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.

Wharram Catamaran Tiki 26 Hulls - new



Wharram Catamaran Tiki 26 Hulls - new

Buy It Now: $25,000.00

Sale

Ends In:
12d 11h 48m

1986 26' Contessa w Trailer



1986 26' Contessa w Trailer

Price: $20,000.00

Sale

Ends In:
3d 20h 29m

Catalina 250 Water Ballast. New 2006



Catalina 250 Water Ballast. New 2006

Price: $17,600.00

Sale

Ends In:
12h 35m

1996 20' Alerion Express Day Sailer Sailboat



1996 20' Alerion Express Day Sailer Sailboat

Buy It Now: $16,000.00

Sale

Ends In:
2d 22h 3m

2001 Macgregor 26x Power Sailer and trailer



2001 Macgregor 26x Power Sailer and trailer

Price: $13,500.00

Sale

Ends In:
3d 21h 36m

J 22 Sailboat Perfect racer, daysailer, weekend cruiser



J 22 Sailboat Perfect racer,  daysailer,  weekend cruiser

Price: $10,100.00

Sale

Ends In:
2d 19h 23m

27 ft Morgan 1975 Sailboat w Outboard



27 ft Morgan 1975 Sailboat w Outboard

Price: $8,500.00
Buy It Now: $11,000.00

Sale

Ends In:
1d 13h 50m

Macgregor 26s.....beautiful boat.....



Macgregor 26s.....beautiful boat.....

