Kent County High School, MD homes for sale & real estate

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ABOUT THIS HOME
Kent County High School, MD Homes for Sale
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering spa

$245,000

— beds2 baths2,718 sq ft

11989 Augustine Herman Hwy, Kennedyville, MD 21645

Large backyard • Desirable location • Built 1883

(410) 275-2118

ABOUT THIS HOME
Kent County High School, MD Homes for Sale
ROCK HALL — ON THE GRID, NOT OFF THE GRID! Discover Eastern Shore living in this beautifully maintained end-unit townhome offering 2,040+ sq ft, a flexible floor plan and a premium oversized lot—with NO HOA! The standout feature is the oversized rear sunroom/4th bedroom, larger than the primary suite, with its own private exterior entrance and direct kitchen access. Ideal as a guest room, home office, studio or additional living space. Inside, enjoy abundant natural light, a fireplace, hardwood flooring, updated lighting, crown molding, generous storage and a plumbed bar area ready for your finishing touches. Outside, enjoy low-maintenance living with plenty of parking and room

$364,900

3 beds2.5 baths2,040 sq ft

21123 Striper Run, Rock Hall, MD 21661

Built 2007 • Listed 129 days

(443) 249-7653

3D WALKTHROUGH

ABOUT THIS HOME
Kent County High School, MD Homes for Sale
Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The l

$359,900

3 beds2.5 baths1,712 sq ft

21124 Striper Run, Rock Hall, MD 21661

Built 2004 • Listed 130 days

(443) 274-1900

FLOOR PLAN

ABOUT THIS HOME
Kent County High School, MD Homes for Sale
Amazing waterfront community on the Sassafras river. This Kentmore Park home was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect year round get away or primary residence. Well maintained. Four bedrooms and two baths. Lower level garage and walk out basement. Enclosed lawn and yard equipment storage space. Rear yard gathering area and room for a garden. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park Community areas. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce

$499,000

4 beds2 baths2,132 sq ft

14136 Kentmore Park Rd, Kennedyville, MD 21645

Waterfront access • Pastoral view • Easy path to beach

(410) 275-2118

ABOUT THIS HOME
Kent County High School, MD Homes for Sale
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversi

$399,000

4 beds2 baths1,247 sq ft

21424 Catholic Ave, Rock Hall, MD 21661

Custom wood cabinets • New lvt • Renovated kitchen

(410) 275-2118

Property at 896 Washington Ave, Chestertown, MD 21620, 3 beds, 1 bath

$325,000

3 beds1 bath1,000 sq ft

896 Washington Ave, Chestertown, MD 21620

(410) 778-0330

Property at 11944 Augustine Herman Hwy, Kennedyville, MD 21645, 4 beds, 2 baths

$399,000

4 beds2 baths2,156 sq ft

11944 Augustine Herman Hwy, Kennedyville, MD 21645

(410) 778-0330

Property at Undisclosed address, Rock Hall, MD 21661, 6 beds, 1.5 baths

$2,950,000

6 beds1.5 baths3,200 sq ft

Undisclosed address, Rock Hall, MD 21661

(410) 778-3779

Property at 117 Water St N Unit 2A, Chestertown, MD 21620, 2 beds, 1 bath

$375,000

2 beds1 bath787 sq ft

117 Water St N Unit 2A, Chestertown, MD 21620

(410) 673-3344

Property at 226 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$898,000

3 beds3.5 baths2,172 sq ft

226 S Water St, Chestertown, MD 21620

(410) 275-2118

Property at 121 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths— sq ft

121 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at 23043 Bay Shore Spur, Chestertown, MD 21620, 4 beds, 3 baths

$385,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

Property at 117 Water St N Unit 2B, Chestertown, MD 21620, 1 bed, 1 bath

$350,000

1 bed1 bath850 sq ft

117 Water St N Unit 2B, Chestertown, MD 21620

(410) 673-3344

Property at 6416 Edesville Rd, Rock Hall, MD 21661, 3 beds, 3 baths

$369,000

3 beds3 baths2,200 sq ft

6416 Edesville Rd, Rock Hall, MD 21661

(410) 639-4003

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

$499,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

Property at 11167 Oak Ln, Worton, MD 21678, 3 beds, 1 bath

$269,900

3 beds1 bath960 sq ft

11167 Oak Ln, Worton, MD 21678

(410) 643-4663

Property at 21090 W Sharp St #133, Rock Hall, MD 21661, 3 beds, 2 baths

$545,000

3 beds2 baths1,650 sq ft

21090 W Sharp St #133, Rock Hall, MD 21661

(410) 639-2118

Property at 106 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$799,900

3 beds3.5 baths2,092 sq ft

106 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #37 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$765,900

