6,883

Chestertown, MD Homes

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    • /36

      Est $914,105 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,352 Sq Ft

      9831 Breezecroft Ln, Chestertown, MD 21620

      9831 Breezecroft Ln, Chestertown, MD 21620
  • /18

    $643,595 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,599 Sq Ft

    3654 Gratitude Way, Chestertown, MD 21620

    TO BE BUILT......Welcome to Ryan Homes at Gilbert Meadows. Offering ranch style & 2-story single family homes with 1st floor primary suites in Harford County, MD. Minutes to Rte. 22 & I-95 - Starting from the low $500's. Our homes are designed to make your life easier with open and modern designs connecting all the spaces you use most! Plus, our homes all offer all the conveniences of main-level

    Tineshia Johnson NVR Services, Inc.

    3654 Gratitude Way, Chestertown, MD 21620
  • /65

    $950,000 Sold Oct 17, 2024

    • 4,730 Sq Ft
    • $201/SF
    • 110 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    7755 Waterview Ln, Chestertown, MD 21620

    This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7755 Waterview Ln, Chestertown, MD 21620
    • /27

      Est $262,725 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • /2

    $135,000 Pending

    • Land
    • 13 Acres
    • $10,030 per Acre

    0 None Unit MDKE2005014, Chestertown, MD 21620

    13.5 wooded acres with very limited access on north side of Chestertown. Should be excellent deer hunting. 16' paper right of way to access.

    William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
  • /76

    $1,362,500 Sold Oct 16, 2024

    • 5,195 Sq Ft
    • $262/SF
    • 457 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1760

    201 N Water St, Chestertown, MD 21620

    SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified

    Nancy McGuire Maryland Heritage Properties

    201 N Water St, Chestertown, MD 21620
    • /30

      Est $450,313 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,304 Sq Ft

      105 S Kent St, Chestertown, MD 21620

      105 S Kent St, Chestertown, MD 21620
  • /2

    $344,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    109 Edmore Rd, Chestertown, MD 21620

    Welcome to 109 Edmore Rd, a beautifully renovated 3-bedroom, 2-bath ranch-style home offering 1,344 sq. ft. of comfortable living space on a 0.34-acre lot. This move in ready home blends modern upgrades with cozy charm. Renovated in 2021 upgrades include HVAC, Roof, Encapsulated crawl space, appliances, reverse osmosis and water conditioner. Features a 16 x 12 screen porch for relaxing outdoors.

    Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
  • /22

    $565,000 Sold Oct 07, 2024

    • 1,146 Sq Ft
    • $493/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1870

    125 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience.Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just

    John Burke Gunther-McClary Real Estate

    125 High St, Chestertown, MD 21620
    • /44

      Est $653,407 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,536 Sq Ft

      225 Washington Ave, Chestertown, MD 21620

      225 Washington Ave, Chestertown, MD 21620
  • /8

    $408,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    200 Hoffman Ln, Chestertown, MD 21620

    Investor’s Dream on the Chester River – 1.75 Acres with Endless Potential!Welcome to a rare opportunity along the stunning Chester River! This unique property combines two parcels totaling 1.75 acres and includes an 1100+ square foot home that’s ready for your vision. Whether you're a seasoned investor, a savvy flipper, or someone dreaming of creating the perfect riverfront retreat—this is the

    Joelle Dolch Cross Street Realtors LLC

    200 Hoffman Ln, Chestertown, MD 21620
  • /27

    $165,000 Sold Oct 04, 2024

    • 1,232 Sq Ft
    • $134/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21320 Persimmon Dr, Chestertown, MD 21620

    Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just the answer. Close to the Bay and all Tolchester offers from it's marina, Shanty beach bar and the best spot for an incredible sunset. Tolchester Village offers the perfect location for those looking for a summer retreat or full

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    21320 Persimmon Dr, Chestertown, MD 21620
    • /32

      Est $499,418 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,700 Sq Ft

      311 Mayfair Dr, Chestertown, MD 21620

      311 Mayfair Dr, Chestertown, MD 21620
  • /95

    $1,495,000 Open Sat 11AM - 2PM

    • 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 of

    Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • /36

    $380,000 Sold Oct 03, 2024

    • 1,625 Sq Ft
    • $234/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    23118 Raleigh Rd, Chestertown, MD 21620

    Welcome to this beautifully updated rancher, offering a perfect blend of classic charm and modern amenities. This home boasts an oversized detached 2-car garage and an inviting in-ground saltwater pool. Inside, you'll find two fully remodeled bathrooms, stunning hardwood floors, and a back screened-in porch where you can relax and enjoy serene country views. Recent upgrades include a newer HVAC

    Kaitlyn Collins Benson & Mangold, LLC

    23118 Raleigh Rd, Chestertown, MD 21620
    • /13

      Est $220,272 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft

      21286 Maine Ave, Chestertown, MD 21620

      21286 Maine Ave, Chestertown, MD 21620
  • /7

    $700,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft

    5594 Langford Bay Rd, Chestertown, MD 21620

    Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.The heart

    Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
  • /13

    $749,000 Sold Oct 01, 2024

    • 3,322 Sq Ft
    • $225/SF
    • 3 Beds
    • 2 Baths
    • Built 1966

    7694 Waterview Ln, Chestertown, MD 21620

    Prepare to be wowed! Stunning house in Country Club Estates. Less than 2 miles from Chestertown and close to the Chester River. One floor living. Large rear and side yards. Easy flow floor plan with spacious rooms. Plenty of storage space. Nothing needed, just bring your suitcase!

