Deck - Chestertown, MD Real Estate & homes for sale & real estate

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OPEN DEC 6, 11AM TO 1PM

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a . 345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-ca

$399,000

3 beds2.5 baths2,034 sq ft

121 Primrose Rd, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1971

(410) 778-0330

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom

$598,000

5 beds3.5 baths3,504 sq ft

311 Devon Dr, Chestertown, MD 21620

Large eat in kitchen • Gas fireplace • Natural light

(410) 810-0010

OPEN SUN, 11AM TO 12:30PM

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
* Days on Market Reporting Incorrectly- Property listed Oct 30, 2025 * Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptio

$515,000

4 beds3.5 baths3,799 sq ft

100 Adela Way, Chestertown, MD 21620

0.32 acre lot • 2 garage spots • Built 2008

(410) 266-0600

OPEN TODAY, 12PM TO 2PM

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Wate

$619,000

4 beds3.5 baths2,008 sq ft

206 S Water St, Chestertown, MD 21620

Sunroom mudroom • Heartland appliances • Waterview deck

(301) 967-3344

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
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. ½ 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 Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitt

$499,900

4 beds2.5 baths2,524 sq ft

8620 Park Dr, Chestertown, MD 21620

1.37 acre lot • Two story colonial • Laundry room

(410) 810-0010

Property at Little Harbor Way #1, Chestertown, MD 21620, 3 beds, 2.5 baths

$1,459,000

3 beds2.5 baths2,231 sq ft

Little Harbor Way #1, Chestertown, MD 21620

(410) 275-2118

Property at 110 Tuxedo Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths1,664 sq ft

110 Tuxedo Rd, Chestertown, MD 21620

(410) 823-0033

Property at 222 Dutchess Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,096 sq ft

222 Dutchess Rd, Chestertown, MD 21620

(410) 275-2118

Property at 134 Char Nor Manor Blvd, Chestertown, MD 21620, 3 beds, 1 bath

$279,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

Property at 300 Hickory Ln, Chestertown, MD 21620, 5 beds, 3.5 baths

$1,198,000

5 beds3.5 baths3,640 sq ft

300 Hickory Ln, Chestertown, MD 21620

(410) 275-2118

Property at 165 Char Nor Manor Blvd, Chestertown, MD 21620, 4 beds, 2.5 baths

$429,999

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

Property at 103 Landing Ln, Chestertown, MD 21620, 2 beds, 2.5 baths

$539,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

Property at 201 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$470,000

3 beds2 baths1,588 sq ft

201 Birch Run Rd, Chestertown, MD 21620

(410) 778-0330

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3D WALKTHROUGH

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Welcome to 24204 Drayton Landing Drive — a beautifully renovated 3-bedroom, 2-bath home set on 2 peaceful acres in the heart of Kent County on Maryland’s Eastern Shore. Nestled within the desirable Kinnairds Point community, residents enjoy a warm neighborhood setting along with exclusive access to two waterfront common areas: a boat launch and a swim beach. These shared spaces provide the perfect opportunity to experience the Chesapeake Bay and the natural beauty of Still Pond Creek and Churn Creek. This single-story residence offers a spacious first-floor primary suite, an attached 2-car garage, a charming screened porch ideal for unwinding, plus a large composite deck and two

$799,000

3 beds2 baths2,176 sq ft

24204 Drayton Landing Dr, Worton, MD 21678

New siding • Screened porch • New roof

(410) 822-6665

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a v

$649,900

4 beds3.5 baths2,944 sq ft

21173 and 21163 Chesapeake Ave, Rock Hall, MD 21661

Side deck • Large shed • 0.26 acre lot

(410) 810-0010

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Welcome to this spacious and beautifully refreshed 5-bedroom home — move-in ready and full of modern comfort! Step inside to discover fresh new paint and plush new carpet throughout, giving the home a bright, inviting feel. The thoughtfully updated lighting adds a warm, contemporary touch to every room. The open-concept main living area flows seamlessly into a large kitchen and dining space, perfect for entertaining family and friends. Step outside to the expansive deck — ideal for cookouts, morning coffee, or relaxing evenings overlooking the yard. With five generous bedrooms, there’s plenty of room for everyone, plus flexible space for a home office. This home combines c

$500,000

5 beds2.5 baths3,088 sq ft

120 Brook Knoll Way, Centreville, MD 21617

Plush new carpet • Fresh new paint • Large kitchen

(703) 891-4520

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Welcome to 233 Northfield Way - A True North Brook Beauty! This stunning Colonial in the highly sought-after North Brook community offers over 3,300 sq. ft. of true living space, beautifully maintained and filled with natural light. As you arrive, you’ll notice the mature landscaping that perfectly complements this home’s curb appeal. Step inside to an inviting open floor plan, to the right, a main-level office with custom built-ins and a large bay window, and to the left, a spacious living and dining room combination, ideal for entertaining. The heart of the home is the gorgeous kitchen, featuring a large island with cooktop, wall oven/microwave combo, tile floors, granite coun

$549,900

4 beds2.5 baths3,374 sq ft

233 N Field Way, Centreville, MD 21617

Main level office • Gorgeous kitchen • Large island

(443) 274-1900

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
Check out this Like New , MOVE IN READY Rancher with an Amazing view ! This beautiful 3-bedroom, 2-bathroom residence offers quality craftsmanship and tasteful upgrades throughout. From the granite countertops to the designer bathroom vanities and recessed lighting, every detail has been carefully selected for both style and function. The kitchen is a standout feature—complete with stainless steel appliances, custom cabinetry, and a center island topped with gleaming granite—perfect for entertaining or everyday living. The spacious primary suite includes a private bath and walk-in closet, offering comfort and convenience. Enjoy peaceful pastoral views of farmland, a pond, and m

