Homes for Sale in 21620

• 

  

  

  /5

  $55,000

  • Land
  • 3 Acres
  • $18,333 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

  

  Retha Arrabal

  Doug Ashley Realtors, LLC

  0 Georgetown Rd SE Unit MDKE2005218, 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

  

  John Burke

  Gunther-McClary Real Estate

  222 Dutchess Rd, 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

  

  John Burke

  Gunther-McClary Real Estate

  7680 Country Club Ln, 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

  

  John Burke

  Gunther-McClary Real Estate

  226 S Water St, 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.

  

  Joe Howerton

  Taylor Properties

  305 Roosevelt Dr, 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

  

  Retha Arrabal

  Doug Ashley Realtors, LLC

  7415 Wilkins Ln, 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

  

  Kristina Hyland

  Coldwell Banker Chesapeake Real Estate Company

  0 Old Morgnec Rd Unit MDKE2004974, 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

  

  John Burke

  Gunther-McClary Real Estate

  108 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

  

  John Burke

  Gunther-McClary Real Estate

  102 Little Harbor Way, 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

  

  John Burke

  Gunther-McClary Real Estate

  36 Landing Ln, 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

  

  John Burke

  Gunther-McClary Real Estate

  0 Little Harbor Way Unit 1, 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

  

  John Burke

  Gunther-McClary Real Estate

  104 Landing Ln, Chestertown, MD 21620
• 

  

  /22

  $329,900

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  22974 Bay Shore Rd, Chestertown, MD 21620

  Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm.Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home

  Mae Nordhoff Benson & Mangold, LLC

  22974 Bay Shore 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /25

  $315,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /45

  $375,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /50

  $1,375,000

  $75K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /8

  $150,000

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

  0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

  Sebrin Adem RE/MAX Allegiance

  0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

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