Pending Listings in 21620, MD

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 21620, MD:
Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

$629,900

3 beds2 baths2,430 sq ft

201 River Rd, Chestertown, MD 21620

Sun room • Pool • Main floor

(410) 778-0330

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 21620, MD:
Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights. A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

$205,000

3 beds1 bath1,341 sq ft

202 Pine St, Chestertown, MD 21620

0.29 acre lot • Built 1955 • Listed 8 days

(410) 778-0330

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 21620, MD:
✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dream

$289,900

2 beds3 baths1,518 sq ft

522 High St, Chestertown, MD 21620

Brick patio • Fountain • Historic home

(410) 822-6665

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 21620, MD:
Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, th

$380,000

3 beds1.5 baths3,292 sq ft

8312 Broad Neck Rd, Chestertown, MD 21620

Picturesque acres • 40 x 60 outbuilding • Three phase electric

(571) 386-1075

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 21620, MD:
Escape to the Eastern Shore! Nestled among mature trees on a . 41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cab

$289,900

2 beds1.5 baths1,500 sq ft

21146 Montana Ave, Chestertown, MD 21620

Oak cabinetry • Wooded lot • Waterfront community

(410) 778-3779

Property at 9126 Fairlee Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$324,000

3 beds1.5 baths1,216 sq ft

9126 Fairlee Rd, Chestertown, MD 21620

(443) 215-4663

Property at 240 Merganser Dr, Chestertown, MD 21620, 3 beds, 2 baths

$365,000

3 beds2 baths1,120 sq ft

240 Merganser Dr, Chestertown, MD 21620

(443) 215-4663

Property at 123 Heath Rd, Chestertown, MD 21620, 3 beds, 2 baths

$349,000

3 beds2 baths1,792 sq ft

123 Heath Rd, Chestertown, MD 21620

(443) 215-4663

Property at 517 Round Top Rd, Chestertown, MD 21620, 3 beds, 1 bath

$299,900

3 beds1 bath1,248 sq ft

517 Round Top Rd, Chestertown, MD 21620

(410) 729-7700

Property at 210 N Queen St, Chestertown, MD 21620, 4 beds, 2.5 baths

$735,000

4 beds2.5 baths2,730 sq ft

210 N Queen St, Chestertown, MD 21620

(410) 778-0330

Property at 101 S Mill St, Chestertown, MD 21620, 2 beds, 2.5 baths

$515,000

2 beds2.5 baths1,476 sq ft

101 S Mill St, Chestertown, MD 21620

(410) 778-0330

Property at 105 N Water St #2, Chestertown, MD 21620, 2 beds, 2 baths

$475,000

2 beds2 baths1,011 sq ft

105 N Water St #2, Chestertown, MD 21620

(410) 465-1770

Property at 222 Mount Vernon Ave, Chestertown, MD 21620, 4 beds, 2 baths

$419,999

4 beds2 baths1,656 sq ft

222 Mount Vernon Ave, Chestertown, MD 21620

(410) 263-3400

Property at 214 Silver Heel Rd, Chestertown, MD 21620, 4 beds, 2.5 baths

$340,000

4 beds2.5 baths1,972 sq ft

214 Silver Heel Rd, Chestertown, MD 21620

(410) 778-3779

Property at 10720 Foreston Rd, Chestertown, MD 21620, 3 beds, 2 baths

$309,000

3 beds2 baths1,412 sq ft

10720 Foreston Rd, Chestertown, MD 21620

(301) 298-1001

Property at 207 Lincoln Dr, Chestertown, MD 21620, 4 beds, 1.5 baths

$135,000

4 beds1.5 baths1,152 sq ft

207 Lincoln Dr, Chestertown, MD 21620

(443) 906-3840

Property at 110 Prospect St, Chestertown, MD 21620, 3 beds, 1.5 baths

$54,900

3 beds1.5 baths2,210 sq ft

110 Prospect St, Chestertown, MD 21620

(877) 328-4400

Property at 407 High St, Chestertown, MD 21620, 3 beds, 4.5 baths

$798,000

3 beds4.5 baths3,047 sq ft

407 High St, Chestertown, MD 21620

(410) 778-0330

Property at 24581 Willow Oak Ln, Chestertown, MD 21620, 3 beds, 2 baths

$229,990

3 beds2 baths1,352 sq ft

24581 Willow Oak Ln, Chestertown, MD 21620

(410) 810-0010

Property at 103 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,280 sq ft

103 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at Buck Neck Landing Rd, Chestertown, MD 21620

$10,000

Land0.55 acre (lot)

Buck Neck Landing Rd, Chestertown, MD 21620

(410) 758-0333

Property at Cromwell Clark Rd, Chestertown, MD 21620

$3,000,000

Land87.34 acres (lot)

Cromwell Clark Rd, Chestertown, MD 21620

(410) 934-3478

Property at Lot 9 Prestwick Dr, Chestertown, MD 21620

$185,000

Land1.95 acres (lot)

Lot 9 Prestwick Dr, Chestertown, MD 21620

(410) 275-2118

Property at 103 Maple Ave, Chestertown, MD 21620, 4 beds, 2.5 baths

$615,000

4 beds2.5 baths4,536 sq ft

103 Maple Ave, Chestertown, MD 21620

(410) 778-0330

Property at 107 Conley Dr, Chestertown, MD 21620, 3 beds, 1 bath

$240,000

3 beds1 bath1,140 sq ft

107 Conley Dr, Chestertown, MD 21620

(410) 822-6665

Property at 611 Cannon St, Chestertown, MD 21620, 2 beds, 1.5 baths

$275,000

2 beds1.5 baths920 sq ft

611 Cannon St, Chestertown, MD 21620

(410) 810-3900

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Pending Listings in 21620

There are currently 26 pending listings for sale in 21620 at a median listing price of $375K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21620 stay on the market for 73 days and receive 1 offers. This map is refreshed with the newest listings in 21620 every 15 minutes.

In the past month, 15 homes have been sold in 21620. In addition to houses in 21620, there was also 1 condo, 18 townhouses, and 1 multi-family unit for sale in 21620 last month. Find your dream home in 21620 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 21620 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21620. If you're looking to sell your home in the 21620 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21620 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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