Kent, MD Homes

/27
$260,000 Sold Aug 22, 2025
- 850 Sq Ft
- $306/SF
- 33 Days On Market
- 2 Beds
- 1.5 Baths
- Built 2010
5810 Judefind Ave, Rock Hall, MD 21661

Adorable Cottage featuring 2BR/1.5BA, just over a quarter acre of land! Built in 2010, cute as a button, large front porch and another on the back to match. Large attic (potential for expansion), on-demand water heater, gutter filters, HVAC, shed in back for storage/lawn mower, mature asparagus bed in front yard! Living space is open with a nicely appointed kitchen and the covered back porch

Retha Arrabal Doug Ashley Realtors, LLC

5810 Judefind Ave, Rock Hall, MD 21661
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More

/7
Est $105,382 Not Listed For Sale
5246 Eastern Neck Rd, Rock Hall, MD 21661

5246 Eastern Neck Rd, Rock Hall, MD 21661

/9
$1,150,000
- Land
- 1.56 Acres
- $737,179 per Acre
206 Cannon St, Chestertown, MD 21620

Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

Brian Gearhart

Benson & Mangold, LLC

(443) 419-7633

206 Cannon St, Chestertown, MD 21620
/41
$685,000 Sold Aug 19, 2025
- 1,400 Sq Ft
- $489/SF
- 4 Days On Market
- 4 Beds
- 3 Baths
- Built 1962
5807 Beach Rd, Rock Hall, MD 21661

Just steps from the Chesapeake Bay this charming rancher offers 3 bedrooms, 1.5 baths all on convenient, one level living. The kitchen is the central gathering space in the house with gleaming quartz countertops and beautifully refinished wood floors. The floorplan is open, yet provides cozy places for reading and relaxing. Owner upgrades include new white 5-panel doors and moldings to accentuate

Cindy Genther Rock Hall Properties Real Estate

5807 Beach Rd, Rock Hall, MD 21661

/9
Est $84,943 Not Listed For Sale
10578 Chesterville Forest Rd, Millington, MD 21651

10578 Chesterville Forest Rd, Millington, MD 21651

/39
$745,000 Under Contract
- 3 Beds
- 3.5 Baths
- 2,492 Sq Ft
110 S Mill St, Chestertown, MD 21620

Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront.The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is

John Burke

Gunther-McClary Real Estate

(410) 514-3490

110 S Mill St, Chestertown, MD 21620
/47
$540,000 Sold Aug 15, 2025
- 2,094 Sq Ft
- $258/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
25244 Wymont Park Rd, Worton, MD 21678

As you walk up to this home, the front porch welcomes you to sit back, relax, and enjoy the peaceful surroundings. Mature plants and gardens create a relaxing feel, the quiet and openness is something you’ll want to take in and appreciate. There’s more great space on the screened porch than it overflows to the outdoor patio, cooking station, and specialty gardens.Inside, this home has

Grace Crockett Doug Ashley Realtors, LLC

25244 Wymont Park Rd, Worton, MD 21678

/35
Not Listed For Sale
- 2 Beds
11430 Lynch Rd, Worton, MD 21678

11430 Lynch Rd, Worton, MD 21678

/45
$698,000 Under Contract
- 2 Beds
- 2 Baths
- 1,460 Sq Ft
9194 N Bayview Ave, Chestertown, MD 21620

Stunning home and property with 180-degree views of the Chesapeake Bay.The home was completely remodeled in 2017 by Taylor Loughry Construction. Boasting a bright open floor plan with high-end finishing, vaulted ceilings with skylights, and beautifully landscaped outdoor space. Two bedrooms and two full bathrooms, open living space with a gourmet kitchen, and a large deck overlooking the

John Burke

Gunther-McClary Real Estate

(410) 650-6367

9194 N Bayview Ave, Chestertown, MD 21620
/20
$246,000 Sold Aug 15, 2025
- 1,000 Sq Ft
- $246/SF
- 17 Days On Market
- 3 Beds
- 1 Bath
- Built 1988
10624 Millbrook Dr, Chestertown, MD 21620

Charming One-Level Living Near the Chesapeake Bay!This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind.Enjoy your mornings on

Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

10624 Millbrook Dr, Chestertown, MD 21620

/52
Est $406,860 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,520 Sq Ft
5785 Liberty St, Rock Hall, MD 21661

5785 Liberty St, Rock Hall, MD 21661

/36
$759,000 New Construction
- 3 Beds
- 3.5 Baths
212 Landing Ln, Chestertown, MD 21620

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

John Burke

Gunther-McClary Real Estate

(410) 883-7032

212 Landing Ln, Chestertown, MD 21620
/16
$270,000 Sold Aug 15, 2025
- 1,628 Sq Ft
- $166/SF
- 28 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1996
21114 Striper Run, Rock Hall, MD 21661

SELLERS CONCESSION OFFERED !!!!!!!!!!Coastal Charm Just Steps from the Water – 3 Bed, 2 Bath Home!Welcome to your dream home, perfectly situated just a short stroll from the water! This 3-bedroom, 2-bath residence offers a blend of comfort, style, and the ultimate coastal lifestyle.Step inside to discover an open and airy floor plan filled with natural light. The spacious

Alyson Anderson Allfirst Realty, Inc.

