Contessa Sailboats
Below is a list of Contessa sailboats and information about each model. If you are interested in purchasing a Contessa sailboat, we regularly scan the internet for Used Contessa Sailboats.
| Model ↕ | Listings ↓ | Year Built ↕ | LOA (ft) ↕ | Beam (ft) ↕ | Draft (ft) ↕ | Displ. (lbs) ↕ | Hull ↕ | Designer ↕ | Rig ↕ | Keel ↕ |
|---|---|---|---|---|---|---|---|---|---|---|
| Contessa 32 | 38 for sale | 1971 | 32 ft | 9.5 ft | 5.5 ft | 9,500 lbs | Monohull | David Sadler | Masthead Sloop | Fin |
| Contessa 28 | 11 for sale | 1977 | 27.67 ft | 9.42 ft | 4.83 ft | 6,970 lbs | Monohull | Doug Peterson | Masthead Sloop | Fin |
| Contessa 26 | 8 for sale | 1965 | 25.5 ft | 7.5 ft | 4 ft | 5,400 lbs | Monohull | David Sadler | Masthead Sloop | Full |
| Contessa Ood 34 | 7 for sale | 1978 | 33.67 ft | 11.08 ft | 6.33 ft | 8,050 lbs | Monohull | Doug Peterson | Masthead Sloop | Fin |
| Contessa 25 | 1 for sale | 1980 | 25 ft | 7.2 ft | 4.1 ft | 4,750 lbs | Monohull | Peter Cole | Masthead Sloop | Fin |
| Contessa 27 | 1 for sale | 1981 | 27.5 ft | 10 ft | 5.42 ft | 5,750 lbs | Monohull | Rob Humphreys | Fractional Sloop | Fin |
| Contessa 33 | 1 for sale | 1984 | 32.67 ft | 11.08 ft | 5.82 ft | 8,988 lbs | Monohull | Rob Humphreys | Fractional Sloop | Fin |
| Contessa 35 | 1 for sale | 1974 | 35.5 ft | 11.42 ft | 6.33 ft | 13,500 lbs | Monohull | Doug Peterson | Masthead Sloop | Fin |
| Contessa 39 | 1 for sale | 1979 | 38.67 ft | 12.25 ft | 7.25 ft | 14,250 lbs | Monohull | Doug Peterson | Masthead Sloop | Fin |
| Contessa 38 | — | 1973 | 38.5 ft | 11.5 ft | 6.25 ft | 15,500 lbs | Monohull | Sparkman & Stephens | Masthead Sloop | Fin |
| Contessa 43 | — | 1977 | 42.75 ft | 12.5 ft | 7.25 ft | 21,000 lbs | Monohull | Doug Peterson | Masthead Sloop | Fin |
Contessa Sailboats between 20 – 30 ft
masthead sloop1980
Contessa 25
- LOA
- 25'
- Beam
- 7.2'
- Draft
- 4.1'
- Displ.
- 5k lb
Median ask$ 2k
For sale1
masthead sloop1965–90

Contessa 26
- LOA
- 25.5'
- Beam
- 7.5'
- Draft
- 4'
- Displ.
- 5k lb
Median ask$ 11k
For sale8
fractional sloop1981

Contessa 27
- LOA
- 27.5'
- Beam
- 10'
- Draft
- 5.42'
- Displ.
- 6k lb
Median ask$ 13k
For sale1
masthead sloop1977

Contessa 28
- LOA
- 27.67'
- Beam
- 9.42'
- Draft
- 4.83'
- Displ.
- 7k lb
Median ask$ 11k
For sale11
Contessa Sailboats between 30 – 40 ft
masthead sloop1971

Contessa 32
- LOA
- 32'
- Beam
- 9.5'
- Draft
- 5.5'
- Displ.
- 10k lb
Median ask$ 33k
For sale38
fractional sloop1984

Contessa 33
- LOA
- 32.67'
- Beam
- 11.08'
- Draft
- 5.82'
- Displ.
- 9k lb
Median ask$ 26k
For sale1
masthead sloop1978–81

Contessa Ood 34
- LOA
- 33.67'
- Beam
- 11.08'
- Draft
- 6.33'
- Displ.
- 8k lb
Median ask$ 22k
For sale7
masthead sloop1974

Contessa 35
- LOA
- 35.5'
- Beam
- 11.42'
- Draft
- 6.33'
- Displ.
- 14k lb
Median ask$ 57k
For sale1
masthead sloop1973–74
Contessa 38
- LOA
- 38.5'
- Beam
- 11.5'
- Draft
- 6.25'
- Displ.
- 16k lb
masthead sloop1979

Contessa 39
- LOA
- 38.67'
- Beam
- 12.25'
- Draft
- 7.25'
- Displ.
- 14k lb
Median ask$ 46k
For sale1
