Sailboats 20-27 feet Sailboats Boats

Are you looking for that perfect sailboats 20-27 feet? This is the perfect place to start shopping. We have built up a great collection of sailboats 20-27 feet, and it has never been easier to find the exact model you are looking for. This is a great size for a boat and allows you the ability to easily tow it wherever you need, and still have plenty of room when you are on board. Whether you are upgrading to sailboats 20-27 feet from a smaller model, or you are brand new to owning a boat, this is a great size to have.

2008 Com-Pac Com-Pac 25



2008 Com-Pac Com-Pac 25

Buy It Now: $79,995.00

Sale

Ends In:
6d 21h 29m

Wharram Catamaran Tiki 26 8m



Wharram Catamaran Tiki 26   8m

Buy It Now: $56,400.00

Sale

Ends In:
17d 22h 42m

Wharram Catamaran Tiki 38 New Hulls and Decks ONLY



Wharram  Catamaran Tiki 38 New Hulls and Decks ONLY

Buy It Now: $42,500.00

Sale

Ends In:
17d 22h 50m

2004 Com-Pac Horizon Cat



2004 Com-Pac Horizon Cat

Buy It Now: $29,995.00

Sale

Ends In:
6d 21h 29m

2009 Harbor 20 sailboat trailer sailed in fresh water



2009 Harbor 20 sailboat trailer sailed in fresh  water

Price: $25,000.00

Sale

Ends In:
1h 17m

1989 Catalina 27 Sailboat & Slip Bimini Roller Furl



1989 Catalina 27 Sailboat & Slip Bimini Roller Furl

Buy It Now: $19,500.00

Sale

Ends In:
4d 22h 26m

242 Sailboat



242 Sailboat

Buy It Now: $16,500.00

Sale

Ends In:
2d 17h 4m

Wharram Catamaran Tiki 26' Hulls 8m



Wharram Catamaran Tiki  26' Hulls 8m

Buy It Now: $13,000.00

Sale

Ends In:
17d 22h 47m

1969 Westerly Cirrus



1969 Westerly Cirrus

Buy It Now: $12,995.00

Sale

Ends In:
5d 4h 19m

1989 Beneteau First 235 Liberty Edition



1989 Beneteau First 235 Liberty Edition

Buy It Now: $11,995.00

Sale

Ends In:
5d 5h 19m

G & S MORC 25 Racing Sailboat



G & S MORC 25 Racing Sailboat

Price: $9,000.00
Buy It Now: $18,500.00

Sale

Ends In:
6d 23h 14m

"Jolly Mon" a 27' Catalina Sailboat in Poulsbo, WA



"Jolly Mon" a 27' Catalina Sailboat in Poulsbo,  WA

Price: $8,995.00

Sale

Ends In:
4d 18h 33m

Lindenberg 26 High Performance Sailboat-1978



Lindenberg 26 High Performance Sailboat-1978

Buy It Now: $7,900.00

Sale

Ends In:
6d 21h 27m

Clean Watkins 25 Cruising Sailboat 1987 Well Equipped!



Clean Watkins 25 Cruising Sailboat 1987 Well Equipped!

Price: $7,200.00
Buy It Now: $9,200.00

Sale

Ends In:
8d 20h 39m

'77 Catalina 25 Swing Keel "Pop-Top" #228 with Trailer!



'77 Catalina 25 Swing Keel "Pop-Top" #228 with Trailer!