21114 Striper Run, Rock Hall, MD 21661

/35
Est $290,714 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
120 N Main St, Galena, MD 21635

120 N Main St, Galena, MD 21635

/33
$797,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,522 Sq Ft
7514 Muirfield Dr, Chestertown, MD 21620

Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

John Burke

Gunther-McClary Real Estate

(443) 206-3727

7514 Muirfield Dr, Chestertown, MD 21620
/36
$375,000 Sold Aug 13, 2025
- 2,302 Sq Ft
- $163/SF
- 1 Day On Market
- 5 Beds
- 3.5 Baths
- Built 2022
206 Silver Heel Dr, Chestertown, MD 21620

Welcome to The Verona in The Village at Chestertown—a beautifully designed, move-in ready home offering 2,302 square feet of flexible living space across three levels. With 5 bedrooms and 3.5 bathrooms, this home perfectly balances comfort, function, and style. Step inside to a welcoming foyer that leads into a spacious family room, ideal for relaxing or entertaining. The open-concept layout

TJ Bennett Samson Properties

206 Silver Heel Dr, Chestertown, MD 21620

/24
Est $276,410 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,220 Sq Ft
5788 Liberty St, Rock Hall, MD 21661

5788 Liberty St, Rock Hall, MD 21661

/22
$1,459,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,315 Sq Ft
0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

John Burke

Gunther-McClary Real Estate

(443) 249-2840

0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
/2
$50,000 Sold Aug 13, 2025
- 1,272 Sq Ft
- $39/SF
- 42 Days On Market
- 3 Beds
- 1 Bath
- Built 1900
26743 Medders Rd, Still Pond, MD 21667

Located in the quaint village of Still Pond. This truly is a "fixer upper". This property is being sold strictly "AS IS". There appears to be some issues with the living room floor. This purchase will probably require a cash buyer.

Doug Ashley Doug Ashley Realtors, LLC

26743 Medders Rd, Still Pond, MD 21667

/44
Est $520,289 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,932 Sq Ft
218 Camelot Dr, Chestertown, MD 21620

218 Camelot Dr, Chestertown, MD 21620

/22
$998,000 New Construction
- 3 Beds
- 3.5 Baths
226 S Water St, Chestertown, MD 21620

Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

John Burke

Gunther-McClary Real Estate

(410) 376-5375

226 S Water St, Chestertown, MD 21620
/68
$1,531,832 Sold Aug 12, 2025
- 3,317 Sq Ft
- $462/SF
- 32 Days On Market
- 5 Beds
- 3 Baths
- Built 1975
6581 Elizabeths Ln, Rock Hall, MD 21661

Private Eastern Shore Waterfront RetreatTucked away on a serene, wooded 5-acre waterfront peninsula, 6581 Elizabeth’s Lane offers an unparalleled private escape on West Fork Langford Creek, feeding into the Chester River. With over 1,000 feet of deep water shoreline and three sides of water frontage, this secluded retreat provides easy access by boat to Rock Hall, Kent Island, Annapolis,

Carol Snyder Monument Sotheby's International Realty

6581 Elizabeths Ln, Rock Hall, MD 21661

/33
Est $697,254 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
209 Landing Ln, Chestertown, MD 21620

209 Landing Ln, Chestertown, MD 21620

/33
$2,750,000 Coming Soon
- 5 Beds
- 4.5 Baths
- 4,305 Sq Ft
7989 Quaker Neck Rd, Chestertown, MD 21620

Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

Peter Heller Coldwell Banker Chesapeake Real Estate Company

7989 Quaker Neck Rd, Chestertown, MD 21620
/50
$370,000 Sold Aug 11, 2025
- 2,414 Sq Ft
- $153/SF
- 12 Days On Market
- 4 Beds
- 2 Baths
- Built 2007
169 Millington Rd, Millington, MD 21651

Welcome to 169 Millington Rd in Mill Village! This stunning home offers effortless living with an open floor plan and gleaming hardwood floors that create a seamless, stylish flow throughout the main level. The spacious kitchen features a breakfast bar and opens to the inviting great room with a cozy fireplace—perfect for entertaining or relaxing. A separate formal dining room provides the ideal

Penny Hollis Keller Williams Select Realtors of Annapolis

169 Millington Rd, Millington, MD 21651

/12
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,426 Sq Ft
20790 Mercer Ave, Rock Hall, MD 21661

20790 Mercer Ave, Rock Hall, MD 21661

/30
$4,850,000
- 5 Beds
- 8 Baths
- 9,852 Sq Ft
23620 Land's End Rd, Chestertown, MD 21620

