Homes for Sale near Kent School

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  /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
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  Explore Kent School

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  /25

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  126 Metcalf Rd, Chestertown, MD 21620

  Amazing deal on this 2 yr old rancher/duplex with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside

  

  Brenda Fornos

  Taylor Properties

  (410) 438-8763

  126 Metcalf Rd, Chestertown, MD 21620
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  /40

  $745,000

  • Studio
  • 2,492 Sq Ft

  110 S Mill St, Chestertown, MD 21620

  Beautiful home in historic Chestertown. This property can be a single family home, or two separate units. The larger apartment features a gourmet kitchen with 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 designed for both comfortable living

  

  John Burke

  Gunther-McClary Real Estate

  (410) 514-3490

  110 S Mill St, Chestertown, MD 21620
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  /93

  $1,550,000

  • 5 Beds
  • 4 Baths
  • 4,167 Sq Ft

  7961 Quaker Neck Rd, Chestertown, MD 21620

  **Exquisite Waterfront Retreat on Chester River**Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre

  

  Gretchen Wichlinski

  Compass

  (443) 320-6559

  7961 Quaker Neck Rd, Chestertown, MD 21620
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  /41

  $569,000

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  103 Landing Ln, Chestertown, MD 21620

  Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

  

  John Burke

  Gunther-McClary Real Estate

  (443) 981-2534

  103 Landing Ln, Chestertown, MD 21620
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  /28

  $725,000

  • 3 Beds
  • 3 Baths

  117 N Water St Unit 1A, Chestertown, MD 21620

  Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

  

  John Burke

  Gunther-McClary Real Estate

  (443) 589-6299

  117 N Water St Unit 1A, Chestertown, MD 21620
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  /20

  $185,000

  • Land
  • 1.95 Acres
  • $94,872 per Acre

  Lot 9 Prestwick Dr, Chestertown, MD 21620

  Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

  

  John Burke

  Gunther-McClary Real Estate

  (443) 806-9518

  Lot 9 Prestwick Dr, Chestertown, MD 21620
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  /28

  $399,000

  • 2 Beds
  • 1 Bath
  • 787 Sq Ft

  117 N Water St Unit 2A, Chestertown, MD 21620

  A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

  

  John Burke

  Gunther-McClary Real Estate

  (410) 824-5609

  117 N Water St Unit 2A, 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
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  /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
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  /27

  $1,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,540 Sq Ft

  0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

  **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!**Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest

  

  John Burke

  Gunther-McClary Real Estate

  (443) 249-2840

  0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
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  /90

  $2,750,000

  • 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
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  /19

  $185,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,136 Sq Ft

  423 Calvert St, Chestertown, MD 21620

  Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add

  Barbara McCaffrey Redfin Corp

  423 Calvert St, Chestertown, MD 21620
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  /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
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  /35

  $745,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,917 Sq Ft

  200 Washington Ave, Chestertown, MD 21620

  Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

  Richard Keaveney Cross Street Realtors LLC

  200 Washington Ave, Chestertown, MD 21620
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  /90

  $595,000

  • 4 Beds
  • 3.5 Baths
  • 5,576 Sq Ft

  103 Adela Way, Chestertown, MD 21620

  Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which flows directly into the rest of the house. Moving forward is the very large den/ family room that

  Barbara McPhail Douglas Realty LLC

  103 Adela Way, Chestertown, MD 21620
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  /39

  $949,900

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft

  492 Pear Tree Point Rd, Chestertown, MD 21620

  Great opportunity to own a waterfront property on the scenic Chester River! This beautifully landscaped 3 bedroom, 2 bath home with a wraparound porch offers stunning views. There is an additional partially finished 700+/- sq ft space over the garage, filled with natural light and river views, ideal for extra bedrooms with bath, master bedroom or an in-law suite. Tucked away in a peaceful,

  Leo Kuneman Meredith Fine Properties

  492 Pear Tree Point Rd, Chestertown, MD 21620
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  /54

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 3,935 Sq Ft

  251 Devon Dr, Chestertown, MD 21620

  Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula

  Debbie Meikle Doug Ashley Realtors, LLC

  251 Devon Dr, Chestertown, MD 21620
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  /54

  $648,750

  • 4 Beds
  • 3.5 Baths
  • 2,008 Sq Ft

  206 S Water St, Chestertown, MD 21620

  Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This versatile home has over 2,000 square feet of finished living space and was rebuilt and expanded with future customizations in mind!* The rear addition includes a sunroom/mudroom with a separate entrance connecting