Buy It Now: $6,795.00

Sale

Ends In:
6d 1h 51m

1985 Catalina 27 Tall Rig Diesel Many recent upgrades



1985 Catalina 27 Tall Rig Diesel Many recent upgrades

Price: $5,000.00
Buy It Now: $11,500.00

Sale

Ends In:
2d 20h 37m

Tanzer 26 sailboat



Tanzer 26 sailboat

Buy It Now: $5,000.00

Sale

Ends In:
7d 17h 15m

1980 MACGREGOR 25 SAILBOAT



1980 MACGREGOR  25 SAILBOAT

Price: $4,700.00

Sale

Ends In:
3d 21h 44m

SailBoat YAMAHA 25 MK II MK 2 YANMAR Diesel YSM 8



SailBoat YAMAHA 25 MK II MK 2 YANMAR Diesel YSM 8

Price: $4,544.44

Sale

Ends In:
6d 22m

Hunter 27 excellent condition like new



Hunter 27 excellent condition like new

Price: $3,999.00

Sale

Ends In:
2d 18h 14m

sailboat 27



sailboat 27

Price: $3,500.00

Sale

Ends In:
4d 3h 4m

26' Chrysler (like 27') sailboat ready to sail, trailer



26' Chrysler (like 27') sailboat ready to sail,  trailer

Price: $3,500.00

Sale

Ends In:
6d 19h

Catalina 22 sailboat



Catalina 22 sailboat

Price: $3,495.00

Sale

Ends In:
1d 5h 32m

1984 Catalina 25 Sailboat at Tower Marine Douglas, MI



1984 Catalina 25 Sailboat at Tower Marine Douglas,  MI

Price: $3,300.00
Buy It Now: $4,200.00

Sale

Ends In:
3h 40m

1972 22" Columbia Sloop w Trailer



1972 22" Columbia Sloop w  Trailer

Price: $3,050.00

Sale

Ends In:
23h 39m

1976 23' Kells Swing Keel



1976 23' Kells Swing Keel

Price: $3,000.00

Sale

Ends In:
3d 5h 10m

Newport Sailboat 27' 1971



Newport Sailboat 27' 1971

Price: $3,000.00

Sale

Ends In:
3d 6h 18m

J-24 TRAILER - Brand New- By: Viking Ttailers



J-24 TRAILER     - Brand New-       By: Viking Ttailers

Price: $2,990.00

Sale

Ends In:
3d 21h 35m

Catalina 25 Sailboat



Catalina 25 Sailboat

Price: $2,600.00
Buy It Now: $4,000.00

Sale

Ends In:
7d 17h 28m

Sailboat Hunter 23' 1986



Sailboat Hunter 23' 1986

Price: $2,550.00

Sale

Ends In:
4d 22h 34m

'82 S2 26' Sloop \\\\\\\



       '82 S2 26' Sloop \\\\\\\

Price: $2,025.00

Sale

Ends In:
4h 46m

23' Sailboat with trailer W D Shock



23' Sailboat with trailer W D Shock

Price: $2,000.00

Sale

Ends In:
2d 1h 52m

1973 Catalina 22 Sailboat w swing keel & trailer



1973 Catalina 22 Sailboat w swing keel & trailer

Price: $2,000.00

Sale

Ends In:
2d 18h

1976 Buccaneer 286



1976 Buccaneer 286

Price: $2,000.00

Sale

Ends In:
6d 4h 29m

Catalina 27 Family Cruiser



Catalina 27 Family Cruiser

Price: $2,000.00
Buy It Now: $4,500.00

Sale

Ends In:
6d 14h 8m

1966 Pace SailBoat



1966 Pace SailBoat

Price: $1,800.00
Buy It Now: $2,495.00

Sale

Ends In:
4d 17h 37m

22' O Day Sailboat with Trailer T152784



22' O Day Sailboat with Trailer T152784

Price: $1,795.00

Sale

Ends In:
6d 4h 26m

Cal 27' Sail Boat in great condition



Cal 27' Sail Boat in great condition

Price: $1,691.26

Sale

Ends In:
1d 4h 50m

1974 26' Santana



1974 26' Santana

Price: $1,600.00
Buy It Now: $2,400.00

Sale

Ends In:
2d 22h

1978 22' sailboat



1978 22' sailboat

Price: $1,495.00

Sale

Ends In:
3d 18h 45m

1982 O'DAY 25 w NEW Mercury 9.9 Outboard



1982 O'DAY 25 w NEW Mercury 9.9 Outboard

Price: $1,225.00

Sale

Ends In:
2d 18h 42m

1969, 24' Morgan Classic



1969,  24' Morgan Classic

Buy It Now: $1,200.00

Sale

Ends In:
4d 21h 26m

1974 COLUMBIA T-26 SAILBOAT



1974 COLUMBIA T-26 SAILBOAT

Price: $1,025.00
Buy It Now: $2,750.00

Sale

Ends In:
2d 4h 15m

'84 Catalina 27 with Cradle ready to Sail! IN MARG 84



'84 Catalina 27 with Cradle ready to Sail!   IN MARG 84

Price: $1,025.00

Sale

Ends In:
3d 6h 19m

Impulse 21



Impulse 21

Price: $1,009.00

Sale

Ends In:
3d 18h 40m

Hunter 25 Sailboat with Hood Rollerfurling Jib



Hunter 25 Sailboat with Hood Rollerfurling Jib

Price: $1,000.00

Sale

Ends In:
4d 3h 44m

J24 Sailboat



J24 Sailboat

Price: $1,000.00
Buy It Now: $6,200.00

Sale

Ends In:
5d 23h 7m

BEAUTIFUL ~1980 CAPE DORY 25' ~ RESERVE LOWERED!