3 beds2.5 baths1,964 sq ft

#37 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 102 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$839,500

3 beds2.5 baths1,964 sq ft

102 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at 104 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$849,900

3 beds2.5 baths1,980 sq ft

104 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at #25 Landing Ln, Chestertown, MD 21620, 4 beds, 3.5 baths

$1,099,900

4 beds3.5 baths2,784 sq ft

#25 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 201 N Lynchburg St, Chestertown, MD 21620, 1 bath

$750,000

— beds1 bath2,045 sq ft

201 N Lynchburg St, Chestertown, MD 21620

(302) 234-3800

Property at 104 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$813,900

3 beds3.5 baths2,192 sq ft

104 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #36 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$753,500

3 beds2.5 baths1,964 sq ft

#36 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #35 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$786,900

3 beds2.5 baths1,964 sq ft

#35 Landing Ln, Chestertown, MD 21620

(410) 275-2118

$289,000

— beds2 baths1,874 sq ft

31001 Chesterville Bridge Rd, Millington, MD 21651

(443) 274-1900

Property at 21008 Rock Hall Ave, Rock Hall, MD 21661

$155,000

Land0.79 acre (lot)

21008 Rock Hall Ave, Rock Hall, MD 21661

(410) 673-3344

Property at Olivet Hill Rd, Galena, MD 21635

$50,000

Land3.90 acres (lot)

Olivet Hill Rd, Galena, MD 21635

(443) 215-4663

Property at Hagy Rd, 5, Edesville, MD 21661

$160,000

Land1.24 acres (lot)

Hagy Rd, 5, Edesville, MD 21661

(410) 643-2244

Property at 27942 Old Morgnec Rd, Chestertown, MD 21620

$89,000

Land5.17 acres (lot)

27942 Old Morgnec Rd, Chestertown, MD 21620

(410) 275-2118

Property at Undisclosed address, Chestertown, MD 21620

$695,000

Land42.59 acres (lot)

Undisclosed address, Chestertown, MD 21620

(410) 810-3900

Property at Towhee Rd, Chestertown, MD 21620

$40,000

Land0.55 acre (lot)

Towhee Rd, Chestertown, MD 21620

(302) 217-6692

Property at Lambs Meadow Rd, Lynch, MD 21678

$25,000

Land1.09 acres (lot)

Lambs Meadow Rd, Lynch, MD 21678

(410) 488-3124

Property at Hynson Rd, Rock Hall, MD 21661

$250,000

Land0.55 acre (lot)

Hynson Rd, Rock Hall, MD 21661

(410) 639-2118

Property at Judefind Ave Lot 2, Rock Hall, MD 21661

$55,000

Land0.29 acre (lot)

Judefind Ave Lot 2, Rock Hall, MD 21661

(410) 639-4003

Property at 620 Cannon St, Chestertown, MD 21620

$85,000

Land3,096 sq ft (lot)

620 Cannon St, Chestertown, MD 21620

(301) 970-2447

Property at 5738 Beach Rd, Rock Hall, MD 21661, 3 baths

$699,900

Land0.96 acre (lot)

5738 Beach Rd, Rock Hall, MD 21661

(302) 426-2211

Property at 8886 Georgetown Rd, Chestertown, MD 21620

$69,900

Land4.03 acres (lot)

8886 Georgetown Rd, Chestertown, MD 21620

(443) 317-8125

Property at 305 Roosevelt Dr, Chestertown, MD 21620

$45,000

Land0.61 acre (lot)

305 Roosevelt Dr, Chestertown, MD 21620

(301) 970-2447

Property at 26765 Dutchtown Rd, Still Pond, MD 21667

$105,000

Land0.50 acre (lot)

26765 Dutchtown Rd, Still Pond, MD 21667

(301) 818-0313

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