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Homes for Sale near Chestertown Christian Academy

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  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 24906 Lambs Meadow Rd, Worton, MD 21678
    24906 Lambs Meadow Rd, Worton, MD 21678
    24906 Lambs Meadow Rd, Worton, MD 21678
    /47

    $319,900

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    24906 Lambs Meadow Rd, Worton, MD 21678

    Closing cost help available. MOTIVATED SELLER!!! BRING ALL OFFERS. NEWLY RENOVATED (Summer-2025)! One of the largest lots in Kent County- NEARLY AN ACRE OF LAND. No HOA!!! This is your single level living oasis home by THE WATER. MOTIVATED SELLER. GREAT OPPORTUNITY to own an UPDATED ALL BRICK rancher home with a fully finished basement ON .78 ACRES. You will enjoy this sun-lit, bright,

    Pamela Dotson Norstar Realty LLC

    24906 Lambs Meadow Rd, Worton, MD 21678
  • 108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    /19

    $315,000

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. Upstairs is a large, sun-filled room with a spacious closet that serves as an office. It could also be a den or sitting room.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /20

    $255,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $167,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, Chestertown, MD 21620
  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    /10

    $62,400

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    132 Prospect St, Chestertown, MD 21620

    Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

    Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • 624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    /3

    $240,000

    • 2 Beds
    • 1 Bath
    • 1,290 Sq Ft

    624 High St, Chestertown, MD 21620

    Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or

    Nicole Stephens Tesla Realty Group, LLC

    624 High St, Chestertown, MD 21620
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /11

    $103,000

    • Land
    • 0.48 Acre
    • $214,583 per Acre

    0 East St, Chestertown, MD 21620

    Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 East St, Chestertown, MD 21620
  • 25034 Lambs Meadow Rd, Worton, MD 21678
    25034 Lambs Meadow Rd, Worton, MD 21678
    /2

    $19,900

    • Land
    • 0.11 Acre
    • $180,909 per Acre

    25034 Lambs Meadow Rd, Worton, MD 21678

    This property, situated on a 0.11-acre lot, offers a blank canvas for your vision. Located in Kent County, the existing structure presents endless possibilities for the right buyer. 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.

    Dustin Parker The Parker Group

    25034 Lambs Meadow Rd, Worton, MD 21678
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /52

    $1,395,500 Open Sun 11AM - 1PM

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

    105 High St, Chestertown, MD 21620

    ***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.***Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /7

    $250,000

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /71

    $649,000

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • 0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    /3

    $20,000

    • Land
    • 0.09 Acre
    • $222,222 per Acre

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
  • 110 Tuxedo Rd, Chestertown, MD 21620
    110 Tuxedo Rd, Chestertown, MD 21620
    /2

    $275,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    110 Tuxedo Rd, Chestertown, MD 21620

    YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.

    Vince Stonesifer Cummings & Co. Realtors

    110 Tuxedo Rd, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    • 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. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, Chestertown, MD 21620
  • 0 will be 11037 Bottom Rd, Worton, MD 21678
    0 will be 11037 Bottom Rd, Worton, MD 21678
    0 will be 11037 Bottom Rd, Worton, MD 21678
    /32

    $315,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    0 will be 11037 Bottom Rd, Worton, MD 21678

    Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single-family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered

    Andy Batch Keller Williams Select Realtors of Annapolis

    0 will be 11037 Bottom Rd, Worton, MD 21678
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /25

    $259,900 New Construction

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this October. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    /70

    $574,000 Coming Soon

    • 5 Beds
    • 4 Baths
    • 3,451 Sq Ft

    302 Rosin Dr, Chestertown, MD 21620

    Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard

    Lori Willis Cross Street Realtors LLC

    302 Rosin Dr, Chestertown, MD 21620
  • 303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    /32

    $363,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    303 E Campus Ave, Chestertown, MD 21620

    Charming Brick Rancher in the Heart of ChestertownDiscover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm,

    Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
  • 10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    /63

    $2,350,000 Coming Soon

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft

    10121 Fairlee Rd, Chestertown, MD 21620

    Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers,

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
  • 8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    /12

    $695,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft

    8951 Orchard Dr, Chestertown, MD 21620

    Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout.The gourmet kitchen features upgraded countertops, cherry cabinetry, stainless steel appliances including double ovens, a gas cooktop, and a tankless water heater. It

    Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /5

    $269,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    318 Lincoln Dr, Chestertown, MD 21620

    Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /19

    $695,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202 — a stunning waterfront retreat in the coveted Chester River Landing community. This beautifully reimagined 3-bedroom, 2-bath condo has been thoughtfully taken down to the studs and rebuilt with high-quality finishes and timeless style. Nearly everything inside is brand new, offering the comfort and peace of mind of a modern build within an established

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • 26994 Branchtown Rd, Worton, MD 21678
    26994 Branchtown Rd, Worton, MD 21678
    26994 Branchtown Rd, Worton, MD 21678
    /3

    $359,900 New Construction

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

    26994 Branchtown Rd, Worton, MD 21678

    Quality built and adorable Cape Cod on Private 1 acre mostly wooded lot. 4 bedrooms, 2 full bathrooms. Stainless steel appliances, 2X6 walls, high efficiency heat pump and central a/c system. Nice deck (10'x14') overlooking peaceful back yard and woods. Extra insulated storage in knee walls thru upstairs bedrooms. Close to Rt 213 and Chestertown. No HOA. Owner agent.

    Jason Dey Kevin Dey Realty

    26994 Branchtown Rd, Worton, MD 21678
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $15,000

    • Land
    • 1.8 Acres
    • $8,333 per Acre

    109 2nd St, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 11/12/2025 @ 10:00 AM. Bidding ends 11/14/2025 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $5,000.This +/- 1.80 acres lot of land located is in Chestertown, MD within Queen Anne’s County. A prior soil evaluation completed by the Queen Anne’s County Health Department (7/17/2009) certified suitability for a conventional mound septic system,

    Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
  • 11054 Austin Ln, Worton, MD 21678
    11054 Austin Ln, Worton, MD 21678
    11054 Austin Ln, Worton, MD 21678
    /16

    $110,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    11054 Austin Ln, Worton, MD 21678

    ONLINE AUCTION: Bidding begins 11/19/2025 @ 10:00 AM. Bidding ends 11/21/2025 @ 12:00 PM. List Price is Suggested Opening Bid. Deposit: $20,000. This single family home is located in the Knights Landing area of Kent County, MD. Residents can enjoy the nearby attractions such as Worton Park, and the many establishments in the Chestertown area. The property is occupied. The location also

    Adam Shpritz Ashland Auction Group LLC

    11054 Austin Ln, Worton, MD 21678

Showing Results 41 - 70, Page 2 of 2

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