  Beth Ostrander Doug Ashley Realtors, LLC

  206 S Water St, Chestertown, MD 21620
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  /64

  $659,899

  • 5 Beds
  • 4.5 Baths
  • 4,870 Sq Ft

  113 Stone Ivy Ln, Church Hill, MD 21623

  Welcome to this stunning 4/5-bedroom, 4.5-bath, 4,870 sq ft home, beautifully maintained and thoughtfully upgraded for modern living. Freshly painted throughout in 2022, with new carpet and premium hardwood floors and new ceiling fans. This spacious residence is move-in ready and shines with pride of ownership.Step into a grand two-story foyer that opens to expansive formal and casual living

  Brett Schrader Taylor Properties

  113 Stone Ivy Ln, Church Hill, MD 21623
• 

  

  /22

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft

  101 Birch Run Rd, Chestertown, MD 21620

  A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a New Encapsulated Crawl Space, New Roof with 50-year shingles and a transferable warranty, new water and sewer lines

  Stacy Kendall Cross Street Realtors LLC

  101 Birch Run Rd, Chestertown, MD 21620
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  /2

  $719,500

  • 5 Beds
  • 3.5 Baths
  • 3,256 Sq Ft

  216 Brix Dr, Church Hill, MD 21623

  Photos and a complete property website will be available shortly. The home is currently undergoing a full interior painting and has new luxury vinyl plank flooring being installed throughout. Stay tuned!

  Chris Rosendale CR Realty

  216 Brix Dr, Church Hill, MD 21623
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  /2

  $515,000

  • 4 Beds
  • 3.5 Baths
  • 3,799 Sq Ft

  100 Adela Way, Chestertown, MD 21620

  Preparing for Market- Don't miss this. Stunning and well maintained home on a corner lot with fenced yard, finished basement, sauna room, private office and 2 car garage. Recently replaced: HVAC, Roof and Water Heater. More details to come- On Market by Sept 15, 2025.

  Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

  100 Adela Way, Chestertown, MD 21620
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  /77

  $614,700 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  334 ( Lot 22) Eagle Manor Dr, Church Hill, MD 21623

  To be built in the community of Condor Manor in Church Hill! This is Red Oak's most popular model with various options avaiable . This Pin Oak model, built by Red Oak Properties, LLC is a must see home featuring LVP flooring all throughout the home, upgraded kitchen oversized Island, perfect for preparing meals or entertaining. Entertaining can continue outside to the maintenance free deck.

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  334 ( Lot 22) Eagle Manor Dr, Church Hill, MD 21623
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  /57

  $975,000 New Construction

  • 5 Beds
  • 3.5 Baths

  0 Finley Creek ( Lot 6) Dr Unit MDQA2014154, Centreville, MD 21617

  Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red Oak Properites . Featuring 3100 +/- square foot home features, a home office on the first floor, gourmet kitchen with Island, wall oven, gas cook top, wine cooler, beverage cooler and gas fireplace sitting

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  0 Finley Creek ( Lot 6) Dr Unit MDQA2014154, Centreville, MD 21617
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  /57

  $940,000 New Construction

  • 5 Beds
  • 3.5 Baths

  0 Eagle Manor Lot 20 Dr, Church Hill, MD 21623

  Another estate style home to be built in the highly desirable community of Condor Manor located just outside of Church Hill. Be one of the first to occupy the beautiful Mossy Oak Model home completed by Red Oak Properties, with all the bells and whistles. This 3100 +/- square foot home features, a home office on the first floor, gourmet kitchen with Island, wall oven, gas cook top, wine cooler,

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  0 Eagle Manor Lot 20 Dr, Church Hill, MD 21623
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  /37

  $639,900 Coming Soon

  • 4 Beds
  • 2 Baths
  • 2,869 Sq Ft

  206 Valley Rd, Chestertown, MD 21620

  Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been

  Peter Heller Coldwell Banker Chesapeake Real Estate Company

  206 Valley Rd, Chestertown, MD 21620
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  /35

  $424,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  600 Rosin Dr, Chestertown, MD 21620

  Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Rosin Creek. Combining classic character with modern updates, the open floor plan creates a warm and inviting flow. Perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas. Updated flooring throughout the downstairs,

  Michele Palmer Doug Ashley Realtors, LLC

  600 Rosin Dr, Chestertown, MD 21620
• 

  

  /29

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  221 Old Bridge Rd, Chestertown, MD 21620

  Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof. The walk-up

  Courtney Chipouras TTR Sotheby's International Realty

  221 Old Bridge Rd, Chestertown, MD 21620
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  /39

  $375,000

  • 4 Beds
  • 3 Baths
  • 1,790 Sq Ft

  7653 Broad Neck Rd, Chestertown, MD 21620

  Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Chestertown in an idyllic country setting. Some improvements include new HVAC, electric, 3 season room , water filter and high-end, smart appliances. Terrific in-ground pool enclosed with privacy brick wall, a large patio and deck are perfect for entertaining or relaxing in the

  Brian Petzold Benson & Mangold, LLC

  7653 Broad Neck Rd, Chestertown, MD 21620
• 

  

  /51

  $389,900

  • Studio
  • 1,728 Sq Ft

  517 High St, Chestertown, MD 21620

  Showings start Friday 09/26Fantastic investment opportunity. Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and

  Kristie Midash L. C. Parker Real Estate

  517 High St, Chestertown, MD 21620
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  /42

  $374,900

  • 5 Beds
  • 3.5 Baths
  • 2,615 Sq Ft

  112 Silver Heel Rd, Chestertown, MD 21620

  Welcome home to this stunning Verona floor plan, built in 2023 — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space.The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The

  Federico Busacca EXP Realty, LLC

  112 Silver Heel Rd, Chestertown, MD 21620
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  /35

  $695,000

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  118 Little Harbor Way Unit 201, Chestertown, MD 21620

  An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and Chester River. It is nearly impossible for the body, mind and spirit of its residents and guests not to be "in a good place" on the cloudiest or most challenging of days. River House, with only five private residences, occupies the best real estate within

  Richard Keaveney Cross Street Realtors LLC

  118 Little Harbor Way Unit 201, Chestertown, MD 21620
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  /2

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  119 Darden Rd, Chestertown, MD 21620

  Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

  Solomon Zaldivar Compass

  119 Darden Rd, Chestertown, MD 21620
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  /69

  $559,000 Open House 10/11

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  103 Landing Ln, Chestertown, MD 21620

  Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

  Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

  103 Landing Ln, Chestertown, MD 21620
• 

  

  /18

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  100 Metcalf Rd, Chestertown, MD 21620

  Like-New Chestertown Ranch: Pristine Condition, Ready Today! $255K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $255,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of

  Dale Hunter Bayside Realty

  100 Metcalf Rd, Chestertown, MD 21620
• 

  

  /18

  $549,900

  • Land
  • 5.53 Acres
  • $99,439 per Acre

  202 Everett Ln, Church Hill, MD 21623

  Great opportunity for an investor or builder. 24 units in established 55+ community. Sewer allocations are available, and the community is served by its own on site well water system. Located in quiet small Eastern Shore town close to parks, and theater. Just minutes to Centreville or Chestertown. 5 Building sites which could be sold separately. $23,000/Unit

  Jason Dey Kevin Dey Realty

  202 Everett Ln, Church Hill, MD 21623
• 

  

  /33

  $410,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  907 N Meadowview Dr, Chestertown, MD 21620

  JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly

  William Sutton Coldwell Banker Chesapeake Real Estate Company

  907 N Meadowview Dr, Chestertown, MD 21620
• 

  

  /7

  $110,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  5700 Johnsontown Rd, Chestertown, MD 21620

  Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless.Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold

  Nicole Stephens Tesla Realty Group, LLC

  5700 Johnsontown Rd, Chestertown, MD 21620
• 

  

  /19

  $315,000

  • 1 Bed
  • 1.5 Baths
  • 936 Sq Ft

  108 S Kent St, Chestertown, MD 21620

  Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. Upstairs is a large, sun-filled room with a spacious closet that serves as an office. It could also be a den or sitting room.

  Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  108 S Kent St, Chestertown, MD 21620

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