$325,000

3 beds2 baths1,200 sq ft

11047 Bottom Rd, Worton, MD 21678

Custom cabinetry • Recessed lighting • Granite countertops

(410) 778-3779

COMING SOON

ABOUT THIS HOME
Deck - Deck - Chestertown, MD Real Estate & Homes for Sale
COMING SOON! Welcome to 21745 Centennial Lane, Rock Hall, MD — a brand-new 1,415 SF coastal-style rancher perfectly situated just minutes from local marinas, waterfront dining, and unforgettable sunsets. Crafted by JAC Homes, this thoughtfully designed 3-bedroom, 2-bath home combines modern comfort with timeless coastal charm. Step inside to discover an open concept living space filled with natural light and featuring durable LVP flooring throughout. At the heart of the home, the kitchen boasts granite countertops, quality cabinetry, and a seamless flow into the dining and living areas — perfect for entertaining or relaxing after a day on the water. The primary suite includes a

$379,500

3 beds2 baths1,413 sq ft

21745 Centennial Ln, Rock Hall, MD 21661

9,496 sq ft lot • Garage • Built 2026

(410) 479-3993

Property at 11969 Augustine Herman Hwy, Kennedyville, MD 21645, 4 beds, 2 baths

$319,000

4 beds2 baths2,520 sq ft

11969 Augustine Herman Hwy, Kennedyville, MD 21645

(410) 810-0010

Property at 12765 Still Pond Rd, Still Pond, MD 21667, 3 beds, 2 baths

$180,000

3 beds2 baths2,048 sq ft

12765 Still Pond Rd, Still Pond, MD 21667

(888) 860-7369

Property at 0 will be 11037 Bottom Rd, Worton, MD 21678, 3 beds, 2 baths

$315,000

3 beds2 baths1,300 sq ft

0 will be 11037 Bottom Rd, Worton, MD 21678

(410) 972-4000

Property at 25135 Smithville Rd, Worton, MD 21678, 3 beds, 1 bath

$294,000

3 beds1 bath960 sq ft

25135 Smithville Rd, Worton, MD 21678

(410) 740-1200

Property at 21336 Haven Rd, Rock Hall, MD 21661, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,684 sq ft

21336 Haven Rd, Rock Hall, MD 21661

(410) 639-4003

Property at 119 Watson Rd, Centreville, MD 21617, 4 beds, 3 baths

$699,900

4 beds3 baths2,628 sq ft

119 Watson Rd, Centreville, MD 21617

(410) 643-2244

Property at 6345 Rock Hall Rd, Rock Hall, MD 21661, 3 beds, 1.5 baths

$310,000

3 beds1.5 baths1,622 sq ft

6345 Rock Hall Rd, Rock Hall, MD 21661

(410) 639-4003

Property at 25209 Wymont Park Rd, Worton, MD 21678, 3 beds, 3 baths

$1,150,000

3 beds3 baths2,874 sq ft

25209 Wymont Park Rd, Worton, MD 21678

(410) 810-0010

Property at 218 Lakeside Dr, Millington, MD 21651, 3 beds, 2.5 baths

$424,900

3 beds2.5 baths2,184 sq ft

218 Lakeside Dr, Millington, MD 21651

(443) 274-1900

Property at 105 Inverness Dr, Church Hill, MD 21623, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths3,062 sq ft

105 Inverness Dr, Church Hill, MD 21623

(410) 827-4663

Property at 109 Recovery Dr E, Centreville, MD 21617, 3 beds, 2.5 baths

$799,900

3 beds2.5 baths1,974 sq ft

109 Recovery Dr E, Centreville, MD 21617

(301) 970-2447

Property at Eagle Manor Lot 20 Dr, Church Hill, MD 21623, 5 beds, 3.5 baths

$940,000

5 beds3.5 baths— sq ft

Eagle Manor Lot 20 Dr, Church Hill, MD 21623

(410) 476-2201

Property at 331 Old Line Dr, Centreville, MD 21617, 3 beds, 2.5 baths

$618,000

3 beds2.5 baths2,648 sq ft

331 Old Line Dr, Centreville, MD 21617

(410) 304-2250

Property at 6119 New St #2, Rock Hall, MD 21661, 3 beds, 3.5 baths

$950,000

3 beds3.5 baths3,000 sq ft

6119 New St #2, Rock Hall, MD 21661

(410) 639-4003

Deck - Chestertown Homes for Sale

There are currently 13 homes for sale matching deck in Chestertown at a median listing price of $450K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestertown stay on the market for 70 days and receive 1 offers. This map is refreshed with the newest listings matching deck in Chestertown every 15 minutes.

In the past month, 4 homes have been sold in Chestertown. In addition to houses in Chestertown, there were also 3 condos, 9 townhouses, and 2 multi-family units for sale in Chestertown last month. Find your dream home in Chestertown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chestertown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestertown. Our Chestertown real estate stats and trends will give you more information about home buying and selling trends in Chestertown. If you're looking to sell your home in the Chestertown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestertown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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