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Boats for sale in Chestertown, MD

23 Boats for sale in Chestertown, MD. Compare listings with market score insights and find your next boat on Boatinho.

Shop boats for sale in Chestertown, MD with trusted market context

Every listing includes normalized specs and price context so you can compare options faster. Filter to Chestertown, MD inventory and prioritize offers with stronger market score signals.

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1983 Bimini 38 Power

Bimini

1983 Bimini 38

$45,000

Complete listing 70/100

Chestertown, MD 21620

38 ft 1983 Used Diesel

38 ft • Chestertown, MD 21620 • Diesel

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1986 Sea Ray 390 express Power

Sea Ray

1986 Sea Ray 390 express

$29,000

Complete listing 70/100

Chestertown, MD 21620

39 ft 1986 Used

39 ft • Chestertown, MD 21620

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2005 Regal 2600 Power

Regal

2005 Regal 2600

$31,500

Complete listing 70/100

Chestertown, MD 21620

24 ft 2005 Used

24 ft • Chestertown, MD 21620

View details →
1986 Sea Ray 39 Power

Sea Ray

1986 Sea Ray 39

$33,300

64% above market

$20,244.38 avg across 32 make & class peers

Complete listing 70/100

Chestertown, MD 21620

39 ft 1986 Used

39 ft • Chestertown, MD 21620

View details →
1986 Sea Ray 390 express Power

Sea Ray

1986 Sea Ray 390 express

$33,300

Complete listing 70/100

Chestertown, MD 21620

39 ft 1986 Used

39 ft • Chestertown, MD 21620

View details →
1986 Sea Ray 390 express Power

Sea Ray

1986 Sea Ray 390 express

$29,500

Complete listing 70/100

Chestertown, MD 21620

39 ft 1986 Used

39 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$8,950

91% above market

$4,693.80 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$7,950

62% above market

$4,893.80 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$999

84% below market

$6,284.00 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$7,450

49% above market

$4,993.80 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$3,485

40% below market

$5,786.80 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1998 Wellcraft 2800 martinique Power

Wellcraft

1998 Wellcraft 2800 martinique

$3,585

38% below market

$5,766.80 avg across 5 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

28 ft 1998 Used

28 ft • Chestertown, MD 21620

View details →
1995 Chaparral 2123 anniversary edition cuddy cabin Power

Chaparral

1995 Chaparral 2123 anniversary edition cuddy cabin

$8,000

19% below market

$9,923.12 avg across 84 make & class peers

Basic listing 50/100

Chestertown, MD 21620

21 ft 1995 Used

21 ft • Chestertown, MD 21620

View details →
1995 Chaparral 2135 anniversary edition cuddy cabin Power

Chaparral

1995 Chaparral 2135 anniversary edition cuddy cabin

$8,000

Basic listing 50/100

Chestertown, MD 21620

21 ft 1995 Used

21 ft • Chestertown, MD 21620

View details →
1995 Chaparral 2135 anniversary edition cuddy cabin Power

Chaparral

1995 Chaparral 2135 anniversary edition cuddy cabin

$7,500

Basic listing 50/100

Chestertown, MD 21620

21 ft 1995 Used

21 ft • Chestertown, MD 21620

View details →
1995 Chaparral 2135 anniversary edition cuddy cabin Power

Chaparral

1995 Chaparral 2135 anniversary edition cuddy cabin

$6,000

Basic listing 50/100

Chestertown, MD 21620

21 ft 1995 Used

21 ft • Chestertown, MD 21620

View details →
2011 Boston Whaler 130 super sport Power

Boston Whaler

2011 Boston Whaler 130 super sport

$14,000

69% below market

$45,458.92 avg across 25 make & class peers

Basic listing 50/100

Chestertown, MD 21620

13 ft 2011 Used

13 ft • Chestertown, MD 21620

View details →
1988 Sea Ray 305 sedan bridge Power

Sea Ray

1988 Sea Ray 305 sedan bridge

$18,900

8% above market

$17,514.29 avg across 7 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

30 ft 1988 Used

30 ft • Chestertown, MD 21620

View details →
1988 Sea Ray 305 sedan bridge Power

Sea Ray

1988 Sea Ray 305 sedan bridge

$17,900

Market average

$17,657.14 avg across 7 make, class & model peers

Basic listing 50/100

Chestertown, MD 21620

30 ft 1988 Used

30 ft • Chestertown, MD 21620

View details →
1987 Sea Ray express cruiser Power

Sea Ray

1987 Sea Ray express cruiser

$23,500

Basic listing 50/100

Chestertown, MD 21620

39 ft 1987 Used

39 ft • Chestertown, MD 21620

View details →

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