80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

Stacy Kendall

23620 Land's End Rd, Chestertown, MD 21620
/10
$65,000 Sold Aug 11, 2025
- Land
- 2.36 Acres
- $27,542 per Acre
- 54 Days On Market
9020 Georgetown Rd, Chestertown, MD 21620

Price improvement!!! Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any

Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

9020 Georgetown Rd, Chestertown, MD 21620

/44
Est $429,245 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,890 Sq Ft
204 N Mill St, Chestertown, MD 21620

204 N Mill St, Chestertown, MD 21620

/37
$509,900
- 4 Beds
- 2 Baths
- 2,220 Sq Ft
515 N Kent St, Chestertown, MD 21620

Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming

Jody Baker Cross Street Realtors LLC

515 N Kent St, Chestertown, MD 21620
/63
$390,500 Sold Aug 08, 2025
- 1,457 Sq Ft
- $268/SF
- 6 Days On Market
- 3 Beds
- 1 Bath
- Built 1874
137 N Main St, Galena, MD 21635

Historic St. Andrews Chapel - Galena, MD - circa 1874. Architecturally stunning one of a kind former Episcopal wayside chapel converted to fabulous residence. From the exterior you will notice the attention to detail that this home has received during massive updates and renovations over the last few years. Full exterior restoration of original board and batten siding, standing seam metal

John Carroll Village Real Estate Company LLC

137 N Main St, Galena, MD 21635

/7
Est $596,076 Not Listed For Sale
- 4 Beds
- 5 Baths
- 3,497 Sq Ft
128 N Queen St, Chestertown, MD 21620

128 N Queen St, Chestertown, MD 21620

/56
$649,000
- 4 Beds
- 5 Baths
- 3,549 Sq Ft
6134 Rock Hall Rd, Rock Hall, MD 21661

Welcome to 6134 Rock Hall Road, a beautifully landscaped property with an expansive four bedroom historic home situated at the entrance of Rock Hall. Although the original home dates from the late 1800s, the majority of the home was designed and constructed by T. Milton Jones, a prominent Baltimore builder, who purchased the property in 1911. Named “Vemmerr” for the first initials of Mr. and

Lynn Hilfiker Gunther-McClary Real Estate

6134 Rock Hall Rd, Rock Hall, MD 21661
/19
$335,000 Sold Aug 08, 2025
- 1,500 Sq Ft
- $223/SF
- 17 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
10578 Tonopah Rd, Chestertown, MD 21620

Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living—featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite

David Moore RE/MAX Executive

10578 Tonopah Rd, Chestertown, MD 21620

/18
Est $230,090 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,088 Sq Ft
114 W Cross St, Galena, MD 21635

114 W Cross St, Galena, MD 21635

/24
$450,000
- 3 Beds
- 2 Baths
- 1,886 Sq Ft
224 Valley Rd, Chestertown, MD 21620

Impeccably maintained! One-level home offers easy living on a quiet street. Thoughtful updates and meticulous care are evident throughout, including a new vapor barrier in the crawl space, new attic fans, the list goes on and on! The spacious primary bedroom features a full en-suite bath, while the exterior boasts a beautifully landscaped yard and a new concrete patio surrounding the in-ground

Casey Scattergood Cross Street Realtors LLC

224 Valley Rd, Chestertown, MD 21620
/53
$600,000 Sold Aug 08, 2025
- 5,001 Sq Ft
- $120/SF
- 0 Days On Market
- 5 Beds
- 3 Baths
- Built 1977
605 Mill Ln, Galena, MD 21635

Bring everyone along to experience this stunning property, offering a combination of space, style, & functionality. The 3-bedroom, 2-bath main home has been thoughtfully designed to cater to both relaxation & entertainment, featuring expansive living areas & high-end finishes throughout. The spacious primary suite is a true retreat at the end of the main hall, thoughtfully designed with comfort

Liddy Campbell TTR Sotheby's International Realty

605 Mill Ln, Galena, MD 21635

/23
Est $407,690 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,356 Sq Ft
101 S Kent St, Chestertown, MD 21620

101 S Kent St, Chestertown, MD 21620

/35
$795,000
- 4 Beds
- 3.5 Baths
- 2,917 Sq Ft
200 Washington Ave, Chestertown, MD 21620

This early 20th C gem of a traditional "Four Square" has been a Chestertown STAND-OUT RESIDENCE since originally crafted by acclaimed master builder Walter Pippin. The flawless flow of its' first floor, with discreet powder room, and the abundance of windows throughout make this corner home, with wrap-around porch, tended landscape and white picket fence an exceptional offering. Four bedrooms,

Richard Keaveney Cross Street Realtors LLC

200 Washington Ave, Chestertown, MD 21620
/24
$285,000 Sold Aug 08, 2025
- 652 Sq Ft
- $437/SF
- 457 Days On Market
- 1 Bed
- 1 Bath
- Built 1886
117 N Water St Unit 3B, Chestertown, MD 21620

A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

John Burke Gunther-McClary Real Estate

117 N Water St Unit 3B, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

Maryland Kent County

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Constant Friendship Homes

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage