107

Chestertown, MD Homes for Sale

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  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /25

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    222 Dutchess Rd, Chestertown, MD 21620
  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    226 S Water St, Chestertown, MD 21620
  • 305 Roosevelt Dr, Chestertown, MD 21620
    305 Roosevelt Dr, Chestertown, MD 21620
    /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • 7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    $5K PRICE DROP
    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Unsuccessful land evaluation

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 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
  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /5

    $60,000

    • Land
    • 3 Acres
    • $20,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    104 Landing Ln, Chestertown, MD 21620
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    102 Little Harbor Way, Chestertown, MD 21620
  • 8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    /38

    $38,200,000

    • 4 Beds
    • 2 Baths
    • 2,330 Sq Ft

    8184 Rock Hall Rd, Chestertown, MD 21620

    Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a

    Joe Hickman Cross Street Realtors LLC

    8184 Rock Hall Rd, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /18

    $295,000

    • 1 Bed
    • 1 Bath

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

    Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    204 Double Creek Rd, Chestertown, MD 21620
    /38

    $545,000

    $67K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,927 Sq Ft

    204 Double Creek Rd, Chestertown, MD 21620

    Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance.The first floor features an open and functional layout designed for everyday

    Grace Crockett Doug Ashley Realtors, LLC

    204 Double Creek Rd, Chestertown, MD 21620
  • 0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:25 AM. The list price is the suggested opening bid. Deposit: $5,000.This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the

    Adam Shpritz Ashland Auction Group LLC

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /10

    $315,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    * SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 533 Round Top Rd, Chestertown, MD 21620
    533 Round Top Rd, Chestertown, MD 21620
    533 Round Top Rd, Chestertown, MD 21620
    /17

    $225,000

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    533 Round Top Rd, Chestertown, MD 21620

    Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your

    Chris Craddock EXP Realty, LLC

    533 Round Top Rd, Chestertown, MD 21620
  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $10,000

    • Land
    • 39,204 Sq Ft
    • $11,111 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    HUGE PRICE REDUCTION on a 0.9-acre Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • 27942 Old Morgnec Rd, Chestertown, MD 21620
    27942 Old Morgnec Rd, Chestertown, MD 21620
    27942 Old Morgnec Rd, Chestertown, MD 21620
    /4

    $89,000

    • Land
    • 5.17 Acres
    • $17,215 per Acre

    27942 Old Morgnec Rd, Chestertown, MD 21620

    Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

    Brett Davis Gunther-McClary Real Estate

    27942 Old Morgnec Rd, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, 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
    /2

    $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
  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    $22K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 233 Merganser Dr, Chestertown, MD 21620
    233 Merganser Dr, Chestertown, MD 21620
    233 Merganser Dr, Chestertown, MD 21620
    /13

    $60,000

    • Land
    • 21,780 Sq Ft
    • $120,000 per Acre

    233 Merganser Dr, Chestertown, MD 21620

    Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

    Barbara Wallace Long & Foster Real Estate, Inc.

    233 Merganser Dr, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /44

    $1,245,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 109 Parma Rd, Chestertown, MD 21620
    109 Parma Rd, Chestertown, MD 21620
    109 Parma Rd, Chestertown, MD 21620
    /55

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    109 Parma Rd, Chestertown, MD 21620

    Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    109 Parma Rd, Chestertown, MD 21620
  • 404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    /11

    $19,500

    • Land
    • 43,124 Sq Ft
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Queen

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /2

    $135,000

    $15K PRICE DROP
    • Land
    • 1.8 Acres
    • $75,000 per Acre

    109 2nd St, Chestertown, MD 21620

    **STARTING 9/5 & ENDING 9/12: For one week only, list price is reduced to $125,000 with all closing costs covered by seller!** Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still

    Katie Stecklair Cross Street Realtors LLC

    109 2nd St, Chestertown, MD 21620
  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /25

    $315,000

    Coming Soon Sep 18
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space.The home

    Joseph A Zang III RE/MAX Chesapeake

    24775 Langford Rd, Chestertown, MD 21620
  • 0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:45 AM. The list price is the suggested opening bid. Deposit: $5,000.This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620
  • 1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    1906 Pondtown Rd, Chestertown, MD 21620
    /4

    $110,000

    • Land
    • 1.93 Acres
    • $56,995 per Acre

    1906 Pondtown Rd, Chestertown, MD 21620

    Build your dream home on this beautiful 1.93-acre wooded, perc-approved lot in Queen Anne's County. Nestled among mature trees, this private homesite offers the perfect balance of seclusion and convenience. Enjoy the peaceful surroundings of Maryland's Eastern Shore while remaining within easy reach of Chestertown, Centreville, local marinas, parks, shopping, dining, and major commuter routes.

    Lonnie Gilmore Keller Williams Flagship

    1906 Pondtown Rd, Chestertown, MD 21620
  • 123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    /45

    $375,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    123 Trafford Dr, Chestertown, MD 21620

    Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    123 Trafford Dr, Chestertown, MD 21620
  • 101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    /35

    $359,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    101 S College Ave, Chestertown, MD 21620

    This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space.Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled

    Michele Palmer Doug Ashley Realtors, LLC

    101 S College 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
  • 104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    104 Conley Dr, Chestertown, MD 21620
    /26

    $239,900

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    104 Conley Dr, Chestertown, MD 21620

    Price Improvement! Now offered at $239,900Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a

    Heather Kooser Cummings & Co. Realtors

    104 Conley Dr, Chestertown, MD 21620
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $9,500

    • Land
    • 14,810 Sq Ft
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /7

    $75,000

    • Land
    • 2.2 Acres
    • $34,091 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location

    Lori Sample RE/MAX Chesapeake

    0 Fairlee Rd, Chestertown, MD 21620
  • 22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    22470 Fairgale Farm Ln, Chestertown, MD 21620
    /50

    $1,450,000

    • 4 Beds
    • 5 Baths
    • 4,257 Sq Ft

    22470 Fairgale Farm Ln, Chestertown, MD 21620

    Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

    Ashton Kelley Gunther-McClary Real Estate

    22470 Fairgale Farm Ln, Chestertown, MD 21620
  • 956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    /29

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 3

Maryland Kent County

Real Estate & Homes for Sale in Chestertown, MD

Why Live in Chestertown

Chestertown, Maryland, is a historic community on the Chester River, known for its maritime heritage and charming downtown. Founded in 1706, Chestertown was once a bustling port and remains a popular destination for homebuyers seeking a quieter lifestyle away from larger cities like Washington or Philadelphia. The town features a mix of Victorian homes downtown and waterfront properties, with river access being a significant draw. Residents enjoy boating on the river, and many homes feature private docks. The private Chester River Yacht & Country Club offers additional amenities such as an 18-hole golf course and a marina. Local parks like Wilmer Park provide walking trails and playgrounds, while the Wayne Gilchrest Trail caters to bikers and joggers. Downtown Chestertown is pedestrian-friendly, hosting boutiques, galleries and locally owned restaurants. Annual events like the Chestertown Tea Party Festival and the Sultana Downrigging Festival celebrate the town's rich history. Washington College, a small liberal arts institution, adds to the vibrant atmosphere. The University of Maryland Shore Medical Center provides health care services, including an emergency room. Chestertown is within driving distance of Baltimore, 75 miles away, and Baltimore/Washington International Airport. With its blend of historic charm, riverfront recreation and local amenities, Chestertown offers a unique living experience.

Learn more about living in Chestertown

Chestertown, MD Home Prices vs. Nearby Neighborhoods

Chestertown, MD Kingstown
Median Home Price
$375,000
$359,900
Median Sale Price
$370,000
+3% YoY
$377,000
+8% YoY
Avg. Price per Square Foot
$218
$235
Median Single Family Price
$386,200
$345,000
Median Townhouse Price
$264,900
--
Median Condo Price
$350,000
--
Total Active Listings
34 listings
5 listings
Market Conditions
4 Months of Supply
Balanced Market
2 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Chestertown, MD?
Homes for sale in Chestertown, MD have an average home price of $444,688.
Are home prices dropping in Chestertown?
Yes, home prices in Chestertown are down 4% in the last 12 months.
How many homes have sold over the last 12 months in Chestertown, MD?
103 homes have sold in Chestertown, MD over the last 12 months.
What are the most popular zip codes in Chestertown, MD?
The most popular zip codes in Chestertown, MD include 21620, 21678, 21623, 21645 and 21667.
What are the most popular neighborhoods in Chestertown, MD?
The most popular neighborhood in Chestertown, MD with the most homes for sale is Kingstown.
How much do you need to make to afford a house in Chestertown?
The median home price in Chestertown is $375,000. If you put a 20% down payment of $75,000 and had a 30-year fixed mortgage with an interest rate of 6.71%, your estimated principal and interest payment would be $1,940 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $83K a year to afford the median home price in Chestertown. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chestertown, MD?
Chestertown, MD has highly rated public and private schools. Some of the best schools in Chestertown based on Niche Grades are Radcliffe Creek School, H.H. Garnett Elementary School and Kent County High School. The neighborhood in Chestertown with the highest rated schools is Kingstown. Browse all the schools in Chestertown, MD to learn more.
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