BEAUTIFUL ~1980 CAPE DORY 25' ~ RESERVE LOWERED!

Price: $1,000.00

Sale

Ends In:
6d 2h 33m

Venture 22 swing keel sailboat (by MacGreggor)



Venture 22 swing keel sailboat (by MacGreggor)

Price: $995.00
Buy It Now: $1,295.00

Sale

Ends In:
6d 1h 1m

Tanzer 7.5 sloop, 25 feet. Priced to sell



Tanzer 7.5 sloop,  25 feet.  Priced to sell

Price: $900.00

Sale

Ends In:
5h 24m

Sailboat Southcoast 22 swing keel



Sailboat Southcoast 22 swing keel

Price: $810.00

Sale

Ends In:
1d 17h

21 Ft Mcgregor



21 Ft Mcgregor

Price: $800.00

Sale

Ends In:
4d 17h 2m

25' 1977 Hunter Sailboat



25' 1977 Hunter Sailboat

Price: $650.00
Buy It Now: $3,250.00

Sale

Ends In:
6d 1m

20' sailboat w slip treasure island sfbay worldcup hq



20' sailboat w slip treasure island sfbay worldcup hq

Price: $601.33

Sale

Ends In:
3d 5h 5m

1983 Sovereigh Sloop 23 Used Sailboat



1983 Sovereigh Sloop 23 Used Sailboat

Price: $600.00
Buy It Now: $850.00

Sale

Ends In:
1d 16h 40m

1967, 27' Classic Irwin Sailboat NO RESERVE AUCTION



1967,  27' Classic Irwin Sailboat NO RESERVE AUCTION

Price: $520.00

Sale

Ends In:
5d 18h 40m

1970 Pearson 26’ Sloop



1970 Pearson 26’ Sloop

Price: $500.00
Buy It Now: $3,000.00

Sale

Ends In:
1d 21h 20m

chrysler 22' sailboat



chrysler 22' sailboat

Price: $500.00

Sale

Ends In:
2d 2h 28m

1978 Catalina 25 Sailboat Swing Keel No Reserve



1978 Catalina 25 Sailboat Swing Keel No Reserve

Price: $500.00

Sale

Ends In:
6d 4h 49m

Cal 27 Sail Boat



Cal 27 Sail Boat

Price: $500.00

Sale

Ends In:
6d 23h 3m

24 foot sloop



24 foot sloop

Price: $441.00

Sale

Ends In:
5h 8m

25 ft sailfoot



25 ft sailfoot

Price: $373.00

Sale

Ends In:
3d 17h 27m

1976 Clark San Juan 21' Used Sailboat - NC



1976 Clark San Juan 21' Used Sailboat - NC

Price: $281.89

Sale

Ends In:
1h 19m

1973 Grampian 26' Used Sailboat - MI



1973 Grampian 26' Used Sailboat - MI

Price: $202.50

Sale

Ends In:
5d 1h 19m

22' Cape Dory Sailboat



22' Cape Dory Sailboat

Price: $200.00
Buy It Now: $2,000.00

Sale

Ends In:
6d 6h 55m

1977 S2 26 ft sailboat - good condition - NO RESERVE!!!



1977 S2 26 ft sailboat - good condition - NO RESERVE!!!

Price: $152.50

Sale

Ends In:
6d 3h 49m

#8972 1980 25' W.D. Shock Santana 25 Sailboat



#8972 1980 25' W.D. Shock Santana 25 Sailboat

Price: $102.50

Sale

Ends In:
1d 17h 49m

1966 Albin Vega 27' Sailboat blue water cruiser



1966 Albin Vega  27'  Sailboat blue water cruiser

Price: $1.25

Sale

Ends In:
2d 24m

Discount & Bargain

By going with sailboats 20-27 feet, you can usually save money on docking fees as well. These boats are very convenient, and still offer a level of comfort that you would expect. Browse through our amazing selection of sailboats 20-27 feet now and see just how many great deals you can find. We’ve made it easy to find just the right sized boat by putting all of our sailboats 20-27 feet in one easy to shop place.
 
You can take advantage of some truly incredible deals on sailboats 20-27 feet by shopping at our boat shop. Whether you need a used sailboats 20-27 feet, or a brand new model, chances are you’ll find it right here and at a significant discount. Start shopping for your new sailboats 20-27 feet right now before they are all sold out. Even though we add them on a continuous basis, our low prices mean that nothing sticks around for long.

Cheap


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