearby shops, dining, and boating. Schedule your tour today!

7655 James Ln, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

25705 Meadow Rd, Worton
$239,000
1 Beds ⋅ 1 Baths
Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous updates, a full, unfinished walk-out basement, and plenty of possibilities! Situated on .63 acres with Village zoning and NO HOA, this property offers the freedom and flexibility you’ve been looking for! Bring your boat, RV, or recreational toys—there’s room to enjoy your property your way! Inside, you’ll appreciate the many improvements, including an updated roof, windows, water heater, water softener, and luxury vinyl plank (LVP) flooring. Step outside onto the beautiful Trex deck with low-maintenance vinyl railings, perfect for relaxing or entertaining. The full unfinished walk-out basement offers excellent storage and potential for additional living space. Conveniently located just minutes from Chestertown, Betterton, and Still Pond, you’ll enjoy peaceful country living while remaining close to shopping, dining, boating, beaches, and everything Kent County has to offer! Whether you’re searching for your first home, looking to downsize, or wanting a weekend getaway, this one deserves a look! Affordable living and valuable updates-all on your own .63-acre property! Property is being sold as-is.

25705 Meadow Rd, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

13852 Sassafras Rd, Galena
$719,500
3 Beds ⋅ 3 Baths
A Private Waterfront Retreat off Maryland’s Sassafras!!! Welcome to your own waterfront retreat and nature sanctuary, a private one-acre property designed around the water, the outdoors and the beauty of its natural setting. With more than 300 feet of waterfront and a 70-foot private dock, this unique property offers exceptional access for boating, kayaking and paddleboarding, via Swantown to the serene Sassafras River and nearby Georgetown Marina. From the moment you arrive along the tree-lined drive, the home feels tucked into its surroundings. An inviting front porch, thoughtfully designed landscaping and extensive hardscaping complement the wooded setting. Multiple outdoor living spaces take full advantage and provide abundant water views. Three levels of rear porches and decks provide sweeping views across the waterfront, creating wonderful spaces for morning coffee, outdoor dining, entertaining or simply enjoying the changing seasons. Inside, the 2,240-square-foot home offers three bedrooms and 2.5 baths, with the water and shoreline remaining the focal point. Full glass doors from the primary bedroom, living room and kitchen bring the landscape into the home and provide abundant views toward the waterfront. The modern, spacious living area boasts crown molding, hardwood flooring and built-ins, which flank the wood burning fireplace. The adjacent spacious kitchen with a large center island designed for gathering and dining, features quartz countertops, stainless appliances including a double oven, under cabinet lighting and a chef-inspired pantry for storage. The second level is home to a primary en-suite with a walk-in closet and full bathroom and connected deck that is perfect spot to enjoy morning coffee and birds, where hummingbirds and eagles regularly visit. Two additional bedrooms and a full updated hall bathroom complete this level. A meticulously maintained one-car garage offers additional storage, work area and additional refrigerator and freezer opportunity. The outside is a nature lover's paradise. The lower deck and waterfront flagstone patio add additional outdoor living space. Just to the right of the home is a private path to your very own private dock - the perfect spot to launch your kayaks, canoes or paddle boards. Enjoy this beautiful property with amazing landscaping and water views; the perfect location for privacy and peacefulness, and a great place to entertain as well. With easy access to Route 301, you are just a short drive to Middletown and Wilmington. Make this stunning home yours - schedule a tour today!

13852 Sassafras Rd, Galena

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

21121 Striper Run, Rock Hall
$330,000
3 Beds ⋅ 3 Baths
Nestled in the serene enclave of Watermans Estates, this exquisite end-of-row townhouse offers a harmonious blend of contemporary design and luxurious living. Spanning 1,628 square feet, this home is a sanctuary of comfort and style, perfect for those seeking an elevated lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, enhanced by plush carpeting and a cozy gas fireplace that beckons for intimate gatherings. The kitchen is a culinary enthusiast's dream, featuring upgraded countertops, a built-in microwave, and a gas range, all designed to inspire your inner chef. Enjoy casual meals in the kitchen's table space or host dinners in the dedicated dining area. This residence boasts three spacious bedrooms, including a convenient entry-level bedroom, ensuring comfort and privacy for all. Each of the three bathrooms is thoughtfully designed, with the master bath featuring a luxurious soaking tub, perfect for unwinding after a long day. The allure of this home extends beyond its interior. Step outside onto the expansive deck or balcony, where you can savor morning coffee or evening sunsets amidst the tranquil sounds of nature. The partly wooded lot, adorned with mature trees, offers a peaceful retreat. Located just three blocks from the stunning Chesapeake Bay, this property invites you to embrace a lifestyle enriched by water-oriented activities. Whether it's a leisurely stroll along the shore or a day of boating, the beauty of the bay is always within reach. Parking is a breeze with a private driveway and an attached garage, ensuring convenience for you and your guests. The home is equipped with modern amenities, including a washer and dryer, ensuring that daily tasks are handled with ease. This property is not just a house; it's a place to create lasting memories. With its blend of luxury, comfort, and natural beauty, this townhouse in Watermans Estates is a rare find, offering an exclusive lifestyle that truly feels like home. Looking for a cash flowing investment? The property has performed exceptionally well as a short-term rental. With no restrictions, this property could be the perfect option. Experience the perfect balance of elegance and tranquility-your dream home awaits.

