101

Chestertown, MD Homes for Sale

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  • 234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    /3

    $100,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • 0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
    /2

    $9,000

    $3K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $244,500

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $750,000

    $45K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $7,500,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, 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 2A, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, 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
  • 105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    105 N Water St Unit 2, Chestertown, MD 21620
    /49

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, Chestertown, MD 21620
  • 0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    0 Round Top Rd, Chestertown, MD 21620
    /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, Chestertown, MD 21620
  • 22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    /88

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    22481 Goose Hollow Dr, Chestertown, MD 21620

    ****Professional photos will be uploaded shortly***** AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides

    Tom Atwood Keller Williams Legacy

    22481 Goose Hollow Dr, Chestertown, MD 21620
  • 103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    103 Trafford Dr, Chestertown, MD 21620
    /65

    $399,900

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,944 Sq Ft

    103 Trafford Dr, Chestertown, MD 21620

    PRICE IMPROVEMENT: Priced below 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Trafford Dr, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $499,900

    • 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. 1⁄2 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 Hot

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
    /3

    $55,000

    • Land
    • 30,492 Sq Ft
    • $78,571 per Acre

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620

    Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Map 36 Parcel 80 Watertower Rd Unit MDKE2006592, Chestertown, MD 21620
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,650,000

    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, 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 1B, Chestertown, MD 21620
  • 23741 L Rd, Chestertown, MD 21620
    23741 L Rd, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • 896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    /2

    $325,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

    A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    $23K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

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