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7694 Waterview Ln, Chestertown, MD 21620
    • /30

      Est $394,525 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,390 Sq Ft

      208 W Campus Ave, Chestertown, MD 21620

      208 W Campus Ave, Chestertown, MD 21620
  • /2

    $220,000 Coming Soon

    • 1 Bed
    • 1 Bath
    • 882 Sq Ft

    619 Cannon St, Chestertown, MD 21620

    Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect for a weekend retreat, investment property, or full-time

    Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
  • /46

    $279,000 Sold Sep 27, 2024

    • 1,456 Sq Ft
    • $192/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    9769 Augustine Herman Hwy, Chestertown, MD 21620

    Panoramic farmland views and a peaceful rural setting invite you to enjoy all that this traditional brick home has to offer. Original oak hardwood floors add classic charm to the spacious traditional floor plan, perfect for both entertaining and everyday living. A large rear-facing garage compliments the home's livability and enhances it's curb appeal. Situated on 1.38 acres, the surrounding yard

    Rosella Hunter Remax Vision

    9769 Augustine Herman Hwy, Chestertown, MD 21620
    • /23

      Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,530 Sq Ft

      114 High St, Chestertown, MD 21620

      114 High St, Chestertown, MD 21620
  • /39

    $575,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    25285 Foxchase Dr, Chestertown, MD 21620

    Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
  • /26

    $398,000 Sold Sep 27, 2024

    • 1,776 Sq Ft
    • $224/SF
    • 45 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    209 Princess Anne Dr, Chestertown, MD 21620

    Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foyer, you'll immediately appreciate the spaciousness and elegance this home offers.This meticulously maintained residence boasts three comfortable bedrooms that provide ample space for relaxation and privacy. The property

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    209 Princess Anne Dr, Chestertown, MD 21620
    • /44

      Est $969,370 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,276 Sq Ft

      9556 Chantilly Farm Ln, Chestertown, MD 21620

      9556 Chantilly Farm Ln, Chestertown, MD 21620
  • /40

    $599,900 Under Contract

    • 5 Beds
    • 2.5 Baths
    • 2,536 Sq Ft

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
  • /9

    $250,000 Sold Sep 27, 2024

    • 1,234 Sq Ft
    • $203/SF
    • 36 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    631 High St, Chestertown, MD 21620

    Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of the few homes on High Street to come with off street parking (up to 4 spaces) accessed by alley way in back. Partially fenced in back yard with privacy

    Michele Palmer Doug Ashley Realtors, LLC

    631 High St, Chestertown, MD 21620
    • /28

      Est $253,676 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft

      545 High St, Chestertown, MD 21620

      545 High St, Chestertown, MD 21620
  • /56

    $749,900 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft

    7988 Aldan Dr, Chestertown, MD 21620

    This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

    Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
  • /24

    $350,000 Sold Sep 27, 2024

    • 2,472 Sq Ft
    • $142/SF
    • 85 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    213 Devon Dr, Chestertown, MD 21620

    Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower – 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible – Be sure to step outside from the dining room through the sliding glass door into the large screened-in deck

    Christopher Buss Weichert Realtors - Blue Ribbon

    213 Devon Dr, Chestertown, MD 21620
    • /47

      Est $321,157 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      9041 S Bayview Dr, Chestertown, MD 21620

      9041 S Bayview Dr, Chestertown, MD 21620
  • /38

    $598,500 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft

    129 N Queen St, Chestertown, MD 21620

    Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

    William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
  • /31

    $394,000 Sold Sep 26, 2024

    • 1,616 Sq Ft
    • $244/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    211 Byford Dr, Chestertown, MD 21620

    Welcome to a hidden oasis, just steps from Downtown Chestertown! This Byford Heights home has been meticulously maintained; featuring main level living, attached oversized garage, home office space, an ample screen porch, fully fenced back yard, and in-ground pool. And, untouched hardwood floors just begging to be uncovered! Open House on Saturday the 24th from 1-3p.

    Liddy Campbell TTR Sotheby's International Realty

    211 Byford Dr, Chestertown, MD 21620
    • /69

      Est $1,200,431 Not Listed For Sale

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

      10069 John Carvill Rd, Chestertown, MD 21620

      10069 John Carvill Rd, Chestertown, MD 21620
  • /52

    $795,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
  • /50

    $1,300,000 Sold Sep 24, 2024

    • 3,345 Sq Ft
    • $389/SF
    • 18 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1943

    10705 Tilden Ln, Chestertown, MD 21620

    Enjoy picturesque water views of Worton Creek from every room. Situated on over 2.5 acres of well maintained and landscaped property with irrigation and enjoy the water from the private pier with 5 ft. of depth and only minutes by boat to the Chesapeake Bay or relax by the water side pool. This five bedroom three bath home has an apartment above the detached 3 car garage with a full kitchen,

    Glenn Sutton TTR Sotheby's International Realty

    10705 Tilden Ln, Chestertown, MD 21620
    • /45

      Est $405,063 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • /48

    $579,900 Under Contract

    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • /24

    $250,000 Sold Sep 23, 2024

    • 864 Sq Ft
    • $289/SF
    • 115 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1930

    235 Burchard Sawmill Rd, Chestertown, MD 21620

    Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new

    John Carroll Village Real Estate Company LLC

    235 Burchard Sawmill Rd, Chestertown, MD 21620
    • /44

      Est $400,236 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      111 Manor Ave, Chestertown, MD 21620

      111 Manor Ave, Chestertown, MD 21620

Showing Results 281 - 320, Page 8 of 18

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