Buy It Now: $7,800.00

Sale

Ends In:
4d 19h 42m

'76 26' Balboa Sloop



'76 26' Balboa Sloop

Buy It Now: $7,500.00

Sale

Ends In:
3d 1h 59m

1986 Sovereign Shoal Keel w new trailer and motor



1986 Sovereign Shoal Keel w new trailer and motor

Price: $7,000.00
Buy It Now: $7,500.00

Sale

Ends In:
17h 23m

Watkins 27' Sailboat 1980



Watkins 27' Sailboat 1980

Buy It Now: $7,000.00

Sale

Ends In:
7d 16h 20m

SAILBOAT - CATALINA 27



SAILBOAT - CATALINA 27

Buy It Now: $6,950.00

Sale

Ends In:
17d 17h 55m

1979 O'Day 25



 1979  O'Day 25

Price: $6,800.00

Sale

Ends In:
3d 1h 47m

catalina



catalina

Buy It Now: $6,500.00

Sale

Ends In:
3d 16h 45m

Sovereign 24' Sailboat



Sovereign 24' Sailboat

Buy It Now: $6,000.00

Sale

Ends In:
2d 13h 51m

1995 Hunter 23.5 Sail Boat



1995 Hunter 23.5 Sail Boat

Price: $5,100.00
Buy It Now: $7,900.00

Sale

Ends In:
2d 1h 33m

DANA 24 - PACIFIC SEACRAFT Bluewater Cruiser 1986



DANA 24 - PACIFIC SEACRAFT Bluewater Cruiser 1986

Price: $5,100.00
Buy It Now: $40,000.00

Sale

Ends In:
5d 21h 37m

27' NAUTICA SAILBOAT READY TO SAIL 3 SETS OF SAILS RARE



27' NAUTICA SAILBOAT READY TO SAIL 3 SETS OF SAILS RARE

Price: $4,950.00
Buy It Now: $5,995.00

Sale

Ends In:
5d 21h 39m

1986 Sea Pearl 21



1986 Sea Pearl 21

Price: $4,050.00

Sale

Ends In:
16h 27m

27' Morgan Sailboat



27' Morgan Sailboat

Price: $3,999.00

Sale

Ends In:
3d 10h 14m

1973 C&C Fixed Keel Sailboat



1973 C&C Fixed Keel Sailboat

Price: $3,900.00
Buy It Now: $5,900.00

Sale

Ends In:
2d 1h 3m

Catalina 22 ft Poptop Retractable Keel



Catalina 22 ft Poptop Retractable Keel

Buy It Now: $3,895.00

Sale

Ends In:
17h 5m

1988 Hunter 23.5 sail boat



1988 Hunter 23.5 sail boat

Price: $3,000.00
Buy It Now: $3,800.00

Sale

Ends In:
1d 23h 5m

Macgregor 26d Water Ballast Sail Boat



Macgregor 26d Water Ballast Sail Boat

Price: $3,000.00

Sale

Ends In:
6d 16h 15m

SAILBOAT- 27' AMERICAN W SHOAL KEEL NEWLY REFURBISHED



SAILBOAT- 27' AMERICAN W SHOAL KEEL NEWLY REFURBISHED

Price: $2,950.00
Buy It Now: $5,600.00

Sale

Ends In:
9d 17h 49m

1975 Bristol 27. Great pocket cruiser. Alberg design



1975 Bristol 27. Great pocket cruiser. Alberg design

Price: $2,900.00

Sale

Ends In:
6d 22h 32m

1980 San Juan 21' Sailboat with Trailer NR



1980 San Juan 21' Sailboat with Trailer NR

Price: $2,500.00

Sale

Ends In:
3d 2h 7m

1974 21' San Juan sailboat



1974 21' San Juan sailboat

Price: $2,500.00

Sale

Ends In:
4d 13h 3m

1983 Catalina 25 Sail Boat Tall Rig Sloop Sailboat



1983 Catalina 25 Sail Boat Tall Rig Sloop Sailboat

Price: $2,500.00

Sale

Ends In:
6d 51m

1981 MacGREGOR 25 Sailboat



1981 MacGREGOR 25 Sailboat

Price: $2,499.00

Sale

Ends In:
1d 11h 34m

1974 HUNTER 25 Sailboat w Pop Top Cabin in Connecticut



1974 HUNTER 25 Sailboat w Pop Top Cabin in Connecticut

Buy It Now: $2,488.00

Sale

Ends In:
2d 11h 12m

81 Catalina 22 ft Sailboat with Sails Trailer Sail Boat



81 Catalina 22 ft Sailboat with Sails Trailer Sail Boat

Price: $2,425.00

Sale

Ends In:
3d 4m

1979 HALMAN POCKET CRUISER- SINGLE HANDED WORLD CRUISE



1979 HALMAN POCKET CRUISER- SINGLE HANDED WORLD CRUISE

Price: $2,135.00

Sale

Ends In:
2d 16h 20m

1984 Catalina 22 Pop Top with CDI Furler and trailer



1984 Catalina 22 Pop Top with CDI Furler and trailer

Price: $2,001.00

Sale

Ends In:
3d 2h 22m

1972 22' Tanzer Sailboat



1972 22' Tanzer Sailboat

Price: $2,000.00

Sale

Ends In:
1d 14h 8m

1988 Melges E-Scow



1988 Melges E-Scow

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

Sale

Ends In:
4d 22h 36m

1980 25' Catalina No Reserve



1980 25' Catalina    No Reserve

Price: $2,000.00

Sale

Ends In:
5d 23h 12m

SANTANA 30 30 SAILBOAT RACER



SANTANA 30 30 SAILBOAT RACER

Price: $2,000.00

Sale

Ends In:
6d 18h 13m

1977 BAYLINER BUCCANEER SAILBOAT 20FT



1977 BAYLINER BUCCANEER SAILBOAT 20FT

Price: $1,995.00
Buy It Now: $2,995.00

Sale

Ends In:
2d 48m

SAILBOAT - SAN JUAN 24



SAILBOAT - SAN JUAN 24

Buy It Now: $1,950.00

Sale

Ends In:
3d 18h 32m

23' 1973 PACESHIP SAILBOAT



 23'  1973 PACESHIP SAILBOAT

Price: $1,900.00
Buy It Now: $2,300.00

Sale

Ends In:
12h 23m

22' MacGregor Venture 222 Sailboat and Trailer T143859



22' MacGregor Venture 222 Sailboat and Trailer T143859

Price: $1,595.00

Sale

Ends In:
3d 3m

SEIDELMAN 25' SAILBOAT



SEIDELMAN 25' SAILBOAT

Price: $1,500.00

Sale

Ends In:
6d 17h 57m

CLASIC 1965 CAL 25, MUST SEE, NO RESERVE, CA



CLASIC 1965 CAL 25,  MUST SEE,  NO RESERVE,  CA

Price: $1,500.00

Sale

Ends In:
8d 20h 22m

24' Sailboat Sail Boat 24ft Windrose Trailer Outboard



24' Sailboat Sail Boat 24ft Windrose Trailer Outboard

Price: $1,499.00

Sale

Ends In:
1d 23h 16m

1976 Pearson 26' Used Sailboat - CA



1976 Pearson 26' Used Sailboat - CA

Price: $1,105.00

Sale

Ends In:
13h 3m

Hunter 27 Yanmar Diesel Furler Teak interior NO RESERVE



Hunter 27 Yanmar Diesel Furler Teak interior NO RESERVE

Price: $1,050.00

Sale

Ends In:
2d 3m

22 ft Catalina sail boat with trailer



22 ft Catalina sail boat with trailer

Price: $1,025.00

Sale

Ends In:
4d 14h 46m

1983 United Sailing Yacht Model: US22 - Sailboat, 22 ft



1983 United Sailing Yacht Model: US22 - Sailboat,  22 ft

Price: $1,025.00

Sale

Ends In:
6d 16h 51m

Nice, with yamaha 8hp motor, 25S Seidelmann (NR)



