Recently Sold Homes in 21690, MD

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SOLD OCT 3, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
SINGLE FAMILY HOME built just 2 years ago at this price! This beautiful home is ready for immediate occupancy. Clean lines and neutral tones make this an easy move-in with nothing to do! Just across the Vintage Chester River Bridge, you will enter a charming little town that surrounds Washington College that has all sorts of new centers and places to go and things to do! The home offers a modern, open-concept layout with plenty of space and style. Large covered front porch with room for seating, plank flooring throughout the main level, lots a light and a bright kitchen equipped with stainless steel appliances and a convenient side breakfast bar. Craftsman-style doors add a touch of eleg

$335,000 Last sold price

3 beds2.5 baths1,856 sq ft

110 Flying Cloud Ct, Chestertown, MD 21620

(410) 505-9700

SOLD OCT 24, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
With almost every inch updated since 2012 - from the roof to the floors - this adorable two bedroom, two and half bath cottage is turnkey. The luxury primary suite, added in 2014 by a sought-after custom contractor, has tall ceilings, a cozy bay window seat, walk-in closet, en-suite bath with heated tile flooring, and spa shower. The cozy family room with wood-burning fireplace opens to the awning covered back patio to extend the living space into the mature English gardens. Just a few short blocks from the waterfront and the farmer's market, amble or ride bikes (or register your golf cart!) to take advantage of all that Downtown Chestertown offers. Ready for showings on Thursday September

$398,000 Last sold price

2 beds2.5 baths1,711 sq ft

221 Richard Dr, Chestertown, MD 21620

(410) 673-3344

SOLD SEP 26, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
The townhouse is the second from the end and has three bedrooms and 2.5 baths. The slider door provides easy access to the patio and there is a stack washer on the main level, kitchen has the needed appliances. Located in Chestertown you can enjoy all of the amenities of this historic town, the Farmer's Market, Washington College is only a couple of minutes away, the many parks, marinas, and public landings. There are fun things to do in Chestertown, enjoy the festivals, the live performances at the Garfield Theater, the shops, art galleries, take art classes or check out what Washington College offers. High Speed Internet is available. Move in ready home -- come see!

$215,000 Last sold price

3 beds2.5 baths1,199 sq ft

304 Hilltop Ln, Chestertown, MD 21620

(410) 810-0010

SOLD SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch. Enjoy the convenience of a patio out back—perfect for relaxing or entertaining. Located just minutes from town, you’ll love the easy access to shopping, dining, and everything Chestertown has to offer. Easy to show—schedule your tour today!

$220,000 Last sold price

3 beds2.5 baths1,200 sq ft

300 Hilltop Ln, Chestertown, MD 21620

(410) 778-0330

SOLD SEP 30, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
Spacious, Stylish, and Designed for Real Life – Discover the perfect blend of comfort, flexibility, and convenience in this expansive 4-bedroom home, tucked into the sought-after Orchard Hill neighborhood in Chestertown. With thoughtful upgrades and versatile spaces, this residence is ideal for those looking to level up their lifestyle—whether you're a young professional seeking work-from-home ease, those looking for room to spread out and make a place their own, or hosting large holiday gatherings under one roof. Enjoy the ease of main level living, including a beautiful 2024 renovation of the custom primary bath that brings spa-level luxury to your daily routine. The chef in t

$680,000 Last sold price

4 beds2.5 baths3,820 sq ft

8978 Orchard Dr, Chestertown, MD 21620

(410) 673-3344

Property at 224 Valley Rd, Chestertown, MD 21620, 3 beds, 2 baths

$455,000 Last sold price

3 beds2 baths1,886 sq ft

224 Valley Rd, Chestertown, MD 21620

(410) 778-3779

Property at 206 Barroll Dr, Chestertown, MD 21620, 3 beds, 2 baths

$438,000 Last sold price

3 beds2 baths1,820 sq ft

206 Barroll Dr, Chestertown, MD 21620

(410) 778-3779

Property at 110 S Mill St, Chestertown, MD 21620, 3 beds, 3.5 baths

$695,000 Last sold price

3 beds3.5 baths2,492 sq ft

110 S Mill St, Chestertown, MD 21620

(410) 275-2118

Property at 205 Pine St, Chestertown, MD 21620, 3 beds, 1.5 baths

$296,337 Last sold price

3 beds1.5 baths2,212 sq ft

205 Pine St, Chestertown, MD 21620

(410) 778-2610

Property at 225 Duke Of Kent St, Chestertown, MD 21620, 3 beds, 2.5 baths

$395,000 Last sold price

3 beds2.5 baths1,850 sq ft

225 Duke Of Kent St, Chestertown, MD 21620

(410) 778-0330

Property at 200 Fey Rd, Chestertown, MD 21620, 3 beds, 2 baths

$375,000 Last sold price

3 beds2 baths1,572 sq ft

200 Fey Rd, Chestertown, MD 21620

(302) 234-1111

Property at 221 Old Bridge Rd, Chestertown, MD 21620, 3 beds, 2 baths

$359,900 Last sold price

3 beds2 baths1,851 sq ft

221 Old Bridge Rd, Chestertown, MD 21620

(410) 673-3344

Property at 209 Rivershore Rd, Chestertown, MD 21620, 2 beds, 1.5 baths

$790,000 Last sold price

2 beds1.5 baths1,401 sq ft

209 Rivershore Rd, Chestertown, MD 21620

(866) 987-3937

Property at 103 Adela Way, Chestertown, MD 21620, 4 beds, 3.5 baths

$585,000 Last sold price

4 beds3.5 baths5,576 sq ft

103 Adela Way, Chestertown, MD 21620

(866) 987-3937

Property at 126 Metcalf Rd, Chestertown, MD 21620, 3 beds, 2 baths

$230,000 Last sold price

3 beds2 baths1,140 sq ft

126 Metcalf Rd, Chestertown, MD 21620

(301) 970-2447

Property at 201 Radcliffe Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$795,000 Last sold price

4 beds2.5 baths2,736 sq ft

201 Radcliffe Dr, Chestertown, MD 21620

(410) 778-0330

$390,000

— beds1.5 baths1,885 sq ft

200 David Dr, Chestertown, MD 21620

$137,700

— beds1 bath972 sq ft

227 Calvert St, Chestertown, MD 21620

Property at 136 Truslow Farm Ln, Chestertown, MD 21620

$560,000 Last sold price

— beds— baths— sq ft

136 Truslow Farm Ln, Chestertown, MD 21620

(443) 215-4663

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SOLD NOV 7, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
* * Exquisite Waterfront Retreat on Chester River * * Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dr

$1,550,000 Last sold price

5 beds4 baths4,167 sq ft

7961 Quaker Neck Rd, Chestertown, MD 21620

(410) 429-7425

SOLD OCT 22, 2025

ABOUT THIS HOME
Recently Sold Home in 21690, MD:
This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the hi

$700,000 Last sold price

2 beds2 baths1,966 sq ft

26889 Morgnec Rd, Chestertown, MD 21620

(410) 778-0330

SOLD SEP 25, 2025

$278,160

— beds3 baths3,418 sq ft

232 River Rd, Chestertown, MD 21620

SOLD NOV 8, 2025

$775,000 Last sold price

4 beds3 baths2,836 sq ft

8293 Brices Mill Rd, Chestertown, MD 21620

(410) 778-0330

Recently Sold Homes in 21690

There are currently 19 recently sold homes for sale in 21690. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in 21690 every 15 minutes.

Find your dream home in 21690 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 21690 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21690. If you're looking to sell your home in the 21690 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21690 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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