21121 Striper Run, Rock Hall

Listing courtesy of Astoria Realty Advisors LLC. Contact:

13950 Huyett Ln, Galena
$689,000
3 Beds ⋅ 2 Baths
Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that invites tranquility and privacy. Built in 2005, this meticulously maintained home boasts 2,748 square feet of thoughtfully designed living space, perfect for those who appreciate both style and functionality. The upgraded countertops and stainless steel appliances in the kitchen elevate the culinary experience, while the formal dining room, adorned with crown moldings and exposed beams, adds a touch of sophistication. Natural light floods the interior through casement windows, enhancing the warmth of the hardwood floors that flow throughout the home. The main level features a convenient entry-level bedroom, perfect for guests or as the primary bedroom. The luxurious bathrooms include a walk-in shower and claw foot soaking tub providing a spa-like retreat at home. For those who appreciate the finer details, the home is equipped with recessed lighting, ceiling fans, and a dedicated wine storage area, ensuring every aspect of your lifestyle is catered to. The laundry room, conveniently located on the main floor, adds to the home's practicality. Outside, the property is beautifully landscaped with a mix of cleared and partly wooded areas, offering a picturesque view of the surrounding trees and woods. The expansive deck provides an ideal space for outdoor entertaining or simply enjoying the peaceful surroundings. With ample parking options, including a paved driveway and a detached garage with space for two vehicles, convenience is at your fingertips. This residence is not just a home; it's a lifestyle. Enjoy the luxury of space, the beauty of nature, and the comfort of a well-appointed interior. Experience the perfect blend of elegance and warmth in this Georgetown gem, where every detail has been thoughtfully curated for your enjoyment.

13950 Huyett Ln, Galena

Listing courtesy of RE/MAX Associates - Newark. Contact:

21305 Haven Rd, Rock Hall
$299,999
4 Beds ⋅ 2 Baths
Selller has made a Major price reduction to move this propperty! Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

21305 Haven Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

24607 Chestertown Rd, Chestertown
$365,000
3 Beds ⋅ 3 Baths
Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

24607 Chestertown Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

07 River Rd, Millington
$94,900
WELCOME TO THE EASTERN SHORE! | 5.46± ACRES | MILLINGTON, KENT COUNTY, MARYLAND Discover the beauty and peaceful charm of Maryland’s Eastern Shore with this beautiful 5.46± acre fully wooded property in Millington, Kent County! Offering excellent road frontage, a private natural setting, and endless possibilities for outdoor enjoyment, this is an incredible opportunity to own your own piece of Eastern Shore paradise. Surrounded by the beauty of nature, this wooded acreage provides an ideal setting for hunting, recreation, weekend adventures, or creating the perfect homesite. Imagine designing your dream home tucked among the trees, enjoying the quiet country atmosphere, and embracing the relaxed lifestyle that makes the Eastern Shore so special. Conveniently located near the many attractions, waterways, charming communities, and outdoor recreation opportunities throughout the region, this property offers a wonderful balance of peaceful country living and access to local amenities. And with the Chesapeake Bay region and Atlantic coast within reach, you can enjoy the coastal lifestyle and ocean breezes that make this part of Maryland so desirable. Whether you're searching for a private hunting retreat, a recreational getaway, or the perfect place to build your dream home, this beautiful 5.46± acre property is ready for your vision. Beautiful wooded acreage. Excellent road frontage. Peaceful Eastern Shore setting. Endless possibilities. Come discover your own slice of the Eastern Shore in Millington, Maryland!

07 River Rd, Millington

Listing courtesy of Charis Realty Group. Contact:

8901 S Bayview Dr, Chestertown
$525,000
3 Beds ⋅ 3 Baths
The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane fireplace, flows beautifully into the dining area to make the space feel inviting and roomy. The eat-in kitchen opens directly onto a back deck, making outdoor grilling and relaxation easy. The highly sought-after primary bedroom is conveniently located on the main level for easy first-floor living. Upstairs includes additional bedrooms, plenty of easy-access storage space, and a versatile, fully finished bonus room over the garage with a convenient interior entrance—ideal for a home office, hobby room, or guest suite. For hobbies and storage, the property excels. The oversized garage offers ample room for parking plus a dedicated project/workshop space. Below, a partial walk-out basement provides exterior access, making it incredibly easy to store gear or access the home's systems. Situated in a desirable water-oriented community, you will enjoy peekaboo views of the Chesapeake Bay right from the house. Best of all, the neighborhood features its own small private beach for easy enjoyment, making it effortless to relax by the water and perfect for collecting sea glass, beachcombing, and watching the sunset. This classic, beautifully refreshed home is ready for its next chapter!