Nice,  with yamaha 8hp motor,  25S Seidelmann (NR)

Price: $1,000.00

Sale

Ends In:
5d 16h 41m

71 Pearson 26 in the water and ready to sail



71 Pearson 26 in the water and ready to sail

Price: $1,000.00
Buy It Now: $2,500.00

Sale

Ends In:
5d 20h 43m

2002 MacGregor 26X sailboat, trailer & 50hp Honda



2002 MacGregor 26X sailboat,  trailer & 50hp Honda

Price: $1,000.00
Buy It Now: $17,000.00

Sale

Ends In:
6d 20h 12m

22 ft O' day 1975 W Trlr, Sails, LOW RESERVE project



22 ft O' day 1975 W Trlr,  Sails,  LOW  RESERVE  project

Price: $810.00

Sale

Ends In:
2d 33m

Balboa 20 with motor and trailer !!!



Balboa 20 with motor and trailer !!!

Price: $800.00

Sale

Ends In:
1d 1h 34m

macgregor 25



macgregor 25

Price: $761.00

Sale

Ends In:
4d 3h 1m

1987 Cal 22 Sailboat



1987 Cal 22 Sailboat

Price: $760.00

Sale

Ends In:
1d 18h 50m

25' Oday sailboat



25' Oday sailboat

Price: $750.00
Buy It Now: $2,400.00

Sale

Ends In:
5d 14h 52m

1972 W D Schock Corp. SANTANA 26 Sail Boat w Cradle!!



1972 W D Schock Corp. SANTANA 26 Sail Boat w  Cradle!!

Price: $610.00

Sale

Ends In:
7d 16h 31m

Possibly WORLD'S GREATEST WEEKEND RACER CRUISER No Res



Possibly WORLD'S GREATEST WEEKEND RACER CRUISER No Res

Price: $550.00

Sale

Ends In:
3d 2h 45m

1973 Jensen Sailboat Cal 25' -NO RESERVE-STK#174701



1973 Jensen Sailboat Cal 25' -NO RESERVE-STK#174701

Price: $530.00

Sale

Ends In:
1d 21h 6m

1976 23' NorthWind sailboat



1976 23' NorthWind sailboat

Price: $525.00
Buy It Now: $1,500.00

Sale

Ends In:
3d 4m

1981 Lockely Newport 27' Used Sailboat - CT



1981 Lockely Newport 27' Used Sailboat - CT

Price: $510.00

Sale

Ends In:
2d 22h 48m

sloop cutter, stable and fun, great weekend sailing



sloop cutter,  stable and fun,  great weekend sailing

Price: $500.00
Buy It Now: $2,400.00

Sale

Ends In:
6d 15h 25m

1978 Catalina 27' Used Sailboat - WI



1978 Catalina 27' Used Sailboat - WI

Price: $466.00

Sale

Ends In:
2d 22h 48m

1982 O'Day 25' Used Sailboat - NY



1982 O'Day 25' Used Sailboat - NY

Price: $352.00

Sale

Ends In:
5d 22h 48m

Harken 0-190 furling system for sailboats up to 26ft.



Harken 0-190 furling system for sailboats up to 26ft.

Price: $343.65

Sale

Ends In:
4d 19h 7m

1977 Venture 25' Used Sailboat - MI



1977 Venture 25' Used Sailboat - MI

Price: $280.00

Sale

Ends In:
1d 23h 3m

NICE S-2 MODEL 8.0B FRESH WATER CRADLE "NO RESERVE"



NICE S-2 MODEL 8.0B FRESH WATER CRADLE "NO RESERVE"

Price: $202.50

Sale

Ends In:
3d 13h 35m

1973 Morgan 27' Sailboat fl mare 73



1973 Morgan 27' Sailboat fl mare 73

Price: $200.00

Sale

Ends In:
6d 23h 3m

Sailboat



Sailboat

Price: $150.00

Sale

Ends In:
5d 23h 14m

1966 Wescomar 25'1" Used Sailboat - CA



1966 Wescomar 25'1" Used Sailboat - CA

Price: $102.50

Sale

Ends In:
5d 22h 48m

1977 O'Day 25' Used Sailboat - RI



1977 O'Day 25' Used Sailboat - RI

Price: $52.55

Sale

Ends In:
5d 22h 3m

1966 Ray Greene Clipper 24' Used Sailboat - OH



1966 Ray Greene Clipper 24' Used Sailboat - OH

Price: $10.00

Sale

Ends In:
1d 22h 3m

1963 Wescomar Victory 21' Used Sailboat - CA



1963 Wescomar Victory 21' Used Sailboat - CA

Price: $10.00

Sale

Ends In:
2d 22h 48m

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