15

Chestertown, MD Homes for Sale under $700,000

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  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    108 Little Harbor Way, Chestertown, MD 21620
  • 10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    10781 Fermoy Rd, Chestertown, MD 21620
    /54

    $429,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    10781 Fermoy Rd, Chestertown, MD 21620

    Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country

    David Moore Real Broker, LLC

    10781 Fermoy Rd, Chestertown, MD 21620
  • 212 Washington Ave, Chestertown, MD 21620
    212 Washington Ave, Chestertown, MD 21620
    212 Washington Ave, Chestertown, MD 21620
    /35

    $675,000

    Open House 10/03 Coming Soon Oct 3
    • 5 Beds
    • 3 Baths
    • 2,838 Sq Ft

    212 Washington Ave, Chestertown, MD 21620

    Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    212 Washington Ave, Chestertown, MD 21620
  • 7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    /45

    $424,900

    Open Sun 2PM - 5PM $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    8630 Elm Rd, Chestertown, MD 21620

    Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore.The home offers five generously sized bedrooms, providing comfortable space for family,

    Lawrence Lessin Save 6, Incorporated

    8630 Elm Rd, Chestertown, MD 21620
  • 1003 Twin Ct, Chestertown, MD 21620
    1003 Twin Ct, Chestertown, MD 21620
    1003 Twin Ct, Chestertown, MD 21620
    /43

    $499,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft

    1003 Twin Ct, Chestertown, MD 21620

    Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and

    Jody Baker Cross Street Realtors LLC

    1003 Twin Ct, Chestertown, MD 21620
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $509,000

    $41K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • 105 N Water St Unit 3, Chestertown, MD 21620
    105 N Water St Unit 3, Chestertown, MD 21620
    /2

    $489,000

    Open House 10/03 Coming Soon Oct 1
    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft

    105 N Water St Unit 3, Chestertown, MD 21620

    Second story, waterfront condo in historic Chestertown. Private boat slip. Many more details and pictures to come. Stay tuned! You won't want to miss this!

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    105 N Water St Unit 3, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    /9

    $450,000

    • Land
    • 12,477 Sq Ft
    • $1,570,925 per Acre

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620

    Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

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

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Listing will be removed September 30 until Spring 2027. 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

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    /10

    $568,900

    Coming Soon Sep 28
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    329 Union Church Rd, Chestertown, MD 21620

    Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own!Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a

    Heather Dolan Chesapeake Real Estate Associates, LLC

    329 Union Church Rd, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

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

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 7712 Waterview Ln, Chestertown, MD 21620
    7712 Waterview Ln, Chestertown, MD 21620
    /2

    $659,999

    Open Sat 10AM - 2PM Coming Soon Sep 23
    • 3 Beds
    • 4 Baths
    • 2,716 Sq Ft

    7712 Waterview Ln, Chestertown, MD 21620

    Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    7712 Waterview Ln, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
Maryland Kent County

Real Estate & Homes in Chestertown, MD under $700,000

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $372,500, up 4% year-over-year. Homes in Chestertown sell in 45 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$372,500
Median Single Family Sale Price
$386,200
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$386,500
Median 1 Bedroom Sale Price
$295,000
Average Price Per Sq Ft
$221
Number of Homes for Sale
15
Last 12 months Home Sales
106
Months of Supply
3.80
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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