8901 S Bayview Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

24110 Kinnards Point Dr, Worton
$675,000
3 Beds ⋅ 3 Baths
Discover the Charm of Kinnairds Point in this beautiful mid-century modern home. A sloping, wooded wonderland just minutes from historic Chestertown, this inviting and energy-efficient home offers the perfect blend of privacy, comfort, and Chesapeake Bay living. Set on just over two beautifully landscaped acres, the property features mature trees, fruit trees, spectacular plantings, and a peaceful, private setting surrounded by nature. Designed for both everyday living and effortless entertaining, the home offers three bedrooms and two updated baths on the main level, along with hardwood floors throughout. The updated gourmet kitchen opens to the dining and living areas, where a wood-burning fireplace creates a warm and welcoming gathering space. The updated screened porch and new, expansive deck bring the outdoors in and provide wonderful places to relax, entertain, and enjoy the natural surroundings. The spacious lower level adds exceptional flexibility, with a comfortable family room, with a wood burning stove, that can be partitioned to create a fourth bedroom or home office, a full bath, laundry area, and a surprising sunroom. With its own outside entrance, this level offers excellent accommodations for guests or additional living space. An oversized two-car garage, ample storage, and a long driveway add to the home's convenience. Kinnairds Point residents have access to two private Chesapeake waterfront areas, each featuring its own beach, pavilion, and kayak storage, with a boat ramp at one location. Just a short walk or golf cart ride away, these waterfront amenities make it easy to embrace the best of Eastern Shore living. Imagine launching your boat, kayaking along the shoreline, setting crab pots, enjoying sunset cruises, or simply unwinding by the water. Private, peaceful, and beautifully situated, this exceptional property offers room to spread out, space to entertain, and a wonderful connection to nature and the water—all just minutes from historic Chestertown, with convenient access to destinations north and south. Come experience the Eastern Shore lifestyle at Kinnairds Point!

24110 Kinnards Point Dr, Worton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

21338 Virginia Ave, Chestertown
$400,000
2 Beds ⋅ 2 Baths
Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms , and two fully appointed bathrooms, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21905 Harrington Park Rd, Rock Hall
$650,000
4 Beds ⋅ 2 Baths
Welcome to this lovely Cape Cod-style, four-bedroom, two-full-bath home situated on .98 acre in Rock Hall, where comfortable living, peaceful surroundings, and the relaxed charm of Maryland Eastern Shore come together. A welcoming front porch invites you inside to a spacious living room featuring carpet and floating flooring, an open ceiling accented by beautiful exposed wood beams, two ceiling fans, and a distinctive two-sided fireplace that brings warmth and character to the space. The kitchen features stainless steel appliances, a pantry, and plenty of room for everyday living and entertaining. The upper level features a spacious primary bedroom with carpet and a ceiling fan, along with a private primary bath complete with a relaxing Jacuzzi tub and separate shower. The second bedroom offers carpet, a ceiling fan, a walk-in closet, and a skylight that fills the room with natural light. Just outside, the Trex deck provides a peaceful place to relax and take in beautiful views of the pool, private backyard, and surrounding farmland. On the main level, the front bedroom features carpet and a ceiling fan and is conveniently located near the full bath, complete with corian and tile finishes, a handicap-accessible walk-in shower, and a storage cubby. The rear bedroom, also featuring carpet and a ceiling fan, provides direct access to the screened-in back porch. With Trex flooring, two ceiling fans, and peaceful views of the pool and surrounding farmland, the porch is an inviting spot to enjoy your morning coffee, relax at the end of the day, or simply appreciate the quiet surroundings. Step outside and discover your own private backyard retreat. The vinyl-lined pool is surrounded by a river-stone patio and beautiful mature landscaping, including Japanese maples and crepe myrtles. Wood and wrought-iron fencing add privacy and character, with a pool shed and an additional shed for lawn equipment provide convenient outdoor storage. For those who enjoy life on the water, this location offers wonderful access to everything the Rock Hall area is known for. Grays Inn Creek Marina is approximately two minutes away, with access to Grays Inn Creek and Harrington Creek, which flow into the Chester River. A public landing and pier are also nearby, making it easy to enjoy some of the Eastern Shore’s favorite pastimes—fishing, crabbing, sailing, and boating. Approximately 2.6 miles to downtown Rock Hall welcomes you with restaurants, quaint shops, marinas, and all the unique character of life along the Chesapeake Bay. Whether relaxing by the pool, taking in the peaceful country views, or spending the day on the water, this home offers a wonderful opportunity to enjoy the natural beauty, coastal charm, and laid-back lifestyle that make Rock Hall and Maryland’s Eastern Shore such a special place to call home.

21905 Harrington Park Rd, Rock Hall

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

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