Chesapeake Landing, MD homes for sale & real estate

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NEW CONSTRUCTION

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main li

$349,900

3 beds2.5 baths1,650 sq ft

23208 Buck Neck Rd, Chestertown, MD 21620

Open living room • Walk-in closet • Granite counters

(855) 450-0442

OPEN SEP 19, 11AM TO 1PM

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

$269,000

3 beds2 baths1,404 sq ft

10540 Tonopah Rd, Chestertown, MD 21620

Laminate flooring • Open concept • Huge master bath

(410) 810-0010

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
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 kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional

$429,900

4 beds2.5 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

Fishing pier • Historic downtown • Cleared lot

(855) 450-0442

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property 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.

$50,000

Land0.55 acre (lot)

Towhee Rd, Chestertown, MD 21620

Spacious lot size

(302) 217-6692

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
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 major traffic artery, Fairlee Rd, connecting to the surrounding areas.

$3,000

Land0.34 acre (lot)

Cogar Rd, Chestertown, MD 21620

Listed 167 days

(410) 488-3124

Property at Lenapah Rd, Chestertown, MD 21620

$3,000

Land0.34 acre (lot)

Lenapah Rd, Chestertown, MD 21620

(410) 488-3124

Property at Tonopah Rd, Chestertown, MD 21620

$3,000

Land0.34 acre (lot)

Tonopah Rd, Chestertown, MD 21620

(410) 488-3124

Property at Kinglet Rd, Chestertown, MD 21620

$5,000

Land0.34 acre (lot)

Kinglet Rd, Chestertown, MD 21620

(443) 215-4663

Property at Clarissa Rd, Chestertown, MD 21620

$10,000

Land0.34 acre (lot)

Clarissa Rd, Chestertown, MD 21620

(866) 825-7169

Property at Beltram Rd, Chestertown, MD 21620

$5,000

Land0.34 acre (lot)

Beltram Rd, Chestertown, MD 21620

(410) 488-3124

Property at Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

$5,000

Land0.34 acre (lot)

Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

(410) 488-3124

Property at Bunting Rd, Chestertown, MD 21620

$5,000

Land0.34 acre (lot)

Bunting Rd, Chestertown, MD 21620

(410) 488-3124

Property at Sheldrake Dr, Chestertown, MD 21620

$10,000

Land0.34 acre (lot)

Sheldrake Dr, Chestertown, MD 21620

(410) 778-0330

Property at Fish Hatchery Rd, Chestertown, MD 21620

$5,000

Land0.37 acre (lot)

Fish Hatchery Rd, Chestertown, MD 21620

(410) 488-3124

Property at Redfield Rd, Chestertown, MD 21620

$38,000

Land0.34 acre (lot)

Redfield Rd, Chestertown, MD 21620

(703) 570-7307

Property at Spinnaker Rd, Chestertown, MD 21620

$38,000

Land0.56 acre (lot)

Spinnaker Rd, Chestertown, MD 21620

(703) 570-7307

Property at Buck Neck Rd, Chestertown, MD 21620

$5,000

Land0.34 acre (lot)

Buck Neck Rd, Chestertown, MD 21620

(443) 215-4663

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Nearby homes that match your criteria

ABOUT THIS HOME
Chesapeake Landing, MD Homes for Sale
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.

$15,000

Land1.00 acre (lot)

23741 L Rd, Chestertown, MD 21620

Plenty of privacy • Peaceful setting

(410) 822-6665

$24,000

Land0.50 acre (lot)

23710 L Rd, Chestertown, MD 21620

Listed 1166 days

(703) 570-7307

Average home prices near Chesapeake Landing, MD

Cities

Zip Codes

21620 homes for sale
$375,000
21678 homes for sale
$354,499

Chesapeake Landing, MD real estate trends

$325K

Sale price

-6.3%
since last year

$261

Sale $/sq ft

+33.4%
since last year

Over list price

Days on market

Down payment

—

Total homes sold

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